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.

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Top guest favorite

Cottage in Petersham

4.98 out of 5 average rating, 199 reviews

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

Guest favorite

Cottage in Becket

4.94 out of 5 average rating, 213 reviews

The Yellow • 1,750ft² (170m²), 2-level cottage • Open concept with 180° view from living room • 3 bedrooms (all queen size beds), 2 full baths • Fully equipped kitchen • Private dock & firepit • Canoe & 2 kayaks • 50" smart TV and 4 Google Smart Speakers • 1 Gigabit Wi-Fi 'gorgeous with amazing views' • Workspace with laptop stand upstairs • Additional full size bed upstairs • Additional queen size sofa bed downstairs • Additional twin trundle downstairs • Washer and dryer with laundry detergent

Guest favorite

Guest suite in Granby

4.91 out of 5 average rating, 147 reviews

Whole place,staycation,3 bedrooms, spacious area

ENTIRE LIVING SPACE: Private spacious 3 bedroom lower level. Near MacDuffie Prep School & 5 prestigious colleges. Couples, solo adventurers, business travelers, families (with kids), and big groups. 14 acre. Private-golf course, pickleball, polypropylene basketball court, badminton, fishing, frisbee golf and tennis courts close by. Nature surrounds you with quiet locations to relax. 1 acre beach pond to cool off. If you are the person who likes to stay busy or relax, this is the place for you.

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Cottage in Shutesbury

4.92 out of 5 average rating, 221 reviews

Lake Wyola House Shutesbury Massachusetts

Bright, airy recently remodeled three Bedroom lakefront home on Lake Wyola. Most rooms have a Lake View. Beds and bedding are new, each bedroom has a ceiling fan. A super place to make awesome memories. Perfect for a family vacation or romantic getaway. (6 people, two cars max) Close to local colleges, Amherst, Northampton and many attractions. Comfortable and relaxing. Big Screen TVs in the living room and master bedroom. Cable and Wifi. Full kitchen, washer & dryer. Sorry no pets.

Guest favorite

Apartment in Woodstock Valley

4.93 out of 5 average rating, 402 reviews

“Tranquillity on the Lake ” Woodstock Valley, CT.

Summer is here !! Enjoy fun relaxing water activities on beautiful Lake Bungee. Enjoy direct waterfront sunrises , 1400 sq ft. Queen bed in Master. Queen sofa in living area. Cozy indoor propane fireplace. Kitchen stove, full refrigerator, microwave. Enjoy your own deck, propane fire pit, gaze at the stars. BBQ propane grill. Stroll around both lakes, see bird sightings,nature’s at its finest. Great local dining & wineries. Each season paints its own stunning beauty. Relax and enjoy Tranquility

Top guest favorite

Cottage in Southwick

4.98 out of 5 average rating, 110 reviews

Lake View, Hot Tub, 4 Kayaks, Central AC, Fire Pit

Congamond House is the perfect lake home getaway. Kayak the calm North Pond. Get your breathtaking pics of the surrounding wildlife. Cuddle up on the deck and enjoy the stars or relax in the hot tub under the deck while gazing upon the lake. This 1500 sq ft cottage is the perfect size for 2 families. (4 adults w/4 kids or 6 adults) Minutes from Six Flags Amusement Park, the Big E and the Basketball Hall of Fame 4 Kayaks that seat 6. Paddles and life vests provided 20 min. from Bradley Airport

Top guest favorite

Apartment in Charlemont

4.99 out of 5 average rating, 158 reviews

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 !

Guest favorite

Camper/RV in Westhampton

4.89 out of 5 average rating, 173 reviews

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.

Guest favorite

Cabin in Guilford

4.95 out of 5 average rating, 169 reviews

Silver Brook Cabin

Waterfront setting in a relaxing, but convenient, location in southeastern Vermont. Photos and captions do the best job of describing our cabin, adjacent brook, and very nearby Green River with its covered bridge and swimming holes. The cabin is 20 minutes from Brattleboro with its many restaurants, shops, movie theater, and galleries. Not only is the immediate area wonderful for swimming, biking, and hiking, you can also simply relax with a good book or two.

Guest favorite

Tiny home in Orange

4.92 out of 5 average rating, 384 reviews

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.

Top guest favorite

Home in Agawam

4.98 out of 5 average rating, 175 reviews

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.

Guest favorite

Cabin in Newfane

4.99 out of 5 average rating, 277 reviews

Log Cabin: Amazing Views, River Frontage, Hot Tub

A sparkling clean, recently renovated log cabin in the woods with beautiful views of river and mountains. Located by the charming villages of Williamsville and Newfane, 12 miles from Mount Snow, and right on the crystal clear Rock River. It's the perfect place for a romantic getaway, a family vacation and quality times with good friends. Now also with outdoor hot tub with views of mountains, river and the wide, open sky above.