Vacation Rentals By Owner In Stockbridge, MA

Experience Stockbridge like a local in this 3-bedroom apartment. Great location on Main Street Stockbridge await you from the comfort of your king suite with attached bath, queen, and twin bedrooms . With amenities like a washing machine, AC, and WiFi, your stay will be hassle-free. Off Street parking for one car. Kickback, relax, and enjoy everything Stockbridge and our apartment has to offer.

Apartment

Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$382.65

My place is close to Stockbridge center, Berkshire Theaters, Great Barrington, Lenox, and the Berkshires in general - great views, the city center, art and culture. You’ll love my place because the view from our home looks down upon the Housatonic river, and the oldest preserve in Massachusetts - the neighborhood, the ambiance, the comfy beds, the light, the outdoors space. My place is good for couples, solo adventurers, business travelers, and families (with kids). The place is newly renovated.

Two Blocks from the Red Lion Inn & next to Berkshire Theater

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$443.9

Hello hip, glamping cabin! Our 2 bedroom 1.5 bath cottage has been fully remodeled. The decor is chic & bohemian cool! Enjoy the large yard & sunny deck. Fieldstone fireplace w/ vaulted ceilings & skylights. The cottage has beautiful pine throughout w/ fabulous interior design picks. Enjoy the sweet reading nook, master bedroom w/ skylights and half bath or put on a favorite record. Kids will love the cozy sleeping loft. A 8-10 minute stroll or 2 minute drive to the lake public beach (The lovely Stockbridge Bowl) Outdoor shower. Weber gas BBQ grill. 6 minutes to Tanglewood and Lenox downtown.

CABIN FEVER IN STOCKBRIDGE

Stockbridge, Massachusetts, United States

3

Bed

Bath

6

Sleeps

$648.49

Beautifully furnished, recently renovated Stockbridge home centrally located 3 miles from Tanglewood, 1 mile from Norman Rockwell, 2 miles from Red Lion Inn. Quiet country setting on 10 wooded acres.brbrExpansive 2-tier deck adjacent to house overlooking manicured grounds and woods. brbrIn-ground pool with pool house overlooking the woods. brbrLarge family room with dining area, spacious living room overlooking woods, and den with fireplace provide three comfortable, nicely furnished living areas. Kitchen, master bedroom with marble bath including spacious marble shower, 2 additional bedrooms, 2nd marble bathroom. brbrCentral air conditioning, hardwood floors throughout house.brbrCaretaker on premises.

Home with Pool on 10 Acres

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$1238.27

The General Williams house is located 2 miles from Stockbridge Center and 5 miles from Lenox Center. Only 7 miles from the Mass Pike it is an easy commute from Boston or New York City. brbrThe house has 8 foot ceilings and provide a nice 'vacation' like feel with every bedroom but one having its own bath. The common areas are designed for fun and socializing with family and friends.brbrThe 6 fireplaces provide ambiance and a feeling of escape into a time long forgotten. Play a game of pool, chess or checkers with your family. Enjoy two kitchens in which to work from, sit together at the 12 person dining area while enjoy a fire in the large hearth as you drink your wine and soak in the feeling of the Berkshires. brbrThis home has it all and it is designed to give you and your group a relaxing and fulfilling vacation.brbrKeywords: The Williams House dates to 1797 and has been completely updated in 2010. This home boasts 6 bedrooms, 5.5 baths, two terraces, 6 fireplaces, two full service cook's kitchens, a billiard room, large family room, dining area and table that seats 12 and a lounge/game area. This is the ultimate vacation rental. The house is situated 2 miles from Stockbridge Center, on 4 acres of pristine land with two patios and large grassy areas for outdoor fun. Enjoy all that the Berkshires offer while staying in luxury with your family and friends.

