Discover a selection of 500 vacation rentals in Jamaica, VT that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including WiFi and swimming pools. Prices start at $100 per night, and houses and cabins are popular options for a stay in Jamaica. Either way, you'll find a rental for everyone's needs.
Destination guide

Get away from it all in Jamaica, Vermont

With a population just barely topping 1,000, this tiny hamlet in the southeastern corner of Vermont is the epitome of small town New England charm and light years away from big city life. You'll feel as though you've stepped into a postcard when you start exploring the quaint houses and picturesque churches that are dotted around the town's tiny main street, which is home to family-run shops that will make you yearn for simpler times. Jamaica is an idyllic base for exploring the refreshing forests and nature of the Green Mountain State.

Things to do

Something for everyone, from waterfalls to women's rights

If want fresh air, your Jamaica vacation rental won't disappoint. Jamaica State Park is on your doorstep, with trails, camping, and swimming holes at every turn. A moderate hike rewards you with views of the cascading waters at Hamilton Falls (plus some prime birdwatching along the way). Drive a few minutes and you're immersed in the lush greenery of Green Mountain National Forest or on the slopes of Stratton Mountain Resort, a mecca for local skiers and snowboarders. Don't forget to stop at the Clarina Howard Nichols Historical Landmark, dedicated to the pioneering 19th-century advocate for abolition and women's rights.


From hiking to shopping, life is stress-free in Jamaica

Be sure to pack some sturdy shoes so you can take advantage of the countless hiking and nature trails that wind through the surrounding countryside. A Jamaica vacation rental puts you in a wonderland of forest, mountains, and streams, plus enough fresh air that you'll be sure to sleep well at night. When you've had your fill of the scenery (if that's possible), get some creative inspiration or nab some local hand-blown glass at the unique shops and galleries on the main street. For snow bunnies, there's some prime skiing nearby.


Cozy winter nights by the fire, and lazy summer nights out

If you're a fan of winter, Jamaica's your place. Particularly from December through March (and maybe even longer), the surrounding countryside is covered in feet of fluffy white snow, making for some great winter activities, or just a spectacular view with a blanket and some hot chocolate. Summers are pleasant and warm, though often humid. Even in the warmest months of June to August, the mercury rarely rises into the 80s -- you might even want a light sweater at night. The blazing fall foliage peaks during the prime leaf peeping months of September and October.

Natural features

Go chasing waterfalls in Jamaica's lush forests

Endless acres of vibrant mountain forests are just waiting to be explored at your Jamaica vacation rental. With Jamaica State Park and Green Mountain National Forest just minutes away, you'll get your fill of hiking trails, towering trees, and native wildlife, especially some pretty feathered friends. The area's crown jewel is Hamilton falls, just one of many secluded watering holes you'll find as you lose yourself in the wilderness. The peaks of Stratton Mountain Resort are a great place to take it all in and get that perfect Instagram shot.

How to get there

How to get to and around Jamaica

The nearest airport is in Springfield, VT (VSF-Hartness State), located 22.3 mi (35.8 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 30.4 mi (48.9 km) away.

How many vacation rentals are available around Jamaica, VT?

Our 2021 property listings offer a large selection of 655 vacation rentals around Jamaica. From 469 house rentals to 31 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the popular point of interests near where I can stay when traveling to Jamaica?

Vrbo offers a large selection of vacation rentals near lovely places in Jamaica. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Ball Mountain Dam: 1,128 vacation rentals
  • Ball Mountain State Park: 1,121 vacation rentals
  • Jamaica State Park: 1,130 vacation rentals
  • Hot Glass Works: 958 vacation rentals
  • Margie's Muse Handweaving & Gallery: 956 vacation rentals

But there are many other points of interest around Jamaica listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Jamaica?

Yes, of course. Vrbo has 469 Houses in Jamaica. Our other popular types of vacation rentals in Jamaica include:

  • Cabins: 31 rentals available
  • Condos/Apartments: 140 rentals available
  • Bungalows: 31 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Chalets and more.

Can I find a vacation rental with pool in Jamaica?

Yes, you can select your preferred vacation rental with pool among our 200 vacation rentals with pool available in Jamaica. Please use our search bar to access the selection of vacation rentals available.