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Jamaica vacation rentals

We found 1,208 vacation rentals — enter your dates for availability

Discover a selection of 43 homes, 11 cabins, and other vacation rentals in Jamaica that are perfect for your trip. Whether you're traveling with a group or just with your pet, vacation homes have the best amenities for hanging out with the people that matter most, which might include WiFi and a fireplace. No matter what you're looking for, you'll find a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Jamaica

Showing deals for:Jun 26 - Jul 3

Image gallery for the farmhouse at Big Picture Farm

Snow and ski sports
10 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)

the farmhouse at Big Picture Farm

Townshend

14% off
Price is $1,770
$12,391 for 7 nights
All fees included
the farmhouse at Big Picture Farm

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Find out more about Jamaica

Why visit Jamaica

  • Outdoor Adventures: Jamaica, Vermont, is perfect for skiing and outdoor sports, providing thrilling experiences for adventure enthusiasts.
  • Scenic Natural Beauty: Enjoy breathtaking mountain views and explore scenic national parks, rivers, and lakes for a tranquil escape.
  • Charming Atmosphere: Experience the friendly, quaint vibe of this rural town, ideal for families and solo travelers alike.
  • Diverse Accommodations: Choose from vacation rentals, cozy cabins, or stylish condos to suit your travel style and preferences.
  • Local Culture: Immerse yourself in the local scenery and culture, making your visit memorable and enriching.

Popular types of accommodation in Jamaica

Discover the perfect getaway with vacation rentals in Jamaica. Whether you prefer a private vacation home, a cozy cabin, or a stylish condo, we have options for every traveler. Enjoy outdoor seating with stunning views, or choose from ideal house rentals and select hotels that cater to your needs. Whatever your plans, you're sure to find the perfect accommodation for an unforgettable Jamaican experience.

  • Houses: Ideal for families or groups, these homes offer plenty of space and amenities for a relaxing stay in Jamaica.
  • Condos: A convenient option, condos provide a blend of comfort and accessibility, perfect for travelers looking for a home-away-from-home experience.
  • Cabins: For nature enthusiasts, cabins present a cozy retreat surrounded by stunning landscapes and outdoor activities.
  • Apartments: Apartments are a practical choice for couples or solo travelers seeking a central location and local vibe.
  • Chalets: These charming lodges offer a unique stay, combining rustic charm with modern comforts in a picturesque setting.**

Top attractions in and around Jamaica

Jamaica, Vermont, offers an exciting blend of ski, adventure, and sports vacations. Visitors can explore scenic national parks, rivers, and lakes, making it an ideal destination for those seeking cultural and outdoor experiences. Whether you're traveling solo, with family, or friends, Jamaica promises a memorable getaway filled with natural beauty and adventure.

  • Jamaica State Park: Experience the beauty of nature at Jamaica State Park, where you can hike scenic trails, enjoy picnicking by the river, and immerse yourself in the tranquil outdoor vibes. Perfect for adventure seekers and nature lovers alike.
  • Golf Club at Equinox: Just 15 miles from Jamaica, this premier golf course offers a challenging layout amid stunning landscapes. Enjoy an exhilarating day on the greens while soaking in the fresh air and beautiful surroundings.
  • Hildene: Also located 15 miles away, Hildene is the historic home of Robert Todd Lincoln. Explore its rich history, beautiful gardens, and cultural exhibits that provide a glimpse into American heritage.

Things to do recommended for couples

Planning a romantic getaway in Jamaica, Vermont? Enjoy a round of golf at the luxurious Brattleboro Country Club, just 19 miles away. Unwind together amidst stunning views and serene landscapes, making it the perfect backdrop for your couple's retreat.

Things to do recommended for families

Families can explore the scenic trails of Jamaica State Park, enjoy a refreshing swim at the local swimming hole, or visit nearby farms for fruit-picking. Don't miss the charming shops and eateries in town that offer local flavors and crafts for everyone to enjoy.

Things to do recommended for groups

Explore the stunning landscapes on a group hike in the gorgeous Green Mountains or enjoy a fun-filled day at the Jamaica State Park, where you can picnic and go swimming. Don't miss the chance to visit local shops for unique crafts and delicious food.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Jamaica

If you're planning a trip with a group, family, pets, or considering an extended stay, be sure to use the appropriate filters to align with your needs. Here are some helpful booking tips for Vrbo.

