
House vacation rentals in Stockbridge
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Top-rated house rentals in Stockbridge
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Popular amenities for Stockbridge house rentals
House rentals with a pool

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres
Lovely place to stay. Close to Hudson, but far enough to feel secluded.

Berkshire Mountain home views, pool, Queechy Lake
The house was very spacious, the kids ranging from 6-10 loved the games, especially cue ball and fuzz ball. The adults loved the fact there was a lower half where the kids can watch movies and play, while the adults did grown up chatting in the living space. A memorable ski weekend that everyone enjoyed to the fulliest and sad it went so fast. We look forward returning one day in the spring or summer to see a different aspect of the area. Thank you!

The Round House w/ Heated Pool
An amazing location when you want to get slightly off the grid for peace and tranquility. Everything you need to truly slow down, dial out and get peace, quiet and rest. An amazing spot for a weekend getaway. If you want to find yourself amongst serene surroundings and a quiet, private wooded area, this is the place. Just enough modern amenities to be comfortable, but just basic enough to make you slow down. Tanner the host was the most responsive and helpful host of any of the airbnbs we've ever stayed. Truly went above and beyond at every turn to make our stay as comfortable as possible. More than accommodating with every request.

Modern Barn on 12 acres w Sauna, FirePit+swimming
there was lots to do inside the house as well as outside. everything was amazing

Farmhouse and Guesthouse w Pool, Pond and Sauna!
Donna was an amazing host and extremely responsive. The property was beautiful and exactly as described in the listing. The pool, pond, sauna’s made the entire experience feel like a special escape from the city. I highly recommend this property and can’t wait to go back!

10 Acre Country Estate with Pool, Hot Tub & Views!
We loved staying here with our family. It worked out perfectly having our daughter’s family on the one side of the house so if the baby cried it wouldn’t wake anyone up. A pack and play was also provided by Justin so we had a place for the baby downstairs as well. The house was roomy and comfortable for everyone. The hot tub wasn’t working right away but they let us know and had it fixed so we were able to use it during our trip. We would definitely stay here again and try it in warmer weather so we could use the pool as well. Thank you for a wonderful place to stay

Peaceful and Private Setting
I have nothing but wonderful things to say about Teva and his lovely home. The house is spacious, tidy, comfortable, and the surroundings are beautiful and peaceful. The beds were comfortable and everything you would need is there. We skied at Catamount which was ~20 minutes away - super convenient. Finally, and most notable, the overall experience and Teva’s attention to his guests’ experience was outstanding. He promptly and proactively reached out with local recommendations, was accessible during our stay for any questions, and made us feel right at home. We hope to come back over the summer for a little getaway.

Family home in the country
We loved staying at Craig’s house. Very warm and inviting with everything you need. Very quiet and peaceful wooded area which we enjoyed very much at the end of the day.
Weekly house rentals

Modern, cozy log cabin in Copake
Our stay at Julia's home was perfect! We all felt right at home, our grand daughter had lots of books, which she loves and other kids toys. The log cabin was more beautiful than pictured and the claw foot tub in the upstairs suite was the icing on the cake.

Stockbridge Cape Near Tanglewood!
Very nice accommodations in a great location. A vehicle needed to get around to plentiful hiking, shops in nearby towns, and cultural sites. Very nice home for family gatherings and with all necessary amenities.

Hudson New York Grey Victorian
This house was perfect for our girls’ weekend in Hudson! It was spacious, clean, and had so much character. The location was great—just a short 5-minute drive to Warren Street. We didn’t walk due to the cold weather but it was definitely close and convenient. Would definitely stay here again!

Secluded Post-And-Beam Retreat
A lovely house in a private location. Our kids loved the games, watching movies on the projector, and watching deer from the window. The kitchen was well equipped and everything was comfortable.

