Waterfront vacation rentals in Jamaica

4.81 out of 5 average rating, 405 reviews

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

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.

4.88 out of 5 average rating, 311 reviews

A cozy living area features a dark sofa adorned with colorful throw pillows. Natural light enters through a window, illuminating the space. A coffee table rests in front, complemented by a comfortable side chair and ottoman. Wall décor includes vintage items, enhancing the inviting atmosphere.

Apartment in Wilmington

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.

4.88 out of 5 average rating, 133 reviews

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

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.

4.81 out of 5 average rating, 201 reviews

A small red cabin is nestled under large trees, surrounded by lush greenery and autumn foliage. The backdrop features distant mountains, creating a serene and natural setting. Soft light filters through the leaves, enhancing the peaceful atmosphere of the landscape.

Guesthouse in Manchester

Glamping Cabin with Private Pond and Mountain View

This little glamping cabin with cozy woodstove is set at the far edge of a field overlooking a wildlife pond, seasonal fountain, and mountain. It is a peaceful place, surrounded by beauty, and special not just for these amenities but because it is improbably located on four private acres right in Manchester Center. The property abuts 70 acres of preserved land, but is steps from Main Street and all the shopping, dining, and outdoor options that this lovely year-round tourist town has to offer.

4.97 out of 5 average rating, 128 reviews

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

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, 40 to Magic Mt!

4.94 out of 5 average rating, 173 reviews

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

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

An aerial view captures a cozy cottage situated along the Connecticut River. Lush greenery borders the water, and a small pathway leads to the cottage. A boat glides along the river, highlighting the serene setting surrounded by forests and rolling hills.

4.85 out of 5 average rating, 373 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.

4.98 out of 5 average rating, 121 reviews

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

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!

4.99 out of 5 average rating, 139 reviews

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

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 .

4.97 out of 5 average rating, 116 reviews

A serene view of a stream surrounded by trees that display autumn foliage in warm hues. A deck area with comfortable chairs is visible by the water, providing a peaceful spot for relaxation amidst the natural landscape.

Chalet in Dover

Mountain Chalet: Private Brook - Hot Tub - Firepit

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.

4.99 out of 5 average rating, 135 reviews

An interior view showcases a modern staircase with wooden steps and a metal railing, leading to a second floor. Natural light floods the space through large glass windows, illuminating the wooden walls and a stone fireplace. A green plant adds a touch of nature.

Home in Londonderry

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).

4.99 out of 5 average rating, 277 reviews

The exterior of a renovated log cabin is presented, featuring a red metal roof and a charming porch with steps leading up. The cabin is surrounded by lush greenery, with rolling hills visible in the background under a clear blue sky.

Cabin in Newfane

Log Cabin: Amazing Views, River Frontage, Hot Tub

A sparkling clean, recently renovated log cabin in the woods with beautiful views of river and mountains. Located by the charming villages of Williamsville and Newfane, 12 miles from Mount Snow, and right on the crystal clear Rock River. It's the perfect place for a romantic getaway, a family vacation and quality times with good friends. Now also with outdoor hot tub with views of mountains, river and the wide, open sky above.

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

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

4.93 out of 5 average rating, 46 reviews

The kitchen features warm wood cabinetry and a countertop with bar seating for two. A stainless steel stove and microwave are included, with utensils hanging above the sink. The mosaic tile backsplash adds texture, while natural light filters in through the window.

Apartment in West Dover

Brookside Hideaway Retreat

DavidRating, 5 stars2 months ago

Charming and cozy place with the river right in the terrace area. Magical! The place had everything needed for a comfortable stay. The kitchen well packed! Super clean and organized. 5mins drive to Mt Snow.

4.89 out of 5 average rating, 57 reviews

A well-designed kitchen corridor features wooden cabinetry and stainless steel appliances. Marble flooring guides the view, complemented by a decorative runner. Natural light illuminates the space, highlighting the open layout leading towards a dining area in the distance.

Apartment in Chester

Spacious, Sunny, Second Story 2 Bedroom Apartment

ArunRating, 5 stars3 months ago

Overall A great place. Would def book it again. -Very spacious. We are a fam of 3 and more than enough for us. Easily could fit a fam Of 5. -Clean.

4.98 out of 5 average rating, 484 reviews

A well-lit kitchen and dining area features a wooden dining table surrounded by six chairs. Light hardwood flooring complements the gray cabinetry. A potted plant sits on the table, and modern appliances are visible in the background, including a refrigerator and stove.

Apartment in Wilmington

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

Magdalene ERating, 5 stars1 month ago

This apartment is adorable, clean, well stocked and located right in downtown Wilmington. Walkable to the famous Dot’s restaurant (a must eat at!) and additional restaurants, shops, liquor stores, etc. Jennifer and her husband were so kind and accommodating with a funny / embarrassing misunderstanding on our part! They went above and beyond to ensure we were comfortable and happy. We loved how well stocked the bathrooms were with toiletries that a traveler may have forgotten at home. Happy to stay at any of their properties again anytime!