  • Traveling to Jamaica with a group: Think about how many bedrooms you'll require, as well as any amenities you might want, like a full kitchen or outdoor space for gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Jamaica with young kids: Traveling with young kids can be a bit demanding. It's important to prioritize their comfort and safety, along with ensuring access to suitable amenities, like a private pool. Additionally, keeping in mind the location of family-friendly attractions can enhance your experience.
  • Taking your pets with you to Jamaica: For many families, a vacation isn't truly fulfilled without their furry companions. If this resonates with you, take a look at Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Jamaica: If you're in search of vacation rentals that offer great deals for stays of a month or longer, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Jamaica

Jamaica, Vermont, is a charming destination perfect for adventure enthusiasts and families alike. Nestled in rural Vermont, this quaint town offers breathtaking mountain views and a friendly atmosphere. Explore nearby neighborhoods for a romantic getaway or a relaxing retreat, where you can immerse yourself in the local scenery and enjoy outdoor sports. A trip to Jamaica promises a delightful blend of adventure and tranquility, making it an ideal Vermont escape.

  • Stratton: Located 7 miles from Jamaica, Stratton is a premier destination for outdoor enthusiasts. Renowned for its ski slopes, this city offers an exhilarating adventure for both seasoned skiers and beginners alike. The Stratton Ski Resort features extensive ski fields and terrain parks, ensuring a thrilling experience for sports lovers. Beyond skiing, the surrounding mountains and serene lakes provide stunning scenery and ample opportunities for hiking and exploration in the nearby national state park. Whether you're hitting the slopes or enjoying the tranquil beauty of nature, Stratton is a must-visit.
  • West Dover: Just 12 miles away from Jamaica, West Dover is another fantastic spot for ski and adventure lovers. This charming city is home to impressive ski resorts and well-maintained ski fields, making it a popular choice for winter sports activities. The breathtaking landscapes, featuring majestic mountains and crystal-clear lakes, are perfect for outdoor exploration. The nearby national state park invites visitors to hike, bike, and appreciate the natural beauty of the region, offering a perfect blend of relaxation and adventure in West Dover.
  • Bondville: Situated 6 miles from Jamaica, Bondville is a quaint city that captures the essence of Vermont's picturesque landscapes. With its close proximity to ski resorts and ski fields, Bondville is a great base for winter sports enthusiasts. The scenic surroundings, including lakes and mountains, provide a captivating backdrop for outdoor activities year-round. Visitors can enjoy hiking, fishing, or simply soaking in the breathtaking views at the nearby national state park, making Bondville an ideal spot for those seeking both adventure and tranquility.

Best time to go to Jamaica

If you're planning a trip to Jamaica, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in July and November to December, while off-peak times, like March to May tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January19.8°F (-6.8°C)Light RainMostly CloudyAverageSlightly High
February21.7°F (-5.7°C)Light RainMostly CloudyAverageSlightly High
March29.7°F (-1.3°C)Light RainMostly CloudyLowAverage
April41.9°F (5.5°C)Light RainMostly CloudyLowSlightly Low
May54.9°F (12.7°C)Light RainMostly SunnyLowSlightly Low
June62.2°F (16.8°C)Light RainMostly SunnyAverageAverage
July68.2°F (20.1°C)Light RainMostly SunnyHighAverage
August66.2°F (19.0°C)Light RainMostly SunnyAverageAverage
September59.4°F (15.2°C)Light RainMostly SunnyAverageSlightly Low
October47.8°F (8.8°C)Light RainMostly CloudyAverageAverage
November35.4°F (1.9°C)Light RainMostly SunnyHighAverage
December26.8°F (-2.9°C)Light RainMostly CloudyHighSlightly High

Booking with Vrbo is simple

Are you hoping to save on your next getaway? Being flexible with your travel dates can help, as prices can vary quite a bit. Additionally, booking an extended stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides you with a convenient space to plan new adventures, keep your travel arrangements on track, or organize your existing bookings. Your saved and booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To check out Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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.