General Williams Estate House Lenox/Stockbridge

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$565.1

Summary:brFeels good staying here! We built this house with our own hands. We chose materials and a design that we loved and we think you will too! There are ash hardwood floors, custom white pine trim and mahogany decks. The interior has an open-concept floor plan inviting abundant natural light. brbrGuests must agree to a rental contract prior to booking.brbrThe Space:brThe house is perfectly located in the center of the Berkshires. It is no more than 10 minutes from Lenox, Lee, West Stockbridge and Great Barrington. Central heating and air conditioning as well as other great features. Guest access to near by swimming, skiing, apple picking, fall foliage views, hiking, theater, and great restaurants. I live near by and I am happy to assist any time there are questions. My Dad is retired in the area and is also available to help. There is a sidewalk in front of the house that goes to town. The neighborhood is great for walking, jogging, or bike riding.brbrGuest Access:brCheck in anytime after 3PM.brbrOther Things to Note:brSpring is an awesome time of the year in the Berkshires. However, we do not see high demand and so the prices are great!

Now Featuring Spring Specials

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$572.68

Absolutely stunning 2018 build less than 1 mile from downtown Stockbridge and an 8 minute drive to Ski Butternut and downtown Great Barrington. This 3 bedroom 3.5 bath is tucked away on a private road with one acre of peace and quiet. The grounds are immaculately maintained with a sitting area surrounding a Solostove firepit and a 6 person hot tub on the private back patio.brEnter on the main level to experience 11ft ceilings spanning the light filled open floor plan. Main floor features the dining area, which seats up to 6-8 people, modern kitchen, and the living room with floor to ceiling stone remote controlled fireplace and a 50 smart TV. This floor also features the primary bedroom with a private bathroom and a large walk in closet. Enjoy the furnished deck off the dining area and utilize the laundry room past the kitchen, as well as the half bath and ample closet storage.brLower level features a large bedroom with a private bathroom, and another bedroom with a full bathroom. Unwind and hangout in the lower den area with a wrap around couch, a 65 smart TV, and ample books and games. Walkout to the hot tub and firepit.brRelax with the quiet woods and peaceful interior, stay connected and entertained with high speed internet and smart televisions, and explore the trails, lakes, mountains, arts and country life of the Berkshires.

Spacious & Modern Berkshires Getaway

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$701.48

Discover a unique getaway in the heart of Stockbridge, Massachusetts, at the historic rectory of St. Joseph's Church. Perfect for families, groups, or anyone seeking a serene escape, this charming property combines timeless elegance with modern amenities for an unforgettable stay.brbrEnjoy spacious, beautifully designed rooms that accommodate 8-12 guests, ideal for gatherings or peaceful retreats. Relax in the tranquil garden or explore local landmarks, including the nearby Divine Mercy Shrine, a haven for reflection and spiritual renewal.brWhether you're planning a weekend escape, a family reunion, or a quiet retreat, this one-of-a-kind Stockbridge gem offers comfort, history, and a truly divine experience. Book your stay today and immerse yourself in the beauty of the Berkshires!br

Historic Rectory Retreat in Stockbridge – Getaway for 8-12 Guests

Stockbridge, Massachusetts, United States

5

Bed

Bath

12

Sleeps

$297.62

Modern family home moments from Tanglewood, the Stockbridge Bowl, the Norman Rockwell and Chesterwood Museums. Just a 10 minute drive to Lenox and only 3 miles from the center of Stockbridge with access to cafes and shops. Enjoy serene walks along Averic Lake. brbrRental is for June 30 - July 31, 2025.brbrProperty sits on about 1 acre of land that is nestled behind the Interlaken Fire House. This is a 3 bedroom home. One master bed and bath, 1 bedroom with a full size bed and one bedroom with a twin and trundle.

