
Waterfront holiday rentals in Jamaica
Find and book unique waterfront rentals on Airbnb
Quick stats about waterfront rentals in Jamaica

Total holiday rentals
Explore 10 holiday rentals in Jamaica

Nightly prices starting at
Jamaica holiday rentals start at €130 per night before taxes and fees

Verified guest reviews
Over 1,640 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
10 of Jamaica holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Jamaica rentals

4.9 Average rating
Jamaica stays are highly rated by guests – averaging 4.9 out of 5!
Top-rated waterfront rentals in Jamaica
Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

The Grafton Chateau
Welcome to the Grafton Chateau, a gorgeous secluded and private country retreat for all of your family and friends. With six bedrooms and a den, four baths, two fireplaces, a sauna and a large private pond beautifully situated on 67 acres of woodlands, the Grafton Chateau is the perfect comfortable home base for ski trips, hiking, antiquing, or just enjoying the scenery while you sit around the fire pit. The garage has outdoor recreation gear, like snowshoes and sleds. The den has a variety of toys, and games for kids and adults. The whole house, sauna house, barn and all 67 acres are all yours! We are always available by phone, text, or email if you have any questions. Grafton is just about the most charming Vermont town you can find and is convenient to four ski mountains and every other outdoor activity you can imagine.

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.

Vermont Mirror House
Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

Romantic Barn Guesthouse in Village Center
Keep it simple at our peaceful and centrally-located hideaway. This rustic and cozy two-story barn guesthouse with fireplace is located on four acres of a 1768 historic homestead right in Manchester Center. Enjoy the pond and mountain views from the bedroom and living room windows; the guesthouse faces a peaceful meadow and wildlife pond which abuts 70 acres of preserved land with hiking trails, yet it's also just steps from Main Street and all of the dining and shopping of Manchester Village.

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.

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!

Brook House: Hot Tub, Fire Pit, Ping Pong, Mt Snow
The Brook House Vermont is set back in the trees and unbelievably cozy. It's a place to reconnect while listening to the brook. To enjoy big meals, conversations, and games by the fireplace. To bask in the sun or do yoga on the deck, or gaze into dark, starry skies from the hot tub and fire pit at night. There's skiing mins away at Mount Snow, swimming at Harriman Reservoir, as well as hiking, golf, mountain biking, antiquing, breweries, and some of the best food southern VT has to offer!

Brook Haven Retreat - Minutes to Mt Snow&Stratton
Welcome to Brook Haven Retreat! We are situated directly on Wardsboro Brook, just minutes away from the best skiing and riding, hiking, biking, fishing and relaxation in Southern Vermont.The property features a private fenced yard and deck to take in all the beauty alongside the brook. The home is fully updated with modern conveniences including three sleeping areas, living room, and a fully stocked kitchen. We love and allow well-behaved furry friends in our home!

Pet Friendly Silk Purse Cottage on Baker Brook
The "Silk Purse" started life in the 60's as a 10x40 mobile home. Easy vehicle access and fast wifi are great for remote work. 20 minutes to Brattleboro, 30 to Stratton, 25 to Mt. Snow, 40 to Magic Mt. ski areas! 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.

Modern 3-bedroom A-frame in Londonderry w/ Pond
This 1970s A-Frame has been newly renovated and is ready to host guests. This home is located on a 2.6 acre property complete with a swimmable pond , outdoor firepit (snow dependent) and dining al fresco. It's located only a few minutes away from amenities such as Londonderry Market, Pingree Park, Lowell Lake and several restaurants. For skiing, this home is in proximity to Magic (8min), Bromley (9min), Okemo (25 min) and Stratton (20 min). STR License 26-23-185

50 Acres · Fall Foliage · West River Valley Views
Walk out the door onto 50 private acres of Vermont farmland, with a half-mile of West River rolling right through your backyard. In fall, the valley views from every window become something else entirely. Stratton Mountain is near by, just 10 minutes away and your furry friend will love the toasty warm wood stove. A private oasis escape. Prindle Cottage is a 1,400sqft rustic countryside cottage offering captivating views that will impress first-time visitors.

The House of Pi
WE now pay your 15.5% Guest Service fee!!! Welcome to The House of Pi π aka Lakefront Loft. One of a kind custom built 34 foot high raised container home overlooking a beautiful southern VT lake with direct lakefront property with your own private dock and Kayaks. Our spacious home custom designed and built with 8 shipping containers boasts every amenity you want. 3 master bedrooms designed with amazing panoramic views. Hot Tub and Custom Cedar Sauna!
Popular amenities for waterfront rentals in Jamaica
Waterfront apartment rentals

River View apartment

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

Globetrotter Retreat - Minutes to the Mountain

Downtown | Waterfront | Walk to Shops

Cozy Brookside Getaway

A Beautiful Secret Den - with a private hot tub!

Spacious, Sunny, Second Story 2 Bedroom Apartment

On the Water at North Bridge Cove, Patio and Sauna
Waterfront house rentals

Pinecone Pond 30 min ski Mt Snow, 45 to Stratton

Secluded cabin on brook near skiing and lakes

Vermont lake house near Mt. Snow-fab 360 views!

VT Cabin sitting above the West River and Village

Lakefront Home - Ski Okemo, Killington and More!

Gorgeous Vermont Lakefront with epic sunsets!

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

The Barn on Main
Other waterfront holiday rentals

The King's Cottage

Pond Cottage at Consider Bardwell Farm

Bear Creek Cabin

Home with a spring fed Koi pond and mountain view

Elegant & Rustic Cabin - A Peaceful VT Getaway.

~Luxury Tiny Cabin~

Connecticut River-Cozy Cottage

Wishing Well Cabin
When is the best time to visit Jamaica?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €276 | €273 | €234 | €239 | €221 | €238 | €215 | €201 | €195 | €217 | €210 | €246 |
| Avg. temp | -5°C | -4°C | 1°C | 8°C | 14°C | 18°C | 21°C | 20°C | 16°C | 9°C | 4°C | -2°C |
Destinations to explore
- New York Holiday rentals
- Montreal Holiday rentals
- Philadelphia Holiday rentals
- Boston Holiday rentals
- Quebec City Holiday rentals
- Jersey City Holiday rentals
- Portland Holiday rentals
- Newark Holiday rentals
- Mont-Tremblant Holiday rentals
- Atlantic City Holiday rentals
- Salem Holiday rentals
- Providence Holiday rentals
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Monadnock State Park
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Dartmouth College
- West Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Killington Resort
- Mount Monadnock
- Emerald Lake State Park
- Bromley Mountain Ski Resort
- Massachusetts Museum of Contemporary Art
- Mount Sunapee Resort
- Montshire Museum of Science
- Mount Greylock
- Camp Plymouth State Park
- Quechee Gorge
- The Montague Bookmill





