Waterfront holiday rentals in Pioneer Valley

Find and book unique waterfront rentals on Airbnb

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Popular amenities for waterfront rentals in Pioneer Valley

Waterfront apartment rentals

Guest favourite
Flat in Wilmington
4.98 out of 5 average rating, 487 reviews

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

SarahRating, 5 stars2 weeks ago
Was the perfect spot to catch our breath after a long drive. Host gifted us with a growler from their market. Was such a treat! Accommodations were super clean and comfortable. The river was gorgeous and it was lovely listening to it while sitting on the deck. We’d love to stay again.
Top guest favourite
Flat in Brattleboro
4.99 out of 5 average rating, 142 reviews

River View apartment

ScottRating, 5 stars6 days ago
Susan's place is exactly as advertised and more. Very comfortable and well-equipped space with nice extras - coffee, tea, snacks, firewood and a grill with grill spatula, etc. Quiet, country setting that is a great value compared to hotels in the area. Would recommend and stay again.
Guest favourite
Flat in East Windsor
4.85 out of 5 average rating, 82 reviews

Modern Cozy Studio

EmilyRating, 5 stars2 weeks ago
The check-in process was so quick and easy! Roger was always quick to respond and ensured I had everything I needed!
Top guest favourite
Flat in Wilmington
4.88 out of 5 average rating, 312 reviews

Globetrotter Retreat - Minutes to the Mountain

JoeRating, 5 stars3 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 favourite
Flat in Newfane
4.97 out of 5 average rating, 456 reviews

Rock River Retreat: VT Oasis Pet Friendly

johnnyRating, 5 stars1 week ago
The place was very nice and the design was well, blend it with the original structure including the floors and complemented with a vintage decor. well, I made the attempt to sound sophisticated, the bottom line is, we had a good time and enjoyed the space very much.
Guest favourite
Flat in Great Barrington
4.95 out of 5 average rating, 76 reviews

King Bed, Wi-Fi, 2m Ski Resort

KirstenRating, 5 stars1 month ago
Lovey room, charming decor, comfortable bed and nice sheets. Great location .
Top guest favourite
Flat in Otis
4.96 out of 5 average rating, 98 reviews

Enjoy every season the Berkshires have to offer.

MicheleRating, 5 stars1 week 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 favourite
Flat 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 favourite
Home in Oakham
5 out of 5 average rating, 167 reviews

Lovely & Peaceful Waterfront Vacation Retreat

RachelRating, 5 stars1 month ago
My family loved this big beautiful house and landscape. The setting is outstanding, with long views down the pond and there are a variety of different ways to enjoy it -- including the lakeside dock, the screened porch, the hammocks, the boats, walking paths, etc. Something for everyone. The house had everything we needed. The architecture felt completely authentic to the place -- beautifully solid wood detailing, extraordinarily wide floorboards, and hand-made furniture. We all wished we could stay longer.
Top guest favourite
Home in Dummerston
4.99 out of 5 average rating, 347 reviews

Pinecone Pond

KathyRating, 5 stars3 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 favourite
Home in Guilford
4.96 out of 5 average rating, 126 reviews

Green River Cottage-A Peaceful Country Retreat

KaylaRating, 5 stars4 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 favourite
Home in Brattleboro
4.93 out of 5 average rating, 215 reviews

Frosted Willows

SafeerRating, 5 stars5 days ago
Perfect place for our family. We’re grateful for the baby proofing and kids toys, and the creek at the back was beautiful. Highly recommend Chelsea’s place!
Guest favourite
Home in Union
4.83 out of 5 average rating, 148 reviews

Antique Home w Private Pond, Sturbridge /Brimfield

JingRating, 5 stars4 days ago
We had a lovely stay, including walks with the pup, through the surrounding quiet, green areas (including the state parks nearby). Dave was quite responsive & welcoming; he is accurate in his description that the home is beside the freeway (the bedroom with the Queen bed is, as described, the quieter of the 3). The yard is large, with various seating areas to enjoy it & the many birds that flit through including egrets & herons. The home is sweet & has everything you might need, we had the relaxing time we needed.
Superhost
Home in Cornwall
4.83 out of 5 average rating, 100 reviews

State Forest Getaway

NicoleRating, 5 stars1 month ago
My girlfriends and I had an amazing stay! The house is stunningly gorgeous—even more beautiful than the photos. Every detail was thoughtfully designed, creating the perfect setting for a relaxing and fun getaway. The space was spotless, well-equipped, and incredibly comfortable. We truly had a great time and felt right at home. Highly recommend for anyone looking for a stylish and memorable escape!
Superhost
Home in Cheshire
4.85 out of 5 average rating, 214 reviews

19th c. Barn in The Berkshires

JohnRating, 5 stars6 months ago
Our party of four adults and two small kids really enjoyed our weekend in this unique and tastefully renovated former barn. The linens, bedding, and towels were all top quality, the kitchen was well equipped, and overall the place was comfortable and spotless. The location is super private and quiet, surrounded by nature and farmland, including an on-site stream and sheep (that's not a typo). A great spot to stay for a visit to the northern Berkshires - Mt. Greylock and Mass MoCA are very nearby. Our visit was on a frigid winter weekend with a ton of snow and outside temps in the 20s, yet our indoor temps were toasty and very comfortable, especially with the wood stove.
Guest favourite
Home in Orange
4.96 out of 5 average rating, 79 reviews

Four Season Cozy Cottage on Lake Mattawa

CricketRating, 5 stars1 month ago
We had a fantastic long weekend on Lake Mattawa. Came to celebrate our son’s graduation from UMass. It was an easy 30 minute drive to campus for graduation. The cottage was a perfect place to hang out as a family…we paddled, fished, played games and cooked. Enjoyed eating on the deck and loved having our morning coffee on the sun porch. Really liked the Quabbin Harvest Coop (awesome local produce and supplies) and had an amazing sandwich at the Corner Cafe. Hope to return!

Waterfront apartment rentals

Superhost
Apartment 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
Apartment in Shelburne Falls
4.9 out of 5 average rating, 49 reviews

Flowers & Falls Spot House

TerriRating, 5 stars3 weeks ago
Always an easy peaceful stay whenever we stay at David’s place. We will be back again
Superhost
Apartment in Lenox
4.8 out of 5 average rating, 10 reviews

Tranquil Lakeside Escape in the Berkshires

GregoryRating, 5 stars1 month 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 favourite
Apartment 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.
Apartment 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.

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