Home Vacation Rentals By Owner In New Marlborough, MA

Showing 20 Of 22 Vacation Rentals
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$502.8

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Private Vacation Home

Hot Tub, Chic Sexy Style booking Summer 26!

New Marlborough, Massachusetts, United States

Aberdeen: Sparkling contemporary, sitting on 6+ acres, one-level living + privacy. 2 bedrooms, 2 full baths, fiber internet, AC, hot tub, outdoor seating, grill, firepit, wood stove, 2 Smart TVs, stainless appliances, forest views, washer/dryer, all linens included. The location is less than 10 minutes to Ski Butternut and under 15 minutes to the center of Great Barrington. Clean. Gorgeous. Sexy. This place has it all. Sleeps 5 in beds, 7 guests max.brbrAberdeen: Sparkling, new, wood and glass, contemporary cabin in the woods, sitting on 6+ acres, offers one-level living, luxury, the ultimate Berkshire lifestyle, plus privacy. Amenities include: 2 bedrooms, 2 full baths, fiber-fast (high speed) internet, good cell service, Central AC, wood stove, fire pit, hot tub, deck with outdoor seating and propane grill, huge Smart TV with access to all subscription channels, all high end stainless appliances, all new glass and tile bathrooms, entryway with organizers for your gear, 6+ acres with forest views, washer and dryer, and of course all linens are included. The location is a bit off the beaten path... but with every convenience, is less than 10 minutes to Ski Butternut and under 15 minutes to the center of Great Barrington. Clean. Gorgeous. Sexy. This place has it all.brSleeps 5 in beds, 7 guests max. brAberdeen is a breathtaking Dwell style home located in New Marlborough, MA. This contemporary spa-themed home has one-level living, luxury, and privacy. Newly constructed in 2018, this gem has undergone a full renovation. Step into the entry foyer, well designed to host and store your 4-season Berkshire gear with hooks to grab your jacket and go, boot trays, and a large closet for the rest of it. The great room is lit with an open-concept kitchen, dining, and living room all under one soaring ceiling. This space has large picture windows and sliding glass doors for that easy indoor/outdoor feel. The kitchen has gleaming quartz countertops and all new stainless steel appliances that include: a 5 burner propane stove, new freezer/fridge, dishwasher, and double sink with forest views. The small appliances include; 2 coffee makers (standard drip + espresso maker) toaster, microwave and oodles of plates, glassware, baking tins, etc. Cook up your gourmet meals at Aberdeen! With counter seating for 4 on the island and a gorgeous dining room set for 6, there is plenty of seating here. The wood stove provides a cozy supplemental warmth when the temperatures dip. The living room has ample seating for all, and stunning natural views. There is also a wall mounted smart TV with access to all your subscription tv channels. Both sofas convert to a full bed for an extra guests. A desk is provided for writing or checking email. The entire house has central heating with AC throughout. Two bedrooms were designed for privacy, located in their own wings. The primary bedroom has a king size bed, walk-in closet and its own smart TV. The ensuite bathroom was designed to feel like you just entered your favorite spa with beautiful non-slip marble tiles. The oversized walk-in shower has a rain shower head, plus a pulsating hand held nozzle. There is an interactive smart mirror with adjustable color tones and an anti-fog setting. Guest room #2 features a queen bed + daybed and a closet with built in storage. This guest room has its own full bathroom with a tiled tub/shower combination. Outside, just off the kitchen, is a large screen porch with 2 sofas, a bar height dining table, large weber Propane BBQ grill and a fan to keep you cool. There is also a large sun deck with ample seating and a fantastic modular sofa/bed/and sun lounger that can be set up however you like! There is also a fabulous 5 to 6 person hot tub available year round, with loads of jets to help relax under the stars or after a day of skiing.brbrClose to Ski Butternut and less than 15 minutes to the center of Great Barrington for shopping, restaurants and entertainment. You are also close to some of the best food in the Berkshires: The Old Inn on The Green and The Southfield Store!brAberdeen is pet friendly, however, pets must be approved and, typically, a $150 minimum pet fee (depending on the pet) applies. brNon Smoking, Thank you!
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Bath 2

