Waterfront vacation rentals in Pioneer Valley

Find and book unique waterfront rentals on Airbnb

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Popular amenities for Pioneer Valley waterfront rentals

Waterfront apartment rentals

Guest favorite
Apartment in Wilmington
4.98 out of 5 average rating, 486 reviews

**Happy Hour! Gorgeous & Modern Downtown Retreat**

SydneyRating, 5 stars3 weeks ago
This place was absolutely awesome!! There’s a lake right down the street, we got in some good fishing over there😁 there’s also a dispensary and liquor store downstairs. Hands down the coolest dispensary I’ve ever been in. Also, love the golden retriever in the liquor store!! The flea market was right down the street as well as a small pink colored coffee shack. They had the best iced lattes and they use espresso cubes for ice! Can’t wait to go back!
Top guest favorite
Apartment in Lanesborough
5 out of 5 average rating, 41 reviews

Cozy Berkshire Waterfront Home

MarkRating, 5 stars4 months ago
Can’t say enough good things about this find near Jiminy Peak in the Berkshires! Stayed for three nights while skiing two days over presidents weekend. Hosts were very thoughtful and flexible. Left cookies and s’mores kit which were a nice touch. During snowstorm steps to the unit and walking areas were kept shoveled and salted. For us and our two teenagers this offered the perfect alternative to pricey on mountain lodging and was only about a 13 minute drive. There was even a bonus game room which could probably serve as a small additional bedroom if someone had the need, it certainly has room for a twin air mattress. Our two kids shared the queen bed with minimal fighting, but that would’ve been our back up plan😂. Anyway, they were super responsive, check in and check out was easy and will certainly look to stay again if we get up there to ski again this year !
Top guest favorite
Apartment in Brattleboro
4.99 out of 5 average rating, 141 reviews

River View apartment

JohnRating, 5 stars4 days ago
If you are in the Brattleboro area, I highly recommend this listing. It was clean, comfortable, and quiet. We were there for just one night, but were very pleased with these accomodations.
Guest favorite
Apartment in East Windsor
4.85 out of 5 average rating, 80 reviews

Modern Cozy Studio

PaulRating, 5 stars2 weeks ago
Pleasant stay in a clean, cozy space. There is a bit of noise from traffic on the nearby road, but not a big issue for us. Would stay here again.
Top guest favorite
Apartment in Wilmington
4.88 out of 5 average rating, 311 reviews

Globetrotter Retreat - Minutes to the Mountain

JoeRating, 5 stars2 weeks ago
We had a great 4 day stay at Nina’s place. The apt is exactly as pictured and described on Airbnb. The space was a nice size, the furniture comfortable with the bed on the softer side, really good Water pressure in the shower, good amount of kitchen ware To create breakfast and lunches and light dinners. We loved the proximity to town and yet how quiet the place was, and there is a river directly in back. Nina was very prompt in responding to questions and gave us great recommendations for hikes in the area. There is a great bookstore and a number of really wonderful gift stores with Vermont artist’s works a block from the apt. And about a mile down the road starfire bakery with truly amazing baked goods. Make it a priority to Go there and try lots of things! We really loved our stay at Nina’s place and hope we can return in the fall or winter.
Top guest favorite
Apartment in Newfane
4.97 out of 5 average rating, 455 reviews

Rock River Retreat: VT Oasis Pet Friendly

Kate-LynnRating, 5 stars1 week ago
It was a wonderful stay. Whether you’re just looking to relax or for a little adventure this stay offers it all. Even though it was a rainy stay they offer plenty of movies, books and games.
Top guest favorite
Apartment in Otis
4.96 out of 5 average rating, 97 reviews

Enjoy every season the Berkshires have to offer.

MicheleRating, 5 stars3 days ago
The space is very clean. I stayed 2 nights and brought my dog with me. The only thing that I was surprised about was that there wasn't a door to the bedroom area. I had looked at the pictures and assumed the door I saw was to the bedroom but it was a closet. The bed area is separated by a partial wall but not an actual door. Something to keep in mind if you have additional people sleeping on the pull out couch.
Guest favorite
Apartment in West Granby
4.9 out of 5 average rating, 131 reviews

Majestic Farmhouse Private & Peaceful Guest Apt.

CindyRating, 5 stars9 months ago
This was a quick trip to the area to break up the drive to a further destination. Joy's little 18thc apartment was perfect. Joy met and explained everything needed, and was very helpful with local suggestions for dining and activities.Was'nt here long enough to experience any of the hiking trails,.etc but truly seems like a place I'd like to return. if you're lucky, you will meet the inimitable Baloo!

