Vacation Rentals By Owner In Great Barrington, MA

$1288.69

Renovated family friendly house close to everything and endless views

Great Barrington, Massachusetts, United States

Bright, comfortable house with pool and comfortable outdoor seating and eating areas, endless mountain views in front and acres of open pasture in back. Four bedrooms and 3.5 baths. Two bedrooms with king sized beds, large closets and en suite newly renovated bathrooms. One bedroom with queen sized bed and twin bed. One bedroom with twin bed and bunkbed. Reading room can serve as extra bedroom. Remodeled, fully stocked kitchen.brbrbrWood burning fire placebrTelevision, cable and internetbrWasher/dryer on ground floorbrTwo car garagebrFully stocked kitchen with 12 place settingsbrPing pong table brChildren's outdoor swingset and slidebrHeated swimming pool with outdoor lounge furniturebrOutdoor shower brOutdoor table with large umbrella brOutdoor fire pit (marshmellows!) with seating brbr3 miles to center of Great Barringtonbr4 miles to Guidos and Big Ybr7 miles to Butternut br7 miles to Catamountbr4 miles to Egermont Country Club (public 18 hole golf course)br12 miles to Tanglewoodbr120 miles from Manhattanbr140 miles from Boston

4

Bed

3

Bath

10

Sleeps

$465.79

/ Nightly

Private Vacation Home

Private Home in the Berkshires with Hot Tub

Great Barrington, Massachusetts, United States

Welcome to your private country escape — a newly renovated 2-bedroom, 1-bath home surrounded by 2 acres of open lawn and 5 acres of wooded area and natural beauty. Tucked away on a quiet road, this serene retreat offers the perfect blend of modern comfort, rustic charm, and total relaxation. Inside, the open-concept design creates a bright and airy feel, with large windows that bring the outdoors in. The fully equipped kitchen flows seamlessly into the cozy living space, making it easy to cook, unwind, and connect. Every detail has been thoughtfully updated — from the stylish finishes and new flooring to the warm, inviting décor that makes you feel right at home. Step outside to your private deck and sink into the bubbling hot tub as you take in the peaceful countryside views. With no city noise or close neighbors, you’ll have all the privacy you need to truly unwind — perfect for sipping wine under the stars or enjoying your morning coffee as the sun rise. Whether you’re looking for a romantic weekend, a family getaway, or a quiet place to recharge, this home is a hidden gem. Explore local trails, lakes, and small-town shops nearby, then return to your private haven where comfort, calm, and wide-open space await.

2

Bed

1

Bath

4

Sleeps

$130.95

/ Nightly

Apartment

Cozy 1-bedroom studio in serene Great Barrington with AC

Great Barrington, Massachusetts, United States

This Great Barrington studio boasts one welcoming bedroom featuring a cozy bunk bed and a comfortable sofa bed. Guests enjoy a quaint bathroom with a refreshing shower, perfect for unwinding after a day of exploring. The space stays comfortable year-round with heating and air conditioning, making it easy to relax no matter the season. Whether you’re here for a quick getaway or an extended stay, this phenomenal studio offers a charming retreat that feels like a home away from home. Make your holiday one for the books with a stay at our place.

Bed

Bath

Sleeps

$646.01

/ Nightly

Cabin

Secluded Forest Sanctuary • Outdoor Living, Yard, Views | Half Moon by AvantStay

Great Barrington, Massachusetts, United States

Kick back among the wooded hills of the Berkshires at Half Moon. The rustic exterior of this log cabin gives way to naturally chic spaces inside. Take in the fresh air from the large deck, complete with plenty of comfortable seating, or grill out and relax in the covered outdoor dining area. Contemporary decor and a colorful kitchen create the perfect atmosphere for playful connection at home, while the charming town of Great Barrington is just a ten-minute drive away with shopping, dining, and entertainment. Surrounded by trees and tucked at the end of a long private driveway, Half Moon is a woodsy retreat packed with style, privacy, and convenience.brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbrLocal Attractions: Berkshire Botanical Gardens, Bidwell House Museum, Mahaiwe Performing Arts Center, Norman Rockwell Museum, Hancock Shaker Village, Historic Deerfield, Jiminy Peak Mountain ResortbrbrVisiting the Berkshires is a must for anyone looking to pair a gorgeous natural landscape with an exciting cultural and culinary experience. The abundance of mountains, lakes, and woods here makes it easy to enjoy a wide range of outdoor activities, from rafting and fishing to ziplining and hiking. Stunning in any season, this region is famous for its food scene, which values local ingredients, and you’ll find many farm-to-table establishments in the southern areas. Explore classic New England architecture, a growing array of performing arts, and dozens of towns and trails. The Berkshires are waiting with variety and beauty you won’t find anywhere else.brbrHome Truths:br- The living room window is cracked and we are waiting for the replacement window to arrive.br- This home allows pets for a fee. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- Please note our occupancy includes an additional two beyond bed count. Trifold floor mattresses and additional linens can be provided upon request.br- This home is located in the Berkshires, so you may encounter wildlife such as bugs and insects.br- The lawn care company comes weekly to service the lawn.brbrParking Details:br- Carport accommodates 2 carsbr- Driveway accommodates 3 - 4 cars maximumbrbrThis home comes with a pack n' play travel crib available. A high chair can be provided upon request with at least 24hrs advanced notice. Just ask and we are happy to accommodate you and your little ones!brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / King bedbrBedroom 2 / King bedbrBedroom 3 / Queen bedbrBedroom 4 / Two queen beds.br+ 2 twin size tri-fold sleeping matsbrbr---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 30 days require a security deposit.brbrWe report and prosecute all Credit Card Fraud.

