Great Barrington Vacation Rentals

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Vacation Rentals in Great Barrington

The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Interior

The Freeman - Newly Renovated 14K SF Estate on 40 Acres

10.0 out of 10, Exceptional, (31)
"We loved the Freeman estate for our wedding!! Daniel and Anna were super helpful and the property was amazing! The house had so many amenities it was beyond our expectations. Our guests were astounded by the home and the surrounding property, would HIGHLY recommend to anyone and everyone. "
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Private Estate, Heated Yearround Outdoor Pool
Fridge, microwave, oven, stovetop

Private Estate, Heated Yearround Outdoor Pool

10.0 out of 10, Exceptional, (14)
"Beautiful property, well-appointed, and comfortable for extended family of 12."
Private Estate, Heated Yearround Outdoor Pool
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
TV, fireplace, DVD player, books

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (41)
"We had expectations of a peaceful rustic cabin in the woods, and this rental checked almost all of the boxes! The quaint town of Great Barrington was just close enough for convenience, but the house was rural enough to help us all relax and enjoy the quiet. We loved the dock and the firepit, and the house was well-stocked with firewood, towels, and toiletries. "
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Peaceful, Post and Beam Loft, Sleeps 9
1 bedroom, iron/ironing board, WiFi, bed sheets

Peaceful, Post and Beam Loft, Sleeps 9

10.0 out of 10, Exceptional, (14)
"House and grounds are large! Firepit is great! Local hiking and restaurants were fantastic! Enjoyed the large rooms and decor and artworks and prints."
Peaceful, Post and Beam Loft, Sleeps 9
Perfect Vacation Get Away - Historical New Marlborough
Property grounds

Perfect Vacation Get Away - Historical New Marlborough

9.4 out of 10, Exceptional, (54)
"It was a pleasure to find this gem of a cabin available for a night so we could attend a concert at Tanglewood, despite living out of state. The location was lovely, convenient and quiet; the cabin was impeccably appointed (thanks for the fresh flowers in every room and bottle of Riesling!) and very clean with every possible amenity; and the hosts were communicative, friendly and helpful. Overall, this was an idyllic mix of quaint/cute/unique and function/comfort/ease. I will absolutely seek out...
Perfect Vacation Get Away - Historical New Marlborough
Minutes from Ski Butternut, Tanglewood, and Downtown Great Barrington
7 bedrooms, free WiFi, bed sheets

Minutes from Ski Butternut, Tanglewood, and Downtown Great Barrington

10.0 out of 10, Exceptional, (25)
"It was a quirky and interesting house!"
Minutes from Ski Butternut, Tanglewood, and Downtown Great Barrington
Great Barrington Get Away
Fridge, microwave, oven, stovetop

Great Barrington Get Away

9.2 out of 10, Wonderful, (22)
"Well-located home, comfortable home with a well-stocked kitchen and plenty of space. We hope to return! "
The price is CA $491
CA $856 total
includes taxes & fees
Jan 2 - Jan 3, 2025
Great Barrington Get Away
Micosta Leisure Inn
Balcony

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (89)
"Fantastic place to stay! So homey, comfortable, and peaceful. Steven was a fabulous host, and his property is wonderful - in a beautiful garden. The room is large and beyond well equipped. No reason to pay more to stay downtown Hudson. We’re on a month-long New England road trip, and this has been our favorite stay! "
The price is CA $187
CA $202 total
includes taxes & fees
Jan 9 - Jan 10, 2025
Micosta Leisure Inn
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (231)
"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "
The price is CA $210
CA $321 total
includes taxes & fees
Dec 30 - Dec 31
Berkshire Village Carriage House - Super Private!!
Peace and quiet on the lake
Interior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (200)
"My family and I really enjoyed our stay at the lake. My kids enjoyed playing outside in the snow. We had such a quality family time playing board games, watching movies and drinking hot cocoa. Justin was such a great host and really helpful when needed. We’re definitely coming back!"
Peace and quiet on the lake
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
TV, fireplace, DVD player

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.8 out of 10, Exceptional, (38)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Pristine Home In Becket Woods
Fridge, microwave, oven, stovetop

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (13)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Exterior

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (209)
"The Cabin Had All The Amenities You Would Need and With A Quiet and Serene Area. For Me It Was Relaxing Stay!"
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Serene Acreage - Pond - Hiking Trails Nearby
Terrace/patio

Serene Acreage - Pond - Hiking Trails Nearby

10.0 out of 10, Exceptional, (6)
"Wonderful accommodation."
Serene Acreage - Pond - Hiking Trails Nearby
Berkshires Cabin 2 Mi to Appalachian Trail!
TV, fireplace, books

Berkshires Cabin 2 Mi to Appalachian Trail!