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$322.23

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Cabin

Cosmo Cabin: Your Cozy Escape

New Marlborough, Massachusetts, United States

Summary:brbrTucked away in the serene woods of New Marlborough, Massachusetts, Cosmo Cabin is a newly renovated 2-bed, 1-bath retreat blending comfort, style & tranquility, under 3 hrs from Boston & just 3 hrs from NYC.brbrbrbrThis cozy country escape features a bright sunroom, a cozy bedroom with an electric fireplace and a spa-like bathroom for ultimate relaxation. Outside, enjoy the deck with a grill or gather around the firepit. With its rustic charm and modern comforts, this is the perfect getaway for couples seeking to unwind and reconnect with nature.brbrbrbrNearby towns: Great Barrington (20mins), Stockbridge (25mins), Egremont (20mins), Catamount Ski Mountain (25mins), Lee (30mins)brbrbrbrThe Space:brbrSurrounded by nature’s beauty, Cosmo Cabin provides a relaxing and stylish atmosphere inclusive of warm wood finishes. As you approach the cabin, step onto the inviting wooden deck complete with outdoor furniture and a BBQ grill where you can bask in the peaceful surroundings. brbrbrbrUpon entering the cabin, you’re greeted by a stylish open-plan kitchen and living area, where warm wood paneling and expansive windows frame peaceful forest views. The kitchen is thoughtfully equipped with high-end appliances, a custom backsplash, and a deep purple farmhouse sink that adds a bold, artistic touch. Just off the kitchen, a charming dining table for four and a cozy daybed create the perfect spots to enjoy a meal or relax while soaking in the tranquil surroundings.brbrbrbrBedroom 1 features a double bed and an electric fireplace to create a cozy, intimate ambiance. With direct access to the screened porch, you can step out for a morning coffee or take in the soothing sounds of nature at any time of day. The sunroom offers year-round enjoyment with its bright and airy design. Whether surrounded by the snowy landscapes of winter, the fiery hues of autumn, or summer’s lush greenery, this tranquil space is perfect for curling up with a book, enjoying quiet conversation, or simply basking in the natural beauty of the wooded setting. The second bedroom offers a comfortable single bed.brbrbrbrThe bathroom is an indulgent retreat, designed to pamper and impress. It features a sleek walk-in shower with natural stone-inspired finishes and modern fixtures, evoking a spa-like atmosphere. The true highlight is the luxurious two-person Stargazer bathtub, perfect for unwinding after a day of exploring the beautiful surroundings.brbrbrbrWhether you're seeking a romantic getaway, a family vacation or a quiet escape with friends, Cosmo Cabin offers the ideal setting to unwind. The tranquil wooded surroundings invite you to enjoy nature while the cabin’s cozy interior offers a haven to relax in comfort. The cabin's ridge-side location provides privacy and proximity to hiking trails, scenic drives, charming towns and local attractions. In the evenings, gather around the fire pit or relax on the deck -whatever your idea of relaxation, Cosmo Cabin provides the perfect place to make it a reality.brbrbrbrThe Neighborhood:brbrCosmo Cabin is 1 mile from the Mill River General Store; filled with local food, produce and staples. It is also close to Sheffield and Great Barrington which have several grocery stores, outstanding restaurants, coffee shops, shopping, yoga and more. You’re close to many hiking trails - access to 72 acres of woods to hike, skiing - Butternut Ski is just 10 minutes away, arts and cultural institutions. With Umpachene Falls and Lake Garfield around the corner, bringing swimsuits in the summer is a must.brbrbrbrGetting Around:brbrCosmo Cabin is under 3 hours from Boston & just 3 hours from New York City. You'll definitely want a car to get there and around the area. In the winter, we recommend a car with four-wheel drive that can handle the snow and gravel roads.brbrbrbrOther Things to Note:brbrCOOLING: There is a mini split above the front door.brbrbrbrThe house has an internet connection and moderate cell service with AT&T, T-Mobile and Verizon. The Berkshires is full of cellular dead zones, so we recommend downloading the region’s online maps to your device prior to arrival or any day while you’re here at the cabin.
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Exceptional(101)

$356.53

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Cottage

Waterfront Cottage 10 Min From Great Barrington

New Marlborough, Massachusetts, United States

A couple's getaway for the books awaits you at this Lake Buel vacation rental. Just 6 miles from Great Barrington's shops, restaurants, and art scene, this 2-bedroom, 1-bath cottage is close to all the Berkshire's excitement, yet far enough for high-quality rest and relaxation. Hike the Appalachian Trail in the summer, ski Butternut Basin during the winter, or enjoy the fall colors from the home's charming deck - and don't forget the amazing stargazing! The ultimate Bay State vacay starts now!brbrThe PropertybrbrDeck overlooking Lake Buel | Fire Pit | Peaceful Neighborhood | Seasonal Fishing Dock | Panoramic ViewsbrbrCraft the ultimate couple's getaway at this charming lakeside cottage - close to Great Barrington dining, arts, and culture, yet rural enough for rest, relaxation, and of course, romance.brbrBedroom 1: Bob-o-Pedic Dual King Adjustable Bed | Bedroom 2 (Updated 9/23/24): Bob-o-Pedic Queen Adjustable BedbrbrOUTDOOR LIVING: Deck, chairs, patio, gas grill, fire pitbrbrINDOOR LIVING: 3 flat-screen TVs, DVD player, vaulted ceilings (washer/dryer available for stays of one week or more.)brbrKITCHEN: Well-equipped, drip coffeemaker, granite countertops, ice maker, dishware & flatware, pots & pans, stainless steel appliances, Crockpot, toaster, kitchen cart. (Countertop dishwasher available for stays of one week or more.)brbrGENERAL: Free WiFi, ceiling fans, towels/linens, canoe, kayaks, SUPs, life jacketsbrbrFAQ: 2 steps to access, no A/CbrbrPARKING: Driveway (3 vehicles)
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Sleep 4

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Exceptional(22)

$626.96

/ Nightly
Private Vacation Home

Massachusetts Lake House w/ Dock - Pets Welcome!

New Marlborough, Massachusetts, United States

150’ Lakefront | Renovated | Great for AnglersbrbrTucked along the shores of Lake Buel — a 192-acre mountain lake — this New Marlborough vacation rental sets the scene for a laid-back Berkshires getaway. Start your mornings on the deck, paddle out in the provided watercraft, and end each day around the fire pit. With 4 bedrooms, 2.5 baths, and easy access to local restaurants, fairways, and wine tastings, it’s as inviting to stay in as it is to head out. Book now!brbr-- THE PROPERTY --brbrC0239292030brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 1 queen bedbr- Bedroom 3: 1 queen bedbr- Bedroom 4: 1 queen bedbr- Sunroom: 1 futonbrbrOUTDOOR LIVINGbr- 65’ dock (seasonal), 2 10' single kayaks, 1 6' single youth kayak, 1 double kayak, 16' canoe, 2 stand-up paddleboards, life vestsbr- Furnished deck w/ Weber gas grill, waterfront view & safety gatebr- Fenced yard w/ fire pit & yard gamesbr- Partially enclosed outdoor showerbr- Picnic tablebrbrINDOOR LIVINGbr- Sunroom w/ refinished floors, 96’ x 40’ 8-person dining farm tablebr- 50 Smart LED TVbr- Simmons Beautyrest mattresses w/ adjustable incline up to 80 degreesbrbrKITCHENbr- Refrigerator, gas range, ovenbr- Drip coffee maker, toaster, toaster oven, microwavebr- Dishware/flatware, trash bags/paper towelsbr- Granite countertopsbrbrGENERALbr- Free WiFibr- Window A/C unit, portable A/C unit, central heating, ceiling fansbr- Full insulationbr- Linens/towelsbr- Iron/boardbrbrFAQbr- Pet fee (paid pre-trip)br- No in-unit laundrybr- Food not providedbr- Pontoon boat not availablebr- Homeowner’s family occasionally on-sitebrbrACCESSIBILITYbr- Single-story home, 2 steps to enterbrbrPARKINGbr- Driveway (3 vehicles max)brbr-- THE LOCATION --brbr- Lakefront activities: kayaking, canoeing, floating, fishing, swimming, 3 miles to public boat launchbr- 1 mile to Les Trois Emme Winerybr- 5 miles to Beartown State Forestbr- 6 miles to Mahaiwe Performing Arts Centerbr- 14 miles to Greenock Country Clubbr- 43 miles to Bradley International Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly with a $100 fee (+ fees & taxes, 1 pet max)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This single-story home requires 2 steps to enterbr- There is no washer or dryer on-sitebr- The dock is installed and removed by a contractor, and the exact date when this occurs is not within the homeowner’s control. It is generally installed around Memorial Day and removed in mid-to-late October. The lake can still be accessed without the dock, and watercraft can be launched from the steps. The lake will be cold in the spring and autumn monthsbr- No food is provided at the propertybr- The homeowner’s family owns a pontoon boat attached to 1 side of the dock, and they may occasionally be present to access it during your stay. The pontoon boat is not included in the rental and should not be boarded by guests
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Exceptional(7)

