Jamaica holiday rentals

We found 1,174 holiday rentals — enter your dates for availability
Discover a selection of 46 homes 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:18 Dec - 25 Dec

Exterior
Exterior
Interior
Sports court
Exceptional
(82 reviews)

Beautiful Lakeview Log Cabin on 60-Acre Property

Peru

8% off
AU$35,135
for 7 nights, 1 home
AU$5,019 per night
includes taxes & fees
Beautiful Lakeview Log Cabin on 60-Acre Property
Exterior
Large living room with endless natural light
Property grounds
New custom kitchen
Exceptional
(17 reviews)

Private 6 bedroom Chalet 5min to Mt Snow

West Dover

8% off
AU$16,103
for 7 nights, 1 chalet
AU$2,300 per night
includes taxes & fees
Private 6 bedroom Chalet 5min to Mt Snow
Dining
Living area
Private kitchen
Room
Exceptional
(35 reviews)

Beautiful log home close to Mt. Snow with hot tub and sauna.

West Dover

8% off
AU$12,606
for 7 nights, 1 cabin
AU$1,801 per night
includes taxes & fees
Beautiful log home close to Mt. Snow with hot tub and sauna.
A look at the main floor family room from above.
Welcome to our 9 bedroom luxury home in the heart of Southern Vermont!
Complete privacy on our property!
Hot tub and firepit are great after a day of fun.
Exceptional
(22 reviews)

Luxury 9BRs Stratton Estate. Views! Hot Tub, Sauna, Game House, Swimming pool!

Bondville

8% off
AU$38,614
for 7 nights, 1 home
AU$5,516 per night
includes taxes & fees
Luxury 9BRs Stratton Estate. Views! Hot Tub, Sauna, Game House, Swimming pool!
Primary bedroom balcony
Interior
Private kitchen
Sitting room looking into the kitchen.
Exceptional
(8 reviews)

Views of Stratton, Minutes from the Slopes, EV Charging Level 2

Bondville

8% off
AU$15,598
for 7 nights, 1 home
AU$2,228 per night
includes taxes & fees
Views of Stratton, Minutes from the Slopes, EV Charging Level 2
Fully equipped kitchen
Front of the house
King bed
Patio chairs and solo stove firepit
Exceptional
(16 reviews)

Chalet Mount Snow/Stratton Skiing/hiking

East Dover

8% off
AU$4,823
for 7 nights, 1 chalet
AU$689 per night
includes taxes & fees
Chalet Mount Snow/Stratton Skiing/hiking
Room
Interior
Dining
Bar (on property)
Exceptional
(79 reviews)

Western Mountain Lodge on River and Close to Stratton

Jamaica

17% off
AU$24,301
for 7 nights, 1 home
AU$3,472 per night
includes taxes & fees
Western Mountain Lodge on River and Close to Stratton
View of the main house from the creek on the property.
Main house top floor river room with sounds of the river out the windows.
Main house top floor river room with deck overlooking the pool and backyard.
2nd - 3rd floor main house stairs
Exceptional
(38 reviews)

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Wardsboro

8% off
AU$22,024
for 7 nights, 1 home
AU$3,146 per night
includes taxes & fees
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
Living area with wood stove.
Kitchen and dining area.
Dry your ski gear on the hooks near the warm wood stove.
Enjoy the infamous Moss Rock!
Exceptional
(26 reviews)

Vermont ski chalet near beautiful Mount Snow and the quaint town of Wilmington

West Dover

8% off
AU$5,497
for 7 nights, 1 chalet
AU$785 per night
includes taxes & fees
Vermont ski chalet near beautiful Mount Snow and the quaint town of Wilmington
Exterior
Interior
Private kitchen
Dining
Exceptional
(55 reviews)

Skylight Ski Lodge VT Rustic Chic Near Stratton

Bondville

8% off
AU$17,730
for 7 nights, 1 home
AU$2,533 per night
includes taxes & fees
Skylight Ski Lodge VT Rustic Chic Near Stratton
Back porch
Living area
Front door
Dining room
Exceptional
(40 reviews)