Quiet 3BR Home, Near Tanglewood in Stockbridge

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$255.26

A lovely, quiet retreat for two or a fun family getaway, just minutes from some of the most iconic spots in the Berkshires! Children welcome!brbrThe Norman Rockwell Museum and Berkshire Botanical Gardens are within walking distance. Chesterwood Museum and Boston Symphony's summer home at Tanglewood are just down the road, along with Herman Melville's Arrowhead, Edith Wharton's The Mount, Ski Butternut and many other local attractions. Fewer than five minutes from Stockbridge's historic main street made famous by Rockwell, this cottage provides the perfect home base for a relaxing and memorable stay exploring all that Western Massachusetts has to offer. brbrThe upstairs king bedroom suite boasts a pastoral view of the spacious grounds and forest beyond. Enjoy a generous living/dining space and relax on the adjoining patio overlooking the groomed lawn and gardens. Kitchenette is equipped with countertop convection oven, coffee pot, four-burner cooktop, and mini-fridge. Upstairs also accommodates a double trundle (two twin beds) for couples with children. Garage bay available with remote for convenient parking, loading/unloading during inclement weather.brbr

Cottage

Springtime in the Berkshires!

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$406.59

Escape to the serene beauty of the Berkshires and stay at this bright and cozy 2-bed, 2-bath cabin! Nestled just a few steps from the Stockbridge Town Beach, the vacation rental is perfectly located for enjoying the area's top attractions, like lake activities, Tanglewood, the Norman Rockwell Museum, and hiking trails - all found within a short drive. Ease into your mornings with a good book and a steamy cup of coffee on the private porch, and later, walk to the lake for a picnic!brbr-- THE PROPERTY --brbrC0077602830 | Free WiFi | Expansive Deck | SunroombrbrIndulge in a leisurely Berkshires lifestyle when you stay at this cozy, light-filled cabin. Ideal for pairs of two looking to escape modern distractions and spend time in nature.brbrBedroom 1: King Bed | Bedroom 2: 2 Twin Beds (Photos Coming Soon) | Sunroom (Not Private): Twin Bed w/ Twin Trundle BedbrbrOUTDOOR LIVING: Large deck w/ outdoor dining table, lounge chairs, gas grill, 2 kayaks, 2 stand up paddleboards, beach chairs, outdoor shower, walk to lakeshore, neighbors nearby (please be respectful of the noise level outside)brINDOOR LIVING: Vaulted ceilings, open layout, high-top counter seating, desk, ample natural light, bright interior, flat-screen Smart TV (no cable), 2 cozy bedrooms, 2 full baths, 800 square feet totalbrKITCHEN: Well equipped, dishwasher, gas range stove, toaster oven, microwave, drip coffee maker, cooking basics, dishware, flatware, pots, pansbrGENERAL: Linens/towels, window air conditioning, first aid kit, Pack 'n Play, washer/dryer, wall heaters, space heaters, ceiling fansbrPARKING: Driveway (3 vehicles max)brbrThis charming seasonal cottage dates back to the 1940s. It still maintains much of its original details and rustic charm, which is balanced nicely by its freshly whitewashed interior, comfortable amenities, welcoming decor, and brand new cedar outdoor shower.brbrThoughtful touches like picnic blankets, beach towels, and even a record player and albums make this cute cabin an easy place to call home during your Berkshire vacation.brbrSituated at the edge of the woods on a shared, dead-end drive, the cottage offers the perfect place to get away (and possibly even see some wildlife!) while being just minutes from Lenox and Stockbridge and walking distance to the lake beach. And, when the wind is just right, you can even hear the faint sounds of Tanglewood's music drifting across the lake on a warm summer night.brbrNote from the owner: We have so many happy memories at 'Elandee,' named after our two daughters, L and E. We hope that if you choose to stay, you have an enjoyable and memorable time here, too!brbr-- THE LOCATION --brbrSTOCKBRIDGE BOWL: Stockbridge Town Beach (0.1 miles - 5-min. walk), BSO Beach (2.3 miles), Stockbridge Bowl Boat Ramp (3.1 miles), boating, swimming, fishing, kayaking, paddle boarding, canoeingbrHIKING: Brothers Trail (3.2 miles), Parsons Marsh Reserve (3.4 miles), Olivia's Overlook (3.8 miles), Burbank Trail (3.8 miles), Stevens Glen Trail Head (4.5 miles), Monument Mountian Reservation (6.2 miles), Appalachian Trail (11.6 miles)brLOCAL ATTRACTIONS: Orleton Farm (0.9 miles), Koussevitzky Music Shed (1.9 miles), Seiji Ozawa Hall (2.0 miles), Frelinghuysen Morris House & Studio (2.0 miles), Tanglewood (2.5 miles), Ventfort Hall Mansion and Gilded Age (3.4 miles), Norman Rockwell Museum (3.8 miles), The Mount, Edith Wharton's Home (4.4 miles), Cranwell Mansion (4.7 miles), The Playhouse (5.5 miles)brSKIING: Ski Butternut (11.3 miles), Catamount Mountain Resort (18.0 miles), Jiminy Peak Mountain Resort (25.4 miles)brAIRPORT: Albany International Airport (51.5 miles)brbr-- 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- No pets allowedbr- No events, parties or large gatheringsbr- Must be at least 23 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This property is best suited for 4 guests, but can sleep a total of 6 with the use of the non-private sunroombr- NOTE: This property is not suitable for children under 12br- NOTE: Your safety matters. This property features 2 exterior security cameras, above the front door and the deck, all facing outward. They do not look into interior spaces

