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Waterfront vacation rentals in Jamaica

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Jamaica

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Cabin in Wardsboro

4.87 out of 5 average rating, 104 reviews

Mountain side acres

10 years of love and affection went into building our 2 bedroom custom home. Sticking with natural products to blend together the beauty of the surrounding area. Lay in bed at night and listen to river that runs the entire length of the property. The house has a full kitchen with seating for 6. Spacious living room for relaxing or admiring one of the many birds that visit all year round. Two upstairs bedrooms and office space. Walkout basement with full entertainment area, hot tub,exercise room.

Home in Jamaica

4.94 out of 5 average rating, 169 reviews

Cozy Riverfront Home in beautiful Jamaica

. Surrounded by tall pines and mountains, with the tranquil sound of the West River outside, here you can escape into nature while still enjoying all the cozy comforts of home. Our newly renovated home has been transformed into a getaway spot for romance, friends or family. The deck, set on the waterfront, is a beautiful, serene space to dine or take a soak in our wood burning hot tub. Put on some records, make a meal and cuddle up in front of the fire after a long day of playing outdoors.

Guesthouse in Springfield

4.86 out of 5 average rating, 352 reviews

Connecticut River-Cozy Cottage

This cozy cottage is located on the beautiful Connecticut River, nestled between fertile farmland and Skitchewaug Mountain with views abound. The cottage design utilizes a small footprint while offering functionality and basic comforts, including a small kitchen. Great for all seasons, close to Okemo, Sunapee, Ascutney and other worthy attractions. Hiking and snowshoeing options at your front door. Secrete fishing and swimming holes located on the property. Boat dock available upon request.

Chalet in Jamaica

4.98 out of 5 average rating, 242 reviews

Vermont Chalet

Escape to our cozy A-frame on 3 private acres in Southern Vermont for a peaceful, secluded retreat. Relax to the soothing sounds of the river across the street while unwinding on the covered, enclosed porch. Enjoy a fully stocked kitchen, updated bathroom, strong WiFi, video games and books by a warm wood stove. Explore local towns, ski & board, or wander through our tranquil forest. With an EV charger, local artisan soaps, and warm woodstove, this is the perfect spot for a serene getaway.

Rental unit in Jamaica

4.98 out of 5 average rating, 110 reviews

West Wing at Mantana Meadows on the West River

Welcome to Mantana Meadows! This 1970's contemporary is able to allow large families and friends a great space to enjoy VT. We are centrally located in Vermont within a half hour of five great ski resorts and all of the shopping Manchester has to offer. The grounds are scenic and peaceful, and the back of the house is 25' away from the West River. Great for Spring, Summer, Fall and Winter recreation and relaxation. We've also got a high speed 50 amp 240 Volt outlet for EV charging!

Home in South Londonderry

4.85 out of 5 average rating, 133 reviews

Lovers Honey Pond Treehouse with hot tub & sauna

This VERY NEW and VERY romantic treehouse is finished!!! The Honey Pond Treehouse is made especially for you and yours! It’s constructed of all natural materials, has breathtaking views, and is outfitted with absolutely everything you need! Lifted high over a stocked trout pond way up in the birch trees…You will enjoy private hot tubbing, sauna time, relaxing, swimming & hammock time. Skylight was designed for stargazing in bed!! Just minutes to the slopes…biking & disc golf at Magic Mnt!

Cabin in Newfane

4.98 out of 5 average rating, 258 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.

Tiny home in Chester

4.99 out of 5 average rating, 113 reviews

Bearfoot Cottage: Tiny House w/ Hot Tub near Okemo

Tiny living at its best! Welcome to Bearfoot Cottage, a custom-designed Tiny House escape nestled on 15 acres in Southern Vermont. Enjoy the entire property to yourself with hot tub, Char-Griller BBQ, & Solostove firepit. Hike or snowshoe Ladybug Trail to our babbling brook. Then explore the best of Okemo Valley all at your fingertips! Ski/Snowboarding (+more Winter sports), biking, hiking, fishing, dining, breweries, and live music/nightlife. Your vacation is what you make it!

Cottage in Newfane

4.97 out of 5 average rating, 117 reviews

Silk Purse Cottage on Baker Brook

The "Silk Purse" started life in the 60's as a 10x40 mobile home. Its placement next to Baker Brook offers a private view out of every window and easy vehicle access. The screened porch is a relaxing place to have coffee or cocktails. Extra windows add interior light in this shaded woodland setting, and a beautiful 12x14 addition with a skylight and a full wall of glass give an unobstructed, private view of the stream. 20 minutes to Brattleboro, 30 to Stratton, 25 to Mt. Snow.

Rental unit in Brattleboro

4.98 out of 5 average rating, 121 reviews

River View apartment

Beautiful completely furnished 1 bedroom apartment with a private driveway and deck. It is located along the west river where every summer you can go tubing, swimming, or kayaking. Across the river is a bike/walking path that leads right to the Marina restaurant on Putney Rd in Brattleboro. Bakery/café, Art Gallery and Retreat Farm all close by. A half hour from skiing and 5 min away from snowmobile trails. A gorgeous view of the river and mountain across the street .

Cottage in Orange

4.93 out of 5 average rating, 160 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.

Tiny home in Orange

4.92 out of 5 average rating, 346 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.

Vacation rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Jamaica waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment rentals

Rental unit in Hartland

4.82 out of 5 average rating, 68 reviews

Private Riverside Studio* Upper Valley*Vermont

Rental unit in Chester

4.9 out of 5 average rating, 50 reviews

Spacious, Sunny, Second Story 2 Bedroom Apartment

Rental unit in Wilmington

4.98 out of 5 average rating, 464 reviews

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

Rental unit in Springfield

4.95 out of 5 average rating, 151 reviews

Connecticut River Odyssey

Rental unit in Wallingford

5 out of 5 average rating, 39 reviews

49 River Street

Rental unit in Clarendon

4.95 out of 5 average rating, 289 reviews

Dog heavenly! Private, beautiful and relaxing.

Rental unit in Charlemont

4.99 out of 5 average rating, 144 reviews

Suite 23 - Spacious Sunny 2-BR with Mountain view

Rental unit in Shelburne Falls

4.98 out of 5 average rating, 105 reviews

River View Apt in Shelburne Falls Historic Village

Waterfront house rentals

Home in Plymouth

4.95 out of 5 average rating, 237 reviews

Top of the World! Jacuzzi! Private Hiking Trails!

Home in Dover

4.93 out of 5 average rating, 82 reviews

Cozy Riverfront Home, 1mi to Mt Snow, On Moover

Home in East Dover

5 out of 5 average rating, 38 reviews

Magical Retreat Cottage - Vermont cabin getaway

Home in Jamaica

4.93 out of 5 average rating, 55 reviews

Large Riverfront Home | Minutes to Stratton!

Home in Cheshire

4.86 out of 5 average rating, 212 reviews

19th c. Barn in The Berkshires

Home in Newfane

4.98 out of 5 average rating, 66 reviews

Riverside Farmhouse

Home in Londonderry

4.9 out of 5 average rating, 62 reviews

VT Cabin overlooking the West River and Village

Home in Grafton

4.93 out of 5 average rating, 69 reviews

Artsy Retreat Near Ski Resorts

Quick stats about waterfront rentals in Jamaica

Total rentals
20 properties
Nightly prices starting at
$100 before taxes and fees
Total number of reviews
1.9K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace

Destinations to explore