Bed

Bath

Sleeps

$590.87

/ Nightly

Private Vacation Home

Modern Victorian Walk to Main Street

Great Barrington, Massachusetts, United States

Lovely 4 bedroom, sleeps 10. 3-story classic Victorian home in family-friendly neighborhood. Clean modern interiors and nature-enjoying exteriors including gardens, covered porch, screened deck and fenced yard. Easy walk to Main Street and Lake Mansfield. brbrLike winter sports This home is a great ski season rental as it's a quick 9 minute drive to Butternut Ski Area and Tubing Center and only 14 minutes to Catamount Mountain Resort. brbrBuilt in 1903, this updated and yet stunning example of Victorian craftsmanship is a perfect place for family and friends looking to find an easy getaway in the Berkshires. The interior is sunny, bright and modern with charming Victorian details throughout. brbrThe house is well appointed on the ground floor level with a large living room, music parlor including a grand piano and large assortment of art and design books, large eat-in kitchen, separate dining room area with large farm table and French café chairs with seating for 8, ½ bath, and large pantry/laundry room with side by side front loading washer and dryer. The living room and parlor comfortably seats 10 guests. brbrThere are inviting touches throughout the house such as: lovely artwork, books, games, puzzles and toys to entertain both children and adults! The kitchen is well equipped with high-end stainless appliances and All-Clad and Le Creuset cookware. All tools needed for baking are available including a Kitchen-aid stand mixer. Kitchen includes a large assortment of high-end small appliances including microwave, food processor, blender, coffee maker and 4-slot toaster. At the kitchen sink, a Multi-Pure water filter system is built-in. The deck and screened porch are accessed from both the kitchen and the living room.brbrThe second floor has 2 bedrooms: the primary suite with a king bed and full bathroom with tub/shower combination, en suite. The second large bedroom has a queen bed and access to the 2nd floor porch. There is a second full bathroom on this floor with a walk-in shower.brbrThe third floor is a delightful converted loft-like attic space with two rooms. One bedroom has 4 twin beds: 2 extra long singles and the third is a twin trundle, which can be made up as a twin, two twins or a king - perfect for a group sleepover or family! The other room, best for children, has one extra-long twin and small trundle bed. All three floors have central air-conditioning and heating. The extra-long twins have organic rubber mattresses. Due to their generous length and quality, these mattresses are very comfortable for adults as well as children.brbrOutside you have a delightful front sitting porch and lovely cottage gardens with pathways leading to the front walk and side parking area. The back sun deck is private, with outdoor seating and a grill for dining al fresco. There is also a cozy screen tea porch on the side of the house, accessed through the family room. The yard is fenced with a delightful playhouse!brbrLocated in the sought after neighborhood called “The Hill”, this home is an easy 5-minute walk to the center of downtown Great Barrington for a meal, shopping, shows, cinema, galleries and much more. This home is also an easy walk (or 3 minute drive) to Lake Mansfield Park for swimming. (There is a sandy beach, children's playground equipment and a lifeguard on duty!) You can enjoy picnicking and having fun on the climber & swing sets. No motorboats allowed but canoes/kayaks are available for rent in town or bring your own! brbrFor music lovers, it's a 25 minute drive to Tanglewood, and for dance enthusiasts it's a 25 minute drive to Jacob’s Pillow.brbrAmenities:brArrival Day FlexiblebrChildren WelcomebrPets ConsideredbrSmoking Not AllowedbrDecked areabrCentral heatingbrAir ConditioningbrTelevisionbrGamesbrToysbrSmart TVbrBooksbrLaptop FriendlybrKitchenbrRefrigeratorbrMicrowavebrCoffee MakerbrDishwasherbrDishes UtensilsbrSpicesbrStovebrHighchairbrToasterbrOvenbrBBQbrFridgebrFreezerbrHeatingbrCarbon Monoxide DetectorbrGrillbrDeck Patio UncoveredbrGardenbrPrivate yardbrBalcony/TerracebrHouse Cleaning OptionalbrWifibrFishing FreshwaterbrHikingbrSkiingbrSnowboardingbrGolf course within 30 min drivebrFamilybrDowntownbrTownbrLive TheaterbrEco TourismbrBathtubbrHigh ChairbrChildren's Books and ToysbrTable Corner GuardsbrPack n Play Travel CribbrRoom Darkening ShadesbrChildren's DinnerwarebrStair Gates

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Bath

Sleeps

$1507.95

/ Nightly

Private Vacation Home

Stunning Renovated Victorian

Great Barrington, Massachusetts, United States

Located in the beautiful Berkshires, MA, the 5000 sqf home is located in a desired neighborhood known as the Hill.” The sun filled house is on a quiet no outlet road and sits on 2.5 acres of landscaping including blueberry bushes, maple tree, lawns, mature flowers, and custom cobblestone. In spite of being only a 15 min walk from downtown, it feels very away from it all with trees in every window and privacy.brbrConnections to the Appalachian trail within 10 minutes. Lake Mansfield is a 15 min walk. The Green River, with a swimming hole, is a 15 min hike through the woods. The Mahaiwe, a movie theater and the great thriving restaurants, boutiques, toy stores and coffee shops of downtown are a 15 minute walk. Tanglewood is a 20 minute drive. Butternut is a 10 minute drive.brbrThe historic home was built in 1905 and was one of the first in Great Barrington to receive electricity. It has been lovingly renovated and restored from the ground up. Many original details were restored to new condition (windows, radiators and the like) and modern conveniences added. There is central air conditioning, whole home audio system, movie room w/ mounted 65 inch 4k television, surround sound, double pane windows, heated floors in the bathrooms and kitchen. There is a second 4k television in the den for when the kids don't want to watch the same movie as the adults - also with high end surround sound. Sony Playstation and multiple streaming devices all updated to 4K technology. The gourmet cook's kitchen includes a large granite prep area, 2 deep sinks, Wolf Stove, large SubZero, and 2 Bosch dishwashers for easy clean up. brbrThe house is oversized but still cozy with brand new sheets from Brooklinen, new towels, lots of blankets, and well designed locally bought furniture and rugs. There are games and a library of classics and NYTimes bestsellers for ages 2 - adult. In keeping with the classic feel, there is a high end record player in the library for afternoons playing chess and cards. Two large wood burning fireplaces make it homey during the winter.brbrEnjoy the fresh summer air on the large screened in porch, play ping pong, or enjoy a meal in the fresh air on the screened porch dining table. Ample lawns and private outdoor space, especially for an in town property. Weber Grill on large stone patio for for preparing summer meals, nine person sunken hot tub on mahogany deck and a wood swing set and slide set up for the kids. brbrNursery was painted and set-up in 2022 and has toddler toys available for use. Farrow and Ball paint and natural fiber rugs used throughout most of the house. Fragrant free and organic or non-toxic cleaners used. Plates and serving ware for 12 from Crate and Barrel, new in Fall 2024.brbrAlso available for seasonal or year-long rental.

