House vacation rentals in Pioneer Valley

Find and book unique houses on Airbnb

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Popular amenities for Pioneer Valley house rentals

House rentals with a pool

Guest favorite
Home in Colrain
4.9 out of 5 average rating, 126 reviews

The 1770 House

BrianRating, 5 stars2 months ago
Another great weekend at Ed’s! It was our group’s second time staying here, and we loved it just as much as the first, which is to say—a lot! Ed is very considerate and responsive, and there’s plenty to do for everyone. We are already looking forward to next year!
Superhost
Home in Egremont
5 out of 5 average rating, 4 reviews

Fabulous Heated Pool, Screen Porch, Ping Pong!

AmyRating, 5 stars10 months ago
We had a wonderful family vacation staying at Stone Hill. The house is absolutely perfect, literally a dream house. The pool and landscaping are beautiful and peaceful. The kitchen has everything you could ever need for cooking big meals. We thoroughly enjoyed the basket with s’mores ingredients and the fire pit. The screened-in porch was the perfect spot to enjoy morning coffee and look out at the scenery and pool. The ping-pong table in the basement was fun for the whole family, as well as a great selection of games and cards in the TV room. These came in handy on our 2 rainy days. The owner was super responsive to a few questions we had. It’s the perfect location, only a short drive to Great Barrington and grocery shopping at Guido’s. There’s also a great dog park in GB if you’re traveling with a dog. We hope to come back to Stone Hill many times in the future.
Superhost
Home in Wilmington
4.87 out of 5 average rating, 171 reviews

Adams Farm-"The Little Farmhouse"

Catherine (Lou)Rating, 5 stars2 months ago
We had an amazing stay! The house is lovely and very comfortable, perfect for going skiing at mount snow and cross country skiing and prospect mountain. We were really glad to have picked it. The house is spacious, we all had a lot of room to ourselves, and the kitchen had everything we needed. The farm is gorgeous. Great grocery stores nearby. Sharon was amazing - so helpful when a winter storm threatened to make it hard for us to drive home. She offered us extra time or even another night discounted, which was really generous. She also communicated with friends to help us determine if the road back to NYC had been cleared. We are so grateful for her help! We hope to return in warmer weather to enjoy the farm even more.
Guest favorite
Home in New Lebanon
4.98 out of 5 average rating, 59 reviews

Berkshire Mountain home views, pool, Queechy Lake

GeorgeRating, 5 stars2 months ago
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!
Guest favorite
Home in Keene
4.93 out of 5 average rating, 208 reviews

The Brick House on Washington Street

KennethRating, 5 stars2 months ago
We had a great stay in Keene. Ruth is a fantastic hostess. Her house is just close enough to Main Street to keep it a walkable distance to multiple restaurants and shopping. The house is a nice cozy spot that was big to accommodate my whole family meeting up for a fun winter weekend in Keene. I would stay there again without hesitation
Guest favorite
Home in Richmond
4.96 out of 5 average rating, 27 reviews

Escape to The Berkshires w/Pool by Evergreen Home

JacobRating, 5 stars2 months ago
Our stay at this beautiful home in the Berkshires was nothing short of fantastic! Even in the winter, the house was warm, inviting, and perfectly set up for a relaxing getaway. The wood-burning fireplace in the living room made for the perfect cozy atmosphere, whether we were reading a book, watching a movie on the large TV, or just enjoying the peaceful mountain views. The house was well-insulated and heated, keeping us comfortable even on the coldest nights. The kitchen was modern and fully stocked, making it easy to cook meals instead of going out in the snow. The beds were incredibly comfortable, and the primary bedroom with its own ensuite bathroom was a great touch. The downstairs living area gave us plenty of space to spread out, making it a great option for groups or families.
Guest favorite
Home in Litchfield
4.94 out of 5 average rating, 16 reviews

Iconic Litchfield Home in Town Center

ClareRating, 5 stars5 months ago
The house was beautiful! We loved the charm of the old floors and the cozy farm style. The house was so clean, we all noticed and appreciated the time it must have taken to clean. Thank you for a wonderful stay!
Guest favorite
Home in Williamstown
4.89 out of 5 average rating, 217 reviews

Hollywood Bungalow in the Berkshires #C0191633410

JohnRating, 5 stars2 months ago
We had a great stay at the Hollywood Bungalow. House was described accurately and had so many thoughtful touches to make us feel welcome. Diana met us upon arrival and walked us around the property and the house. Such a great host! She had generously provided snacks, treats and gave a thorough overview for our stay. We were primarily focused on skiing at Jiminy Peak which was a short 20 minute drive. We also brought our 5 year-old rescue who had the best vacation of her life. She was able to use the fenced-in backyard to run around off leash and even meet a new friend when Jackson's dog visited. Diana even shoveled walking paths in the yard throughout our stay so we could get around in the high snow. The Screening Room is awesome and provided hours of entertainment. Quiet street and picturesque location. We will definitely return.

Weekly house rentals

Superhost
Home in Rindge
5 out of 5 average rating, 3 reviews

Secluded lakefront vacation home

ClaudiaRating, 5 stars2 months ago
Beautiful home. Well kept. Hosts super accessible and very friendly. We felt like home and house is super cozy
Top guest favorite
Home in Stockbridge
4.93 out of 5 average rating, 41 reviews

Stockbridge Cape Near Tanglewood!

