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Compare Vacation Homes in Stockbridge with updated reviews, rates, and availability.

Private Lake House in the Berkshires
Lake Side
Private Lake House in the Berkshires
9.8 out of 10, Exceptional, (15)
"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
Hearts Desire is a furnished whole house in a small, colorful garden center.
Exterior
Hearts Desire is a furnished whole house in a small, colorful garden center.
10.0 out of 10, Exceptional, (66)
"Probably one of the cleanest places I have ever stayed. The house is perfect. Beautiful views!"
Hearts Desire is a furnished whole house in a small, colorful garden center.
Cozy Retreat on Copake Lake in our Charming Home
Front of the house
Cozy Retreat on Copake Lake in our Charming Home
9.6 out of 10, Exceptional, (31)
"My family and I came in for a wedding weekend. The property was clean and spacious. We all really enjoyed"
Cozy Retreat on Copake Lake in our Charming Home
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Peaceful Retreat Compound 10 Minutes to Great Barrington!
Heated pool
Peaceful Retreat Compound 10 Minutes to Great Barrington!
10.0 out of 10, Exceptional, (11)
"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!"
The price is AED 2,204
AED 3,980 total
includes taxes & fees
5 Jun - 6 Jun
Peaceful Retreat Compound 10 Minutes to Great Barrington!
Tranquil 3-BR Waterfront Retreat
HRDSC00175.jpg
Tranquil 3-BR Waterfront Retreat
10.0 out of 10, Exceptional, (7)
"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
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
Amazing Entertainment Space
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
10.0 out of 10, Exceptional, (128)
"Our stay at The Barn in New York was unforgettable. This luxury home, converted from a barn and situated at the end of a back road, is surrounded by 50 acres of picturesque fields and has every amenity. With many restaurants a short drive away and only 20 minutes to Great Barrington, MA, and Hudson, NY, we were never short on dining options and The Prairie Whale was our favorite and also dog friendly. The area offered endless adventures with hiking trails, antique stores, galleries, and outdoor...
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Living area
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.8 out of 10, Exceptional, (7)
"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 AED 584
AED 1,225 total
includes taxes & fees
30 Jun - 1 Jul
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
A pictureque outdoor dining table on the patio makes al fresco meals a breeze.
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
8.8 out of 10, Excellent, (3)
"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!
Waterview Home in the Berkshires: Near Hiking
Sheffield Vacation Rental | 3BR | 2BA | 2,262 Sq Ft | 2 Steps to Enter
Waterview Home in the Berkshires: Near Hiking
9.2 out of 10, Wonderful, (14)
"Lovely house and kind owner. We had a great time. The view is amazing."
Waterview Home in the Berkshires: Near Hiking
Private Cabin On Over 12 Acres Of Woods!
Private Cabin On Over 12 Acres Of Woods!
10.0 out of 10, Exceptional, (3)
"The cabin is cozy and absolutely beautiful. We had everything we needed for a a relaxing stay in The Berkshires. Thanks for the comfort and welcoming hospitality."
Private Cabin On Over 12 Acres Of Woods!
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Beautiful open concept for Entertaining friends and family
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
10.0 out of 10, Exceptional, (105)
"We attended our daughters wedding in Philmont. House was perfect. Views were amazing! Enjoyed morning walks and sitting outside on the deck. Very tranquil!"
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Historic New Lebanon Hideaway on 33 Private Acres!
New Lebanon Vacation Rental | 5BR | 5BA | 3,600 Sq Ft | Stairs Required
Historic New Lebanon Hideaway on 33 Private Acres!
10.0 out of 10, Exceptional, (1)
Historic New Lebanon Hideaway on 33 Private Acres!
Charming historic farmhouse minutes to Great Barrington MA and Salisbury CT
Front view of house
Charming historic farmhouse minutes to Great Barrington MA and Salisbury CT
10.0 out of 10, Exceptional, (3)
"Our family had the pleasure of staying at this home during our child’s graduation from the nearby Berkshire school. It was the perfect situation for us in an idyllic setting very close to the campus. The home is over 250 years old and has been lovingly updated. The kitchen has seemingly all new appliances and gorgeous wood plank countertops with an adjacent windowed sitting area with a large hearth. The old and new are beautifully combined. Our family members spent a lot of time looking at the...
Charming historic farmhouse minutes to Great Barrington MA and Salisbury CT
Berkshire Manor for Lasting Memories
Berkshires Manor
Berkshire Manor for Lasting Memories
10.0 out of 10, Exceptional, (2)
"Leah was a wonderful host to us. She provided easy-to-follow instructions for getting into the house, offered good suggestions on things to do and where to eat. Although the house was a bit larger than we needed, we chose it because of the location, the generous sized and comfortable looking (from photos) casual spaces, the kitchen and the number of bathrooms so we each had our own. This house did not disappoint! It has lots of New England charm, the beds were comfortable, as were the several...
Berkshire Manor for Lasting Memories
Berkshires sanctuary w/ outdoor living area & fire pit. Minutes from Tanglewood!
Exterior
Berkshires sanctuary w/ outdoor living area & fire pit. Minutes from Tanglewood!
The price is AED 1,322
AED 2,808 total
includes taxes & fees
5 Jun - 6 Jun
Berkshires sanctuary w/ outdoor living area & fire pit. Minutes from Tanglewood!
Pristine Home In Becket Woods
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (7)
"My wife and young daughters live in central CT, and the drive to Becket was both scenic and relatively short at around an hour and a half. The property offers great privacy in a remote wooded setting in the heart of the always beautiful Berkshires. We brought our dog along, and we all were able to relax by the fire, read our favorite books, as well as peruse interesting titles on the impressive bookshelf built into the living room wall—a book lover’s delight. We admired the openness and light...
Pristine Home In Becket Woods
Peace and quiet on the lake
Exterior
Peace and quiet on the lake
9.6 out of 10, Exceptional, (184)
"My husband and I had a very peaceful and relaxing long weekend at this lake house! It was very clean and has everything you need. We spent the majority of our time on the wonderful screened-in porch. The location was great and there was a little store/restaurant only a couple minutes walk up the street that was convenient and the food was really good! Overall, a great place to stay!"
Peace and quiet on the lake
Private Estate, Heated YEARROUND Outdoor Pool
Private Estate, Heated YEARROUND Outdoor Pool
10.0 out of 10, Exceptional, (8)
"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
Fox Hollow Luxury Ranch Laurel Lake
Property grounds
Fox Hollow Luxury Ranch Laurel Lake
9.4 out of 10, Exceptional, (12)
"Generous facility, nicely located, accommodating host."
Fox Hollow Luxury Ranch Laurel Lake
The Meadows House @ Otis Ridge w/ 7-person hot tub
7 person Artesian Grand Cayman hot tub with all the bells and whistles.
The Meadows House @ Otis Ridge w/ 7-person hot tub
9.8 out of 10, Exceptional, (20)
"Relaxing get away. Great hot tub, table shuffleboard. 3 floors of comfort."
The Meadows House @ Otis Ridge w/ 7-person hot tub
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See all available properties in Stockbridge
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 Stockbridge

