Waterfront vacation rentals in Jamaica

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Top-rated waterfront rentals in Jamaica

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

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Guest favorite
A charming red farmhouse exterior is framed by lush green trees, displaying a welcoming entrance with a simple front door and steps leading up. Large windows allow light to flood into the interior, inviting guests to explore within.
Home in Jamaica
4.81 out of 5 average rating, 415 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.

Guest favorite
The custom home features warm wood siding and a welcoming porch with flower boxes. A spacious deck with rustic railings extends from the second floor, while a covered area includes seating. Surrounding greenery enhances the natural setting, creating a serene outdoor ambiance.
Cabin in Wardsboro
4.85 out of 5 average rating, 164 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.

Guest favorite
A cozy bedroom features a metal bed frame adorned with a colorful quilt. Soft pillows are arranged at the head of the bed, and a bedside lamp provides gentle illumination. An angled ceiling creates an intimate atmosphere, complemented by a framed landscape picture on the wall.
Guesthouse in Manchester
4.75 out of 5 average rating, 287 reviews

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.

Guest favorite
A cozy cabin is presented, featuring a wraparound deck and surrounded by lush greenery. Trees with autumn foliage add splashes of color to the landscape. The structure is elevated, inviting guests to enjoy the view from the deck.
Home in Dover
4.93 out of 5 average rating, 101 reviews

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

The Riverhouse at Mount Snow is 1 mile from the mountain (2 min car ride) or take the FREE MOOver. NEW AC. This cozy cabin has open main floor plan and sleeps 6 comfortably with 3 bedrooms, 2 baths, den, living room with wood fireplace. Washer/dryer, gametable, yard games, gas grill, deck overlooking a river with a swimming hole, private firepit area, privacy fence. Easy in/out right off Rt 100 - Walk to restaurants/brewery. Mt. Views from the front porch/yard. 15 Mins from Lake Whittingham.

Guest favorite
The image captures a view from a wooden deck illuminated by string lights. A cozy seating area features an Adirondack chair and a gas fire pit, with the West River flowing nearby, reflecting the soft light of dusk.
Home in Jamaica
4.94 out of 5 average rating, 186 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.

Top guest favorite
A winter landscape is depicted, showing a house surrounded by snow-covered trees. Steps lead down from the house towards the water, which is also blanketed in snow. The warm glow of the house's lights contrasts with the cool white surroundings.
Cabin in Poultney
4.93 out of 5 average rating, 368 reviews

Waterfront Vermont Lake House w/ Panoramic Sauna

We invite you to come stay and experience all of the beauty that Vermont has to offer at Lake St. Catherine. Located on the west side of the lake off a quiet private drive with almost 100ft of lake frontage, there are few spots with a better view. Watch the sun rise each morning from either our private decks. Explore the lake by canoe or kayak; both available for our guests. If the dates you're looking for are booked, message us for availability at our second location! Follow us @vtlakehouse

Top guest favorite
A comfortable living area features a dark leather sofa with two accent pillows and a coffee table atop a patterned rug. A dining table with four chairs is positioned nearby, and natural light enters through a window dressed with light curtains. Wall decor includes vintage skis and decorative deer antlers.
Apartment in Wilmington
4.92 out of 5 average rating, 148 reviews

Globetrotter Retreat too - Minutes to the Mountain

Newly renovated, fully furnished 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 on 2nd floor sleeps 4 people in comfort. Private balcony overlooks tranquil woods & rolling river. Steps to restaurants, bars & shopping. Supermarket is a short walk. Free Moover bus stop across the street ride for free to local destinations! 18 years or older guests only.

Top guest favorite
Aerial view of a contemporary wooden house surrounded by trees, highlighting two main sections with large windows. A patio area is visible with outdoor seating, and a clear path of steps leads to the entrance, blending seamlessly with the natural landscape.
Apartment in Jamaica
4.98 out of 5 average rating, 128 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!

Guest favorite
The image captures the West River, with its clear waters gently flowing over smooth stones. Lush greenery borders the riverbank, while a bright blue sky and scattered clouds create a serene backdrop. Sunlight glimmers on the water, enhancing the tranquil natural setting.
Cottage in Jamaica
4.87 out of 5 average rating, 113 reviews

50 Acres of solitude & 1/2 mile on the West River

A private oasis escape. Prindle Cottage is a 1,400sqft rustic countryside cottage nestled on 50 acres of historic farmland, offering captivating views that will impress first-time visitors. Cozy up by the fireplace with your furry friend, soak up the warmth in the sunroom, or explore the many trails along the West River. There are stunning long-range valley views that overlook the pastures, this pet-friendly cottage is the ideal retreat for both intimate getaways and grand gatherings.

Top guest favorite
Two white lounge chairs are positioned around a small black fire pit in a grassy area. Lush greenery and trees define the backdrop, while an open space creates a sense of privacy and tranquility.
Apartment in Brattleboro
4.99 out of 5 average rating, 172 reviews

River View apartment

Beautiful completely furnished 1 bedroom apartment with a private driveway and deck. Less than a half hour from skiing and 5 min away from snowmobile trails. 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 gorgeous view of the river and mountain across the street .

Top guest favorite
Chalet in Dover
4.97 out of 5 average rating, 145 reviews

Private Brook Chalet: Hot Tub - Fire pit - Ski

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 VT has to offer.

Top guest favorite
A spacious bedroom features a skylight that allows natural light to fill the space. A bed is adorned with a colorful floral quilt, while a cozy armchair and table create a relaxing sitting area by glass doors that offer a view of the surrounding greenery.
Cottage in Newfane
4.97 out of 5 average rating, 145 reviews

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.

Popular amenities for Jamaica waterfront rentals

When is the best time to visit Jamaica?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$66,633 GYDG$63,918 GYDG$58,487 GYDG$44,701 GYDG$50,132 GYDG$49,505 GYDG$51,803 GYDG$48,460 GYDG$46,998 GYDG$53,265 GYDG$57,860 GYDG$58,905 GYD
Avg. temp-5°C-4°C1°C8°C14°C18°C21°C20°C16°C9°C4°C-2°C

Quick stats about waterfront rentals in Jamaica

  • Total vacation rentals

    Explore 20 vacation rentals in Jamaica

  • Nightly prices starting at

    Jamaica vacation rentals start at G$35,510 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,810 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Jamaica vacation rentals include wi-fi 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!

Destinations to explore

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