Choose from 96 vacation rentals located in Jamaica, Vermont. Top filters in Jamaica include Internet / Wifi, Kitchen / Kitchenette, and Laundry. Prices range from $73 to $3,862 per night. Our most popular vacation rental types near Jamaica are Hotel and RV.

Top vacation rentals in Jamaica

The deck faces the river in the back yard
4.7
Outstanding(64 Reviews)
Chalet
 in Jamaica
Two Bedroom Chalet, Charming, Quiet, River Front
4 guests · 2 bedrooms · 1 bath
Kitchen / Kitchenette · Internet / Wifi · Parking

Experience vacation in Jamaica with our Chalet, Two Bedroom Chalet, Charming, Quiet, River Front . Enjoy amenities such as Dishwasher, Fireplace and Internet / Wifi, and more.

$$$$
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A beautiful retreat but close to everything.
5.0
Outstanding(56 Reviews)
House
 in South Londonderry
Beautifully Maintained Custom Built Home on 7 acres - 3 mi from Stratton Access
6 guests · 3 bedrooms · 2 baths
Garden · Pets allowed · Kitchen / Kitchenette

Enjoy the best of Jamaica in our House, Beautifully Maintained Custom Built Home on 7 acres - 3 mi from Stratton Access. A stunning property with amenities including Dishwasher, Fireplace and Internet / Wifi, and more.

$$$$
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Exterior
5.0
Outstanding(67 Reviews)
House
 in Jamaica
Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton
8 guests · 4 bedrooms · 2 baths
Garden · Kitchen / Kitchenette · Internet / Wifi

Business stays, family stays, couples stay, getaway vacation, and rental in Jamaica at Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton for $500 for your next trip.

$$$$
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View from house of West River and Ball Mountain
4.9
Outstanding(55 Reviews)
House
 in Jamaica
Western Mountain Lodge on River and Close to Stratton
14 guests · 5 bedrooms · 7 baths
Garden · Kitchen / Kitchenette · Internet / Wifi

This House in Jamaica, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

$$$$
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Vacation rentals with internet & wifi in Jamaica

Front of chalet with plenty of parking
4.7
Outstanding(44 Reviews)
Chalet
 in South Londonderry
Minutes from Stratton Mountain for Less Money
6 guests · 3 bedrooms · 2 baths
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Are you ready to indulge in a relaxing getaway? Our Chalet in Jamaica has everything you need for a rejuvenating stay. Treat yourself to Minutes from Stratton Mountain for Less Money's exceptional amenities, such as Air conditioner, Dishwasher and Fireplace.

$$$$
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Main living area
4.8
Outstanding(36 Reviews)
Cabin
 in Jamaica
Secluded, cozy and affordable! Beautiful setting in the woods
6 guests · 3 bedrooms · 2 baths
Pets allowed · Kitchen / Kitchenette · Internet / Wifi

Looking to create some memories in Jamaica? Look no further than our Cabin, Secluded, cozy and affordable! Beautiful setting in the woods. Enjoy top-rated amenities including Dishwasher, Internet / Wifi and Laundry, and more.

$$$$
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Exterior
4.8
Outstanding(34 Reviews)
House
 in Jamaica
Privacy in the Green Mountains! Hike, bike, swim and enjoy VT all summer.
8 guests · 4 bedrooms · 3 baths
Garden · Pool · Pets allowed

Discover the beauty of Jamaica with a stay at Privacy in the Green Mountains! Hike, bike, swim and enjoy VT all summer. , a top rated House with amenities such as Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Property view
5.0
Outstanding(7 Reviews)
House
 in Jamaica
Warm & Inviting Jamaica Cabin w/ Grill: Ski & Hike
6 guests · 2 bedrooms · 2 baths
Garden · Kitchen / Kitchenette · Internet / Wifi

When traveling to Jamaica, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $200 per night.

$$$$
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city photo
Jamaica

Jamaica travel guide

Let us help you plan your perfect Jamaica vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Jamaica, and more.

Frequently asked questions

What do I need to know before visiting Jamaica, VT?

Before visiting Jamaica, VT, you should be aware of a few important things.

  • Jamaica is a small, rural town, located in the Windham County of Vermont.
  • The area is known for its rolling hills and scenic views.
  • The town is home to the Jamaica State Park, a popular spot for hiking and swimming.

When visiting Jamaica, be sure to dress appropriately for the season and bring any necessary supplies. Additionally, it is important to be respectful of the local wildlife and to be mindful of the rules and regulations of the town.

What are the must-visit tourist attractions in Jamaica, VT?

Jamaica, VT is a small town in the Green Mountain State with plenty of attractions for tourists to explore. Here are some of the must-visit tourist attractions in Jamaica, VT:

  • Jamaica State Park
  • Jamaica Covered Bridge
  • Jamaica Falls
  • Jamaica Wildlife Refuge

Visitors to Jamaica, VT can enjoy outdoor activities like camping, fishing, and hiking in the State Park, take a leisurely stroll across the historic Covered Bridge, admire the beauty of Jamaica Falls, or observe the local wildlife in the Wildlife Refuge.