5 out of 5 average rating, 65 reviews

A cozy seating area is presented, featuring a patterned rug beneath a wooden coffee table. A sofa with light-colored cushions and decorative pillows is accompanied by a lamp providing warm light. A chest of drawers and a framed artwork add character to the inviting space.

Apartment in Wallingford

49 River Street

RaquelRating, 5 stars1 week ago

Immaculate place. Everything you might need! Very charming town. Close to Green Mountain and Appalachian trail hiking. This was our second stay here and we love it. Also, definitely go to Sweet Birch coffee shop while in town. :)

4.95 out of 5 average rating, 309 reviews

An open living space is captured, featuring a comfortable couch, a colorful chair, and a round coffee table. Natural light brightens the room, highlighting a kitchenette area and coordinating furnishings across the suite. High ceilings contribute to an airy atmosphere, creating a welcoming environment.

Apartment in Clarendon

Dog heavenly! Private, beautiful and relaxing.

MarindaRating, 5 stars1 week ago

Our second stay here was great, river was a little higher but we wanted a peaceful weekend with friends and dogs. Apartment was warm given the unseasonable cold weather and we had all the amenities we needed even dog towels for wet pups. Did not see the host during our stay but she was in contact as needed.

4.99 out of 5 average rating, 158 reviews

A modern kitchen features a central island with bar stools, stainless steel appliances, and white cabinetry. Natural light floods the space through a skylight and large windows, highlighting the open layout. A dining area with dark chairs sits adjacent to the kitchen.

Apartment in Charlemont

Suite 23 - Spacious Sunny 2-BR with Mountain view

MichelleRating, 5 stars2 months ago

We had another wonderful weekend at Barbara & Chad's suite. We've stayed there multiple times and love it for our family of four. The hosts are always responsive and so very helpful. We also love the nearby Berkshire East Mountain resort and nearby local towns. Looking forward to our next visit!

Apartment in Shelburne Falls

A cozy living room features a brown leather sofa adorned with patterned cushions. A coffee table with decorative items sits in front of the sofa, while a large window allows natural light to illuminate the space. A potted plant and artwork decorate the room, enhancing its charm.

4.98 out of 5 average rating, 121 reviews

River View Apt in Shelburne Falls Historic Village

JuliaRating, 5 stars3 weeks ago

shelburne Falls is an adorable town, and this Airbnb has a small table with 3 chairs on a back porch that looks out on the river and bridge— very nice . Cute apartment over the the owner’s store and perfect location to walk around town . crystal was a great host…. proactive before our arrival responsive

4.89 out of 5 average rating, 9 reviews

A well-lit bedroom features a spacious bed covered with a floral quilt. Above the bed, a shelf is filled with various books, adding character to the space. Wooden flooring and light-colored walls create a calm environment, while storage provided by a closet and hooks ensures convenience.

Apartment in Londonderry

A Beautiful Secret Den - with a private hot tub!

SeanRating, 5 stars29 months ago

Beautiful location, great host! We loved the hot tub and the proximity to Magic Mountain. We will definitely be back!

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Waterfront house rentals

4.93 out of 5 average rating, 176 reviews

An open-concept living room is presented with large windows offering views of the lake. A red leather chair is positioned next to a wooden table, while a dining table accompanies wooden chairs. Exposed beams and a light fixture enhance the rustic charm of the space.

Home in Argyle

High Oaks Lodge on Cossayuna Lake

MicalaRating, 5 stars1 week ago

Martha’s place is the perfect waterfront property to stay at for a relaxing weekend! The amenities are great and it is a cozy/updated camp with everything you need! It is close to neighbors and situated in a walkable community with friendly people. Great for a summer getaway with family or friends!

4.94 out of 5 average rating, 123 reviews

A spacious deck extends from the house, equipped with an umbrella and several chairs, providing a view of the encompassing greenery and mountains. The home's exterior features warm brown siding and solar panels on the roof, set against a bright blue sky.

Home in Brattleboro

Spacious Brattleboro home on river, walk to town

ThomasRating, 5 stars1 month ago

It was perfect for my overflow guests attending a weekend family reunion!

4.96 out of 5 average rating, 126 reviews

The cottage, constructed with a rustic red facade, is surrounded by vibrant greenery. A metal roof complements the structure, while nearby ferns and trees enhance the natural setting. Windows invite light into the space, showcasing a serene, wooded atmosphere.

Home in Guilford

Green River Cottage-A Peaceful Country Retreat

KaylaRating, 5 stars3 months ago

we will definitely be back here in warmer/fall weather. it was so peaceful and the kids loved it, so did my husband and I. the home was beautiful and I loved the fully stocked spices and bathroom of things you may not think to bring with you on vacation.