Bed

Bath

Sleeps

$577.12

/ Nightly

Private Vacation Home

Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.

Great Barrington, Massachusetts, United States

**WINTER** Hit the slopes in minutes. Less than 10 minutes to Ski Butternut and less than 15 minutes to Catamount Ski Mountain**Adventure Awaits in Every Season. Hike. Ski. Swim. Relax. Repeat****brCombining the beauty and solitude of our 5+ acres of wooded hills, all the while sitting conveniently just 0.7 miles from the magnificent town of Great Barrington. Sleeps 10 | Wi-fi | 2 Zone AC and Heating| Private Outdoor HOT TUB.brbr---THE PROPERTY---brNestled by trees and tucked at the end of a long private driveway. Tons of yard space provide fresh views while sitting on the large front porch or sipping your favorite drink in the ultra-comfortable screened in back porch. Cap off the night sharing stories and making memories by the outdoor firepit. Warm up after a long day slope side in the brand new Outdoor Hot Tubbrbr**Easy One Level Living in this Simple & Modern Ranch with Outdoor Hot Tub***br**Complimentary Spectrum Cable + Wi-Fi + Smart TV | 2 zone AC and Heating system**brbrAll Bed Linens and Bathroom Linens are providedbrbrBedroom 1: King Bed + Large Sofa and Walk in Closet + DresserbrbrBedroom 2: King Bed + Closet + DresserbrbrBedroom 3: Two Double Beds + Closet + DresserbrbrLiving Room: 1 Pull out Queen SofabrbrBathroom 1: Master Bathroom with double sinks, closet, and Large ShowerbrbrBathroom 2: Large Bathroom with Bathtub & ShowerbrbrKitchen: Dine in or Entertain with your friends in this open concept Kitchen. Quartz Countertops, Stainless Steel Appliances, Toaster, Coffee Maker, Dishwasher, Dishes, Glasses, Pots, Pans, Serving Platters, Cooking utensils, + plenty of silverware. 2 Counter Stools + Dining Table seats 6brbrLiving Room: Offers plenty of seating with the overly large sectional sofa. Pick a spot to unwind after a day of exploring. Smart TV + Spectrum Cable + DVD Player + Wi-fibrbrOutdoor Amenities: Large Front Porch | Screened in Porch | Outdoor Grill and Dining Area | Lawn Games in Deck Box | Fire Pit| Outdoor Hot Tubbrbr**Dogs are on a case by case discretion and needs the Owners approval. $50 per Dog FeebrbrParking for 3-6 VehiclesbrbrWasher | Dryer | Iron available brbr**Complimentary Pack n Play with Mattress + Portable Booster Seat available**brbr---THE LOCATION---brSitting on nearly 6 acres, enjoy the sights as you may encounter wildlife such as bugs, birds, bears, bobcats, and deer just to name a few.brLess than 1 mile to downtown Great Barrington & Lake Mansfield. br--- POLICIES----br- Property Registration Number C043443113Ebr- No Smokingbr- Onsite parties or group events are strictly prohibitedbr- Notice that no excessive noise shall occur after 8:00 PM or earlier than 8:00 AMbr- Must be at least 25 years old to bookbr- Government-issued photo identification and credit card, debit card, or cash deposit may be required at check-in for incidental charges.br- Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteedbr- NOTE: This unit has exterior-facing cameras. They do not look into interior spaces within the propertybrSAFETY FEATURES: Fire Extinguisher | Smoke Detector | First Aid Kitbr-----LOCAL ATTRACTIONS----brGreat Barrington, Lenox, Stockbridge, Lee, Tanglewood, & Pittsfield. Fun in any season. Take your pick. The abundance of lakes, mountains, and woods provides a variety of outdoor activities from trail hiking, biking, fishing, ziplining, kayaking, Skiing, Snowboarding, snowshoeing, festivals, music concerts, apple and berry picking, farmers markets, and theatrical performances. Fill up with the famous Berkshire food scene showcasing a variety of cultural and culinary experiences. Want more Explore the infamous New England architecture, homes, and historical sites. Chill out to some local and some famous performers. The experiences are unlike anywhere else. The

Bed

Bath

Sleeps

$569.67

/ Nightly

Private Vacation Home

Outdoor Sauna, Hot tub, Fire Pit, Dogs Welcome!