Wishing Well Cabin

Jamaica

8% off
AU$3,752
for 7 nights, 1 cabin
AU$536 per night
includes taxes & fees
Wishing Well Cabin
Terrace/patio
Large open-concept living and kitchen area
Dining area
Bedroom 1: Queen Bed
Exceptional
(18 reviews)

Leonard’s Log Cabin— Mt. Snow/Stratton Ski House

Wardsboro

8% off
AU$8,524
for 7 nights, 1 cabin
AU$1,218 per night
includes taxes & fees
Leonard’s Log Cabin— Mt. Snow/Stratton Ski House
Porch - Winter
Porch -Summer
Antique Cabin
Antique Cabin
Exceptional
(89 reviews)

Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton

Jamaica

8% off
AU$5,962
for 7 nights, 1 home
AU$852 per night
includes taxes & fees
Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton
Dining
Exterior
Living area
Games room
Exceptional
(39 reviews)

Beautiful Four Season Family Vacation Home

West Dover

12% off
AU$10,711
for 7 nights, 1 home
AU$1,530 per night
includes taxes & fees
Beautiful Four Season Family Vacation Home
Dining
Exterior
Plenty of room for relaxing.
Private kitchen
Exceptional
(33 reviews)

Winterfell chalet - quiet, relaxing & private with Stratton on your doorstep.

Bondville

8% off
AU$9,192
for 7 nights, 1 chalet
AU$1,313 per night
includes taxes & fees
Winterfell chalet - quiet, relaxing & private with Stratton on your doorstep.
kitchen
Jacuzzi hot tub
foyer for all skiing and outdoor stuff
main level living room sitting area
Exceptional
(26 reviews)

True Vermont Log Cabin Home at Mount Snow

West Dover

8% off
AU$9,448
for 7 nights, 1 cabin
AU$1,350 per night
includes taxes & fees
True Vermont Log Cabin Home at Mount Snow
Exterior
Terrace/patio
Interior
Interior
Exceptional
(57 reviews)

Modern mountain home - Vermont Ski House close to Stratton

East Dorset

8% off
AU$10,122
for 7 nights, 1 home
AU$1,446 per night
includes taxes & fees
Modern mountain home - Vermont Ski House close to Stratton
South side of house, deck and hot tub
Living area
Loft with surround sound Entertainment
Dining
Exceptional
(32 reviews)

Perfect Get-Away House - 6 Miles from Stratton & Mount Snow

West Wardsboro

5% off
AU$8,734
for 7 nights, 1 home
AU$1,248 per night
includes taxes & fees
Perfect Get-Away House - 6 Miles from Stratton & Mount Snow
living room
Outdoor dining
main entrance
Stratton mtn fire tower view
Exceptional
(39 reviews)

Cozy Manchester Getaway with Amazing Views!!!

Bondville

8% off
AU$5,501
for 7 nights, 1 home
AU$786 per night
includes taxes & fees
Cozy Manchester Getaway with Amazing Views!!!
Screened in porch dining area
Property grounds
Private kitchen
Exterior
Exceptional
(20 reviews)

Cozy Vermont Home Near Mount Snow & Stratton

West Wardsboro

8% off
AU$5,462
for 7 nights, 1 home
AU$780 per night
includes taxes & fees
Cozy Vermont Home Near Mount Snow & Stratton
Wood burning stove 1
Large dining area accommodates family sized gatherings
Living Room
Welcome to Tallwood Timber VT
Exceptional
(13 reviews)

Tallwood Timber: a Family Friendly Ski House in Southern Vermont

Londonderry

8% off
AU$6,492
for 7 nights, 1 home
AU$927 per night
includes taxes & fees
Tallwood Timber: a Family Friendly Ski House in Southern Vermont
Room
Exterior
Living area
Pool
Exceptional
(21 reviews)

Skiing, snowboarding, tubing, snowshoeing and all the other winter activities!

Bondville

8% off
AU$12,880
for 7 nights, 1 home
AU$1,840 per night
includes taxes & fees
Skiing, snowboarding, tubing, snowshoeing and all the other winter activities!
Interior
Available weekend, weekly or monthly spring or summer rental.
Private kitchen
Interior
Exceptional
(32 reviews)

Ski condo a mile from Stratton Mtn, shuttle bus and wood included. No Pets.