Rushing Rapids Cottage – a birdwatcher's paradise
We loved staying at Jeffrey and Juan’s quiet home on the rushing Chittenden Creek! Jeff is a communicative, friendly, and accommodating host and would absolutely recommend his place to others. I surprised myself at how much I loved the bird watching (don’t worry, Jeff has binoculars and a book to guide you!). Don’t miss out on the Empire trail for early evening walks! My husband and I stayed at their home for two weeks as we both work remotely and there was plenty of space to spread out and take calls. The plant room in their home is so beautiful that people complimented my ‘digital’ background on zoom! Would absolutely stay again.

Large Secluded Berkshire Home
We thoroughly enjoyed our stay and the accommodations were exactly as stated, comfortable, roomy, very clean and convenient to amenities. The sleeping accommodations were perfect and the beds were comfortable even for older adults and children. The surroundings were incredibly picturesque, beautiful yard for outdoor activities and lovely mountainous views. The host was very accommodating to our needs and for that we are very thankful. We would definitely stay again.

Hudson BoHo
Our group of 3 felt right at home! Nice decorator touches - Dash and Albert linens and rugs & lovely soaps added a luxurious feel. We were too busy exploring Hudson to miss the TV, but if that’s important to you, take note. Hosts were super responsive. We can’t wait to return!

Modern and spacious Berkshires 5bdr retreat.
Wonderful accommodations—homey and beautifully furnished. We especially enjoyed the well stocked kitchen as our family loves to cook! Very responsive hosts. They even had a Christmas tree for our young grandchildren! Great for all ages!
Private house rentals

A Magic Spot: Booking year round.
the airbnb is very homey, well stocked, and easy to navigate. we had one slight issue with a mess that was not found by the cleaning crew, but robert was friendly and shared our concern about this.

The Berkshires Mountain Terrace LUX Home Sleeps 7
This was a beautiful and well kept home and was a delight to stay in. Natalia was also a lovely and communicative host. We had no issues and would happily stay there again.

Airy 5Br-2Ba,Kids Rm, 6TVs,Pvt Fence-yard&Parking!
Rashawn's place was great! Near downtown Albany, and plenty of sleeping space. Great for any size groups.

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary
This was our second time staying at the Hupi House and loved it. House is perfect for 2 families with kids, super comfortable, spacious and cosy, well equipped and lots of things to do in the area. This time we went skiing at the Butternut resort just 10 mins away and was a great experience. Lucas a very friendly and responsive host.

Log Cabin sleeps 30 bunk style on 350 acres
Beautiful time, we can't wait to come again.

Spacious Lake Front Home
Beautiful location in Otis, right on the lake and so peaceful. The house is very spacious and easily accommodated our family ( 7 adults and 2 children). All the windows in the house provided great views of the lake, especially from the deck. Our host Nick was very responsive when we had questions or any concerns. Would be nice to come for a stay during the summer.

Peaceful Berkshire Getaway (A/C, Lake Access)
Becky’s house was exactly as listed with plenty of space to relax and enjoy the area. Her gardens are beautiful and the house is convenient to the Berkshires without the stress of the downtown areas. We are extremely appreciative of all that was provided!

Cheerful Home with Stunning Views
This was a great location with wonderful views. The home was clean and well stocked and the photos do not do the views justice. We enjoyed the fire place and there was plenty of supplied wood. The grounds were great to explore for us and our dog. The team was very proactive cleaning the driveway of snow and ice. It was a very relaxing and enjoyable time.
Quick stats about house rentals in Stockbridge
Total rentals
70 properties
Nightly prices starting at
$100 before taxes and fees
Total number of reviews
2.7K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
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- Jiminy Peak Mountain Resort
- Windham Mountain
- Catamount Mountain Ski Resort
- Albany Center Gallery
- Berkshire East Mountain Resort
- Six Flags New England
- Taconic State Park
- Zoom Flume
- Mohawk Mountain Ski Area
- Bushnell Park
- Mount Sugarloaf State Reservation
- Opus 40
- John Boyd Thacher State Park
- Mount Greylock Ski Club
- Hartford Golf Club
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Bash Bish Falls State Park
- Beartown State Forest
- Otis Ridge
- Norman Rockwell Museum
- Naumkeag
- Bright Nights at Forest Park
- Rockledge Golf Club
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