Great Barrington, Massachusetts, United States

Relax with the whole family or escape with your partner for a romantic getaway to Lovers Lane. Surrounded by trees and set against the backdrop of Monument Mountain, you'll have everything you need in this quiet, private setting to fully enjoy some time away.brbrSoak in the hot tub and relax in the outdoor sauna while taking in the beautiful view of Monument Mountain.brbrIt's a short drive to downtown Great Barrington & Stockbridge where you will find cute shops & great dining. Go skiing at Butternut, see live music at Tanglewood or hike Monument Mountain. Good times await at Lovers Lane in the Berkshires.brbrThis house was built in 2022 and everything is brand new. The original building was a tannery that made and fit the saddles for the Budweiser Clydesdales. Open floor plan living so plenty of room for the whole family to gather for a meal or in front of the TV for movie night. There is plenty of space to get away for some alone time to nap in one of the bedrooms or take a nature walk in the woods on the property. The house sits back from the street down a private driveway nestled in the trees.brbrWe are right next door to the Little Lion Motel so if you are traveling with extended family and have a big group that needs additional lodging, book them there! It's just a short walk across the backyard from our house.

3

Bed

2

Bath

6

Sleeps

$291.21

/ Nightly

Private Vacation Home

Great Barrington Farmhouse near Lake Mansfield

Great Barrington, Massachusetts, United States

72 CHill Road is a cozy 1860’s farm house with mid-century modern flair. A 7-minute drive to downtown or Butternut, this calm Berkshire refuge is the perfect place for a country vacation with all the amenities of town life. The house has 3 bedrooms, living room, fully equipped kitchen, dining room and sun porch. Out back you will find expansive views, mature trees and close to an acre of lawn with spaces to lounge, practice yoga under the willow or relax in the hammock overlooking East Mountain.

Bed

Bath

Sleeps

$11193.94

/ Nightly

Cabin

Charming Cabin On Scenic Road

Great Barrington, Massachusetts, United States

One bedroom, one bathroom cottage on beautiful rural road. Wood burning stove and recently renovated kitchen makes it ideal for a country get away. Lovely in all seasons.brbrPrivate garden and screened-in porch. Two miles to shops and restaurants of downtown Great Barrington, voted best small town in America by Smithsonian Magazine. Enjoy nearby skiing, cycling, fishing, hiking and golf.brbrJust 20 minutes from Tanglewood.

Bed

Bath

Sleeps

$1386.64

/ Nightly

Private Vacation Home

Berkshires Estate w/ Heated Pool by Evergreen Home

Great Barrington, Massachusetts, United States

Evergreen Home Vacation Rentals invites you to your private 60-acre Berkshires paradise. Ideally located 10 minutes from Great Barrington and Stockbridge, this estate features private trails, a heated saltwater pool, and a pool house with a kitchenette.brbrWith stunning views and ample space, this retreat is perfect for large groups. Enjoy easy access to Tanglewood and Jacob’s Pillow, or simply unwind in your own secluded sanctuary. Experience the ultimate Berkshire escape—book your stay today!brbrIf you have any questions please message via your booking platform. Our goal is always for our guests to enjoy a relaxing stay at a beautiful home.brbrbrThe home is set far off a main road in Great Barrington, the setting is rural and you cannot see the neighbors or see / hear any car traffic.brbrGuests will have private access to the home, and property during their stay.brbrThis is an established 5-star rental property —check the photos to see the glowing reviews!brbrThe open concept main floor of the house features a fully stocked chefs kitchen with a large island, high ceilings, and everything you could need for meals at home. The kitchen also includes a large dining table that can seat up to 8 guests. Cozy up in the family room located off the kitchen and enjoy the view of the property through the large windows.brbrDown the hall, the spacious living room provides the perfect space to enjoy a movie or play a board game with the whole family. Large windows throughout the room allow for natural light to pour into the living area. Attached to this room is the sun porch which contains additional seating and dining areas as well as a small book collection. brbr3 of the 5 spacious bedrooms are located on the first level of the home. The primary bedroom features a king bed, sunlit seating area, and ensuite bathroom. The other two bedrooms on the first floor also contain king sized beds and both have a pullout couch to accommodate different sleeping arrangements. There are two half baths and one full bath with a walk in shower located on the first floor.brbrThe second floor of the home contains the other two bedrooms, one with a king bed and the other with a queen bed. There is a full bathroom with a tub/shower combo upstairs.brbrThe lower level of the house includes the washer and dryer units, pool table, and workout equipment. brbrStart your morning on the front deck, sipping coffee and taking in the sounds of nature. Spend the day on the back deck lounging in the sun or under the awning while enjoying the views of the property. brbrCool off in the salt water pool and keep your food and beverages in the detached pool house equipped with a sink, dishwasher, refrigerator and bathroom. There is also an outdoor shower to rinse off post pool. Explore the private trails maintained around the property.brbrSpend the evening grilling and sitting around the fire pit on the back patio, head into town to one of the many restaurants or bars, or hire an incredible private chef to come in for a gourmet meal. The options are unlimited!brbrLocated 10 min from downtown Great Barrington or Stockbridge, 5 min from Butternut Basin, and 20 min from Tanglewood and Jacob's pillow.brbrHaving a car will greatly enhance your ability to explore the Berkshires effectively.brbr⭐️ LOCATION: This home is set far off a main road in Great Barrington, offering a peaceful, rural setting with no visible neighbors or traffic noise.brbr⭐️ PETS: No pets allowed.brbr⭐️ PARKING: Free on-site parking is available.brbr⭐️ POOL: Open seasonally May through October, with exact dates determined by weather.br• June 1–Labor Day: Heated to 82°F at no additional cost. Guests may request a higher temperature for an extra fee—please contact us in advance.br• May & after Labor Day: Pool heating may be available for $150/day, but is not guaranteed. Advance notice required to ensure readiness.br• Heating above 82°F during June–Labor Day is available for an additional fee; please contact us prior to arrival.brbr⭐️ WORKOUT EQUIPMENT: Guests may enjoy a Peloton (bring your shoes!), TRX, and resistance bands during their stay.brbr⭐️ COMMERCIAL USE: Owners may allow commercial photography or filming with prior permission. Additional fees may apply—please inquire before booking.brbr⭐️ DAMAGE PROTECTION: Your reservation includes a $20 accidental damage insurance fee, allowing you to relax and enjoy your stay with peace of mind. If any damage occurs, please notify us so we can arrange timely replacements for the next guest.