Waterfront house rentals

Top guest favorite
Home in Brattleboro
4.94 out of 5 average rating, 123 reviews

Spacious Brattleboro home on river, walk to town

ThomasRating, 5 stars1 month ago
It was perfect for my overflow guests attending a weekend family reunion!
Guest favorite
Home in Becket
4.94 out of 5 average rating, 150 reviews

Lake front retreat - Stylish Berkshire home

ShaiRating, 5 stars2 weeks ago
We had a wonderful time at this beautiful lake house! The home itself is lovely—spacious, comfortable, and perfect for a family getaway. The lake and boats were a big highlight for us, offering plenty of fun and relaxation. Our host was incredibly responsive and helpful throughout our stay. While there were a few small things that needed fixing, she addressed them right away and was very communicative, which we really appreciated. Overall, it was a great experience and a memorable holiday for our family. We’d definitely love to come back!
Top guest favorite
Home in Dummerston
4.99 out of 5 average rating, 347 reviews

Pinecone Pond

KathyRating, 5 stars2 weeks ago
We had the most lovely stay at Pincone Pond. The house is absolutely spotless and well stocked with everything you need in the kitchen, shampoo and condition in the bathrooms and throw blankets for the cool evenings. The house is so homey and comfortable and the grounds are stunning. Beautiful yard and pond which were well cared for. Catherine has thought of everything including chairs for sitting by the pond or fire pit. Just a lovely, peaceful spot.
Top guest favorite
Home in Guilford
4.96 out of 5 average rating, 126 reviews

Green River Cottage-A Peaceful Country Retreat

KaylaRating, 5 stars3 months ago
we will definitely be back here in warmer/fall weather. it was so peaceful and the kids loved it, so did my husband and I. the home was beautiful and I loved the fully stocked spices and bathroom of things you may not think to bring with you on vacation.
Guest favorite
Home in Brattleboro
4.93 out of 5 average rating, 212 reviews

Frosted Willows

TyRating, 5 stars3 days ago
We had a lovely stay, while in town celebrating our friend’s marriage! We really enjoyed the creek in the backyard! We would recommend this wonderful home ☺️
Guest favorite
Home in Becket
4.96 out of 5 average rating, 26 reviews

New Shaw Pond Skytop Retreat in the Berkshires

NancyRating, 5 stars5 months ago
We stayed here on our way to Stowe to break up our long drive with an 8 and 2 year old. It ended up being a wonderful mini trip that we didn't want to leave. The house exceeded our expectations in terms of quality, cleanliness, and amenities. And the location was excellent - about 10 to 12 min to the nearest grocery store and downtown with restaurants, Edith Wharton's estate about 20 min away, and Great Barrington/Stockbridge were easily accessible for day trips. We plan to come back for skiing, and to take advantage of the lake activities in the summer. The only downside was the busy road, as mentioned in the listing, but the traffic quieted down in the evening and it didn't affect our sleep at night with the bedrooms located in the back of the house (husband is a very light sleeper; we did bring and use sound machines just in case).
Guest favorite
Home in Stamford
5 out of 5 average rating, 34 reviews

Comfortable Entire Farmhouse close to North Adams

LisaRating, 5 stars1 week ago
We can’t say enough about the comfort and beauty of this home. Maura communicated with us regularly and provided coffee, tasty treats for breakfast, and snacks! The kitchen is fully stocked and was very helpful for our family to make our own meals. Sleeping on the porch was a joy! . I’m glad we got to briefly meet Maura; if we ever come back to the area, we hope to stay here again!
Guest favorite
Home in Cornwall
4.92 out of 5 average rating, 268 reviews

Secluded modern forest cabin with private brook

ClaraRating, 5 stars3 weeks ago
The charming house is in the most beautiful settings - tall trees with a creek running through. So peaceful! Secluded, but a short drive to cute shops and restaurants.

Waterfront condo rentals

Superhost
Condo in Lenox
4.63 out of 5 average rating, 8 reviews

Peaceful 1BR Condo with Pond View

VeraRating, 5 stars5 months ago
Very nice and clean 1-bedroom apartment with a great view and everything you need for cooking meals. Wonderful location and very kind hosts
Superhost
Condo in Shelburne Falls
4.92 out of 5 average rating, 48 reviews

Flowers & Falls Spot House

TerriRating, 5 stars2 weeks ago
Always an easy peaceful stay whenever we stay at David’s place. We will be back again
Superhost
Condo in Lenox
4.8 out of 5 average rating, 10 reviews

Tranquil Lakeside Escape in the Berkshires

GregoryRating, 5 stars3 weeks ago
Beautiful property. We enjoyed very much the tranquility. There was an issue with the kitchen light but maintenance was going to address it. The exterior of some of the buildings needs to be worked on, but overall the place was great.
Top guest favorite
Condo in Springfield
4.95 out of 5 average rating, 115 reviews

Welcome to Honey Spot!

PernellRating, 5 stars9 months ago
The Honey Spot was breath taking. The lighting through out the entire space along with the art work on the wall gave me an experience that I wasn't expecting. It was fantastic! I took advantage of the top shelf amenities that was provided with this space. Everything was clean and well organized. I had no problems locating anything. I felt safe and all of my needs were accommodated. The media system, and sound system were the highlight of my stay. Bravo Ricardo! My stay exceeded my expectations! Thank you for being a gracious and phenomenal host.
Condo in Harrisville
5 out of 5 average rating, 3 reviews

Private condo w/stunning view of lake frontage

MitchellRating, 5 stars22 months ago
great place. good for family. one criticism: no place to get rid of garbage and recycling. At a minimum there should be instructions as to where to take it.

Destinations to explore