Sightseeing in and around Jamaica

Are you hoping to discover things to do while you're in town? Venture out of your cozy vacation rental and check out everything that makes Jamaica a one-of-a-kind vacation spot. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Stratton Mountain Resort (6.6 mi / 10.6 km)
  • Mount Snow (12 mi / 19.4 km)
  • Jamaica State Park (3.5 mi / 5.6 km)
  • Stratton Mountain Golf Course (5.4 mi / 8.7 km)
  • Magic Mountain Ski Resort (6.6 mi / 10.7 km)
  • Bromley Mountain Ski Resort (11.6 mi / 18.6 km)

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.

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.

Traveling to and around Jamaica

The nearest airport is in Springfield, VT (VSF-Hartness State), located 21.1 mi (34 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 30.7 mi (49.4 km) away.

Frequently asked questions

What is the best area to stay in Jamaica, Vermont, United States of America when booking a vacation rental?
When looking for the best area to stay in Jamaica, Vermont, you'll want to consider the charming neighborhoods surrounding the village. One popular area is close to the scenic Jamaica State Park, which offers beautiful trails and stunning views, making it a fantastic spot for outdoor enthusiasts. This area features a variety of vacation rental properties, providing plenty of options for visitors.

Another delightful neighborhood to explore is near the quaint downtown area, where you can find local shops and cozy eateries. This location is superb for those who enjoy a more community-oriented atmosphere, with easy access to local events and attractions. The nearby Stratton Mountain Resort is also a highlight, offering skiing in the winter and hiking in the summer, ensuring that there's always something to do no matter the season.
How much does it cost to rent a vacation home in Jamaica?
Prices for vacation rentals in Jamaica vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Jamaica to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Jamaica vacation house rentals?
You can find great discounts on house rentals in Jamaica on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Jamaica ski resort rentals?
For renting ski accommodations in Jamaica, Vermont, travelers should focus on the vicinity of Stratton Mountain Resort, which is just a short drive away. This area offers a variety of vacation rentals, including cozy chalets and mountain cabins that typically feature amenities such as fireplaces, fully equipped kitchens, and spacious living areas ideal for relaxing after a day on the slopes. Many properties also boast outdoor decks with scenic views of the surrounding mountains, providing a great backdrop for unwinding.

In Jamaica itself, visitors can find quaint inns and lodges that provide a more intimate experience. These often include convenient amenities like complimentary breakfast, hot tubs, and access to local trails for cross-country skiing or snowshoeing. The charming village atmosphere of Jamaica enhances the experience, with local shops and restaurants adding to the appeal.

Additionally, the nearby Green Mountain National Forest offers opportunities for winter hiking and snowmobiling, making it easy for travelers to enjoy a range of winter activities.
What is the most popular type of vacation rental accomodation in Jamaica?
In Jamaica, vacation houses are the most popular type of rental, with about 36 available in the area. These properties are often situated in tranquil surroundings, providing a spacious and comfortable environment for travelers. Most vacation houses come equipped with fully functional kitchens, cozy living areas, and outdoor spaces such as decks or patios for enjoying the beautiful Vermont scenery.

In addition to vacation houses, there are around 10 cabins, which offer a rustic charm and are superb for those looking to immerse themselves in nature. Several chalets and cottages are also available, typically featuring warm, inviting atmospheres with amenities like fireplaces and scenic views. For those seeking a more compact option, several condos provide convenient stays, often located near local attractions.
Are there any family house rentals in Jamaica?
In Jamaica, Vermont, there is a great selection of family-friendly house rentals, with about 45 available throughout the area. This charming town is located in the Green Mountains, making it an attractive destination for families seeking outdoor adventures. Many of the vacation homes feature spacious living areas, fully equipped kitchens for preparing meals, and cozy dining spaces great for family gatherings. Additionally, you can find properties with amenities like game rooms, fire pits, and even outdoor decks where families can enjoy the beautiful scenery.