MarkRating, 5 stars5 months ago
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.
Top guest favorite
Home in Northampton
4.94 out of 5 average rating, 184 reviews

Historic Williams House

KerryRating, 5 stars2 weeks ago
This house is drop dead gorgeous, clean, comfortable, and anything else you could ask for in an Airbnb. They do not supply coffee but they do have a French press and drip coffee machine - the only piece of info I wish I knew before coming. 10/10 experience would love to stay again.
Top guest favorite
Home in Keene
5 out of 5 average rating, 150 reviews

Downtown Hot Tub Escape

SophieRating, 5 stars4 days ago
We loved our stay here! The house was cute & cozy and Rebecca was super responsive to any questions I had.
Guest favorite
Home in Wilmington
4.9 out of 5 average rating, 220 reviews

Wilmington A-Frame- Cozy and Convenient

AveryRating, 5 stars3 weeks ago
This spot is absolutely perfect to be on a quite spot to enjoy nature but still right within walking distance of the center of Wilmington. The cabin itself is beautifully appointed, gorgeous, and super comfortable. Due to rain we ended up spending most of our time inside relaxing and watching movies, and have zero regrets about it. The host was also extremely friendly, helpful and responsive. I'll definitely be coming back again and recommend this for a Wilmington get away weekend!
Guest favorite
Home in Sturbridge
4.96 out of 5 average rating, 168 reviews

Cedar Lake 3 Bed 3 1/2 Bath Home Sturbridge MA

JillRating, 5 stars6 months ago
This was our second time to stay. It had a gorgeous view surrounded by beautiful trees. It was so peaceful and relaxing with everything we needed. James is so easy to work with and very responsive. Highly recommended!
Superhost
Home in Fitzwilliam
5 out of 5 average rating, 7 reviews

Large summer home on Laurel Lake NH

BetsyRating, 5 stars69 months ago
This is a place that gives families the time, simplicity, and space to relax together and reconnect. All of the happiness and love of many generations fills the air. This is a wonderful setting for extended families and friends to gather. There is a lot for everyone to do at the house, the lake, and in the Monadnock region. This is a one of a kind property that is very special today more than ever.
Top guest favorite
Home in Holyoke
4.97 out of 5 average rating, 328 reviews

Explore Holyoke from this charming 3 Bedroom house

VirginiaRating, 5 stars4 days ago
This was a perfect place for us to stay at, the place feels like home. My daughter had so much fun jumping in the backyard and playing around. We had a convening really closed by, and the host was super nice with letting us do our debrief meeting at the house. We super appreciated being able to charge our car over night as well. Great folks!> Thank you.

Private house rentals

Superhost
Home in Stephentown
4.8 out of 5 average rating, 76 reviews

A Magic Spot: Booking year round.

PhilRating, 5 stars6 months ago
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.
Guest favorite
Home in Keene
4.92 out of 5 average rating, 49 reviews

Little House with Lots to Offer

ColleenRating, 5 stars1 month ago
I stayed at the Tiny House with my significant other and our dog for a small, private getaway during our anniversary. It was a nice, cozy little home for us which we all enjoyed. It was also great to be right next to a grocery store and near downtown Keene for food and activities.
Top guest favorite
Home in Brattleboro
4.94 out of 5 average rating, 121 reviews

Spacious Brattleboro home on river, walk to town

DebbieRating, 5 stars2 months ago
Absolutely incredible place! Tons of room, bathrooms for each bedroom was a big hit. Amazing location. Views were magnificent after 8 inches of snow and some freezing rain. Perfect excuse to not leave the house and enjoy the peaceful serenity over a nice margarita. Fall views must be totally awesome. Don’t need to bring anything except you, your friends and some food. The home has everything you need, all set and ready to go, and I mean everything you’ll need. The house manager Teri was an absolute peach. Her connection to the house and knowledge of the local history was amazing. 5 STARS doesn’t do this place justice. Already planning a return visit.
Guest favorite
Home in Monterey
4.97 out of 5 average rating, 34 reviews

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

GallianeRating, 5 stars2 months ago
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.
Guest favorite
Home in Colebrook
4.96 out of 5 average rating, 74 reviews

Log Cabin sleeps 30 bunk style on 350 acres

RomaricRating, 5 stars8 months ago
Beautiful time, we can't wait to come again.
Guest favorite
Home in Otis
4.93 out of 5 average rating, 15 reviews

Spacious Lake Front Home

JeanRating, 5 stars5 months ago
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.
Guest favorite
Home in Woodford
4.91 out of 5 average rating, 34 reviews

Green Mountains Lake Retreat - Hidden Gem

SarahRating, 5 stars1 month ago
Great little house close to trails. Was perfect for our visit to the Mt Prospect Nordic center. The house was very comfortable and we enjoyed the games and books in our downtime. Would recommend a stay here!
Guest favorite
Home in Wilmington
4.89 out of 5 average rating, 27 reviews

Brand new, 5 BR, next to Hermitage Club&Hermt Inn

MargaretRating, 5 stars8 months ago
We loved this house! And plan to come back again soon! Beautiful home with great amenities. Host was very responsive. We had a great visit!

Destinations to explore