$804.33

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Private Vacation Home

Lake Buel Waterfront - 4 Bedrooms with private dock

New Marlborough, Massachusetts, United States

Idyllic Berkshire lakeside 4 bedroom cottage offering swimming, fishing, water sports and hiking. Waterfront location with your own private dock 5' in front of the house.brbrLocated directly on the shore of Lake Buel in New Marlborough MA just minutes away from Tanglewood, Jacobs Pillow and many other attractions. Our family home boasts a 30-foot screened in porch for dining and enjoying the beautiful lake.brbrAll rooms are on one floor. You can drive right up to the front door. Great for older people or families with little kids.brbrThe Living room dining room combination is knotty pine finish with a 14 foot stone, wood burning fireplace (decorative only, not used for heating). The kitchen is fully equipped with a gas stove (built-in air fryer) dishwasher, microwave, toaster, refrigerator and coffee station. Included are linens and blankets, towels, cookware, dishes, an outdoor Gas BBQ grill with associated cooking utensils. The family room has a large sectional and a dining table that seats 8.brbrThis lake front cottage has it's own private dock for swimming and boating and has a beautiful grass lawn in front. Located on a 3/4 mile private dirt road just off Lake Buel Road with a short 10 minute ride to Great Barrington that has the best shops, restaurants and theaters in the Berkshires . brbrBreathtaking, tranquil Summer lakefront getaway. You will truly fall in love with this amazing summer home. It is a family friendly environment and home. brbrThe Red House is a Summer Cottage and it is available for rent only during the Summer season. brbrThe Red House is part of our 4 acre family compound on Lake Buel. Our family has owned this property since 1935. Generations of children have had their whole life defined by our Summers at the lake. This house is one of four on the property. The other three are occupied by the extended family members.brbrYou are right on the lake, beautiful screened in porch, one floor, no stairs in or out. Parking is on the same level as the house. You will spend much of your time lounging around or enjoying your meals on the 30' long screened-in porch that runs the width of the house. Plenty of comfortable seating on the porch and a dining table that seats 8. Bring your own boat and tie it up your private dock. When not enjoying the screened porch, the Great Room will be the activity center of the house. It starts with the Fireplace area and our friend 'the moose'. The great room sliding glass doors open to the screened in porch to bring the summer breezes into the house. Use the two ceiling fans or the room air conditioner to make it comfortable on the warm summer days.
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$1718.26

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Private Vacation Home

Hot tub, Sauna, Game Room, Fireplaces + Heated Pool in Summer!

New Marlborough, Massachusetts, United States

Berkshire Rental Properties is delighted to offer Casa Mia – a dynamic rental property, well equipped and set up with fun amenities for family and friends to enjoy. Amenities include 5+ bedrooms, 4 full baths, sleeps 12 in beds and 14 max. There is a 45' X 19' heated (seasonal) pool with outdoor seating, sun umbrellas, patio with luxurious seating and outdoor grill, fire pit and bocce field, walking path, hot tub (available year round) sauna, double-sided fireplace, Mini Split ACs, high speed internet, strong cell service, chef's kitchen with high end stainless appliances, a crib, high chair, ping-pong, foosball, board games, and a short slightly-steep hike to a big view!brbrThis fully renovated contemporary post and beam has an open floor plan for guests to enjoy. As you enter you are greeted by floor to ceiling windows, a massive stone fireplace, and a sparkling chef's kitchen. A smart portrait TV is hung over the double sided fireplace for you to sit back and enjoy a show on the huge sectional sofa. There is a chess set that entertains, and additional seating in the living room that is ample and inviting. The double-sided fireplace warms both the living room and the dining room. The dining table seats 8, plus there is more counter seating available on the kitchen island. The dining room has easy access to the back sun deck with a large gas BBQ grill, many seating options, umbrellas for cover and the sunken hot tub that is available year-round! The well equipped kitchen is a dream with its sparkling quartz countertops and stainless steel appliances. There is a 6 burner gas range, dishwasher, large fridge, microwave, blender, toaster, and Keurig coffee maker, along with many small appliances, gadgets, glassware, dishes, serving platters and more. brbrWhere you will sleep: brMain floor bedroom #1 with a Queen bed (sleeps 2)brMain floor bedroom #2 with twin bunks and a twin cot. (sleeps 3).brThese main floor guest rooms share a full bathroom with a tub/shower combo.brSecond floor Bedroom #3 (Primary, ensuite) with a King bed, stone fireplace, balcony, and ensuite bathroom with soaking tub and walk-in shower. (sleeps 2)brSecond floor Bedroom#4 has a Queen bed and a twin daybed (sleeps 3)brSecond floor Bedroom #5 has a Queen bed. (sleeps 2)brGuest rooms 4 and 5 share a full bathroom with a walk-in shower.brThe second floor also has a Queen sofa bed in the loft area that sleeps 2.br*Casa Mia sleeps up to 14 guests, but no more than 10 adults is preferred. brbrThe lower-level game room has a smart TV, 2 sofas, ping-pong, foosball, board games and more. There is a fabulous sauna to enjoy after a day on the ski slopes as well as the 4th full bathroom with a tub/shower combo. Also located on this floor is the laundry room with a washer and dryer available to guests. brbrOutside you will discover the fabulous heated pool! This is available from Memorial Day Weekend to Columbus Day Weekend. There is comfortable poolside seating, striped pool towels, outdoor umbrellas, a fire pit and a bocce ball court! The screened poolhouse is a great place to sit back and watch the kids swim in the pool. There is a dry bar with stools inside it along with an ice chest for drink storage. Take a short walk up a slightly steep path to take in a big Berkshire view. The large sundeck just outside the great room has 2 dining tables, an outdoor sofa, additional chairs and a large hot tub open all year!brbrGreat Location: 10 minutes to the center of Great Barrington with shops, food, bars, art, ice cream, candy, specialty coffee, toys, and less than 10 minutes to Ski Butternut. There is great hiking and all Berkshire activity close by - please ask for more details.brbrPets are considered with a pet fee. No Smoking please!
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Exceptional(23)

