House vacation rentals in Great Barrington
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Top-rated house rentals in Great Barrington
Guests agree: these houses are highly rated for location, cleanliness, and more.
Home in Lee
4.89 out of 5 average rating, 234 reviewsCozy Berkshires Cottage
Stay in a cozy Berkshires 1920's cottage! The bedroom occupies the entire second floor with peaceful views of the surrounding field and yard. The cottage is set back from the main road, easily accessible yet private. - Zoned air conditioning & heating makes every room comfortable year-round. - Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. - Ideal for couples, solo adventurers, business travelers, and furry friends (pets). (Note: MA requires 11.7% tax added to charges)
May 8 – 15
Home in Lee
4.9 out of 5 average rating, 202 reviews1817 Berkshire Farmhouse- Close to Everything.
*Close to ski resorts & tubing! We are nestled at the foot of October Mountain State Forest, yet close to the centers of Lee, Lenox, & Pittsfield. Our charming house was built in 1817- original wood beams, wood floors, and quite a history. Whether you enjoy skiing, exploring local restaurants & downtowns, venturing outdoors or experiencing the local art scene, the Berkshires has something for everyone. Our little farmhouse serves as the perfect "home base" for all of your Berkshire adventures.
Sep 4 – 11
Home in Great Barrington
4.96 out of 5 average rating, 137 reviewsElegant Year-Round Lakeside Retreat with AC
The Haven, an elegant cottage surrounded by woods, located on a pristine lake with private dock. 4 bedrooms, 3 baths. This year-round vacation cottage with hot tub provides an experience in the Berkshires you won’t forget! Leaf-peep in fall, ski in winter, hike in spring, kayak & swim in summer, or browse the boutique shops in quaint towns like Great Barrington, Lenox and Stockbridge. Newly installed mini-splits provide AC in all bedrooms and LVR/DR/Kitchen common area. 1 house-trained dog ok.
Jan 6 – 13
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Great Barrington house rentals
House rentals with a hot tub
Home in Chester
4.96 out of 5 average rating, 307 reviewsRiverfront Getaway
Dec 9 – 16
Home in Pittsfield
4.98 out of 5 average rating, 100 reviewsHidden Oasis in the Mountains by Evergreen Home
Dec 12 – 19
Home in Craryville
4.98 out of 5 average rating, 184 reviewsModern Home in Woods | Hot Tub | 20 mins to Skiing
Dec 1 – 8
Home in Otis
4.85 out of 5 average rating, 160 reviewsThe Meadows House @ Otis Ridge w/ 7-person hot tub
Jul 12 – 19
Home in Copake
4.88 out of 5 average rating, 108 reviewsDreamy Hudson Valley Lakehouse with Hot Tub
Apr 5 – 12
Home in Catskill
4.95 out of 5 average rating, 132 reviewsHEAVEN ON EARTH - Hudson Riverfront Home
Aug 20 – 27
Home in Colebrook
4.99 out of 5 average rating, 200 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Dec 16 – 23
Home in Craryville
4.93 out of 5 average rating, 218 reviewsThe City Farmers Upstate. Farm house with hot tub
Oct 7 – 14
Home in Hudson
4.95 out of 5 average rating, 246 reviewsLivingston Farmhouse Escape with hot tub and sauna
Apr 3 – 10
Home in Highland
4.96 out of 5 average rating, 106 reviewsHouse in Highland: Secluded Retreat
Mar 11 – 18
Home in Saugerties
4.93 out of 5 average rating, 333 reviewsCatskills Oasis | Hot Tub, Fire Pit, Fenced Yard
Apr 14 – 21
Home in Saugerties
5.0 out of 5 average rating, 131 reviewsUpstate Modern Scandinavian Barn in the Catskills
May 15 – 22
House rentals with free parking
Home in Egremont
4.96 out of 5 average rating, 102 reviewsThe Berkshires Mountain Terrace LUX Home Sleeps 7
Nov 10 – 17
Home in Canaan
5.0 out of 5 average rating, 132 reviewsCountry Cottage
Mar 12 – 19
Home in Great Barrington
4.9 out of 5 average rating, 111 reviewsYour own private Berkshires retreat
Oct 15 – 22
Home in Stockbridge
4.95 out of 5 average rating, 103 reviewsSun-filled, Charming Stockbridge Classic- In Town!
Nov 14 – 21
Home in Great Barrington
4.93 out of 5 average rating, 107 reviewsFormer Sunset View Inn
Jan 11 – 18
Home in Germantown
4.95 out of 5 average rating, 359 reviewsScandinavian Barn Featured in Airbnb Magazine
May 28 – Jun 4
Home in Egremont
4.9 out of 5 average rating, 109 reviewsCozy Berkshire Cape
May 15 – 22
Home in Chatham
4.9 out of 5 average rating, 143 reviews2BR Chatham Vlg Home Wi-fi Park@Door Keyless 55"TV
Dec 13 – 20
Home in Sheffield
4.97 out of 5 average rating, 115 reviewsGorgeous Sheffield Home
Apr 3 – 10
Home in Sheffield
4.93 out of 5 average rating, 111 reviewsA Private Peninsula Retreat In The Berkshires!
Mar 3 – 10
Home in Kingston
4.97 out of 5 average rating, 269 reviewsThis New House
Dec 16 – 23
Home in Woodstock
4.91 out of 5 average rating, 634 reviewsDutch Touch Woodstock Cottage
Feb 9 – 16
House rentals with a pool
Home in Ghent
4.87 out of 5 average rating, 264 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Oct 12 – 19
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
May 2 – 9
Home in New Paltz
4.98 out of 5 average rating, 434 reviewsMid Century Mod *fireplace walk to rail trail/town
Sep 3 – 10
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Oct 20 – 27
Home in Litchfield
4.93 out of 5 average rating, 162 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
Jun 24 – Jul 1
Home in Staatsburg
4.98 out of 5 average rating, 105 reviewsHilltop Escape ~ 25 acre private retreat
Mar 19 – 26
Home in Saugerties
4.96 out of 5 average rating, 150 reviewsLux 1800's renovated farmhouse w/hot tub+pool
Apr 24 – May 1
Home in New Paltz
4.93 out of 5 average rating, 121 reviewsHarrison Field Pool BikeRailTrail 2 Town FirePit
Jan 26 – Feb 2
Home in Cottekill
4.95 out of 5 average rating, 240 reviewsPeace & Privacy - High Falls (hot tub & salt pool)
Nov 23 – 30
Home in Woodstock
4.92 out of 5 average rating, 153 reviewsWoodstock Home Close to 3 Towns, Hiking and More
Apr 12 – 19
Home in Woodstock
4.85 out of 5 average rating, 191 reviews*March Special* Woodstock Retreat Heated Pool
May 23 – 30
Home in Catskill
4.93 out of 5 average rating, 162 reviewsThe Grandview | Catskill, NY
May 5 – 12
Quick stats about house rentals in Great Barrington
Total rentals | 150 properties |
---|---|
Rentals with a pool | 10 properties have a pool |
Pet-friendly rentals | 70 properties allow pets |
Family-friendly rentals | 140 properties are a good fit for families |
Total number of reviews | 3.8K reviews |
Nightly prices starting at | $20 before taxes and fees |
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