Cabin

Cozy Stockbridge Cabin - Walk to Beach & Lake!

Stockbridge, Massachusetts, United States

4

Bed

Bath

4

Sleeps

Select Dates for Price

2 Bedroom 2 Bath fully furnished home steps from Main St. This charming house has been totally renovated and has an open, airy feel with a cathedral ceiling in living/dining area. Spacious bedrooms with large closets. $6,000 per month, all inclusive.

One block from Main St Stockbridge

Stockbridge, Massachusetts, United States

Bed

Bath

3

Sleeps

$306.58

Unwind in Stockbridge in this charming house, under 5 miles from Tanglewood. The house boasts 3 bedrooms and 2 full bathrooms. The beds include 1 king, 1 queen, and 1 full bed, guests will have plenty of space to relax. The house also features a wonderful, private screened porch. An additional office space with a twin bed offers flexibility for guests. Enjoy your time in Stockbridge at our lovely house. Parking is off street.

Charming 3-bedroom house steps from the Red Lion Inn in delightful Stockbridge

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$473.8

Charming new construction home located in neighborhood community that has a private beach on the Stockbridge Bowl. Just completed in Spring of 2020, the home is open and airy and the perfect place to relax and enjoy being in the country while having all the modern conveniences of a brand new home. Whether you enjoy walks, hikes, swimming, kayaking, skiing, museums, shows, concerts or dining at great restaurants, it is all just minutes away. brbrThis four bedroom, two bath home has an open kitchen, dining, living room layout with high ceilings and great light. The master bedroom and a second bedroom are also on the first floor, with two kids bedrooms and play/lounge areas upstairs, creating a bit of separation when it is time to wind down. The home is a short walk to the community beach, where you are free to use our kayaks located right at the lake on the neighborhood’s kayak rack or just lounge at the beach. Downtown historic Lenox and the town of Stockbridge are each 3 miles from the home, with dozens of food options, great shopping and many area attractions. brbrThe home is equipped with central heat/air conditioning, internet, washer/dryer, gas fireplace, dishwasher and a tankless water heater, ensuring a comfortable stay.