Bed

Bath

Sleeps

$774.25

/ Nightly

Private Vacation Home

Jaw dropping mountain & lake views in this stylish mountain home….

Great Barrington, Massachusetts, United States

Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. brbrPrivate mountain top adventure awaits.. brbrCentrally located in Southern Berkshire County: 10 minutes from Butternut ski, 15 minutes to Great Barrington, 20 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.brbrGreat Room: Spacious open floor plan great for entertaining friends and family. Living room is furnished with 2 comfortable deep seated sofas, accent chair and 2 ottomans and 2 large coffee table’s, Relax and enjoy collection of movies on dvd players, listen to music on the stereo system or play games (we have a variety of board and card games).brbrFamily room (downstairs) with large sectional and daybed for extra sleeping. There is a TV and dvd player. brbrChef’s Kitchen: Stainless steel appliances, large island that seats 6 and dining table that seats six...brbr4 Bedrooms: 1 King size, 3 queen size all with luxury mattresses and bedding.brbr2 Bathrooms: Master bathroom (upstairs) features with shower and deep soaking tub.br*we are building an additional 3rd bathroom off the hallway, but for now the bathroom upstairs is in the master bedroom that is shared with the guest bedroom.brbrScreened sunroom nestled amongst the woods with beautiful views of the lake… Provides a comfortable setting to relax and includes a sectional sofa, chair & ottoman and table with 4 chairs to enjoy the outdoors.brHammock’s, fire pit, hot tub and grill set up weather permitting… brbrNOTE: brDriveway: The house is located on the top of a long private gravel road, it gets snow plowed when the snow reaches 4” but it’s best to have a car that suitable in the snow. brbr We have updated home to include Central Heat & Air Conditioning Fall 2019.brbrInternet: Wifi throughout the home.brbrMovies & Cable TV:br2 Large Flat Screen TV’s equipped with Smart TV's and DVD players including premium’s like Netflix, HBO, SHOWTIME and STARS. brbrStereo system with speakers is set up in the great room with record player and aux cord to hook your phone to play any music on your phone library. brbrPhone:brThere is also no house phone some cell phone providers work better than others. brbrWe will be providing all our guests with our How to's, House Rules and an inventory list that each guest must read and email back with confirmation that they have read and understand.brbr* ID verification required before booking.

Bed

Bath

Sleeps

$648.95

/ Nightly

Private Vacation Home

Beautiful House in the Woods: Huge Yard, Hot Tub

Great Barrington, Massachusetts, United States

Experience the charm of country living year-round on 4+ acres of peaceful land, tucked away on a private lane just minutes from Downtown Great Barrington and Tanglewood. brbrThis inviting home offers seamless indoor-outdoor living with abundant natural light, a spacious 1,000+ square foot deck, expansive yard, vibrant gardens, and a relaxing outdoor hot tub. Perfect for families, groups of friends, and even your well-behaved pup, this Berkshires retreat is a one-of-a-kind getaway.brbrWelcome to your home away from home in the heart of the Berkshires—where comfort meets adventure. This spacious retreat is perfectly located just a short, scenic drive from some of the region’s most beloved destinations:brbr- Great Barrington/Stockbridge/Lenox for shopping, dining, and culturebr- Tanglewood and Jacob’s Pillow for unique live performancesbr- Norman Rockwell Museum, The Clark, and Mass MoCA for world-class artbr- Lakes, rivers, trails, and nature preserves for outdoor lovers of all kindsbrbrAfter a day of exploring, gather in the chef’s kitchen—a true standout of the home. Outfitted with premium appliances including a Thermador induction stove, KitchenAid dual oven, Liebherr fridge/freezer, wine fridge, Chemex and electric coffeemakers, and All-Clad pots/pans, it’s fully stocked with everything you need to cook and serve memorable meals. The countertops—crafted from Vermont Danby marble and soapstone—are as elegant as they are functional.brbrStep right outside from the kitchen to a 1,000+ square foot deck surrounded by lush grapevines, hummingbirds, and peaceful woods. Enjoy morning coffee in the sun, dinner al fresco at the large dining table, or a soak in the outdoor hot tub under the stars. There's also a gas grill, fire pit, lounge seating, and a generous yard for games or relaxing.brbrEach floor has its own full bathroom for maximum privacy and convenience.brbrSleeping arrangements:brbrThis home sleeps up to 8 guests across 4 bedrooms, with 3 full bathrooms and 1 half bath:brbr- Main level primary suite: King bed with en suite bathroom (tub + shower)brbr- Upstairs Bedroom 1: Queen bedbrbr- Upstairs Bedroom 2: Two twin bedsbrbr- Lower level Bedroom: Full bedbrbrOther highlights include:brbr- Central A/Cbr- Cozy wood-burning fireplace in the living roombr- Smart TVs in the living room and upstairs bedroom (stream Netflix, Hulu, Prime, etc.)br- Dining table for 10 + kitchen island seating for 4br- Rapid ice maker on top of the beverage fridge (freezer ice maker is off)br- Washer/dryer, hotel-quality linens and towelsbr- Stocked with shampoo, conditioner, and body washbr- Parking for 4–6 cars across two drivewaysbr- Hardwood floors on main/upstairs levels; tile and carpet on the lower levelbr- Easy access for guests with limited mobility: just five stairs to enter, and primary suite on main levelbrbrOne well-behaved dog (1+ year old) is welcome for a $75 pet fee per stay.brbrWhether you're here for culture, quiet, or quality time, this thoughtfully designed home is the perfect Berkshires basecamp year-round.

