Great Barrington Vacation Rentals

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Browse Select Great Barrington Vacation Homes

Waterview Home in the Berkshires: Near Hiking
Outdoor dining
Waterview Home in the Berkshires: Near Hiking
9.2 out of 10, Wonderful, 14 reviews
"Lovely house and kind owner. We had a great time. The view is amazing."
Waterview Home in the Berkshires: Near Hiking
Private Lake House in the Berkshires
Pool
Private Lake House in the Berkshires
9.8 out of 10, Exceptional, 15 reviews
"This was our first VRBO experience, and we are hooked. We had a wedding in Pittsfield with events over three days, so we decided to try this lakeside retreat, and it was a treat! The Berkshires in the fall are absolutely beautiful and Hinsdale is a pretty little town. Ozzie's is definitely worth the trip for breakfast. The lake is lovely and we were looking forward to kayaking and fishing. Unfortunately the weather was not on our side, but we still got one fish! Mary is a wonderful host who is...
Private Lake House in the Berkshires
Cozy Retreat on Copake Lake in our Charming Home
Pool
Cozy Retreat on Copake Lake in our Charming Home
9.6 out of 10, Exceptional, 32 reviews
"Great stay. A short walk to everything the lake has to offer."
Cozy Retreat on Copake Lake in our Charming Home
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Exterior
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.8 out of 10, Exceptional, 7 reviews
"We had a great stay while skiing for 2 days at nearby Catamount ski resort. The kitchen and house were fully stocked with all essentials. Netflix access enabled us to enjoy a family movie after a long day of skiing. Cozy house and quiet area.......nice to wake up to hear birds chirping!!"
The price is CA $218
CA $459 total
includes taxes & fees
Jul 1 - Jul 2
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Peaceful Retreat Compound 10 Minutes to Great Barrington!
Interior
Peaceful Retreat Compound 10 Minutes to Great Barrington!
10.0 out of 10, Exceptional, 11 reviews
"The property was fabulous and had lots of activities on site(basketball hoops,pickleball court and pool). Excellent location close to Great Barrington downtown which has an amazing selection of restaurants. Overall,fantastic stay!"
Peaceful Retreat Compound 10 Minutes to Great Barrington!
Spectacular views and close to Great Barrington.
Living area
Spectacular views and close to Great Barrington.
Spectacular views and close to Great Barrington.
Tranquil 3-BR Waterfront Retreat
Exterior
Tranquil 3-BR Waterfront Retreat
10.0 out of 10, Exceptional, 7 reviews
"The house is immaculate! One of the cleanest properties we've stayed in. The house was the perfect size for my family of 4 (2 adults, 2 teens) with room for more. The beds are comfortable, and there were plenty of linens and towels. The linens and towels are high quality, very soft. The kids had fun fishing in the pond and made good use of the kayak (they caught some bass, pickerel and sun fish). The neighborhood is nice and quiet, dirt roads, no traffic...great for taking walks. We used the...
Tranquil 3-BR Waterfront Retreat
Hearts Desire is a furnished whole house in a small, colorful garden center.
Terrace/patio
Hearts Desire is a furnished whole house in a small, colorful garden center.
10.0 out of 10, Exceptional, 68 reviews
"What an amazing find to stay at while attending a yoga festival at Jiminy Peak. The house was immaculate and didn't miss a thing! Not only was there a bottle of wine waiting, but an adorable history of the home. The house was HUGE and the beds very comfortable. I wouldn't call it a 3 bedroom house though, it's a 2 bedroom with a pull out sofa in the living room. The hot tub is amazing and watching the starts and fireflies in the backyard at night was magical. Highly recommend and would stay...
Hearts Desire is a furnished whole house in a small, colorful garden center.
Le Soleil Suite -- Pool and views 10 min. from downtown Hudson
Private kitchen
Le Soleil Suite -- Pool and views 10 min. from downtown Hudson
10.0 out of 10, Exceptional, 7 reviews
"Le Soleil Suite was just as it was pictured. It was very pretty, neat and clean. Sarah provided everything that we needed for our stay and she was very responsive if we had any questions.It was so quiet and peaceful. We truly enjoyed our stay!"
Le Soleil Suite -- Pool and views 10 min. from downtown Hudson
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Fridge, microwave, oven, stovetop
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
10.0 out of 10, Exceptional, 25 reviews
"Beautiful property- well maintained and excellent location."
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Pristine Home In Becket Woods
Fridge, microwave, oven, stovetop
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, 8 reviews
"I really loved my stay at this beautiful property surrounded by nature and peacefulness in the Berkshire mountains. The owners were great too with communication and making things easy for check in and check out. Highly recommend this place!"
Pristine Home In Becket Woods
Peace and quiet on the lake
Interior
Peace and quiet on the lake
9.6 out of 10, Exceptional, 186 reviews
"The house was clean and cozy. The kitchen was well stocked, especially important as we like to cook at home. Justin was responsive when I contacted him with questions. Love that the house was dog friendly with a fenced in back yard. The house has been updated inside but the deck needs some TLC, which I am sure are in the plans. A perfect get away!"
Peace and quiet on the lake
Chic Pittsfield Home With A View!
Property grounds
Chic Pittsfield Home With A View!
9.0 out of 10, Wonderful, 4 reviews
"Nicely decorated and clean. It had everything we needed, including kitchen supplies and detergent for the washer/dryer. Great rental for our family getaway."
Chic Pittsfield Home With A View!
Beautiful retreat to the woods to enjoy the winter season.
Aerial view
Beautiful retreat to the woods to enjoy the winter season.
10.0 out of 10, Exceptional, 31 reviews
"Very nice, well stocked and away from the hustle and bustle of city life. We had a great time."
Beautiful retreat to the woods to enjoy the winter season.
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Property grounds
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
8.8 out of 10, Excellent, 3 reviews
"My family and I stayed and so enjoyed our time. The kitchen had everything we could have needed and the location was amazing to explore all neighboring towns. The beds were so comfortable and we even got out to enjoy the fire pit! Would absolutely come back again!"
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
Fridge, oven, stovetop, dishwasher
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
10.0 out of 10, Exceptional, 2 reviews
"The barn was amazing and just perfect for our weekend away. Ricky was really great to communicate with and very responsive. We can’t wait to go again soon!"
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
Private Access To Laurel Lake, Enjoy Lake Life
Property grounds
Private Access To Laurel Lake, Enjoy Lake Life
10.0 out of 10, Exceptional, 6 reviews
"My brother and I came to honor our late father, our family used to own property on Laurel lake so it was especially meaningful to us to have access to it for kayaking. The house has central ac which is harder to find, it's got plenty of bedrooms, two of which are on the first floor."
Private Access To Laurel Lake, Enjoy Lake Life
Private Cabin On Over 12 Acres Of Woods!
Fridge, microwave, oven, stovetop
Private Cabin On Over 12 Acres Of Woods!
9.6 out of 10, Exceptional, 4 reviews
"The property was perfect for our weekend in Becket. The house was very comfortable and the grounds quite beautiful. We enjoyed our visit."
The price is CA $1,055
CA $1,854 total
includes taxes & fees
Jul 6 - Jul 7
Private Cabin On Over 12 Acres Of Woods!
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Game room
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
10.0 out of 10, Exceptional, 107 reviews
"Our party of four adults found ample space to spread out and relax at this property. There are quite a few stairs to access all three stories, including the main living space on the second story and the four bedrooms on the third story. The kitchen is well equipped and there is a charcoal grill (bring your own charcoal). There is a very nice deck overlooking the lovely and sprawling grounds below the house. A fire pit was situated behind the house. There is a balcony and patio also off the...
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Cottage at Copake Lake
Property grounds
Cottage at Copake Lake
9.8 out of 10, Exceptional, 57 reviews
"What an amazing property this was to stay in. Plenty of space but felt cosy. It was cold and snowy when we stayed so couldn’t take advantage of the proximity of the lake, but did get to use the fireplace. Cottage is isolated enough to feel like we were well away from the city but close enough to where we wanted to visit. Close to Bash Bish falls, Rodger’s Book Barn, Coopers Daughter and, of course, the supermarket and Stewart’s. Will definitely book again for our next trip"
Cottage at Copake Lake
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See all available properties in Great Barrington
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.