Stockbridge Bowl Lake Community

Stockbridge, Massachusetts, United States

4

Bed

Bath

7

Sleeps

$461.18

Berkshire Retreat - A stone's throw to downtown LenoxbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrPrivacy and peace abound in this beautiful Stockbridge home! Conveniently located about a mile to downtown Lenox and close to Stockbridge when you want to get out to the arts, explore, eat, play, and shop- you can The house is only minutes to Tanglewood, Shakespeare & Co., Kripalu, Great Barrington and the Stockbridge Bowl. In fact, the house has Stockbridge parking access! On days you would rather stay close to home, sit outside and soak in the sun from the home's spacious outdoor area. Surrounded by lush greenery and mature landscaping, this place is one of peace.brbrInside, the light-filled living room is cozy and kept warm thanks to the wood stove. Snuggle up while tuning into your favorite TV shows and movies. The adjacent well-equipped kitchen boasts all the appliances you'll need to whip up delicious dishes. When mealtime rolls around, dine as a family at the large, wooden dining table.brbrFollowing the charming wood finishes and vaulted ceilings, walk into the lovely bedrooms each furnished with soft linens and homey fixtures. The 3rd bedroom is an actual private studio type room with a private bath and kitchenette. The screened porch off the main bedroom opens to the back of the property, bringing the sounds of nature.brbrHouse Rulesbr-This home is not equipped with central air-conditioning, however window air conditioning is provided.brbrThis Vacasa Guestworks vacation rental is operated and managed locally by an independent host.brPrior to your arrival, you will receive local host contact information, who will manage your guest reservation. Your local host will provide in-stay support, secure entry, and arrange pre- and post-stay housekeeping services.brIf you need anything during your stay, the home’s independent local host is ready to help 24/7! Guestworks is a service offering of Vacasa that allows homeowners to smoothly and efficiently manage their own properties.brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. If you would like to add more dogs, please contact us. The pet fee is per stay and ranges between $150 and $200, depending on the bedroom count, and will apply for each additional dog.brbrParking notes: There is free parking available for 4 vehicles.brbrSecurity camera details: There is one Ring camera and one spotlight camera in front of the home.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Berkshire Retreat- Stone's throw to downtown Lenox

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$458.25

Summary:brBeautifully renovated three bedroom in Stockbridge with a great layout and energy throughout the home. In addition to the large and very pretty screened in porch, there is a newly created area off the back that has pavers with a modern fire pit, a new Weber Genesis grill and four wood and wicker chairs - a great area to relax. Clean, updated and cozy all at once.brbrThe Space:brLiving room is inviting and nicely decorated. There is plenty of seating for all with a comfy couch and ottoman (that can be used to make a chaise at one end of the couch) and two swivel chairs.The large 55 inch tv has basic cable and a roku for sound and streaming apps such as Netflix, Hulu, Amazon Prime, etc with your log in information. Original artwork can be found all around the home, along with some framed vintage posters. brbrVery nice flow and layout in the kitchen; easy to use with updated appliances and well equipped; leads right to the dining area inside or the lovely screened in porch outside that has a lovely teak round dining table. Large galley kitchen with a gas stove, new appliances and lots of white quartz counter space, perfect for large meals for the whole crew. New dishwasher to make cleaning a breeze. Essentials including microwave, drip coffee maker, toaster and kettle available for use. brbrWell stocked kitchen with all the necessary cooking/serving items including cookware, pots, pans, plates, bowls, glasses, mugs, silverware and even children's dinnerware.brbrThe dining room has round table seating for eight with the table leaf. There is space for two at the kitchen island. An additional table with chairs is located in the large screened in porch. brbrThere are a total of three bedrooms to accommodate guests during your stay, for easy planning here are the bedroom layouts:brBedroom 1: master with king bed, dresser, desk, full length mirror, en suite bathroom and small walk in closetbrBedroom 2: queen size bedbrBedroom 3: single day bed with another single pull out trundle bedbrbrThere are two full size bathrooms. The en suite in the master has a large walk in shower with tile and marble shelves; there is one vanity with drawers and counter space and a large mirror and a medicine cabinet with mirror on the side of the vanity. brbrSeamless indoor outdoor living including, screened in porch with round teak dining table,; peaceful back yard, fire pit with plenty of seating and a new Weber Genesis grill. brbrOther things to get excited about:br-Only four small steps up to the front door of this one floor home, perfect for guests with limited mobility.br-Hardwood floors throughout the home and tile floors in bathrooms.br-Washer and dryer with plenty of detergent and dryer sheetsbr-There are two AC splits: one in the living room and one in the masterbr- Parking for two cars in the driveway and street parking is availablebr-Bring your furry friends, up to two dogs allowed, $50 per dog, must be at least 1 year old, sorry no puppies!brbrGuest Access:brEverything you need for a great stay, toiletries, linens, towels, hairdryer, iron and ironing board, washing machines, detergent, and more!brbrThe Neighborhood:brFood and Drink favorites:brRed Lion Inn, StockbridgebrOnce Upon a Table, StockbridgebrThe Lost Lamb, StockbridgebrBistro Zinc, LenoxbrAmici, West StockbridgebrFour Brothers Pizza, Great BarringtonbrAegean Breeze, Great BarringtonbrZichotencati, Great BarringtonbrCafe Adam, Great BarringtonbrNaji’s, Great BarringtonbrMarketplace Kitchen Table, Great BarringtonbrGreat Barrington BrewerybrbrCulture and Wellness : brJacob’s Pillow, Dance brShakespeare and Company brTanglewood brKripalu Center for Yoga and Health brMiraval Berkshires Resort & Spa brShaker Mill Books brTanglewood brDowntown Lenox brBerkshire Botanical Garden brNaumkeg brChesterwood brNorman Rockwell Museum brThe Mount, Edith Wharton’s Estate brHerman Mellville’s Arrowhead br brSkiing, Snowboarding and tubing:brButternut Ski Area and Tubing CenterbrCatamount Mountain Resortbr brLakes: Close to public lakes for swimming, kayaking, fishing or lounging by the water: brCard Pond brLake Mansfield brLake Garfield brBenedict PondbrUmpachene Falls brLake Onota br brHiking:brMonument MountainbrHousatonic FlatsbrOctober Mountain State ForestbrBeartown State Forest brTyringham Cobble brAshintully GardensbrHousatonic FlatsbrbrOther Things to Note:brWe look forward to welcoming you soon! brStandard rules like no smoking, no partying, and being respectful of the neighbors apply.brBring your furry friends, two dogs are allowed. $50 per dog per stay. Dogs must be at least one year old, sorry no puppies!brbrNo 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. brbrPets: Damage caused by pets is not covered by the accidental damage waiver.