Bed

Bath

Sleeps

$310.72

/ Nightly

Cottage

Romantic Berkshires Cottage - Stunning Views, Pool

Great Barrington, Massachusetts, United States

This unique cottage--30' away from our home on a fenced, three-acre property--has its own entrance and its own parking space. The pool is shared with us, but you will have it to yourselves for most of the day--just ask for private time. brbrThere are windows on three sides, a ceiling fan and a window fan. brbrThe Berkshires in spring, summer and fall are alive with beauty, and we offer glorious views of the rolling hills and verdant meadows. Nature lovers, artists, writers and all who cherish tranquility will take particular delight in this unique spot. brbrPerfect for any couple (can accommodate a small child, too), this gem of a cottage offers a romantic break that will appeal whether you are an active hiker or biker, or just want to sit under the trees or by the pool with a good book and savor the unsurpassed scenery. You'll be on a secluded country lane, but only minutes from downtown Great Barrington with its restaurants, music, theater and shopping. It's an easy drive to all area attractions and great Appalachian Trail hikes. The area roads are also ideal for biking. brbrBedroom/sitting room, kitchenette with toaster oven, electric kettle, toaster, microwave and full-size fridge, but no stove. Full bath with bathtub and shower. Non-smoking only. Check our rates for week-long specials. brbrWe do not accept reservations for longer than two weeks. brbrWe can also assist you in finding just the right activity for your stay, whether it's hiking the state's highest peak, Mt. Greylock, a picnic at Bartholomew's Cobble or just lounging on the bench outside the cottage. brbrStudio offers complimentary bottle of wine, use of two kayaks, excellent wifi coverage, hair dryer, onsite parking, TV, microwave, electric kettle, Ninja coffee maker, toaster, toaster oven, full-sized fridge. brbrPlease note that taxes of 11.7% include 6% Great Barrington tax and 5.7% Mass. tax.

1

Bed

1

Bath

3

Sleeps

$411.97

/ Nightly

Private Vacation Home

Available in June! Mountain Views, Fire Pit, AC, High Speed Internet!

Great Barrington, Massachusetts, United States

Renovated cottage with vast mountain views. 3 bedrooms, 2 full baths, sleeps 6. Amenities: backyard patio with seating, cafe lights, fire pit (wood included), propane BBQ grill, main floor bedroom with king bed and en suite bathroom, High speed internet/WiFi, 3 Smart TVs, washer/dryer, pack-n-play, highchair, fenced dog run, large backyard with outdoor games: soccer nets, balls, corn hole, bocce ball and the Appalachian trail just steps away! Central location! Pets considered with fee.brbrFirst Floor Features:brRenovated eat-in kitchen (seats up to 6) with pantry storage for your food, solid pots and pans, utensils, dishware, platters, etc. Perfect for longer stays!brKitchen appliances include: Dishwasher, Gas range/oven, microwave, toaster oven, toaster, blender.brCoffee station (Keurig, standard drip + French press) with kitchen lounge seating with mountain views: Plus 4 bar stools!brLiving room with sofa and club chair seating, reading nook, gorgeous nature views, and a 65 Smart TV.brMain floor Primary with king bed, ensuite bath with walk-in shower, TV, dresser, closet and Smart TVbrSecond bathroom with tub/shower combination and storagebrAttached 1 car garage with direct entry into the mud roombrFront entry mudroom, well organized for all your Berkshire gear, year round.brAttached garage with direct entry, automatic door clicker, room for 1 car, and ski storage. brbrSecond Floor:brGuest Room #2 with a full bed, dresser and closet.brGuest Room #3 with 2 twins, dresser and closet, and Smart TV + a few toys for the kiddos.brbrLower level:brThe washer and dryer is located in the laundry room in the basement.brbrOutdoor Features:brVast mountain viewsbrPatio with dining set, 4 wood Adirondack chairs a sectional sofa. 2 chaise loungers are avaialble for sunbathing or star gazing at night! brFire pit. (wood included)brBig backyard, flat, and perfect for outdoor games: 2 soccer nets, soccer balls, Cornhole, Bocce Ball included!brPropane BBQ grill and sun umbrellabrCafé lights set the mood! brFenced dog run - dogs must not be left and shall be monitored.brbrHiking: access to the Appalachian trail, is just steps away from Dixon CottagebrbrAdditional Features:brHigh Speed Spectrum cable internet and Wifi provided.brThe home is thoroughly checked prior to your arrival for an easy check in.brAll linens are provided.brProfessionally managed property - So you know you're in good hands!brBaby gear: highchair, pack-n-play - guest bring their own sheets, please brTanglewood picnic accessories: rolling cooler, and foldable chairsbrbrLocation: br5 minutes to downtown Great Barringtonbrless than 5 mins. to The Barn for live musicbr5 minutes to downtown Sheffieldbr15 minutes to Ski Butternutbr10 minutes to Catamount Skibr25 minutes to TanglewoodbrbrPets: Well behaved, trained pets are welcome with a $150 pet fee, per pet.

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Sleeps

$258.07

/ Nightly

Private Vacation Home

Cozy Riverside Berkshires Retreat

Great Barrington, Massachusetts, United States

Stay in our charming historic New England home right on the Housatonic river. This private half of a duplex offers river views, a fenced-in yard for relaxing outdoors, a fully equipped kitchen and easy access to the Berkshires. Downtown Great Barrington is a quick five minute drive and Tanglewood is only fifteen! brThe real treat is Studley, the sweet and much‑loved resident cat and “host with the most,” who lives on the property and is always happy to greet guests.

