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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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Cottage in Shutesbury

4.93 out of 5 average rating, 199 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 bed room 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 livingroom and master bedroom. Cable and Wifi. Full kitchen, washer & dryer. Sorry no pets.

Apartment in Woodstock Valley

4.93 out of 5 average rating, 340 reviews

“Tranquillity on the Lake ” Woodstock Valley, Ct.

Summer is around the corner. Enjoy the beautiful view from your private lakeside suite. 1,400 sq feet of living space. The sunrises are breathtaking. 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 moon & stars. BBQ propane grill. Enjoy scenic walks around both lakes . Enjoy swimming, a boat ride, bird sightings, nature’s finest. A few dates remain available, welcome !!

Guest suite in Granby

4.9 out of 5 average rating, 121 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.

Cottage in Petersham

4.99 out of 5 average rating, 152 reviews

Cider House Cottage

Antique guest cottage on a country 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.

Cottage in Orange

4.94 out of 5 average rating, 133 reviews

The Lake Cottage: A Sweetwater Stay

Welcome to Mattawa Cove! Originally built as an Ice Fisherman's shack, this tiny house is unapologetically elegant and understated. The private dock can be viewed from the wall of windows in the open living space. Walk to the shore, sit with your feet in the water, swim, fish, or kayak. It’s the ultimate, all-year romantic getaway. With excellent Wi-Fi, you can stay as connected as you'd like to the outside world. 1.5 hours from Boston or Providence. 3.5 hours to NYC.

Cottage in Becket

4.95 out of 5 average rating, 133 reviews

Cozy lakeside cottage

Two-bedroom cottage on the lake with a dock nestled in the woodsy Sherwood Forest Community. Relax with the whole family at our quiet and peaceful oasis. You can swim, fish, kayak, and canoe in the water right from our private beach. Great place for a lakeside campfire at night. Our dock is perfectly situated for practicing yoga, meditation or quiet contemplation. Please note that accessing the house as well as getting down to the dock requires climbing stairs.

Tiny home in Orange

4.93 out of 5 average rating, 302 reviews

The Photographer's Hut: A Sweetwater Stay

The Photographer's Hut is the twin to the Writers Retreat. Fitted with two porches, space for four guests, and decorated with photography memorabilia and antique cameras. A beautiful spot ideal for daydreaming and looking out onto the serenity of the pond. 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.

Apartment in Charlemont

5.0 out of 5 average rating, 128 reviews

Suite 23 - Spacious Sunny 2-BR with Mountain view

Our happy place is a short walk to Berkshire East and the Deerfield River. You’ll love our large yard, the brook, private picnic area, enjoy an outdoor fire. This town awaits fun-filled adventures biking, skiing, leaf peeping, fishing , tubing, whitewater rafting, snowmobiling. We reside at the single family home on property and we’re excited to share our place with you.

Cottage in Sturbridge

4.93 out of 5 average rating, 123 reviews

Cozy Cottage on Cedar Lake- "Cottage Cheeze"

Our petite (648 sq. ft.) lakeside cottage is the perfect place to unwind, relax and explore. Enjoy the spectacular unobstructed views of the sunset from the spacious deck (750 sq. ft.) from the comfort of your easy chair. The location of our cottage provides the tranquility of the lake, close to major routes and you will be minutes away from all that Sturbridge has to offer.

Apartment in Northampton

4.92 out of 5 average rating, 546 reviews

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!

Guesthouse in Williamstown

4.97 out of 5 average rating, 149 reviews

Brookside Cottage

Drift off to the sound of a babbling brook outside the bay window in this cozy country cottage. Minutes from Downtown Williamstown, North Adams and Bennington, VT. We are about 20 minutes away from Jiminy Peak for downhill skiing. The trails behind our house are ideal for snowshoeing, nordic skiing, and snowman building.

Guesthouse in Putney

4.97 out of 5 average rating, 204 reviews

Cozy cottage loft and retreat

Relax and recharge in our peaceful Vermont cottage. Enjoy this sweet getaway with hardwood floors, fast wifi, a fully equipped kitchen, a quiet sleeping loft with a queen size bed, gorgeous natural light, views of surrounding hills and pond, gardens, and your own private entrance and back deck next to the Putney Brook.

Vacation rentals for every style

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Convenient locations with everyday essentials

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Quaint homes, peaceful surroundings

Popular amenities for Pioneer Valley waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment rentals

Apartment in West Granby

4.89 out of 5 average rating, 118 reviews

Majestic Farmhouse Private & Peaceful Guest Apt.

Apartment in Newfane

4.97 out of 5 average rating, 407 reviews

Rock River Retreat: Pets Welcome

Apartment in Wilmington

4.88 out of 5 average rating, 279 reviews

Globetrotter Retreat - Minutes to the Mountain

Apartment in Wilmington

4.98 out of 5 average rating, 438 reviews

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

Apartment in Williamstown

4.96 out of 5 average rating, 303 reviews

New Studio In Town, By the Water

Apartment in Williamstown

4.86 out of 5 average rating, 199 reviews

Williamstown Apt. on Green River Walk to Williams!

Apartment in Millers Falls

4.97 out of 5 average rating, 29 reviews

Riverfront Unit with fire pit, access to the river

Apartment in East Windsor

4.84 out of 5 average rating, 19 reviews

Modern Cozy Studio

Waterfront house rentals

Home in Huntington

4.9 out of 5 average rating, 111 reviews

Private house on the River

Home in Becket

4.93 out of 5 average rating, 118 reviews

Lake front retreat - Stylish Berkshire home

Home in Vernon

4.99 out of 5 average rating, 117 reviews

Luxe Bolton Lake!

Home in Sturbridge

4.94 out of 5 average rating, 214 reviews

Lake Front Home Sleeps 6-8 on a private Peninsula!

Home in Coventry

5.0 out of 5 average rating, 109 reviews

Waterfront 10 min to Uconn outdoor tv gas fire pit

Home in Brimfield

4.94 out of 5 average rating, 139 reviews

Brimfield Lakeside Home Away from Home

Home in Leicester

4.94 out of 5 average rating, 113 reviews

Cozy Lake House

Home in Sturbridge

4.96 out of 5 average rating, 115 reviews

LAKE Retreat! Lakefront Home with Amazing Views!

Destinations to explore