$361.1

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Cottage

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

New Marlborough, Massachusetts, United States

Recently renovated home in the exclusive Lake Buel community very close to the Appalachian Trail, Butternut Ski Area, Downtown Great Barrington, Tanglewood, Kripalu, The Norman Rockwell museum and so many more Berkshires attractions. Our rural retreat is well equipped with modern comforts including a well-stocked kitchen, radiant heat floors in the basement, WiFi, central heat & A/C and smart tvs. Enjoy our lake rights at the community dock a short walk away: swimming, kayaking & fishing await you! brThe spacebrYou'll love our comfortable home as it has plenty of space to spread out with cozy bedrooms with comfortable beds (upstairs bedrooms have Queen beds, downstairs has a King bed). 2/3 bedrooms have a smart t.v.s with remote control, sufficient lighting and nearby bathrooms. Both upstairs bedrooms have ceiling fans. There are two separate interior areas to sit and relax. There is a dedicated dining space off of the kitchen with additional bar seating, and numerous outdoor seating areas including a spacious deck with table and chairs. Our kitchen appliances include a full sized refrigerator, electric oven, dish washer and two coffee makers (one traditional drip in the kitchen and one Keurig in the basement bedroom). Our fireplace is equipped with a heat propelling propane insert and will operate at the flip of a switch!brGuest accessbrYou'll have access to the entire home except for the utility room. The shed in our yard is yours to use to store bikes/gear or additional items you bring with you during your stay. We have a propane BBQ for your use on the front porch as well as plenty of outdoor seating.brOther things to notebrEnjoy Lake Buel living in this peaceful enclave where your hardest choice each day might be to kayak or hike the nearby Appalachian Trail. For recommendations on what to do, where to eat, etc please be sure to view our personalized Pine View Cottage Guide which will be sent to you when you book!brbrWe are a rural destination which will require some planning before you arrive. It's a good idea to make a stop at the grocery store for essentials before you arrive (the nearest one is Price Chopper at 300 Stockbridge Road in Great Barrington).brbrOur water is well, so it's great for drinking straight out of the tap!brbrUnfortunately there are no food delivery services in our area at this time.
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Exceptional(4)

$418.0

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Private Vacation Home

Steepletop: Nature Lover’s Paradise w/Rec Room

New Marlborough, Massachusetts, United States

Summary:brbrWelcome to Steepletop Lodge, a beautiful 4 bed/ 2 bath modern retreat with endless opportunities to unplug and forest bathe.brbrbrbrA wall of windows overlooks serene woods and wetlands, and the screened porch welcomes a full three seasons of respite, situated to catch Summer breezes; with a fireplace to keep cozy in the Fall. Modern, bright, well-appointed, and stocked with games, Steepletop Lodge is a special place to reconnect with both nature and your loved ones!brbrbrbrThe Space:brbrFollowing the stone path up to the front door, a spacious foyer welcomes you and seamlessly connects to the open-concept living area, with tall ceilings and flooded with natural light from a wall of windows showcasing the property's wooded views.brbrbrbrThe living room features a woodburning stove and comfy seating, creating a cozy atmosphere within the open layout. Adjacent to the living room, find an enclosed porch with a fireplace, dining table and lounge area, perfect for enjoying nature in any weather. The kitchen is efficiently laid out and fully equipped, with an island and breakfast bar for easy meal prep and casual dining. A repurposed bowling lane serves as the dining table, inviting guests to gather for memorable meals.brbrbrbrThree bedrooms and two baths occupy one side of the main floor. The primary bedroom offers a queen bed, a reading nook, and an ensuite bath with a walk-in shower. Large glass doors open directly onto your private deck. A second bedroom with a full bed and a twin trundle includes a convenient desk area. A full bathroom serves the bedrooms, featuring a bathtub/shower combo. A third bedroom, with twin beds, boasts a cozy reading area and charming decor.brbrbrbrDownstairs, enjoy recreational and fitness options including a stationary bike, treadmill, ping pong table, and cozy seating area with a TV for relaxation. A fourth bedroom offers a queen bed with and convenient work space for remote work. Lastly, a laundry room completes the lower level of the home.brbrbrbrSteepletop Lodge has been a beloved family gathering place for years, offering the perfect setting to create lasting memories with loved ones.brbrbrbrGuest Access:brbrThere is a lockbox and a key inside the screened in porch. We will provide you the code during your check in process.brbrbrbrThe Neighborhood:brbrThe property itself offers much nature to explore, and just across the road is a reserve (also called Steepletop, after the flowers that grow plentifully in the area) with trails to enjoy.brbrbrbrThere is so much to enjoy nearby, including candlelit dinner at the Old Inn on the Green, breakfast at the Southfield Store (also a great place for a quick coffee and picking up local provisions), and many hikes and nature spots. Not far from Southfield is Umpachene Falls–an excellent destination for hiking and swimming.brbrbrbrSteepletop is also close to both Sheffield and Great Barrington which have several grocery stores, restaurants, coffee shops, shopping, yoga, and more. You're also close to hiking and cultural institutions.brbrbrbrGetting Around:brbrSteepletop Lodge is approx. 2.5 hours from Boston and 3 hours from New York City. To enjoy the expansive beauty of the region, you'll need a car to get here and get around--and the drive will be stunning! Since cell service can be inconsistent in the country, we recommend that you download the region's online maps to your phone before your trip.brbrbrbrWe strongly advise using or renting a car that has all wheel or 4 wheel drive to access the property, especially in the colder months.brbrbrbrOther Things to Note:brbr*NOTE: The house does not have air conditioning; however, ceiling fans are installed in each bedroom, and additional portable fans are available throughout the home.brbrbrbr*Please also note that two of the three first-floor bedrooms have curtains, while the third first-floor bedroom and the fourth (basement) bedroom do not have window coverings.
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Exceptional(13)

