
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.

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.

Lovers Honey Pond Treehouse with hot tub & sauna
Guest Favorite VERY romantic abode…The Honey Pond Treehouse is made 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…Enjoy private hot tubbing, sauna time, swimming & hammock time. Skylight was designed for stargazing in bed!! Just minutes to the slopes or enjoy our own groomed trails for Xcountry & snowshoes & nature walks!! High speed WiFi 🐣

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!

Cozy Lakeside Tiny Home, Near Skiing
Hot Breakfast and Lunch INCLUDED every day in your stay. Our general store, located 5 minutes away, will make you fresh egg sandwiches, pastries, and coffee. For lunch, come in and get fresh made subs or our famous brick oven pizza slices. A perfect getaway for couples, friends, or family in every season. Enjoy kayaking, fishing, ice skating and boating on serene Sadawga Lake. It's a quick drive to skiing at Mount Snow, shopping and dining in Wilmington, and direct access to the VAST trail.

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.

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

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!

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.

Private Brook Chalet: Hot Tub, Fire pit, 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 VT has to offer.

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!

Kingsley Grist Mill Waterfall & Private Beach OMG
One of the "World's Most Amazing Vacation Rentals " as seen on the exciting NetFlix series, s.2, ep.7 and on HGTV's "You Live in What?, s.2, ep.1. Join us this season for the romance, the history, the breakfast, the natural mineral spring tap water, the concert, the rafting, the architecture and the legacy of the KGM, Vermont's Wright-esque falling water masterpiece. No cleaning fees added. Come make history with us ! Near Killington & Okemo Mtns.
Popular amenities for Jamaica waterfront rentals
Waterfront apartment rentals

Cozy Brookside Getaway

Downtown River Retreat, Walk to Shops and College

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

Connecticut River Odyssey

49 River Street

Dog heavenly! Private, beautiful and relaxing.

Suite 23 - Spacious Sunny 2-BR with Mountain view

River View apartment
Waterfront house rentals

Stratton Ski House

Top of the World! Jacuzzi! Private Hiking Trails!

Spacious Brattleboro home on river, walk to town

Pinecone Pond 30 min ski Mt Snow, 45 to Stratton

Pristine Magical Retreat Cottage 15 min to Mt Snow

Historic Mill • Near Okemo • Fireplaces • Wi-Fi

Riverside cabin

Vermont lake house near Mt. Snow-fab 360 views!
Other waterfront vacation rentals

Brookside Cottage

Willow Tree Cottage on Peaceful Mountain Lake

Wishing Well Cabin

Rustic Cabin: 8 min to Stratton 10 min to Mt. Snow

Cozy Cottage Loft and Retreat

Brook Haven Retreat - Minutes to Mt Snow&Stratton

Historic Riverfront 3BR Farmhouse, Pet-Friendly

Silver Brook Cabin
When is the best time to visit Jamaica?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ1,172 | ﺩ.ﺇ1,124 | ﺩ.ﺇ1,028 | ﺩ.ﺇ786 | ﺩ.ﺇ881 | ﺩ.ﺇ870 | ﺩ.ﺇ911 | ﺩ.ﺇ852 | ﺩ.ﺇ826 | ﺩ.ﺇ918 | ﺩ.ﺇ889 | ﺩ.ﺇ1,043 |
| 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 |
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 ﺩ.ﺇ624 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!
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- Waterfront rentals Windham County
- Waterfront rentals Vermont
- Waterfront rentals United States
- Okemo Mountain Resort
- Stratton Mountain
- Killington Resort
- Saratoga Race Course
- Pats Peak Ski Area
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Magic Mountain Ski Resort
- Monadnock State Park
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Mount Snow Ski Resort
- West Mountain Ski Resort
- Fox Run Golf Club
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Crotched Mountain Ski and Ride
- Dartmouth College
- Montshire Museum of Science
- Emerald Lake State Park
- Mount Sunapee Resort
- Mount Greylock
- Southern Vermont Arts Center