9.6 out of 10, Exceptional, (10)
"The hosts were extremely responsive and helpful, providing us with hiking ideas, questions regarding the house and suggesting best shopping spots for incidentals. The living room was cozy, seating five comfortably. The kitchen was well stocked so cooking a Thanksgiving meal was a pleasure. We thoroughly enjoyed ourselves."
Berkshires Cabin 2 Mi to Appalachian Trail!
Antique Farmhouse Totally Restored
Exterior

Antique Farmhouse Totally Restored

10.0 out of 10, Exceptional, (83)
"I'd describe the house as elegantly eclectic. The owner is clearly a collector of interesting items which they arrange in a way that enhance (rather than potentially clutter) the interior. The kitchen and living spaces are open and easy to mingle around. The four bedrooms and three bathrooms easily and comfortably accommodated two couples and two singles. Our stay could not have been better! "
Antique Farmhouse Totally Restored
Private Island - Largest Fresh Water Reservoir in Mass....
Outdoor dining

Private Island - Largest Fresh Water Reservoir in Mass....

9.0 out of 10, Wonderful, (7)
"From beginning to end, could not have dreamed of a better island getaway, in the Berkshire’s none-the -less. Bill was a wonderful host. Very friendly, responsive and helpful. Super welcoming. The home was simple, quaint, and super cozy. Perfect for a nice long relaxing weekend for both the dogs and people. The views from the sun room were lovely. The deck/patio area had a beautiful view of the water. The fire pit was a nice perk in the evening. Surrounded by water, the place felt so private....
Private Island - Largest Fresh Water Reservoir in Mass....
Quintessential 6-BR Berkshires Lodge
Exterior

Quintessential 6-BR Berkshires Lodge

9.8 out of 10, Exceptional, (8)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
Quintessential 6-BR Berkshires Lodge
Berkshire Lake access
Lake

Berkshire Lake access

10.0 out of 10, Exceptional, (48)
"The house worked was exceptionally clean and worked great for us. The landowner was exceptionally helpful in providing suggestions. We loved visiting the Norman Rockwell Museum and walking around Lenox. Thanks for everything!"
Berkshire Lake access
Beautiful 5-Star Private Estate! Inquire about our Early Booking Reduced Rates!
Fridge, microwave, oven, stovetop

Beautiful 5-Star Private Estate! Inquire about our Early Booking Reduced Rates!

9.6 out of 10, Exceptional, (85)
"We had fun! Game room great! Spacious and comfortable. Never got to enjoy outdoors, so maybe another trip in the future!"
Beautiful 5-Star Private Estate! Inquire about our Early Booking Reduced Rates!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Great Barrington you may be interested in

Quality Inn
Standard Room, 2 Queen Beds, Non Smoking

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1000)
"Friendly staff"
The price is CA $121
CA $136 total
includes taxes & fees
Jan 2 - Jan 3, 2025
Quality Inn
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Standard Room

Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel

2.5 star property
8.8 out of 10, Excellent, (577)
"Great comfortable stay. Front desk, breakfast and cleaning staff are the BEST!"
The price is CA $179
CA $201 total
includes taxes & fees
Jan 1 - Jan 2, 2025
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Lobby lounge

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.2 out of 10, Wonderful, (675)
"Clean, updated room and bathroom, great price, free breakfast was decent too. Close to downtown but must drive to. "
The price is CA $228
CA $255 total
includes taxes & fees
Dec 25 - Dec 26
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Can I find a vacation rental in Great Barrington?

Yes, there are vacation rentals close to the most popular points of interest in Great Barrington, or you can select a secluded option if you're looking for relaxation. Visitors like the top-notch restaurants and live music in Great Barrington. Leave some time to check out the ski slopes and theater scene during your trip.

What are some of the best vacation rentals in Great Barrington?

Private Estate, Heated Yearround Outdoor Pool: This highly rated vacation home rental in Great Barrington offers a balcony, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the books in this rental home to help you unwind. Our travelers also rate Lakefront Berkshires Retreat w/ Deck, Dock & Boat! as a favorite home for rent in Great Barrington.

How many vacation rentals are there in Great Barrington?

With 93 Expedia vacation rentals, you're sure to find just the right place for your Great Barrington stay.

What can I see and do in Great Barrington?

Cultural attractions include Mahaiwe Performing Arts Center and Art et Industrie, whereas Housatonic River Walk and Housatonic River are a couple of picturesque spots to enjoy the outdoors. Lake Mansfield Park and Ski Butternut are other places to visit while you're in town.

What are vacation rentals like in Great Barrington?

Vacation rentals are privately owned properties you can reserve for several days or more in Great Barrington. Vacation rentals offer extras such as patios, hot tubs, and fire pits so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for a family getaway.