Jamaica Vacation Rentals

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Make Jamaica your next getaway

While its name evokes a tropical island setting, in this case, it couldn’t be further from the truth for the town of Jamaica, Vermont. Meaning “beaver” in the Algonquin native language from which it was named, this quaint Southern Vermont hamlet doesn’t offer any palm trees or sandy shores, but what it does offer is no less compelling: an all-seasons destination far from crowds but close to limitless outdoor recreation in the Green Mountains.

Explore Jamaica house rentals, condo rentals, cabins, and more


House rentals

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Condo rentals

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Jamaica vacation rentals for every getaway

Dog-friendly Hot tub Internet
Potter's Place
2 Bedroom | 1 Bath | Sleeps 4

Potter's Place - Jamaica, VT

$165 avg / night
A Very Vermont Vacation
2 Bedroom | 2 Bath | Sleeps 6

A Very Vermont Vacation - Jamaica, VT

$154 avg / night
Birchside Cabin in the Woods
4 Bedroom | 2 Bath | Sleeps 8

Birchside Cabin in the Woods - Jamaica, VT

$240 avg / night
Under the Willow
2 Bedroom | 1 Bath | Sleeps 6

Under the Willow - Jamaica, VT

$276 avg / night
Sweet Berry Farm
6 Bedroom | 4.5 Bath | Sleeps 11

Sweet Berry Farm - Jamaica, VT

$781 avg / night

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Recent Jamaica vacation rental reviews

Great property near stratton mountain. excellent for a weekend getaway
Rebecca S. | Apr 2024
The house was very clean.
Carla R. | Mar 2024
Everything worked
David B. | Mar 2024
Jamaica vacation rental FAQ

Yes, 38 of our Jamaica homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 109 of our Jamaica vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >

Some of the most popular amenities in our Jamaica vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Jamaica team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Jamaica, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

Now you can experience all the best activities of this charming town with a stay in one of our Jamaica vacation rentals!

Where is Jamaica, VT?

Perched by the southeast foothills of the Green Mountains, Jamaica is tucked into a lush valley between rolling hills and the West River. Situated along Route 100, the town’s close proximity to the world-class ski slopes at Winhall’s Stratton Mountain Resort has long appealed to winter vacationers, and it’s also a popular destination for exploring Southern Vermont and its many other quaint towns, including historic Windham 11 miles to the north, and leafy Dover 18 miles to the south.   

Things to Do in Jamaica, VT

Rising from 688 feet to a high point of 2,542 feet above sea level, Jamaica’s 50-square-miles of lush landscape includes beautiful forest, quaint colonial buildings, and pastoral views at every corner.

Lace up some sturdy shoes and head over to all 772 acres of Jamaica State Park for lush trails reaching picturesque lookouts over the dense Green Mountains. For a particularly beautiful payoff, take the heart-pounding uphill hike to Hamilton Falls, where you’ll be rewarded with cascading pools, incredible cliff-top views, and nature in full bloom.

Refuel back in town with a fresh-baked New York-style pie paired with a Vermont microbrew at Tony’s Pizza. Or, quench your appetite with a delectable “Vermont as Funk” burger made at Honeypie, a farm-to-table restaurant serving up delicious dishes with locally-sourced ingredients.

Continue your tour of town browsing one-of-a-kind paintings and sculptures made by Vermont artists at Elaine Beckwith Gallery and Main Street Studio, or find a unique hand-blown glass keepsake at Hot Glass Works. Retire home with your bounty, ready for some rest in your conveniently located Jamaica vacation rental. 

Day Trips from Jamaica, VT

During any season, no trip to Jamaica is complete without a visit to the outdoor wonderland of Stratton Mountain Resort, home of Vermont’s first World Cup ski races. In the winter, the resort offers 97 ski trails of beginner to expert terrain that’ll test your mettle, along with trick parks, dog sled rides, snowmobile tours, and much more. After a day of rocketing down the slopes, enjoy après-ski entertainment with live music, locavore dining, and boutique shopping in the vibrant Village Square at the base of the mountain.

History buffs will find plenty to love on a visit to Windham. Wind around hilly Windham Hill Road to explore 13 historic buildings dating back to the early 1800s. To get your fill of city culture, including museums, a variety of dining options, and public green spaces, head 42 miles north to Rutland, Vermont’s second largest city.

A quaint gateway to the Green Mountains, Jamaica welcomes your next Vermont getaway with plenty of small-town charm and action-packed adventures. Our vacation rentals put you close to all of the town’s best activities in the beauty of Southern Vermont! 

Photo Credit: redisant via Flickr