
House holiday rentals in Jamaica
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Top-rated house rentals in Jamaica
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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!

Lawrence Cottage
Deep in the West River Valley region of Windham County, Lawrence Cottage is in a gorgeous and uncluttered setting upon Windham Hill. If you long for solitude, serenity and beauty, we have the perfect escape for you. We are convenient to all local amenities and activities and an easy drive from Boston or New York. We are near Townshend, Jamaica and Lowell Lake State Parks, Magic Mountain, Mount Snow and Stratton Mountain Resorts. This is Vermont--of course we welcome people of all backgrounds.

Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly
Reilly's Rest is a private home located on its own 6 acres in a prime location to SKI, HIKE, FISH, SWIM, KAYAK, WALK, + RELAX in the Green Mtns! 11/19 New floors-windows-appliances! The home is just 7 miles to Magic, 10-Bromley, 15-Stratton , and under 20 to both Okemo & Manchester. Reilly's Rest provides a peaceful + cozy stay on 6 acres with Mtn. views. Our Vermont contemporary-style home is sure to impress with warm wood interiors and an upstairs with open floor plan and beautiful views!

Summit View Ski and Golf Retreat w/hot tub & Sauna
Summit View Chalet @ Stratton is the ideal VT retreat, Minutes from Manchester, directly across the entrance from Stratton's 27 Hole Championship Golf Course. Beautifully remodeled! Relax in the hot tub on the deck with direct summit views in any season. Enjoy shuttle access to lifts, minutes from snowmobiling, hiking, fine dining and shopping. Comfortable accommodations for 6 adults and 5 children. Perfect for 2 families to enjoy any season in Southern Vermont's beautiful Green Mountains!

Country Colonial Home with rolling fields & stream
This wonderful colonial home offers wide open space on 21 acres of rolling fields with paths leading to the Green River. In the summer build your own dam or in the winter cross country ski along the edges of the stream and get a full view of the West Arlington valley. Swearing Hill is located within a mile of an old country store for all types of immediate supplies. The town of Arlington is 5 miles away, and Manchester, Vt. Is 14 miles, offering golfing, shopping, and wonderful restaurants.

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.

Modern Cabin with Hot Tub & EV Charging Station
Welcome to the Tea House - a retreat in the woods of Vermont. Set on nearly 5 acres, the location is private and peaceful without feeling remote. Just minutes to skiing at Stratton Mountain, Bromley and Magic. A short drive to Manchester with shops and restaurants. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat

Yellow Sweetie at the Base of Stratton
Our adorable home, The Yellow Sweetie, is located in a convenient setting at the base of Stratton Mountain, just 1 minute to the Stratton Resort access road and 8 mins to the slopes. Explore Vermont's many historic towns with classic architecture and covered bridges, as well as its breathtaking mountains, rivers and lakes. The Yellow Sweetie offers stylish country living-meets-shabby chic comfort and coziness. Escape to the fresh Vermont mountain air where life feels a little bit simpler!

Quaint One-Story Vermont House with Mountain View
From our quaint one-story house, you can see a variety of scenery, from the bright changing colors of the leaves in the autumn to the soft piles of snow in the winter. Experience the quiet of the nearby woods, and see roaming animals such as deer or turkey. Make sure to stop at one of the nearby lakes, each of which offers a variety of amenities, and lush scenery. In the winter, keep warm in the cozy living room next to the fireplace, while having a chat with your friends and family.

Vermont Farmhouse •Walk to Village & Hiking Trails
Experience the magic of this restored 1860s Vermont farmhouse, where historic charm meets modern luxury. This 1,700 sq ft retreat offers 2 cozy bedrooms, 2.5 baths, and sun-drenched living spaces. Relax in Adirondack rockers on the expansive deck, explore 280 acres of woodland trails right outside your door, or take a short stroll into the village. Later, gather at the fire pit for s’mores under the stars. Welcome to your quintessential New England escape at The Vermont Farmhouse.

The Equinox Cottage
The Equinox Cottage is a quick 3 minute drive to the Equinox Hotel and the heart of Historic Manchester Village. Enjoy the shops, outlets, restaurants, cafes, golfing, and relaxed summer vibe. The Cottage is also an easy walk to the trails in the Equinox Pond preserve. Enjoy this pristine wilderness oasis, plus hiking up Equinox Mountain and surrounding trail system without having to step into your car. This peaceful, spacious, serene spot is ideal for summer relaxation.

The Gate House--Experience Vermont!
The Gate House is a historic property located at the foothills of Mt Anthony. Built in 1865, the original structure of the house served as the gate house to the Colgate Estate, one of the most beautiful properties in Southwestern Vermont. Our home is just a few short miles to downtown where you can find local restaurants and breweries. We are not far from some of the best skiing/riding in the Northeast at Mt Snow, Bromley, Stratton and Prospect Mountains.
Popular amenities for Jamaica house rentals
House rentals with a pool

Stratton/Mt Snow minutes away! Hot tub + Game room

Magical Farm Getaway - a must visit!

The 1770 House

Adams Farm-"The Little Farmhouse"

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Woodsy Retreat Near Skiing, Private Pool in Summer

Wander In | Close to Mount Snow & Stratton

Hollywood Bungalow in the Berkshires #C0191633410
Weekly house rentals

Charming Vermont Schoolhouse

2-Bedroom Home, 7 Minutes From Stratton Mountain

Mountain Log Cabin near Stratton

In Town Delight

The Old Pine House

Pristine Magical Retreat Cottage 15 min to Mt Snow

Secluded cabin on brook near skiing and lakes

Cozy 3BR Vermont Artistic Retreat w/ Trails
Private house rentals

Charming New England Cape

Idlewoods

Cozy Home in Pownal VT

Mount Snow & Stratton Riverfront Cozy Ski Cottage

Family, Friends, and Fun! Relax on 4 Private Acres

A-Frame w/ Hot Tub | Ski & Board Stratton 10min

Cabin away from it all.

Four Bedroom Home Close to Stratton & Mt. Snow
When is the best time to visit Jamaica?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $870 NZD | $848 NZD | $702 NZD | $546 NZD | $555 NZD | $533 NZD | $478 NZD | $499 NZD | $492 NZD | $529 NZD | $575 NZD | $802 NZD |
| 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 house rentals in Jamaica

Total holiday rentals
Explore 120 holiday rentals in Jamaica

Nightly prices starting at
Jamaica holiday rentals start at $153 NZD per night before taxes and fees

Verified guest reviews
Over 4,540 verified reviews to help you choose

Family-friendly holiday rentals
110 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
120 of Jamaica holiday 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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- Family-friendly rentals Jamaica
- Rentals with a fireplace Jamaica
- Pet-friendly rentals Jamaica
- Chalet rentals Jamaica
- Rentals with a patio Jamaica
- Fitness-friendly rentals Jamaica
- Rentals with a hot tub Jamaica
- Waterfront rentals Jamaica
- Cabin rentals Jamaica
- Rentals with outdoor seating Jamaica
- Rentals with an EV charger Jamaica
- Rentals with a washing machine and dryer Jamaica
- Rentals with a fire pit Jamaica
- Villa rentals Jamaica
- Rentals with pools Jamaica
- House rentals Windham County
- House rentals Vermont
- House rentals United States
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Killington Resort
- Pats Peak Ski Area
- 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
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Crotched Mountain Ski and Ride
- Montshire Museum of Science
- Dartmouth College
- Mount Sunapee Resort
- Emerald Lake State Park
- Mount Greylock
- Southern Vermont Arts Center
- Massachusetts Museum of Contemporary Art