Visitors to Jamaica can explore nearby attractions such as the Jamaica State Park, which offers hiking trails, picnic areas, and opportunities for swimming in the West River. The local area also boasts quaint shops and eateries for a taste of the local culture.
Can I rent a vacation home with a pool or hot tub in Jamaica?
In Jamaica, Vermont, there are several vacation homes available for rent that feature pools and hot tubs. This charming town, surrounded by the picturesque Green Mountains, offers a tranquil setting for relaxation and outdoor activities. Many of these rentals come equipped with private pools, hot tubs, and spacious outdoor areas, superb for unwinding after a day of exploring the beautiful landscape or skiing in the nearby resorts.
Can I find long-stay vacation rentals in Jamaica?
A long-stay vacation rental in Jamaica is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Jamaica?
In Jamaica, Vermont, there are several pet-friendly house rentals available, providing a welcoming environment for travelers with pets. Many of these rentals are situated in scenic locations, offering amenities such as fully equipped kitchens, outdoor spaces for pets to roam, and cozy living areas for relaxation after a day of exploring.

The area is known for its beautiful landscapes and outdoor activities, making it ideal for those traveling with furry companions. Nearby, you can find parks and trails suitable for hiking and walking, ensuring that your pets have plenty of opportunities to enjoy the great outdoors. Additionally, the community often hosts pet-friendly events and gatherings, ideal for pet owners.
Are there any remote work vacation rentals in Jamaica?
In Jamaica, Vermont, there are plenty of options for remote work vacation rentals, with around 59 available in the area. These accommodations often come equipped with essential amenities for productivity, including high-speed Wi-Fi and designated workspaces, such as desks and comfortable chairs, ensuring that you can stay connected while enjoying your getaway. Many properties also feature cozy living areas and full kitchens, allowing for a comfortable and convenient stay.

The picturesque surroundings of Jamaica offer a serene environment, superb for balancing work and leisure. The area is close to natural attractions, such as the Jamaica State Park, where you can explore hiking trails and beautiful landscapes during your downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Jamaica vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Jamaica with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Jamaica?
In Jamaica, Vermont, popular vacation rental amenities include fully equipped kitchens, ideal for those who prefer to prepare their own meals. Many rentals also feature cozy fireplaces, superb for warming up after a day of outdoor activities. Guests can enjoy the fresh air on decks or patios that are common in these properties, providing space for relaxation or dining outdoors. Onsite parking is typically available, making it convenient for travelers with vehicles. Additionally, many rentals are equipped with coffee and tea makers, ensuring that guests can enjoy their morning brew at their leisure.
When is the best time to visit Jamaica for a vacation rental?
The best time to visit Jamaica for a vacation rental is during the peak season from October to December, with December being particularly popular among travelers. This vibrant period attracts visitors seeking to enjoy the picturesque landscapes and outdoor activities, as the weather is pleasantly warm, with temperatures ranging from the low 40s to mid-60s Fahrenheit. Travelers can indulge in activities like hiking, exploring the local culture, and soaking in the natural beauty that Jamaica has to offer.

During December, you'll find a bustling atmosphere filled with festive events and community celebrations, making it an ideal time for those looking to immerse themselves in the local culture while enjoying outdoor adventures. The scenic trails and stunning views create a great backdrop for activities like hiking or leisurely walks.

If you're considering a more budget-friendly option, April is a great month to visit. While it marks the start of the low season, you'll still experience mild weather and fewer crowds, allowing for a more tranquil exploration of Jamaica. The lush greenery and blooming flowers during this time enhance the natural beauty of the area, making it a great choice for nature enthusiasts.
How early should I book a Jamaica vacation rental?
Book your Jamaica vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Jamaica, Vermont, United States of America?
In Jamaica, Vermont, visitors can enjoy a variety of attractions that highlight the natural beauty and charm of the area. The Jamaica State Park is a major draw, offering picturesque hiking trails that wind along the West River, with opportunities for swimming and fishing during the warmer months. The park is also a great spot for leaf-peeping in the fall.

The nearby Stratton Mountain Resort, approximately a short drive away, provides year-round activities, including skiing and snowboarding in the winter and mountain biking and hiking in the summer.

For those interested in local culture, the quaint town center features unique shops, galleries, and cozy eateries, where travelers can experience the local Vermont cuisine.
Can I change or cancel my Jamaica home rental booking on Vrbo?
To find Jamaica vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Jamaica vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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