$984.8

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Country House

5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home

New Marlborough, Massachusetts, United States

Renovations just finished on this unique home, that originally dates to the 1700s. Great for families and big groups, with space to spread out, inside & out. Charming historic details include stone fireplaces, bay windows, a 3-season room, and a dedicated library. Newly modernized kitchen and updated bathrooms. 5 bedrooms, including a kids' bunk room. Set in a very remote, quiet location, but a quick drive to New Marlborough or Great Barrington. The large in-ground pool is targeted to be open by July.brbrABOUT THE HOUSE: brDownstairs: the space has plenty of room to hangout and entertain, including 3 fireplaces. Large 'great room' with flat-screen TV and large fireplace, and comfortable seating for the whole group. The dining room seats 8-12. The kitchen is open to the breakfast nook, which has an additional indoor fireplace and banquette seating. The library has lots of books, and pocket doors that close to make it a dedicated, quiet office space. There's a 3-seasons room with a 3rd fireplace and sliding glass doors that look over the stone back patio and the backyard. There is also a large mud room, directly accessible from the kitchen & outside, perfect for all your ski or summer gear and with a brand new washer/dryer.brUpstairs: on one side, you'll find 3 bedrooms including 2 with king beds and 1 with a queen bed. On this side, there is also a full bathroom. In the other wing of the upstairs is the other king-size bedroom, the bunk room, an additional full bath, and a small powder room. There is also a large walk-in closet that's been converted to a flex space to be used as an office or baby room with a crib. The layout of the two wings makes it easy for multi-families or groups to share and have their own space. Each bedroom has new mattresses, linens, and blackout shades.brbrOUTSIDE: brThe backyard is large and overlooks the pool. The pool is large, fully fenced in, and is not heated. Pool will be open mid June to at least mid September for 2023. There's a wraparound driveway that surrounds the property, perfect for kids to bike or scoot in, and a basketball hoop. Yard is not fenced.brbrAMENITIES: brThis house is set up for the owners' multi-generational family, and you'll find plenty of amenities that you're welcome to use. Plenty of books, board games, and puzzles. The kitchen is fully stocked. For kids, there are cribs and all the other baby gear you'd need as well as toys, games and outdoor equipment like scooters, pool toys and more.brbrTHE AREA: brThere are great places all around the Berkshires to enjoy fishing, hiking, boating, swimming, kayaking, trail running, mountain biking, camping, skiing, sledding, skating, and more. The Berkshires is a center for music and dance (Tanglewood, Yale Music School), theater (Shakespeare & Company), arts and local craft (downtown Great Barrington, farmers markets), dining (many exceptional local and farm-based restaurants), and hospitality (Inn on the Green, Gedney Farm, Red Lion Inn, etc.). There are no Ubers or Lyfts or taxi services. Cell reception can be spotty at best. Wifi is available in most cafes and stores.brbrLocated in the small village of Southfield, this house is just a 2 minutes drive from a lovely general store called the Southfield Store. It's also conveniently located to Butternut Mountain, Great Barrington, and Stockbridge. The perfect launchpad for whatever you'd like to do in the Berkshires -- antiquing, hiking, skiing, lakes or more. Explore the cute downtowns of the various towns nearby and then come back to the quiet and peaceful village of Southfield!brbrbrOTHER THINGS TO NOTE: brThe house is in a rural country area - there is limited cell reception, and the area can be prone to power outages. Many areas of the home were recently updated, and renovations were completed in 2023. However, this home still has many of the original historic elements that may make it unsuitable for some guests. Examples- the staircases are steep, 2 of the bedrooms upstairs and the powder room have sloped / low ceilings, slate patio on the back deck is not fenced, and would not be suitable for unsupervised toddlers. Please read the house rules and note the descriptions in the photo captions, and reach out with any questions or concerns you might have, prior to booking.
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Exceptional(2)

