Jamaica holiday lettings

We found 1,163 holiday rentals — enter your dates for availability

Discover a selection of 37 homes, 10 cabins and other holiday rentals in Jamaica that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday homes have the amenities that you need and want for your stay, such as Wi-Fi and cable TV. Whatever you're looking for, you're sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Jamaica

Showing deals for:2 Jan - 9 Jan

Image gallery for the farmhouse at Big Picture Farm

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

the farmhouse at Big Picture Farm

Townshend, VT

12% off
Price is £10,405
for 7 nights, 1 room
£1,486 per night
includes taxes & fees
the farmhouse at Big Picture Farm

Find spaces that suit your style

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  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Jamaica

Find out more about Jamaica

Adventurous Jamaica will entice you

The area's art galleries and monuments are just some of the reasons to come on holiday to Jamaica. This city's sledging, horse riding and mountain views draw many visitors. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Jamaica

Do you want to discover attractions to see in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Jamaica a fun place to get away to. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Jamaica State Park (3.6 mi / 5.7 km)
  • Stratton Mountain Resort (6.6 mi / 10.6 km)
  • Stratton Mountain Golf Course (6.6 mi / 10.7 km)
  • Magic Mountain Ski Resort (6.6 mi / 10.7 km)
  • Bromley Mountain Ski Resort (11.6 mi / 18.6 km)
  • Mount Snow (12 mi / 19.4 km)

Exploring the natural features in Jamaica

Whether you're an active traveller or just want to spend some time taking in the scenery, Jamaica is a great place to spend some time outside. These are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Lowell Lake State Park (8.5 mi / 13.7 km)
  • Lye Brook Falls (13.3 mi / 21.5 km)
  • Battenkill River (14.6 mi / 23.4 km)
  • Lake Raponda (15.7 mi / 25.3 km)
  • Equinox Preservation Trust (16.2 mi / 26.1 km)
  • Hogback Mountain Conservation Area (16.7 mi / 26.8 km)

Travelling to and around Jamaica

The nearest airport is in Springfield, VT (VSF-Hartness State), located 21.1 mi (34 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to 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 when booking a holiday rental?
When considering a holiday rental in Jamaica, Vermont, a delightful choice would be the area surrounding the charming village centre. This quaint neighbourhood is great for those looking to immerse themselves in the local atmosphere while enjoying easy access to various amenities and attractions.

Within this vicinity, visitors can explore the stunning landscape of the Green Mountains, which offers a number of outdoor activities, from hiking and mountain biking in warmer months to skiing and snowboarding during the winter. Additionally, the nearby Jamaica State Park is a true gem, featuring scenic trails and picturesque picnic spots alongside the West River, ideal for both relaxation and adventure.

Another appealing area to consider is the outskirts of Jamaica, where you can find a more tranquil setting amidst nature. Here, you can enjoy a serene escape with the backdrop of lush forests and rolling hills. This area tends to have a good selection of properties, allowing you to choose from rustic cabins to charming cottages, suiting a variety of preferences and group sizes.
How much does it cost to rent a holiday home in Jamaica?
Prices for holiday 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 holiday 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 the best ski resort rentals in Jamaica, Vermont, travellers should focus on the area surrounding the Stratton Mountain Resort, which is a short drive away. The town of Jamaica itself offers a variety of charming accommodations, including rustic cabins and cosy lodges that provide a warm, friendly space after a day on the slopes. Many of these properties feature amenities such as wood-burning stoves, fully equipped kitchens, and outdoor spaces for enjoying the serene natural setting.

In the nearby village of Stratton, visitors can find more modern ski-in/ski-out condominiums that cater to families and groups, often equipped with hot tubs, ski storage, and communal areas for relaxation. These rentals typically provide easy access to the ski lifts and are conveniently located near local shops and restaurants, making it easy to enjoy a full holiday experience.
What is the most popular type of holiday rental accomodation in Jamaica?
In Jamaica, holiday houses are the most popular rental option, with around 34 available throughout the area. These properties typically provide spacious interiors, featuring multiple bedrooms, fully equipped kitchens, and outdoor areas for relaxation, making them great for families or groups. Additionally, there are several cabins, chalets, and cottages scattered around, offering a more rustic and cosy experience, often located in nature. Many of these rentals include amenities such as fireplaces, BBQ facilities, and access to nearby hiking trails, ensuring guests enjoy a comfortable stay amid the beautiful Vermont scenery.
Are there any family house rentals in Jamaica?
In Jamaica, Vermont, there is a substantial selection of family-friendly holiday rentals, with around 43 homes available for those seeking a getaway. The area is known for its charming atmosphere and proximity to outdoor activities, making it ideal for families. Many of these properties offer spacious living areas where families can relax together, as well as fully equipped kitchens for preparing meals.
Can I rent a holiday home with a pool or hot tub in Jamaica?
In Jamaica, Vermont, there are several holiday homes available for rent that come equipped with pools and hot tubs. This picturesque town, located in the Green Mountains, offers a tranquil setting for travellers looking to relax. Many of the rentals feature private pools, hot tubs, and spacious outdoor areas, great for soaking up the natural beauty surrounding the area.
Can I find long-stay holiday rentals in Jamaica?
A long-stay holiday rental in Jamaica is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Jamaica?
In Jamaica, Vermont, there are several pet-friendly house rentals available, with around 29 options to choose from. Many of these properties come equipped with amenities that cater to both human and furry guests, such as spacious backyards, outdoor seating areas, and fully stocked kitchens for preparing meals.
Are there any remote work holiday rentals in Jamaica?
In Jamaica, Vermont, there are numerous holiday rentals suitable for remote work, with around 51 options available. These properties typically come equipped with essential amenities such as Wi-Fi, dedicated office spaces, and comfortable desk setups, including desk chairs and computer monitors, allowing for a productive work environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Jamaica holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Jamaica with parking available—perfect for families or travellers 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, holiday rentals typically feature a range of popular amenities that cater to travellers' needs. Most accommodations include a fully equipped kitchen, which allows guests to prepare their own meals. Additionally, you can expect cookware, dishware, and utensils to be provided, making it convenient for self-catering. Refrigerators are standard in the rentals, allowing for easy storage of perishable items, while stovetops and microwaves offer flexible cooking options.
How early should I book a Jamaica holiday rental?
Book your Jamaica holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Jamaica home rental booking on Vrbo?
To find Jamaica holiday 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 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 travellers 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 cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Jamaica holiday 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.

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