
Waterfront vacation rentals in Western Massachusetts
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Western Massachusetts
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.
Woodstock Historic Artist Estate - The Pond House
Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

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

The Red Cabin-Secluded Getaway with backyard Brook
Welcome to our secluded mid-century cabin nestled in the foothills of the Berkshires in Northwestern CT! When you stay here you'll find over three private acres of ferns, forests, wild flowers and a native trout brook a stone's throw from the backdoor with your private hot tub to relax in. Beyond the brook are hundreds of acres of state forest preserve. Enjoy great hiking, fishing, skiing, antiques and restaurants minutes away. Only 2 hours from NYC and 8 minutes to Historic Norfolk Center.

Foliage Lake Views from Hot Tub, Fire Pit & Kayaks
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

Peaceful Mill on the Water - Home Away from Home
Immerse in tranquility at our serene mill retreat in Southern NH. This historic space, adorned with original timber, rustic brickwork, and lofty 11 ft ceilings, offers a spacious 2,650 sq ft sanctuary. Relax in the soaking tub, or savor the calming waterfall views from the deck. Conveniently near downtown, but distant enough for undisturbed peace. Welcome to your soothing retreat for rest and rejuvenation. A remote worker's dream office with high speed connectivity and dedicated workspace.

Rustic Pond Cabin: Nature, Stars & Serenity
Serene rustic cabin in Colebrook, Ct in beautiful Litchfield County! Cozy King bed under skylight, queen downstairs, woodstove and all the comforts of home. Pure clean pond- swim, fish, canoe n kayak! Sits far from main roads on quiet back road. Can walk, run or bike to local trails or stay and walk the trail around the pond, have campfires outside in firepit! Cleaned by me, no crazy rules n and surrounded by nature! Private Great WIFI! Close to quaint ski resorts n dispensaries

Riverfront, Fireplace & Fire Pit -20 min to Hudson
Modern Scandinavia-style riverfront bungalow on 8 acres. Sit on your deck with twinkle lights for coffee/dinner filled w sounds & views of a rushing river; walk across the river into your own private swimming spot! Perfect for a nature retreat, hiking, swimming, fishing (stocked every April), skiing, work w mountain views or write that novel you have always wanted to finish. 2 hrs from the George Washington Bridge. Level 2 EV charger. Hate has no home here-all are welcome.

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.

Twin Lakes Designer A-frame Stone Cottage
*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

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.

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.

Hill-Ross Guest Suite
You'll have the Guest Suite at The Historic Hill-Ross Homestead with private entrance all to yourself. Guest Suite is the renovated carriage house ell off the main farmhouse which houses 2 bedrooms, 1 kitchen, 1 living room and 1 bathroom including your own private patio. One bedroom has a queen bed and second bedroom has a full bed and a single bunk bed. Hill Ross Homestead is a short, 5 minute walk into downtown Florence.
Popular amenities for Western Massachusetts waterfront rentals
Waterfront apartment rentals

Suite 23 - Spacious Sunny 2-BR with Mountain view

Sunny Peaceful Home

Globetrotter Retreat too - Minutes to the Mountain

River View apartment

River View Apt in Shelburne Falls Historic Village

Hudson River Beach House

King Bed, Wi-Fi, 2m Ski Resort

DeMew Townhouse in Historic Kingston
Waterfront house rentals

Upstate Waterfront Saugerties Retreat-Near HITS

Pinecone Pond

Cozy cottage 5 minutes from UConn

Romantic Getaway at The Lake!

Idyllic family retreat - spacious lake home,

Secluded modern forest cabin with private brook

Private Waterfront! Views, Hot Tub, King Bed

Lakefront, view of ski mtn, fireplace, sauna
Waterfront condo rentals

Lake Winnisquam Condo

Flowers & Falls Spot House

Hunter creekside condo with mtn. view

Cozy Vacation Villa 5 minutes from Mohegan

Updated 2nd floor 2BR condo @ Mt Snow / HayStack

King Bed - hot tub - saunas - 1 mile Mohegan Sun

Trailside Tranquility at Hunter Mountain

Perfect Catskills hiking getaway with fireplace
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Mount Pocono Vacation rentals
- The Hamptons Vacation rentals
- Capital District, New York Vacation rentals
- Loft rentals Western Massachusetts
- Aparthotel rentals Western Massachusetts
- Cottage rentals Western Massachusetts
- Farmstay rentals Western Massachusetts
- Vacation home rentals Western Massachusetts
- Rentals with a fireplace Western Massachusetts
- Rentals with a home theater Western Massachusetts
- Apartment rentals Western Massachusetts
- Lakehouse rentals Western Massachusetts
- Luxury rentals Western Massachusetts
- House rentals Western Massachusetts
- Fitness-friendly rentals Western Massachusetts
- Tiny house rentals Western Massachusetts
- Beachfront rentals Western Massachusetts
- Smoking-friendly rentals Western Massachusetts
- Bed and breakfasts Western Massachusetts
- Rentals with a sauna Western Massachusetts
- Rentals with an EV charger Western Massachusetts
- Rentals with lake access Western Massachusetts
- Townhouse rentals Western Massachusetts
- Rentals with a kayak Western Massachusetts
- Rentals with beach access Western Massachusetts
- Rentals with a fire pit Western Massachusetts
- Rentals with pools Western Massachusetts
- Rentals with breakfast Western Massachusetts
- Ski-in/ski-out rentals Western Massachusetts
- Guesthouse rentals Western Massachusetts
- Rentals with a hot tub Western Massachusetts
- Rentals with a washer and dryer Western Massachusetts
- Rentals with an accessible height toilet Western Massachusetts
- Boutique hotels Western Massachusetts
- Family-friendly rentals Western Massachusetts
- Hotel rooms Western Massachusetts
- Rentals with outdoor seating Western Massachusetts
- Condo rentals Western Massachusetts
- Cabin rentals Western Massachusetts
- Chalet rentals Western Massachusetts
- Rentals with a patio Western Massachusetts
- Pet-friendly rentals Western Massachusetts
- Private suite rentals Western Massachusetts
- Waterfront rentals Massachusetts
- Waterfront rentals United States
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Kent Falls State Park
- Catamount Mountain Ski Resort
- Bushnell Park
- Brimfield State Forest
- Taconic State Park
- Norman Rockwell Museum
- Bigelow Hollow State Park
- Wintonbury Hills Golf Course
- Mount Snow Ski Resort
- Mount Sugarloaf State Reservation
- Bright Nights at Forest Park
- Bousquet Mountain Ski Area
- Talcott Mountain State Park
- Hartford Golf Club
- Dinosaur State Park
- Mount Tom State Reservation
- Mohawk Mountain Ski Area
- Beartown State Forest
- Berkshire Botanical Garden