$5776.08

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Private Vacation Home

Sunset Falls: A Berkshire Mountain Luxury Retreat

New Marlborough, Massachusetts, United States

Welcome to Sunset Falls, where luxury meets nature in this modern architecturally significant home on 167 private acres. Open-concept living areas, floor-to-ceiling windows, and spacious great room. Breathtaking mountain views and full-service luxury amenities. Perfect for family gatherings and romantic getaways, this private oasis provides a serene escape, promising a unique, pampered experience with concierge service, ensuring a stay beyond the typical experience.brbrbrTHE SPACE:brbrThis luxurious mountain retreat is nestled in the picturesque Berkshires of western Massachusetts just 20 minutes from Great Barrington. Surrounded by the soft silhouettes of the Berkshires, this unique home offers an unparalleled experience. Unwind on the sundeck by the hot tub, relax in the steam room, explore hiking trails located on the property. Radiant heated floors and zoned heating/AC ensure comfort throughout. brbrInside, the living room features floor-to-ceiling windows, allowing nature's beauty to seamlessly become a part of your surroundings. A curving roof adds a touch of architectural elegance, creating a haven of comfort and style. The great room and sunroom provide additional spaces to unwind and soak in the breathtaking views. Surround yourselves with nature while enjoying peace and serenity. brbrBEDROOMS:brbrEach bedroom in Sunset Falls is designed for ultimate comfort and tranquility. Enjoy plush Italian cotton linens, custom robes, and ensuite bathrooms with deluxe amenities. Unwind in front of 50” smart TVs or savor a glass of wine at the private wine bar in the primary bedroom. Blackout blinds ensure a restful night's sleep, and individual temperature control adds a personalized touch. Bathroom amenities include: towels (bath, hand, washcloth), soap, shampoo, conditioner, hair dryer, and makeup mirror.brbr(Second floor)br• Primary Bedroom: King size bed, Ensuite bathroom with stand-alone shower & bathtub, Alfresco shower, Television, Balconies (Mountain View and Pond View), Fireplace, Refreshment Bar with Wine Cooler and Coffee Maker, Television, Seating Area with Recliners, Mountain view. brbr(First floor)br• Guest Bedroom #1: Queen size bed, Ensuite bathroom with stand-alone shower, Television, Terrace, Mountain view.br• Guest Bedroom #2: Queen size bed, Ensuite bathroom with stand-alone shower, Television, Terrace, Mountain view.brbr(Ground floor)br• Guest Bedroom #3: Queen size bed, Ensuite bathroom with stand-alone shower, Television, Terrace, Mountain view.br• Guest Bedroom #4: Queen size bed, Ensuite bathroom with stand-alone shower, Television, Terrace, Mountain view.br• Kids “Bunk” Room (Bedroom): 6 Queen over queen size bunk beds - sleeps 12brbrCHEF’S KITCHEN & ENTERTAINMEMT HUB:brbrOur fully equipped kitchen is a culinary haven, featuring Subzero refrigerators and freezers, wine fridge, a Wolf 6-burner gas range with grill, and three Bosch dishwashers. The great room located on the ground floor serves as an entertainment hub, complete with a pool table, foosball, shuffleboard table, darts, arcade games, an 85” TV, and a wet bar with a wine fridge and a kegerator. (*Alcohol not included. Please note that for the use of the kegerator, advanced notice is required. Custom kegs need to be ordered in advance to ensure delivery for your arrival.) For quieter moments, explore the library or children’s nook with an array of books and games.brbrINDOOR & OUTDOOR DELIGHTS:brbrImmerse yourself in luxury with radiant floor heating throughout, three indoor fireplaces, and access to a 2-car heated garage. Step outside to a spacious deck with an 8-person hot tub and a gas fire table or enjoy the 4-person steam and adjoining cedar lined changing area located adjacent to the 4 season sunroom which can extend your outdoor living space. Enjoy the serenity of nature and the breathtaking views from every corner of the property.brbrFITNESS & RECREATION:brbrMaintain your fitness routine in our well-equipped gym, featuring a Bowflex treadmill, tread climber, elliptical, cable trainer, free weights, and yoga mats. Unwind in the steam room or indulge in a soothing massage, available upon request. The property also offers easy access to nearby hiking trails for those craving outdoor adventures.brbrCONCIERGE SERVICES & BEYOND:brbrSunset Falls provides a full-service experience, including concierge services, housekeeping touch-ups, and grocery delivery. Elevator access, in-house massage (Total cost will be determined by the massage therapist. *Note- There is an administrative fee of $50 per massage for this service.), chef services (The total cost will be determined by the chef. *Note- There is an administrative fee of $100 per meal for this service.), and seasonal farm-to-table dining are available upon request, ensuring a tailored and memorable stay. brbrEXPLORE THE BERKSHIRES:brbrSunset Falls is conveniently located just 20 minutes from Great Barrington and surrounding towns. Explore nature, local waterfalls and walking trails minutes from the home. Whether you're seeking cultural experiences, outdoor adventures, or simply a quiet retreat, our mountain oasis promises an unforgettable escape. Your concierge can provide all the details needed to enhance your stay in the beautiful Berkshire Mountains.
Bed 6

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Bath 6

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Sleep 16

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Exceptional(36)

$547.4

/ Nightly
Private Vacation Home

Private Woodland Getaway minutes from Ski Butternut

New Marlborough, Massachusetts, United States

Set in the heart of fifteen peaceful wooded acres and fronted by a private meadow, this beautiful chalet-style home with airy, open floor plan is perfect for family vacations or a romantic get-away any time of the year. brbrTHE LOCATIONbrJust seven minutes to Ski Butternut and fifteen minutes to downtown Great Barrington. Tanglewood, Jacob's Pillow, Berkshire Theater Festival, historic homes, and many other attractions are all within convenient driving distance as well. Foodies will delight in the abundant and diverse culinary offerings of the area, including two excellent restaurants just down the road in New Marlborough.brbrStep out the back door to a private trail that connects to miles of hiking or snowshoeing on two nature preserves adjacent to the house property. Hop in the car for a short ride to the Appalachian Trail, Monument Mountain, lakes, swimming holes, waterfalls, and other natural attractions. brbrTHE HOUSEbrPrivate driveway wends through 1/3 mile of woods before opening to the large secluded meadow that fronts the house. Entrance hallway leads to the modern kitchen and a great room with cathedral ceilings and stone fireplace. Floor-to-ceiling windows provide expansive views of nature and flood the home with natural light. Kitchen is well appointed with stainless steel appliances, gas stove and peninsula seating area. Cozy den with sleeper sofa and television opens off the kitchen and entrance hall. Across the hall is a half bath with front-loading washer and dryer. Sonos sound system fills the entire main living area with music. brbrLuxurious first floor master bedroom features king size bed, beautiful stone fireplace and spa-like white marble en suite bathroom complete with oversized tub, separate shower and double sinks. brbrHuge deck extends across the front of the house, from great room to master bedroom, with sliding door access from both, offering elevated views of the meadow and surrounding woods. The ridge line of East Mountain State Forest is visible through the trees to the West.brbrSecond floor features queen size bedroom with en suite full bathroom. The wide hallway contains an alcove with a Shaper Image massage chair, and leads to a roomy Kids' Dormintory with twin-over-full bunk beds, a queen bed, and separate twin size built-in window bed. Perfect for children to play and hang out!
Bed 3