Stockbridge Home, Come Experience The Berkshires!
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (12)
"We have a lovely stay, house is super clean and has all you need to relax and enjoy the space. I loved the fact we could take our small dog with us to make it a lovely family’s vacation. The house is central to everything and all towns in the Berkshires which we appreciated so much. We will return and would recommend to other highly also."
Stockbridge Home, Come Experience The Berkshires!
Rockspring by AvantStay | Huge Berkshires Estate
Welcome!
Rockspring by AvantStay | Huge Berkshires Estate
8.8 out of 10, Excellent, (10)
"We stayed with friends and family and had plenty of room. The separate game room is great! The house was as pictured and described. It is close to a few ski mountains and Great Barrington. We would happily stay at RockSpring or a different AvantStay again!"
Rockspring by AvantStay | Huge Berkshires Estate
Find your Sanctuary at The Rectory at Stockbridge
Exterior
Find your Sanctuary at The Rectory at Stockbridge
10.0 out of 10, Exceptional, (2)
"I stayed here with seven girlfriends, all aged 25-30, for a weekend, and we found it incredibly homey and nice. As a Catholic, it was lovely staying at the rectory, visiting the beautiful altar in the backyard, and knowing that any proceeds from our stay were going to a good cause. All the rooms have saint names, and there is a lot of thoughtful charm throughout. Samantha was very helpful and great at communicating through the entire process. Highly recommend this stay in the heart of...
The price is AED 2,567
AED 4,168 total
includes taxes & fees
20 Jun - 21 Jun
Find your Sanctuary at The Rectory at Stockbridge
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.

Recent reviews of Stockbridge hotels
Expedia verified reviews

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

5/5 Excellent
"This resort is an excellent place for families to relax and spend time together without having to worry about anything, just focus on having fun. The staff were great!"
A verified traveler stayed at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Posted 11 hours ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel