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Waterfront vacation rentals in Jamaica

Find and book unique waterfront accommodations on Airbnb

Top-rated waterfront accommodations in Jamaica

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

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Home in Jamaica

4.81 out of 5 average rating, 395 reviews

1850's VT Farmhouse on the River

Step Back in Time at this 1850s Farmhouse with a Private Riverfront Backyard Nestled amidst the breathtaking landscapes of Southern Vermont, this lovingly restored 1850s farmhouse offers a unique blend of rustic charm and modern conveniences. With its original wide pine floors, plaster walls, slate roof, and classical lines, this property embodies the essence of Vermont's architectural heritage. Just 10 mi from Stratton, experience the tranquility of Jamaica State Park and the West River Falls.

Sep. 11 – 18

$548 CAD per night

Guest favourite

Apartment in Wilmington

4.88 out of 5 average rating, 279 reviews

Globetrotter Retreat - Minutes to the Mountain

Newly renovated, fully furnished apt in heart of quaint mountain village; minutes to Mount Snow, Green Mountains & lakes. Year round outdoor activities: snow sports in winter, watersports/hiking in summer. Quiet 1 bedroom apt sleeps 4 people in comfort. Private balcony overlooks rolling river. Steps from many restaurants, bars & shopping. Supermarket is a short walk. FreeMoover bus stop across the street - leave your car parked & ride for free to local destinations! No guest under 18 years old.

Oct. 14 – 21

$187 CAD per night

Home in South Londonderry

4.85 out of 5 average rating, 100 reviews

Lovers Honey Pond Treehouse with hot tub & sauna

This stunning & romantic treehouse was just built and I’m proud to call it finished!!! The Honey Pond Treehouse is made especially for you and yours! It’s constructed of all natural materials, has breathtaking views, and is stocked with absolutely everything you need! The treehouse is lifted up high over a stocked trout pond up in the beautiful birch trees! You will enjoy private hot tubbing, sauna time, relaxing and swimming!! The skylight was custom designed especially for stargazing in bed!!

Nov. 26 – Dec. 3

$640 CAD per night

Guest favourite

Home in Jamaica

5.0 out of 5 average rating, 101 reviews

Stratton Spa House with Man Cave

MANAGED BY A 5 STAR TEAM WITH MULTIPLE 5 STAR HOMES Perched on a babbling brook this 4700 square ft. contemporary has all your needs covered. Smart tech, 3 fireplaces, man cave, streaming entertainment, home theater, spa suite, hot tub, sauna, pool table, darts, poker room, dueling xbox room, giant master suite, big guest suite with wood burning stove, large dining table, fully equipped kitchen, Keurig, screened porch, 3 private acres, sun deck, bbq, 1/4m walk to water falls and swimming hole.

May 7 – 14

$643 CAD per night

Guest favourite

Guesthouse in Springfield

4.86 out of 5 average rating, 321 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.

Nov. 11 – 18

$142 CAD per night

Guest favourite

Apartment in Jamaica

4.98 out of 5 average rating, 108 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!

Oct. 11 – 18

$333 CAD per night

Guest favourite

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.

Mar. 23 – 30

$420 CAD per night

Guest favourite

Cottage in Whitehall

4.99 out of 5 average rating, 161 reviews

Hillside Cottage @ The Mettawee Retreat

The Hillside Cottage is a luxury cabin with views of the Mettawee River. Located on 26 acres on a back road, it is peaceful & private. Enjoy fishing, swimming, kayaking or relax on the deck. This riverside retreat includes a king bed, jacuzzi tub & a kitchenette. Sitting around the fire pit with dinner cooked on the grill is the perfect ending to a long hike. Whether it’s a quick get-away or an extended vacation, the Hillside Cottage is a simple solution from a complicated life.

Oct. 11 – 18

$224 CAD per night

Guest favourite

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.

Nov. 19 – 26

$207 CAD per night

Guest favourite

Tiny homes in Orange

4.92 out of 5 average rating, 310 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.

Dec. 25 – Jan. 1

$240 CAD per night

Guest favourite

Cabin in Newfane

4.93 out of 5 average rating, 189 reviews

Riverrun Cottage

Cozy cabin newly renovated tucked away on the banks of Rock River. Easy access to Mount Snow, Green Mountain National Forest, hiking trails, swimming holes and ponds, and walking distance to the nationally acclaimed Williamsville Eatery. Twenty minutes from Brattleboro where you will find unique shops, art galleries, first-class dining, music, locally brew'd beer and so much more.

Jul. 18 – 25

$307 CAD per night

Guest favourite

Apartment in Newfane

4.97 out of 5 average rating, 406 reviews

Rock River Retreat: Pets Welcome

You are welcome here with fresh air & room to run - your pet, too, when registered as an extra person! Your private guest suite awaits in a 1790's colonial on the Rock River in the quiet village of South Newfane, VT. Note: Recent floods in Vermont have thankfully not affected our home or guest experience. ❤️ PLEASE READ THE ENTIRE DESCRIPTION BELOW re: kitchenette & pet details.

Aug. 3 – 10

$237 CAD per night

Vacation rentals for every style

Get the amount of space that is right for you.

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space that's all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Popular amenities for Jamaica waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment rentals

Guest favourite

Apartment in Wilmington

4.98 out of 5 average rating, 436 reviews

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

May 28 – Jun. 4

$358 CAD per night

Guest favourite

Apartment in Charlemont

5.0 out of 5 average rating, 128 reviews

Suite 23 - Spacious Sunny 2-BR with Mountain view

Jun. 3 – 10

$355 CAD per night

Guest favourite

Apartment in Williamstown

4.96 out of 5 average rating, 255 reviews

2-Bdr Apt In Town, By the Water

Apr. 18 – 25

$326 CAD per night

Apartment in Williamstown

4.86 out of 5 average rating, 198 reviews

Williamstown Apt. on Green River Walk to Williams!

Aug. 25 – Sep. 1

$317 CAD per night

Guest favourite

Apartment in Dover

4.97 out of 5 average rating, 31 reviews

Brookside Hideaway Retreat

Jul. 18 – 25

$201 CAD per night

Guest favourite

Apartment in Brattleboro

4.99 out of 5 average rating, 74 reviews

River View apartment 30 minutes to Mt Snow.

Mar. 19 – 26

$221 CAD per night

Guest favourite

Apartment in Millers Falls

4.96 out of 5 average rating, 28 reviews

Riverfront Unit with fire pit, access to the river

Aug. 7 – 14

$213 CAD per night

Apartment in Dover

4.75 out of 5 average rating, 8 reviews

Updated 2BR ski condo 1.5 miles from Mt Snow

May 12 – 19

$241 CAD per night

Waterfront house rentals

Guest favourite

Home in Grafton

4.97 out of 5 average rating, 130 reviews

Ephriam Bruce House- ON RIVER IN VILLAGE CENTER

Sep. 16 – 23

$547 CAD per night

Guest favourite

Home in Dummerston

4.99 out of 5 average rating, 323 reviews

Pinecone Pond

Nov. 6 – 13

$624 CAD per night

Guest favourite

Home in Manchester

5.0 out of 5 average rating, 101 reviews

The Barn on Main

Aug. 18 – 25

$569 CAD per night

Home in Argyle

4.93 out of 5 average rating, 151 reviews

High Oaks Lodge on Cossayuna Lake

Jun. 17 – 24

$466 CAD per night

Guest favourite

Home in Poultney

4.93 out of 5 average rating, 275 reviews

Waterfront lakehouse with incredible views!

Sep. 19 – 26

$598 CAD per night

Home in Tinmouth

4.82 out of 5 average rating, 114 reviews

Vermont Lakefront Getaway "The Wild Loon"

May 1 – 8

$506 CAD per night

Guest favourite

Home in Grafton

4.92 out of 5 average rating, 59 reviews

Grafton Artist Retreat With Pond Near Skiing

Nov. 20 – 27

$302 CAD per night

Guest favourite

Home in Jamaica

5.0 out of 5 average rating, 16 reviews

Greek Revival Farmhouse with Hot Tub Near Stratton

Jun. 7 – 14

$652 CAD per night

Waterfront condo rentals

Guest favourite

Condo in Manchester

4.88 out of 5 average rating, 104 reviews

Battenkill River Condo Home, South unit

Nov. 15 – 22

$423 CAD per night

Condo in Shelburne Falls

4.88 out of 5 average rating, 33 reviews

Flowers & Falls Spot House

Jun. 5 – 12

$421 CAD per night

Condo in Plymouth

4.64 out of 5 average rating, 70 reviews

Spacious 4BR Lakefront | Deck | Pool

Jun. 25 – Jul. 2

$863 CAD per night

Condo in Ludlow

4.64 out of 5 average rating, 28 reviews

2BR Riverfront 2nd-Floor | Balcony |

Oct. 9 – 16

$363 CAD per night

Quick stats about waterfront rentals in Jamaica

Total rentals
10 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
1.6K reviews
Nightly prices starting at
$165 CAD before taxes and fees

Destinations to explore