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Bath 2

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Sleep 8

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Exceptional(24)

$305.83

/ Nightly
Private Vacation Home

Peaceful, Post and Beam Loft, Sleeps 9

New Marlborough, Massachusetts, United States

Summary:brbrEnjoy our lovely home for your next stay in the Berkshires! brbrThe list goes on but this house is the total package: COMFORT, TRANQUILITY and WARMTH all in one place!brbrNear plenty of outdoor activities for you to enjoy year round: Ski Butternut is only an 8-minute drive, Dry Hill (a 206 acre-nature preserve) is just a 7-minute ride and Tanglewood is only a quick 25-minute drive.brbrbrbrThe Space:brbrThe classic and peaceful vibe of this lovely home, will make you want to stay longer. brbrbrbrThis house can sleep eight, here are the bed layouts for easy planning:brbrBedroom 1: a private bedroom with one queen bed.brbrLoft 1: 2 queens, 1 full size bed, and 1 queen size air bed brbrbrbrA spacious living area is located on the first floor, with Samsung TV that can access Netflix and other streaming apps plus access to basic TV channels so you can relax and enjoy the indoors as well.brbrbrbrThe full bathroom is tranquil with a double headed shower and a 2-person Jacuzzi tub. There is also a separate half bathroom in the house. brbrbrbrThe kitchen is complete with everything you need to make a home cooked meal including gas stove, and dishwasher. It is stocked with all the necessary cooking/serving necessities including: cookware, pots, pans, plates, cups, and silverware. brbrbrbr Hardwood flooring, washer & dryer, hotel-like linens and parking for six round out this Berkshire’s gem!brbrbrbrPlease keep in mind:brbr-The booking guest must be at least 25 years old and must remain present at the property for the entire duration of the stay.brbrbrbrGuest Access:brbrEverything you need for a great stay, toiletries, linens, towels, hairdryer, iron and ironing board, washing machines, detergent, and more!brbrbrbrThe Neighborhood:brbrNew Marlborough is a quintessentially Berkshire’s town. brbrSeveral rivers, including the Konkapot River, Umpachene River, and Whiting River, flow through town.brbrSki Butternut is only an 8-minute drive, Dry Hill (a 206 acre-nature preserve) is just a 7-minute ride and Tanglewood is only a quick 25-minute drive. brbrbrbrThe town grew as a combination of agriculture in the area around the town center, and mills along the rivers. brbrYou can find plenty of grocery stores, and scrumptious cafes and restaurants in New Marlborough, Here are some places to go:brbrbrbrRestaurants Old Inn On The Green, is a 6-minute drive.brbrMill River General Store, is a 7-minute drive.brbrPlaza Package Great Barrington, 9- minute drive. brbrBaba Louis Pizza Great Barrington, 11-minute drive.brbrCVS Great Barrington, 12-minute drive.brbrCafe Adam Great Barrington, 12-minute drive.brbrbrbrThe nearest bus service and small airport is in Great Barrington, and the nearest rail service (along the Lake Shore Line of Amtrak) is in Pittsfield. Approximately a 10-15 minute drive from the home.brbrbrbrOther Things to Note:brbrWe look forward to welcoming you soon! brbrStandard rules like no smoking, no partying, and being respectful of the neighbors apply.brbrBring your furry friends, two dogs are allowed. $50 per dog per stay. Dogs must be at least one year old, sorry no puppies!brbrbrbrNo sweat on accidental & reported damage! Your rental includes an accidental reported damage waiver fee up to a maximum of $800. The cost to repair any accidental and reported damage to the rented property including any missing or broken items up to a maximum of $800 will be covered at no charge to you as long the damage is reported to your Host before you depart.brbr*Damage caused by pets is not covered by the accidental damage waiver.brbrbrbrInteraction with Guests:brbrAlways available on Airbnb during the day and by phone at night.
Bed 1

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Bath 2

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Sleep 9

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Exceptional(1)