4.93 out of 5 average rating, 209 reviews

A dining area is showcased with a round wooden table surrounded by four white chairs. Natural light illuminates the rich hardwood floors, while a wooden cabinet with glass doors adds storage. The kitchen is visible in the background, featuring modern appliances and a warm atmosphere.

Home in Brattleboro

Frosted Willows

RonaldRating, 5 starstoday

The place had great scenery and was comfortable. Weather was horrible throughout the weekend but we managed to have a great time in the home anyway. Chelsea was very responsive and helpful.

5 out of 5 average rating, 49 reviews

The exterior of the cottage is partially obscured by tall, colorful wildflowers swaying in the breeze. Sunlight illuminates the scene, highlighting the serene setting surrounded by greenery and trees, with a clear blue sky in the background.

Home in East Dover

Magical Retreat Cottage - Waterfalls Everywhere

ManpreetRating, 5 stars3 months ago

Gene was the absolute best from before our trip started until the very end! His retreat was beautiful and very well kept with great amenities, looking forward to check it out in the summer!

4.85 out of 5 average rating, 214 reviews

A rustic red barn stands among lush greenery, featuring large glass doors inviting natural light inside. The path leading to the barn is lined with gravel, and a stack of wood is neatly arranged beside the structure.

Home in Cheshire

19th c. Barn in The Berkshires

JohnRating, 5 stars6 months ago

Our party of four adults and two small kids really enjoyed our weekend in this unique and tastefully renovated former barn. The linens, bedding, and towels were all top quality, the kitchen was well equipped, and overall the place was comfortable and spotless. The location is super private and quiet, surrounded by nature and farmland, including an on-site stream and sheep (that's not a typo). A great spot to stay for a visit to the northern Berkshires - Mt. Greylock and Mass MoCA are very nearby. Our visit was on a frigid winter weekend with a ton of snow and outside temps in the 20s, yet our indoor temps were toasty and very comfortable, especially with the wood stove.

4.93 out of 5 average rating, 75 reviews

A charming artist cabin is nestled among lush greenery, showcasing a unique architectural design. The entrance is framed by well-maintained landscaping, including manicured bushes and vibrant flowers. A stone pathway leads to the front door, inviting guests to explore the serene surroundings.

Home in Grafton

Artist Forest Retreat

MiraRating, 5 stars3 months ago

Really lovely cabin with beautiful open design and decor. Reasonable drive to Magic Mountain and the surrounding area for skiing and other winter sport activities, and a great bathtub for your sore muscles afterward. Heat was super effective, hot water didn't run out even with four of us showering back-to-back, kitchen was well-supplied and there's a nice big driveway with plenty of room to park and turn around. There was even a closet full of boardgames; we played a lot of Scrabble. Of note — like much of Vermont, this is on a gravel/dirt road and it would be a bit sketchy to get there without good tires and four wheel drive. It also snowed a couple times while we were there and the stairs up to the house get very icy. So generally, if you're going in winter, be prepared.

4.9 out of 5 average rating, 102 reviews

Home in Whitingham

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

JinsonRating, 5 stars1 week ago

Elizabeth is a very kind and responsive host! Her house and the bedrooms were spacious and clean, surrounded by beautiful nature. It was a great treat to spend a weekend there!

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Waterfront condo rentals

A sandy lakeside beach is framed by vibrant autumn foliage under a bright sun. Two lightweight chairs face the tranquil water, which reflects the surrounding landscape. A wooden dock extends into the lake, inviting leisurely activities and exploration.

Condo in Plymouth

4.62 out of 5 average rating, 73 reviews

Spacious 4BR Lakefront | Deck | Pool

HannahRating, 5 stars3 months ago

Nice house, very comfy

The kitchen features light wood cabinetry and a large granite countertop with bar seating. Black appliances, including a microwave and stove, complement the warm tones of the tongue and groove pine walls. Ample natural light fills the space, enhancing its inviting atmosphere.

Condo in Harrisville

5 out of 5 average rating, 3 reviews

Private condo w/stunning view of lake frontage

MitchellRating, 5 stars21 months ago

great place. good for family. one criticism: no place to get rid of garbage and recycling. At a minimum there should be instructions as to where to take it.

A spacious living area features a large sectional sofa adorned with cozy throw pillows. A wooden coffee table sits in front of a stone fireplace, while a wall-mounted TV is visible. Natural light filters through the windows, creating a bright and inviting atmosphere.

Condo in Ludlow

4.66 out of 5 average rating, 38 reviews

2BR Riverfront 2nd-Floor | Balcony |

ZachRating, 5 stars3 months ago

Great stay if you’re looking for something close to the mountain but still right in town! Walkable to everything on Main Street. The apt was as advertised and easy to access and had everything we needed to enjoy a ski weekend.