Stockbridge Home, Come Experience The Berkshires!

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$1549.84

Escape to the Berkshires and indulge in the ultimate experience at this luxurious 4-bedroom, 3.5-bathroom house. Situated on 22 acres of pristine land, this vacation rental offers unrivaled privacy and tranquility. Take a dip in the private pool, soak in the hot tub, shoot some hoops, play some pickleball, or a play game of ball hockey on our private court. Or, explore nearby attractions such as the Norman Rockwell Museum, Tanglewood, and the hiking trails of the Stockbridge area.brbr-- THE PROPERTY --brbrMassTaxConnect ID #: C0437672830 | 22-Acre Property | Modern Interior | Gas Fireplace | Private Heated Pool (Depth 3.5’-9’)brbrBedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: Full Bed | Bedroom 4: Queen Bed | Den: 2 Twin Futons (converts to King Bed)brbrOUTDOOR LIVING: Patio, screened-in porch, hot tub, basketball & pickleball court, gas grill, beach chairs, beach towels, deck, garden, hammock, outdoor shower, outdoor speakers, pool toys, patio heater, gas fire pitbrINDOOR LIVING: Board games, piano, Smart TVs, DVD player, books, ceiling fans, walk-in closet, dining table, printerbrKITCHEN: Air fryer, drip coffee maker, dishwasher, microwave, knife set, dishware & flatware, ice maker, spices, toaster, cooking basicsbrGENERAL: Free WiFi, linens & towels, hair dryer, complimentary toiletries, keyless entry, washer & dryer, central heating & air conditioningbrFAQ: Steps required, Ring doorbell (facing out)brPARKING: Driveway (4 vehicles)brbr-- THE LOCATION --brbrOUTDOOR ADVENTURE: Monument Mountain Reservation (6 miles), Berkshire Rivers Fly Fishing (6 miles), Olivia's Overlook (8 miles), Otis Ridge (17 miles) brHITTIN' SLOPES: Butternut Ski Area and Tubing Center (7 miles), Bousquet Mountain Ski Area (12 miles), Catamount Mountain Resort (14 miles), Jiminy Peak Mountain Resort (28 miles) brTIME TRAVEL: Naumkeag (2 miles), Norman Rockwell Museum (3 miles), Ventfort Hall Mansion and Gilded Age Museum (7 miles), Thomas Cole National Historic Site (40 miles), Olana State Historic Site (40 miles) brAIRPORTS: Albany International Airport (51 miles), Bradley International Airport (68 miles)brbr-- 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- No pets allowedbr- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The property requires stairs to accessbr- NOTE: Your safety matters. This property features a Ring doorbell device with an exterior security camera facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video when motion is detected by the device or when the video doorbell button is pressed

