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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, 197 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.

Apr 10 – 17

G$71,708 GYD per night

Cottage in Petersham

4.99 out of 5 average rating, 151 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.

Jan 20 – 27

G$28,951 GYD per night

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.

Feb 4 – 11

G$22,601 GYD per night

Apartment in Woodstock Valley

4.93 out of 5 average rating, 339 reviews

“Tranquillity on the Lake ” Woodstock Valley, Ct.

UCONN Graduations coming soon, celebrate, relax. Enjoy the beautiful view from your private lakeside suite. 1,400 sq feet of living space. Featuring Queen bed in Master. Queen sofa in living area. Cozy indoor propane fireplace. Kitchen stove, full refrigerator, microwave. Enjoy private deck, propane fire pit, gaze at the moon & stars. Cook-Propane grill. Enjoy scenic walks around the lakes. Wake up to amazing sunrises. Pretty flowers, trees surrounding!! Now open-Woodstock Valley Country Store

Dec 16 – 23

G$32,892 GYD per night

Loft in Peterborough

5.0 out of 5 average rating, 100 reviews

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.

Jun 20 – 27

G$51,772 GYD per night

Cabin in Newfane

4.98 out of 5 average rating, 239 reviews

Log Cabin: Amazing Views, River Frontage, Hot Tub

Come stay in our sparkling clean, renovated log cabin in the woods with beautiful views of river, mountains and stars. Located by the charming village of Williamsville, close to historic Newfane village, 12 miles from Mount Snow for skiing, and right on the refreshingly cool and clear Rock River. It's the perfect place for a romantic getaway, a family vacation or quality times with dear friends. Recent addition: outdoor hot tub with views of mountains, river and open sky above.

Apr 22 – 29

G$54,141 GYD per night

Cottage in Orange

4.94 out of 5 average rating, 132 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.

Dec 15 – 22

G$25,126 GYD per night

Tiny home in Orange

4.92 out of 5 average rating, 311 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.

Mar 21 – 28

G$28,840 GYD per night

Guest suite in Agawam

4.95 out of 5 average rating, 155 reviews

The Waters Edge

Contemporary home located on the scenic Ct River. Centrally located between Bstn & Htfd. Within 2 miles of Six Flags, 15 min from Basketball or Volleyball Hall of Fame, MGM Casino, Eastern States Exposition, Downtown Spfld & Bradley Intnl Airport. Adjacent CT River is home to beautiful wildlife. Protected lands provide a stunning backdrop to picturesque views guests love! Rest's, museums, hiking, shopping & much more nearby. NO SMOKING ON PROPERTY.

Oct 5 – 12

G$26,380 GYD per night

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.

Sep 23 – 30

G$46,910 GYD per night

Cottage in Sturbridge

4.93 out of 5 average rating, 122 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.

Jun 5 – 12

G$52,561 GYD per night

Apartment in Northampton

4.92 out of 5 average rating, 542 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!

Jun 16 – 21

G$26,469 GYD per night

Vacation rentals for every style

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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, 116 reviews

Majestic Farmhouse Private & Peaceful Guest Apt.

Dec 16 – 23

G$29,641 GYD per night

Apartment in Newfane

4.97 out of 5 average rating, 406 reviews

Rock River Retreat: Pets Welcome

Oct 27 – Nov 3

G$29,082 GYD per night

Apartment in Wilmington

4.88 out of 5 average rating, 279 reviews

Globetrotter Retreat - Minutes to the Mountain

Oct 18 – 25

G$23,418 GYD per night

Apartment in Williamstown

4.96 out of 5 average rating, 300 reviews

New Studio In Town, By the Water

Apr 1 – 8

G$37,858 GYD per night

Apartment in Wilmington

4.98 out of 5 average rating, 438 reviews

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

Sep 8 – 15

G$46,801 GYD per night

Apartment in Williamstown

4.86 out of 5 average rating, 198 reviews

Williamstown Apt. on Green River Walk to Williams!

Nov 19 – 26

G$39,488 GYD per night

Apartment in Millers Falls

4.97 out of 5 average rating, 29 reviews

Riverfront Unit with fire pit, access to the river

Oct 11 – 18

G$25,599 GYD per night

Apartment in South Hadley

4.92 out of 5 average rating, 37 reviews

River front property

Mar 31 – Apr 7

G$67,722 GYD per night

Waterfront house rentals

Home in Huntington

4.9 out of 5 average rating, 109 reviews

Private house on the River

Mar 22 – 29

G$39,459 GYD per night

Home in Winchendon

4.8 out of 5 average rating, 144 reviews

Waterfront home 2 bedrooms withdeck beach and dock

Sep 27 – Oct 4

G$31,003 GYD per night

Home in Cornwall

4.92 out of 5 average rating, 229 reviews

Secluded modern forest cabin with private brook

Jan 21 – 28

G$47,656 GYD per night

Home in Sturbridge

4.94 out of 5 average rating, 213 reviews

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

Nov 6 – 13

G$69,411 GYD per night

Home in Becket

4.93 out of 5 average rating, 118 reviews

Lake front retreat - Stylish Berkshire home

Sep 12 – 19

G$119,785 GYD per night

Home in Vernon

4.99 out of 5 average rating, 115 reviews

Luxe Bolton Lake!

Jan 21 – 28

G$105,820 GYD per night

Home in Sturbridge

4.96 out of 5 average rating, 115 reviews

LAKE Retreat! Lakefront Home with Amazing Views!

Oct 7 – 14

G$144,119 GYD per night

Home in Sturbridge

4.95 out of 5 average rating, 154 reviews

Sturbridge MA 3 BR 2 1/2 Bath Home on Cedar Lake

Oct 22 – 29

G$73,456 GYD per night

Destinations to explore