$595.18

/ Nightly
Private Vacation Home

Hilltop Escape with Views & Hot Tub

New Marlborough, Massachusetts, United States

Summary:brbrContemporary Berkshire retreat with stunning mountain views, two king suites, media room, hot tub, and wraparound deck. Enjoy sunsets, nearby skiing, hiking, Tanglewood, and Great Barrington. Features include a chef’s kitchen, gas fireplace, fast WiFi, fire pit, and office space. Surrounded by nature on 3.5 wooded acres, just minutes from top attractions. The perfect blend of luxury, privacy, and convenience.brbrbrbrThe Space:brbrWelcome to Hilltop, a serene and stylish Berkshire escape where privacy, luxury, and nature come together in perfect harmony. Perched atop a wooded ridge on 3.5 acres, this contemporary two-story home offers sweeping views of the tree-covered valleys and rolling Berkshire Mountains from nearly every room. Whether you’re here for a romantic getaway, an adventurous family vacation, or a peaceful work-from-home retreat, Hilltop delivers an unforgettable experience in every season.brbrbrbrFrom the moment you arrive, you’ll feel immersed in the tranquil beauty of the Berkshires. Watch the sunset light up the hills from the expansive wraparound deck or unwind in the seven-person hot tub beneath a canopy of stars. Located just 12 minutes from downtown Great Barrington and within 20–25 minutes of Stockbridge and Lenox, you’ll enjoy quick access to top attractions like Tanglewood, Butternut Ski Resort, Lake Buel, and the area’s world-class dining, shops, hiking trails, and art venues.brbrbrbrInside, Hilltop features 2,370 square feet of bright, open living space with two luxurious primary suites, 2.5 bathrooms, and a media room that doubles as a third sleeping area. The main level showcases floor-to-ceiling west-facing windows that fill the home with natural light and frame the incredible mountain views. Thoughtfully designed with a mix of modern furnishings and regional antiques, the décor reflects the character and creativity of the Berkshires.brbrbrbrThe living room is perfect for gathering, with a soaring ceiling, cozy gas fireplace, and 70” HDTV equipped with Roku for you to connect to your favorite streaming services. The open-concept kitchen and dining area allow everyone to stay connected while preparing meals or enjoying a glass of wine. Chef’s will enjoy the four-burner gas cooktop, double oven, new smart refrigerator with ice maker and in-door filtered water, microwave, dishwasher, and Breville Smart Oven Pro. A French press, Keurig K-Duo Hot and Iced Single Serve and Carafe Coffee Maker to ensure your mornings are off to a delicious start.brbrbrbrThe dining room comfortably seats six and is surrounded by windows, making even a casual meal feel special. For those who need to get a bit of work done, the dedicated office/library offers a small desk, computer monitor, reading nook, and 1GB speed WiFi—ideal for remote work or study. This space also connects to the lower-level primary suite and can be used for a pack-n-play if needed.brbrbrbrThe main-level primary bedroom features a king-size bed, 55” TV, walk-in closet, and breathtaking views. The spa-inspired en suite bathroom offers dual vanities, a soaking tub, glass-enclosed rain shower with multiple spray options, and a private bidet-equipped toilet room. You’ll also find an all-in-one washer/dryer conveniently located inside the walk-in closet.brbrbrbrUpstairs, the second primary bedroom is a peaceful retreat with vaulted ceilings, exposed beams, four skylights, and west-facing windows that frame treetop and sunset views. A 60” HDTV provides entertainment, and a stylish shared bathroom with glass-enclosed shower and oversized vanity completes the upper level.brbrbrbrThe media room offers a 77” HDTV and an oversized modular sectional that converts into a queen bed or two full beds, making it the perfect third bedroom or movie-night hideaway. With five TVs throughout the home, everyone can enjoy their favorite shows, games, or streaming services at any time.brbrbrbrStep outside to enjoy the best of outdoor living: a Blackstone gas griddle, fire pit, dining area, and of course, the private hot tub overlooking the mountain ridge. Thoughtful touches like a selection of spices, high-quality kitchenware, plush linens, and a variety of board games make it easy to settle in and feel at home.brbrbrbrGuests have full access to the home, with the exception of the locked, unoccupied basement. Please note: the bedroom skylights do not have window treatments—early risers will love the natural light, while light sleepers may wish to bring an eye mask.brbrbrbrFor easy planning, here are the bedroom layouts:brbrBedroom 1: King Bed (Main Level Primary Suite)brbrBedroom 2: King Bed (Upper Level Primary Suite)brbrMedia Room: Configurable Sectional (Two Full Beds or One Queen Bed)brbrbrbrAt Hilltop, you’ll find yourself surrounded by beauty, comfort, and the rich cultural offerings of the Berkshires. Whether you’re catching a show at Tanglewood, hiking nearby trails, skiing at Butternut, kayaking on a mountain lake, or simply savoring a sunset from the deck, this special home provides the perfect setting to relax, recharge, and reconnect.brbrbrbrPlease keep in mind:brbr-The booking guest must be at least 25 years old and must remain present at the property for the entire duration of the stay.brbrbrbrThe Neighborhood:brbrLocated between the historic village of New Marlborough and Great Barrington.brbrOnly 12 minutes from downtown Great Barrington, 25 from Lennox and 20 from Stockbridge.brbrbrbrOther Things to Note:brbrWe look forward to welcoming you soon!brbrStandard rules like no pets, no smoking, no partying, and being respectful of the neighbors apply.brbrbrbrHot Tub: You must sign the pool waiver form in order for us to access to the hot tub area. If your reservation is not in the peak summer we make no assumptions that the pool will be open during your stay. Please ask us before reserving to clarify this.brbrbrbrNo sweat on accidental & reported damage! Your rental includes an accidental reported damage waiver fee up to a maximum of $800. The cost to repair any accidental and reported damage to the rented property including any missing or broken items up to a maximum of $800 will be covered at no charge to you as long the damage is reported to your Host before you depart.brbrbrbrInteraction with Guests:brbrSupport team available 24 hours a day.
Bed 3

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Bath 2

Bath

Sleep 6

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Exceptional(40)

$285.39

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Private Vacation Home

Converted Berkshire schoolhouse on a quiet river

New Marlborough, Massachusetts, United States

Renovated schoolhouse on a quiet river in the Berkshires. This is the perfect place to unwind. Great for families and friends to relax and reconnect. Take a walk to the waterfalls, play croquet or volleyball on the lawn, gather dinner from our seasonal garden and enjoy 'smores around the fire pit. Very private and woodsy, but close to Butternut for skiing, Great Barrington for shopping and access to all the music and art the Berkshires has to offer. We are very close to some well known restaurants like Cantina 229, Old Inn on the Green and Gedney Farm. Home is stylish, comfortable and inviting. This house is perfectly cozy and you many never want to leave it! We provide all the basic staples ranging from bandaids, shampoo and an iron to coffee, tea, oil, vinegar and some necessary baking items. You will have all the pots and anything in the fridge and cabinets. We have wifi but you can easily unplug if that's what you're looking for. Smart TV to access your own accounts, Great DVD collection for all ages (no cable tv), games like Monopoly and Scrabble, CD collection, BBQ gas grill and charcoal and room to unwind. Don't forget to sign the walls in the downstairs bathroom! Our house is not suitable for toddlers and young children and is not child proofed, we are on a quiet road but there is a river so you will need to use your judgment and be safe. As for pets, we are not equipped for them and not a suitable place for them. We don't even bring our own dogs and cat. We are surrounded by beautiful serene woods but those woods have poison ivy and ticks. You don't want your lovely animals to mess with all that and suffer. And we don't want them bringing those elements inside the house. Thank you for your understanding.
Bed 3

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Bath 1

Bath

Sleep 5

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