Stockbridge Retreat w/ Pool & Hot Tub!

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$466.05

Introducing Woodland Zen: where modern luxury meets secluded tranquility in the heart of the Berkshires.brbrThis sleek, contemporary escape will take your breath away from the moment you arrive. Surrounded by lush greenery, its modern exterior is a unique contrast with the natural landscape. Step onto your spacious deck, complete with comfortable seating and a BBQ grill, and immerse yourself in the serenity of the surrounding woodland.brbrFloor-to-ceiling windows flood the living spaces with natural light, offering stunning views of the picturesque landscape. The bright, open living room features a large fireplace, plush seating, and a TV. Need more space Discover a second sitting area with an additional sofa and TV.brbrEntertain in style in the sleek dining area, nestled next to the windows and overlooking the patio. With seating for 8, it's perfect for gatherings. Plus, there's another dining table in the adjacent sunroom with seating for 6.brbrCooking is a breeze in the fully equipped kitchen, boasting stainless steel appliances, a gas range, and ample counter space. Additional barstool seating ensures everyone has a place to gather.brbrRetreat to one of three comfortable bedrooms, each featuring a plush queen bed. The primary suite boasts an attached ensuite bathroom and access to the patio, perfect for enjoying your morning coffee in peace.brbrConveniently located just 10 minutes from Great Barrington, you'll have easy access to dining, shopping, wine tasting, and outdoor adventures.brbrWith in-home laundry and parking, Woodland Zen offers the ultimate blend of luxury, privacy, and convenience for your Berkshire getaway.brbrAvantStay provides an upscale experience with services that elevate your stay and save time so you can enjoy every moment. Guests have access to a 24/7 support team and a tech-enabled concierge to book services, such as fridge stocking, mid-stay cleanings, and private chefs. For anything you need (or never knew you needed), we’re at your service!brbrA visit to the Berkshires in western Massachusetts is a treat for anyone looking to pair stunning rural landscapes with an exciting cultural and culinary experience. The abundance of mountains, lakes, and woods provide a wide range of outdoor activities, from rafting and fishing in the summer to skiing and tubing in the winter. Stunning at any season, this New England region is also famous for its farm-to-table food scene and local breweries. Come see for yourself!brbrLocal Attractions: Berkshire Botanical Gardens, Bidwell House Museum, Mahaiwe Performing Arts Center, Norman Rockwell Museum, Hancock Shaker Village, Historic Deerfield, Jiminy Peak Mountain ResortbrbrHome Truths:br- Please note our occupancy includes an additional two beyond bed count. Trifold floor mattresses and additional linens can be provided upon request.br- Unfortunately, pets are not allowed in this home. If undisclosed pets are brought into the home without AvantStay's approval, there is a fine of $500 per pet.brbrParking Details:br- Parking is available onsite for 4 vehicles in the carport and driveway.br- No street parking is permitted.brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / Queen bed w/ ensuitebrBedroom 2 / Queen bed w/ ensuitebrBedroom 3 / Queen bed w/ ensuitebrbr---brbrAccidental Damage Protection: A non-refundable accidental damage protection plan has been included in the price of your reservation. Under this plan, you will not be held responsible to pay for accidental damage or loss to the rental property resulting from you or others in your party up to $2000. This plan does not cover intentional acts of a guest, gross negligence, or willful and wanton conduct, and/or damages caused by pets. This plan is not available for reservations 28 days or longer or reservations that require a security deposit.brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation.brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees.brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. All bookings over 28 days require a security deposit.brbrWe report and prosecute all Credit Card Fraud.