Jamaica

8% off
AU$4,353
for 7 nights, 1 apartment
AU$622 per night
includes taxes & fees
Ski condo a mile from Stratton Mtn, shuttle bus and wood included. No Pets.
rear of house
deck
entrance view
Living area
Exceptional
(8 reviews)

Accessible Manchester Home with Amazing Views!

Manchester Center

8% off
AU$7,262
for 7 nights, 1 home
AU$1,037 per night
includes taxes & fees
Accessible Manchester Home with Amazing Views!

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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)
  • 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)
  • Emerald Lake State Park (16.9 mi / 27.2 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 the best area to stay in Jamaica, Vermont, for a holiday rental, the charming village itself is a delightful choice. This picturesque area is known for its stunning natural surroundings, making it a haven for outdoor enthusiasts. You'll find a variety of properties available, ranging from quaint cottages to larger homes that cater to families and groups.Jamaica is particularly well-placed for those who wish to explore the scenic beauty of the Green Mountains. Just a short drive away, you can visit the famous Stratton Mountain Resort, which offers excellent skiing in winter and hiking trails in the warmer months. The nearby Jamaica State Park is also a highlight, providing opportunities for walking, picnicking, and enjoying the tranquil sounds of the West River.Staying in Jamaica allows you to experience the local culture and community vibe, with unique shops and eateries that reflect the area's charm.
Where are the best Jamaica ski resort rentals?
For the best ski resort rentals in Jamaica, Vermont, travellers should focus on the areas surrounding the Stratton Mountain Resort, which is a short drive away and offers a variety of winter sports activities. In the Jamaica village itself, visitors can find charming cabins and lodges that provide a cosy atmosphere and easy access to the slopes. Many of these properties feature amenities such as fireplaces, full kitchens, and outdoor spaces for après-ski relaxation.Additionally, the nearby Town of Stratton offers a range of holiday rentals, from modern condominiums to spacious chalets, often equipped with amenities like hot tubs, ski storage, and access to community facilities such as heated pools and fitness centres. These accommodations are ideal for families and groups looking to enjoy a comfortable stay after a day on the mountain.For those who enjoy a bit of local flair, the Jamaica area is also known for its quaint shops and eateries, where guests can experience the charm of small-town Vermont.
What is the most popular type of holiday rental accomodation in Jamaica?
In Jamaica, holiday houses are the most popular type of holiday rental, with approximately 108 available throughout the area. These properties are often spacious, featuring multiple bedrooms, fully equipped kitchens, and inviting living areas, making them ideal for families or larger groups. Many holiday houses also boast outdoor spaces such as decks or patios, allowing guests to enjoy the scenic surroundings. Additionally, there are around 30 cabins and 24 chalets, which offer a more rustic experience and often include amenities like fireplaces and proximity to nature trails. For those looking for a quaint stay, about 15 cottages provide a charming atmosphere, while several condos are also available, typically featuring modern conveniences and easy access to local attractions.
Are there any family house rentals in Jamaica?
In Jamaica, Vermont, there are numerous family-friendly holiday rentals available, with around 45 options to choose from. The area is well-suited for families, offering a mix of spacious cabins and charming homes, many of which come equipped with amenities such as full kitchens, large living areas, and outdoor spaces superb for kids to play.Visitors can enjoy the beautiful natural surroundings, with nearby attractions including the Jamaica State Park, which features scenic hiking trails and access to the West River for summer activities. Additionally, families can explore the local community and its quaint shops and restaurants, enhancing the overall experience.
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 feature pools and hot tubs, making it an excellent choice for travellers looking to relax and unwind. The area is known for its picturesque landscapes, and many properties come with amenities such as spacious outdoor decks, private swimming pools, and inviting hot tubs, great for enjoying the serene surroundings after a day of exploring.Visitors can find rentals located in tranquil settings, often equipped with fully stocked kitchens for self-catering, comfortable living spaces, and sometimes even game rooms for family entertainment. The peaceful atmosphere of Jamaica provides an ideal backdrop for a leisurely getaway, with opportunities for hiking, biking, and enjoying the natural beauty of the Green Mountains nearby.
Are there pet-friendly house rentals in Jamaica?
