
Waterfront vacation rentals in Pioneer Valley
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Pioneer Valley
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

Cider House Cottage
Antique guest cottage on a becountry farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub
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Vermont Mirror House
Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!
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Hadley Hay House | No Cleaning fees!
Rest easy in this picturesque, very spacious tranquil home ready for you for a relaxing stay. Minutes from umass, 10min to either Amherst or Noho. Not only will you have access to the hot tub and walk in the hay fields behind the house but we are directly across from the Connecticut River. Perfect spot for swimming or kayaking. Enjoy a beautiful view of the mountains/hay and corn fields from multiple rooms in the house. This space is above an all female wood working shop, happy to give tour!
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Suite 23 - Spacious Sunny 2-BR with Mountain view
Our happy place is a 5 minute walk to Berkshire East/Thunder Mountain . An 8 minute walk to the Deerfield River for guided fishing tours with Hilltown Anglers, kayaks, ,whitewater rafting. 10 minute walk to town and shuttle for tubing. A 5 minute drive to local wedding venues. We provide a full kitchen with all cooking essentials, a private picnic area with charcoal grill (charcoal provided). We reside at the single family home on property and we’re excited to share our Suite 23 !
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AirbytheStream waterfront, private, clean and cozy
Beautiful private camper with outdoor deck on the water. All the creature comforts but half the price. Very private yet 15 minutes to Northampton or Easthampton. Kitchen sink, 2 burner stove, refrigerator, toilet and shower, one queen bed and twin bunk beds, dinette can also turn into a bed. Pots and pans, silverware and cooking utensils are provided. Camper has power and water as well as heat and air conditioning. There is a Blackstone griddle for outdoor cooking.
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Berkshire Treehouse Retreat
Escape, unwind and recharge in this double treehouse. A live tree runs through the interior connecting you directly with nature while in the comfort of home. Built with refurbished, materials and hand curated with care and love. Feel like you’re in the middle of nowhere, yet it’s only minutes to the town of Great Barrington for shopping dining or just a walk around town. Use these dreamy separate spaces for sleeping, writing or drawing in peace. LGBTQ+ owned and operated.
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The Writer's Retreat: A Sweetwater Stay
Located on the shore of Tully Pond, The Writers Retreat is a newly designed 325sqft lake side cottage with breathtaking views of Tully Mountain. This 4-season cottage is built with salvaged barn wood; up-cycled maple floors and custom built furniture and lighting. It's the little sister to The Fishing Cottage. You'll find this intimate home has everything you need to relax, write the next Great American Novel, connect with a lover, or just plain chill.
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The House of Pi
WE now pay your 15.5% Guest Service fee!!! Welcome to The House of Pi π aka Lakefront Loft. One of a kind custom built 34 foot high raised container home overlooking a beautiful southern VT lake with direct lakefront property with your own private dock and Kayaks. Our spacious home custom designed and built with 8 shipping containers boasts every amenity you want. 3 master bedrooms designed with amazing panoramic views. Hot Tub and Custom Cedar Sauna!
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Sunrise on the Water's Edge - Riverside Bungalow
Cozy riverside bungalow celebrates panorama views of the peaceful Connecticut River. Multiple levels of outdoor living space, open-air and screened-in. Just minutes from all major points of interest in the Pioneer Valley - including Six Flags New England, MGM Casino Complex, Big E Fairgrounds, Basketball Hall of Fame, and the Greater Springfield Metro area. Only 20 minutes from Bradley International Airport (BDL) in Windsor Locks.
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Hilltown Cabin Hideaway: A River Runs Through It!
Rediscover peace in the Hilltowns of Western Mass. Charming 3BR cabin in nature, with full kitchen, bath, laundry, TV and Wifi! Relax in a serene, wild and beautiful place. Cook a meal with friends. Take a riverside hike, or explore an Old Growth Forest nearby. Go fishing. Watch fireflies. Jump in a swimming hole. Lie in the meadow. Watch the clouds. Enjoy the Hot Tub for two. *Breath the free air again!*
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Sunny Peaceful Home
This is a home-away-from-home! The space includes a full kitchen, laundry, wireless Internet, a queen-size bed, and more. Located in a safe, quiet, residential neighborhood, there is a river out back for swimming and many books and toys in the apartment if you're traveling with small children. You'll also have a beautiful view of the river from the 2nd-floor back deck!
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Vintage Riverview Cottage
Take it easy at this unique and tranquil getaway. As you experience nature at it’s best. Located on the Connecticut River, wake up each day to breath taking views of the river, accompanied by the chirping of birds. Your experience is only Serenity. Enjoy!!!
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Popular amenities for Pioneer Valley waterfront rentals
Waterfront apartment rentals

Inn at Highland Lake: 1st Fl Suite w/ Dock
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Modern Cozy Studio
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River View Apt in Shelburne Falls Historic Village
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3 BR with Private Balcony & Deck
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Riverside Retreat – Cozy 2-Story Getaway!
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Enjoy every season the Berkshires have to offer.
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Lakeside Getaway
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Riverfront White Beauty Home 2BD
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Waterfront house rentals

Serenity Ashford Lake
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Green River Cottage-A Peaceful Country Retreat
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Lake - King - Gym - Kayak - Fire Pit - Pets Allowed - WD
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Idyllic family retreat - spacious lake home,
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Antique Home w Private Pond, Sturbridge /Brimfield
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19th c. Barn in The Berkshires
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Cedar Lake 3 Bed 3 1/2 Bath Home Sturbridge MA
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Gorgeous Vermont Lakefront with epic sunsets!
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Other waterfront vacation rentals

“Elm” Cozy Pond-side Cabin w/wood stove
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The King's Cottage
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The Lake Cottage: A Sweetwater Stay
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Lake Wyola House Shutesbury Massachusetts
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Hill-Ross Guest Suite
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Cheerful cottage by Little Alum Lake & Sturbridge
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Rustic Pond Cabin: Nature, Stars & Serenity
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Cozy Cottage on Cedar Lake- "Cottage Cheeze"
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- Six Flags New England
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Monadnock State Park
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Taconic State Park
- Bash Bish Falls State Park
- Mohawk Mountain Ski Area
- Bousquet Mountain Ski Area
- Dcu Center
- Mount Monadnock
- University of Massachusetts Amherst
- Clark University
- Naumkeag
- Massachusetts Museum of Contemporary Art
- Norman Rockwell Museum
- Connecticut Convention Center
- Mount Greylock
- Hancock Shaker Village
- Mount Holyoke College
- Berkshire Botanical Garden
- Naismith Memorial Basketball Hall Of Fame
- Kripalu Center for Yoga & Health