Woodland Zen by AvantStay | Modern Design + Patio

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$337.76

Elevate your Stockbridge experience by staying at this 3-bedroom, 1.5-bath vacation rental house! Boasting a private deck, fireplace, in-unit laundry, and 114 acres of property to explore, this home-away-from-home can’t be beat! When you aren’t enjoying the stunning exterior space on the expansive deck or spotting wildlife like owls, foxes, and deer, venture off-site for skiing at Butternut Basin or swimming at Stockbridge Bowl. Whether snowy or sunny, endless adventures await!brbr-- THE PROPERTY --brbr1,600 Sq Ft | Pets Welcome | Free WiFibrbrNestled within the serene forests of the Berkshires, ‘The Redway House’ is the quintessential setting for your next Massachusetts retreat, complete with tranquil privacy and modern comforts. brbrBedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: 2 Twin Beds brbrOUTDOOR LIVING: Gas grill, 114 acres of hiking trailsbrKITCHEN: Fully equipped, drip coffee maker, Keurig coffee maker, toaster, electric pancake skillet, ice cube maker, cafe tablebrINDOOR LIVING: 2 TVs, HD TV, fireplace, dining table, Apple Mac-Mini computer, cell phone charging stationbrGENERAL: Washer & dryer, towels, linens, complimentary toiletries, central air conditioning/heat, keyless entry, pet fee (paid pre-trip)brSUITABILITY: Stairs requiredbrPARKING: Driveway (2 vehicles), detached garage (1 vehicle), outdoor area (1 vehicle)brbr-- THE LOCATION --brbrSTOCKBRIDGE BOWL (4.0 miles): Stockbridge Town Beach, BSO Beach, Stockbridge Bowl Boat Ramp, boating, swimming, fishing, kayaking, paddle boarding, canoeingbrHIKING: 114 acres on-site, Stevens Glen Trail Head (4.8 miles), Monument Mountain Reservation (4.8 miles), Olivia's Overlook (5.5 miles), Brothers Trail (6.0 miles), Burbank Trail (6.2 miles), Parsons Marsh Reserve (6.5 miles), Appalachian Trail (12.1 miles)brLOCAL ATTRACTIONS: Norman Rockwell Museum (1.4 miles), Orleton Farm (3.7 miles), Tanglewood (5.6 miles), Koussevitzky Music Shed (5.8 miles), Seiji Ozawa Hall (6.7 miles), Frelinghuysen Morris House & Studio (6.7 miles), The Playhouse (6.9 miles), Ventfort Hall Mansion and Gilded Age (7.4 miles), The Mount, Edith Wharton's Home (7.5 miles)brSKIING: Ski Butternut (9.9 miles), Catamount Mountain Resort (14.6 miles), Jiminy Peak Mountain Resort (25.8 miles)brAIRPORT: Albany International Airport (48.0 miles)brbr-- 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- Massachusetts Tax ID: C0214960870br- No smokingbr- Pet friendly w/ $75 fee (+ fees & taxes, maximum 3 pets allowed)br- No events, parties, or gatherings of more than 6 peoplebr- No fireworks allowed on the propertybr- Must be at least 25 years old to bookbr- Garage is unavailable during winter months (11/15-4/15)br- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: Access to the home requires stairs

Tranquil 3 BR Stockbridge House w/ Private Deck!

Stockbridge, Massachusetts, United States

3

Bed