In Jamaica, Vermont, there are several pet-friendly house rentals available, providing an inviting space for travellers with pets. Many of these holiday homes are situated in scenic locations, offering easy access to the beautiful landscapes of the Green Mountains. Expect amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can play.The area is close to various outdoor activities, including hiking and skiing in the winter months, making it a great destination for those looking to explore nature with their furry companions. Additionally, the nearby Jamaica State Park offers trails that are pet-friendly, allowing for enjoyable walks and adventures in the outdoors.
Are there any remote work holiday rentals in Jamaica?
In Jamaica, Vermont, there is a substantial selection of remote work-friendly holiday rentals available, with around 177 options to choose from. Many of these properties are well-equipped to accommodate remote workers, featuring amenities such as high-speed Wi-Fi, dedicated workspaces, and printers. This ensures that guests can maintain productivity while enjoying the scenic beauty of the Green Mountains.The area is known for its charming rural atmosphere, with easy access to outdoor activities such as hiking, skiing, and exploring local trails. Properties often include comfortable living areas, fully equipped kitchens for self-catering, and outdoor spaces to unwind after a day of work or adventure. Jamaica's proximity to various points of interest, including state parks and quaint local shops, adds to its appeal for those seeking a balance of work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Jamaica?
In Jamaica, Vermont, holiday rentals typically feature a variety of popular amenities suiting comfort and convenience. Most properties come equipped with kitchens for self-catering, allowing guests to prepare their own meals. Many rentals also include inviting fireplaces, superb for creating a cosy atmosphere after a day of exploring the area. Outdoor spaces such as decks or patios are common, providing a lovely spot to enjoy the natural surroundings. Onsite parking is usually available, making it easy for travellers with vehicles. Additionally, rentals often feature coffee and tea makers, ensuring that guests can start their day with a warm beverage at their leisure.
When is the best time to visit Jamaica for a holiday rental?
The best time to visit Jamaica, Vermont for a holiday rental is during the peak season from October to December. This period welcomes visitors with vibrant autumn foliage and offers an abundance of outdoor activities amidst stunning natural landscapes. As the leaves change, the region transforms into a picturesque setting, great for hiking and exploring the nearby Green Mountains.December, in particular, is a popular month, as it combines the charm of winter with a festive atmosphere. With average temperatures ranging from -6 to 4 degrees Celsius, visitors can enjoy activities like skiing at local resorts or simply soaking in the quaint winter wonderland. The holiday spirit is palpable, making it an ideal time for families and friends to gather.For those seeking a more budget-friendly option, consider planning your trip in April. While the snow has melted, the spring season presents a beautiful opportunity to witness the rebirth of nature, with blooming flowers and milder temperatures. This quieter time allows for a more relaxed exploration of the area's attractions without the hustle and bustle of peak tourist traffic.
What are the top attractions in Jamaica?
In Jamaica, Vermont, visitors can enjoy a range of attractions that showcase the area's natural beauty and outdoor activities. The Jamaica State Park is a highlight, offering picturesque hiking trails and access to the West River for kayaking and fishing, making it ideal for nature enthusiasts. The park features scenic picnic areas and beautiful views, superb for a relaxing day outdoors.Another attraction is the nearby Stratton Mountain Resort, which attracts visitors year-round. In the winter months, it's a popular destination for skiing and snowboarding, while in the summer, it offers mountain biking and hiking trails.The quaint village of Jamaica itself boasts charming shops and local eateries, where travellers can experience the warmth of the community.
Are all fees included in the Jamaica holiday homes prices shown on Stayz?
Stayz 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.
Are there any Jamaica holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Jamaica holiday homes?
You can find great discounts on holiday homes in Jamaica on Stayz, 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.
Can I change or cancel my Jamaica holiday home booking on Stayz?
To find Jamaica holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Jamaica?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a Jamaica holiday home?
Book your Jamaica holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Jamaica?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Jamaica to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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