Bed

Bath

Sleeps

$405.84

/ Nightly

Private Vacation Home

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

Great Barrington, Massachusetts, United States

New 3 BR rustic-yet-elegantly modern 2300 sq ft country castle set on on 3.5 secluded acres in Manor Lane, a private compound off Hurlburt Road in Great Barrington, MA, this property offers the perfect balance of peaceful seclusion and year-round convenience. We call it the GreatBarringtonCastle House, but it's much more farmhouse/luxury villa. Take the time to read the full description below -- you won't be disappointed.brbrCentrally located in the heart of the Berkshires in Smithsonian Magazine's Best Small Town in America 2015, Great Barrington. An idyllic basecamp to take advantage of spectacular hiking, biking, skiing, and views, with one of the longest, richly colored fall foliage seasons in the country, from September deep into October. When the winter snows fall, take out your snowshoes and experience the drifting silence of the woods. In summer, enjoy long days in nature and leisurely evenings. Fabulous local shops and restaurants rival any in the big cities. Great, quiet escape from NY City or Boston (or anywhere else). A great gathering spot for a family or group of friends.brbrThis private country home is spacious, extraordinarily comfortable, bright, cheery, uplifting, modern but not art deco, and not cookie-cutter. You’ll find that our house, the property, and the location are even better than in the pictures. The location is literally the best in Great Barrington, and the house is one of the most beautiful and unique homes in town, of any size. That's because we built our house specifically so we would never have a disappointing vacation rental ever again -- and you won’t either!brbrThe house is located on a beautiful, quiet country road, and still close to town. You don't have to choose between rural country life privacy and convenience when staying at this home -- it offers the best of both! Just down the road from Simon’s Rock, and 2 miles to famous Guido's or the center of downtown Great Barrington. The Appalachian trail or a swim at Lake Mansfield with a beach and lifeguard are just 5 minutes away, and it's 15 miles to the music and cultural events of Tanglewood to the north. ....Also makes an ideal ski haus, given that it's 5 miles to Butternut and Catamount ski areas, with an easy in, easy out property that's plowed with every snowfall, a ski rack in the garage to hold your skis, a spacious mudroom with plenty of hooks for your ski gear, the great room with rustic gas heating fireplace that lights up with the flip of a switch as soon as you come home from the mountain, and the chef's kitchen for ravenous appetites. All in all, a perfect four-season getaway!brbrNo expense was spared in rebuilding this home. Charming, bright, spacious modern farmhouse interior, with beautiful large windows throughout. A real gourmet chef’s kitchen with cathedral ceiling, pro range, SubZero fridge, and farmhouse sink, that's fully stocked with everything you could need, including a cabinetfull of spices, papergoods, three coffeemakers, and all the dinnerware, flatware, cookware and kitchenware you’ll need to entertain. And the water in the house is quadruple filtered, so the water coming out of the kitchen faucet is the best you've ever tasted! Seat up to 10 around the large, expandable rustic dining table. Beautiful, comfortable cathedral-ceilinged living room with huge premium sectional sofa, enough seating for a crowd. On rainy days or cold winter getaways, cozy up in front of the rustic fireplace. The grand master bedroom on the main floor has 11’ ceilings and a beautiful, large master bathroom. Another guest bedroom is on the main floor, and a third bedroom is up in the high tower, a favorite of adults and especially kids. All three bedrooms have outstanding, comfortable mattresses. (Another reason we built this house was because we couldn’t find a rental with comfortable mattresses!) Each bedroom has a beautiful private bathroom, with fully tiled shower with heavy glass shower door and Hotel-quality bath and bed linens. There's a well-appointed den with comfortable sofa, large desk, and computer monitor and laser printer to hook up to your laptop. Three large flat-screen TV’s are tastefully installed in the living room, master bedroom, and den, with excellent cable TV, internet, and cellular service, and high speed triband wifi throughout the house, along with direct ethernet jack plug-in to the network if you need it.brbrGas heat throughout the house ensures that you’ll stay toasty warm during the colder months. During the summer months, the main and second floors remain cool with the stone and wood floors and central air. The bedroom in the high tower has its own split unit for heating and cooling. There’s a new full size LG Washtower washer & dryer in a nice laundry/utility room. Plenty of books to keep you occupied, and dozens of cookbooks with recipes to try. Out back, there's a large patio with comfortable table and chairs, and Weber gas grill for summer meals. As Manor Lane is a rural, forested area, we have the house professionally treated with pet- and child-safe products every month by Orkin for ants, bugs, mosquitos, bees, and other critters, so you'll be comfortable and bug free dining outside at night on the patio. There's a single car garage for your use, with direct entry via mudroom into the house. The house has a keypad front door lock and wifi Liftmaster garage door, so you won't need any keys!brbrOur house was especially designed for weekly, monthly and longer term rentals, but we do accommodate 3-day weekend booking requests. We offer a 5% discount for weekly stays or more, and a 10% discount for monthly stays. Note that for stays less than 31 days, VRBO collects Massachusetts excise tax of 5.7% and Great Barrington tax of another 6%, for a total tax of 11.7%. The bright side is, stay 31 days and there's no tax, you save 11.7%! brbrNo smoking, and please inquire about children AND PETS before booking a stay. Sorry, we allow only one pet, and we can't allow cats.

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Bath

Sleeps

$997.6

/ Nightly

Private Vacation Home

Beautiful Berkshire Farm House on 160+ Acres

Great Barrington, Massachusetts, United States

Don't hesitate reach out about availability even if dates look unavailable. We are happy to review avails with you.brbrA working farm located on more than 1000 feet of the Green River. Over 160 acres of beautiful woods and agricultural fields. Large indoor gymnasium with full basketball court, also good for indoor skating and roller blading. Babbling stream with pond right out the side door. A summer time wonder—but close to the local mountains for ski season.brbrbrNo weddings, parties, or events.