How can I get around in Jamaica, VT?

You can get around Jamaica, VT in the following ways:

  • By car or bike
  • By foot
  • By public transportation

If you're looking for car rental options, Jamaica has several rental companies to choose from. For public transportation, Jamaica is served by the Windham Regional Transit Authority, which offers bus service within the town and to nearby towns.

Where can I find affordable accommodation in Jamaica, VT?

Jamaica, VT offers a variety of affordable accommodation options for travelers. Here are four of the best:

  • The Jamaica Inn: Located on Route 30, this inn offers a range of rooms and suites, all with access to a seasonal outdoor pool and hot tub.
  • The Jamaica Inn Motel: This motel is located on Route 30 and offers comfortable rooms with access to a seasonal outdoor pool.
  • The Jamaica House: This historic inn offers a range of rooms and suites, all with access to a seasonal outdoor pool.
  • The Jamaica Inn Bed & Breakfast: Located in the heart of Jamaica, this bed and breakfast offers comfortable rooms with access to a seasonal outdoor pool and hot tub.

What is the culture like in Jamaica, VT?

The culture in Jamaica, VT is a mix of outdoor recreation, small-town charm, and a strong sense of community. Here are 5 key elements of the culture in Jamaica, VT:

  • Outdoor recreation: Jamaica, VT is a great place to explore nature with its numerous trails, parks, and rivers.
  • Small-town charm: Jamaica, VT is a small town with a population of just over 800 people, making it a great place to get to know your neighbors.
  • Strong sense of community: Jamaica, VT has a vibrant community that comes together for events such as the annual Jamaica Covered Bridge Festival.
  • Arts and culture: Jamaica, VT has a thriving arts and culture scene with numerous galleries, museums, and performing arts venues.
  • Local cuisine: Jamaica, VT has a wide variety of locally-owned restaurants, cafes, and pubs serving up delicious food and drinks.

Is Jamaica, VT safe to travel to?

Jamaica, VT is generally a safe place to travel to. Here are some tips to keep in mind when visiting:

  • Be aware of your surroundings and take precautions to stay safe.
  • Avoid walking alone at night.
  • Keep valuables out of sight.

What are the popular shopping destinations in Jamaica, VT?

Popular shopping destinations in Jamaica, VT include:

  • Jamaica Country Store
  • The Jamaica Covered Bridge
  • Jamaica General Store

These stores offer a variety of items, from handmade crafts to locally-sourced produce and more.

What are the best neighborhoods to visit in Jamaica, VT?

The best neighborhoods to visit in Jamaica, VT are:

  • Stratton Mountain
  • Londonderry
  • Rawsonville
  • West Townshend

These neighborhoods offer a variety of activities, from skiing and snowboarding at Stratton Mountain to exploring the outdoors in Londonderry. Rawsonville is a great place to explore the local culture, while West Townshend is home to the historic West Townshend Country Store.

Where is Jamaica, VT?

Jamaica, VT is located in the southeastern part of the state of Vermont, in Windham County. It is bordered by the towns of Stratton, Winhall, Londonderry, and Wardsboro. Jamaica is a small town, with a population of just over 500 people.

What are the most popular vacation rental amenities in Jamaica, VT?

The most popular vacation rental amenities in Jamaica, VT, include:

  • Fully-equipped kitchen
  • Fireplace
  • Hot tub
  • Outdoor deck or patio
  • High-speed internet

These amenities are highly sought after by visitors to Jamaica, VT, as they help to create a comfortable and enjoyable atmosphere during their stay. Fully-equipped kitchens allow guests to prepare meals in the comfort of their rental, while fireplaces provide a cozy atmosphere. Hot tubs are a great way to relax after a long day of exploring the area, and outdoor decks and patios provide the perfect spot for taking in the beautiful views of Jamaica, VT. High-speed internet is also a must for many visitors, as it allows them to stay connected while away from home.

What are the top things to do in Jamaica, VT?

Jamaica, VT is a great place to explore and enjoy the outdoors. Here are the top things to do in Jamaica, VT:

  • Visit Jamaica State Park
  • Go fishing and boating on Ball Mountain Reservoir
  • Hike the trails of Jamaica Wildlife Refuge
  • Enjoy the views from Jamaica Peak

There is something for everyone in Jamaica, VT. Whether you're looking for an outdoor adventure, some relaxation, or just a beautiful view, Jamaica, VT has it all!

What is the price range for rentals in Jamaica?

Vacation rentals in Jamaica have a price range between $73-$3,862. The average price for rentals in Jamaica is $319 per night.

What are the most popular vacation rental amenities in Jamaica?

  • Internet / Wifi
  • Kitchen / Kitchenette
  • Laundry

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