Other property types in Great Barrington

The Freeman - Newly Renovated 14K SF Estate on 40 Acres
7 bedrooms, iron/ironing board, cribs/infant beds, travel crib
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, 29 reviews
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
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, 8 reviews
"The pictures simply do not do this place justice, it’s an incredible home. Our friend group was cozy all weekend! We loved the hot tub/pool, the really interesting artwork, the driving range mat and basketball hoop. Plenty of towels and kitchen supplies. The in law apartment (which we didn’t use as sadly part of our group was unable to join us) is attached to the main home and is so cute. We had a small issue upon arrival and the hosts were immediately responsive with us troubleshooting and...
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, 39 reviews
"This house was the perfect get away house for out family! The place was clean and the kitchen well stocked! We had wonderful large family dinners and enjoyed heading into town for meals and fun too. We had the best hikes with are wonderful dog that we got to include, it was a very special week. Great location and the most peaceful and amazing views from the deck and the dock. Would stay here again for sure! Thank you for sharing your home."
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
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.

Great Barrington Vacation Homes information

Number of reviews
591
Accommodation
452 Vacation Homes
Lowest Price
CA $218
Highest Price
CA $1,055

Recent Reviews in Great Barrington
Expedia verified reviews

Life House Berkshires

Life House Berkshires

5/5 Excellent
Comfy & Pretty!
"Loved my stay! “Front Desk” Team was so friendly and warm - Bobby, Alex, Chris. Room was clean and comfy and space is really pretty and well-done"
A verified traveller stayed at Life House Berkshires
Posted 3 days ago
Life House Berkshires