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Sleeps

$1414.9

/ Nightly

Private Vacation Home

Country Castle-Total privacy-just a few minutes from center of Great Barrington

Great Barrington, Massachusetts, United States

brbrWelcome to the Country Castle! This expansive home, boasting 7000 square feet, sits on 20 private acres less than five minutes (~2-miles) from downtown Great Barrington. It is also ~10-12 minute drive (~6 miles) to either Butternut or Catamount for a day on the slopes. The home is extremely private yet convenient to all Berkshire amenities. You can also meander from the backyard directly onto multiple hiking and snowshoeing trails to enjoy for hours.brbrThe space:brSet back from the road on 20 acres, a half mile long driveway leads you to this fabulous property with plenty of parking for your whole group. The main living space is open concept and is bathed in sun light and includes a large wood burning fireplace, connecting the kitchen, living room and dining room, creating the perfect space for a memorable occasion. The back deck is equipped with a BBQ and ample seating.brbrPerfectly designed with multiple rooms to stretch out and share time with family and friends. Amenities include an entertainment room with 75” TV and theater seating, pool table, and 9 foot tabletop shuffleboard game. A complete chef’s kitchen for the culinary enthusiast, equipped with stainless steel Viking appliances and all cooking essentials. A small gym with peleton style bike and weights. The residence includes a fire pole, drawing room, and meditation space accessed by a ladder in the main living room. There is also a large elevated deck located off of the main living space as well as a lower deck with a small fire pit and even more seating. Multiple offices allow for remote work away from your group during your reservation.brbrSix bedrooms and three baths, with plenty of private spaces to rest after a long day of exploring. The primary bedroom includes a king sized bed and full bath. Bedroom 2 and 3 both have queen sized beds and are connected with a Jack and Jill bathroom. Additionally bedroom 2 has a trundle bed, providing two single mattresses. Bedroom 4 and 5 both have queen sized beds, and share a bathroom in the hall. Bedroom 6 is accessed by a circular staircase and has connected twin beds. perfect for the little ones.brbrGuest access:brGuests will have complete access to the home, except for the plunge pool and the garage.brbrOther things to note:brThis home has stairs throughout and might not be satisfactory for guests that are disabled.brbrWe allow 2 well behaved dogs, and charge a $100 fee for either 1 or 2 dogs. Please include your pet when making your reservation.brbrNo cats please.brbrWe offer monthly discounts. Please make a booking inquiry for monthly rates as they vary through the seasons.

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Bath

Sleeps

$878.16

/ Nightly

Private Vacation Home

Sunsets On Blue Hill, Newly Renovated Farmhouse

Great Barrington, Massachusetts, United States

Summary:brbrWelcome to Great Barrington! The heartbeat of the Berkshires!brbrbrbrThis newly remodeled home is conveniently located in a quiet neighborhood on 1 acre, 5 min drive to downtown Great Barrington, and 5 min drive to Butternut Ski. Convenient to all South County attractions, culinary experiences, cultural and artistic events!brbrbrbrThe Space:brbrOur wrap around porch with sunset views is the perfect place for your group to enjoy you’re morning coffee or evening cocktail. Open floor plan with a fully equipped chef’s kitchen. Stainless 6 burner Viking stove, Viking commercial grade hood, farmer’s sink, stone countertops, dishwasher, and ice maker complete the kitchen, making it a dream for culinary enthusiasts. brbrbrbrStylish mud room has radiant floor heating. Cubbies and hooks for all your coats and hiking boots, as well as a 3/4 bath for a quick shower after your hike, bike ride or rinse off your four legged friend.brbrbrbrLiving room/dining room space is ideal for a family gathering after an exciting day of exploring. Large dining room table as well as abundant seating, allows everyone to spread out and relax. Open, airy, and filled with natural light this space creates a perfect atmosphere for any occasion! Easy access to the wrap around porch, furnished with Adirondack rocking chairs, allows you multiple places to enjoy the view!brbrbrbrSmall bedroom/playroom is right off the kitchen, includes one twin bed in addition to books, games and children’s toys.brbrbrbrLeading up the homes original stairway, you will find three bedrooms, two baths and laundry.brbrbrbrThe primary bedroom features a king sized bed, flat screen smart tv, remote work station, private balcony and luxurious bathroom. The bathroom includes a walk-in shower, soaking tub, top quality linens, and radiant heated floors. Reflect on the balcony with a cup of tea while taking in the evening air, or cuddle up and watch a movie in privacy.brbrBedroom 2 includes a comfortable queen sized bed, and sunset view.brbrBedroom 3 includes a full, and queen size bed. Perfect spot to group all the kiddos in. brbrbrbrAn additional bathroom on second floor with walk in shower, radiant heated floors and stylish finishes. Washer/Dryer on second floor. Thoughtful toiletries for each guest in case anything was left at home.brbrbrbrOutside you will find a large fenced yard for children and pets to play. Wide gravel driveway, stone patio, fire pit with seating and BBQ, great for summer cook outs.brbrbrbrWe have enjoyed creating this space, and are excited to share it with you! We hope to make your reservation a special one for you and you’re whole family!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:brbrGuests will have access to the entire home and property, except for the basement.brbrbrbrThe Neighborhood:brbr4 min drive to downtown Great Barrington, and a 5 min drive to butternut ski mountain, our home is convenient to town. Our home is in a pleasant neighborhood on the north side of town.brbrbrbrGetting Around:brbrWe have parking for up to 5 cars.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.brbrbrbrDamage: 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. Damage related to pets is not covered under this waiver. brbrbrbr-Bring your furry friends, two dogs are allowed. $50 per dog per stay. Dogs must be at least one year old, sorry no puppies!brbrbrbrInteraction with Guests:brbrWe live in the area and can offer assistance if necessary, but will respect your privacy and will not visit the property during your reservation.

4

Bed

3

Bath

9

Sleeps

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