Jamaica vacation rentals

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Top-rated vacation rentals in Jamaica

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Jamaica

4.82 out of 5 average rating, 464 reviews

Forest Cottage ~ 7min to Stratton, Private, Views

Authentic Vermont post & beam cottage with privacy. 3 miles to Stratton's Sun Bowl, a 7-minute drive. Nearby swimming hole at the brook on the property. Dogs welcome, $30 fee per dog. No cats due to allergies. Vinyl record player, VCR/DVD player, board games, Starlink Satellite Internet 20-100 mbps. Heat options: 2 gas wall furnaces & wood stove. Front porch, propane BBQ, fire pit, picnic table & spectacular views of Stratton Mountain. Back deck surrounded by woods with hammock, table & chairs.

May 8 – 15

G$22,883 GYD per night

Guest favorite

Cabin in Londonderry

4.93 out of 5 average rating, 308 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond in S Londonderry, VT. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery and hiking right outside your front door. The Cabin has an open floor plan with a galley kitchen, dining/living area with pullout futon couch & 1 full bathroom. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

Nov 5 – 12

G$21,367 GYD per night

Guest favorite

Home in Jamaica

5.0 out of 5 average rating, 100 reviews

Stratton Spa House with Man Cave

MANAGED BY A 5 STAR TEAM WITH MULTIPLE 5 STAR HOMES Perched on a babbling brook this 4700 square ft. contemporary has all your needs covered. Smart tech, 3 fireplaces, man cave, streaming entertainment, home theater, spa suite, hot tub, sauna, pool table, darts, poker room, dueling xbox room, giant master suite, big guest suite with wood burning stove, large dining table, fully equipped kitchen, Keurig, screened porch, 3 private acres, sun deck, bbq, 1/4m walk to water falls and swimming hole.

May 12 – 19

G$84,042 GYD per night

Guest favorite

Cabin in Jamaica

4.99 out of 5 average rating, 185 reviews

New Cabin in Jamaica

Recently constructed 500sq ft passive solar cabin, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

Sep 16 – 23

G$31,453 GYD per night

Guest favorite

Guesthouse in Jamaica

4.95 out of 5 average rating, 133 reviews

The Chick Inn

This is a two-story, renovated barn adjacent to the chicken coop in rural Vermont with views of the forests. It has brand new floors, a new kitchenette, and fresh look. (Some renovation is still taking place.) The chicken coop is just next door but the birds are free-range and range they will. Enjoy a private, hot shower in the garden, just outside. This listing is only suitable for people comfortable with dogs, cats, and chickens which will undoubtedly greet you outside during your stay.

May 29 – Jun 5

G$20,263 GYD per night

Guest favorite

Apartment in Jamaica

4.84 out of 5 average rating, 199 reviews

The Getaway

Nestled in the woods but yet only; 10 min. (5.3 mls) to Stratton Mtn, 11 min. (7.6 mls) to Bromely Mtn, 26 min. (18.2 mls) to Magic Mtn, 33 min. (19.2 mls) to Mount Snow, 50 min. (38.2 mls) to Okemo and 68 min. (51.2 mls) to Killington. Also only minutes away from Southern Vermont golf resorts, Appalachian, Long and West River Trails, beautiful ponds rivers and falls, state parks, Manchester outlet shopping and the Equinox, fine dining and the most brilliant foliage in New England.

Mar 18 – 25

G$28,183 GYD per night

Guest favorite

Barn in Marlboro

4.95 out of 5 average rating, 263 reviews

The Studio With a View. Bring your dog, too!

Our stylish Studio, a not so tiny Tiny House, is nestled into the Southern Vermont hillside and surrounded by nature. Enjoy the view from the deck, and cozy up in the newly renovated flower barn with a cup of coffee or tea and a great book. Well-mannered dogs are welcome, they will enjoy the fenced-in area right off the deck. Features: efficiency kitchen and dining area, cozy living space, queen-size bed, and a full bathroom. The large covered porch overlooks fields and trees.

Jan 7 – 14

G$29,244 GYD per night

Guest favorite

Barn in Chester

4.99 out of 5 average rating, 493 reviews

Inviting studio apartment above barn in Vermont

This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. We are as close or as far away as you would like us to be with our house right next door.

Aug 31 – Sep 7

G$21,418 GYD per night

Guest favorite

Apartment in Brattleboro

4.95 out of 5 average rating, 150 reviews

Contemporary forest eco-retreat, mountain views

This is an open, light-filled one-Bdm apartment on the lower level of our hillside home, surrounded by forests, with stunning views. Your space is 719 sf + access to laundry. We are fully vaccinated, and ask the same of guests. If you think you may have Covid please tell us. We welcome all kinds of people, regardless of race, ethnicity, gender, etc. We may ask questions before accepting people who don’t have many prior reviews. We don't take pets, sorry.

May 1 – 8

G$24,704 GYD per night

Guest favorite

Tiny home in Jamaica

4.85 out of 5 average rating, 214 reviews

Hot Tub Farmhouse - Buttercup Studio - Jamaica VT.

The calendar is accurate. Hot Tub accommodates 2-3 people comfortably. This private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, and porch. Comfortable for up to 4 people. We are committed to AirBnB's enhanced cleaning protocol. All high-touch surfaces are sanitized. We provide extra cleaning supplies for our guests to use as they desire.

Oct 22 – 29

G$21,739 GYD per night

Guest favorite

Apartment in Andover

4.98 out of 5 average rating, 386 reviews

Private Hilltop farm apartment

Our cozy apartment is located on a beautiful hilltop farm with views out from the porch across horse pasture and to the mountains as far away as New Hampshire. There are over 100 acres of field to walk through as well as a mile long trail running down through our property. We are 15 minutes from Chester, Ludlow and Weston. We also have very fast internet!

Sep 16 – 23

G$23,383 GYD per night

Guest favorite

Apartment in Londonderry

4.94 out of 5 average rating, 333 reviews

Cozy Suite in a Historic Building Near Ski Resorts

Located on the second floor of a historical building in the Village of South Londonderry, Vermont, this renovated studio suite features unique touches of modern amenities but with a Vermont feel. Your room will include a 65 inch Smart TV, WiFi, electric fireplace, lush queen bed, full renovated bathroom, small kitchenette, as well as on site parking.

Jun 27 – Jul 4

G$26,892 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Jamaica vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Jamaica's top sights

Honeypie122 locals recommend

Winhall Brook Campground4 locals recommend

Workhorse Cafe35 locals recommend

Hamilton Falls27 locals recommend

Ungrounded Coffee Roasters27 locals recommend

Fran's Kitchen & Diner18 locals recommend

Other great vacation rentals in Jamaica

Guest favorite

Chalet in Dover

4.93 out of 5 average rating, 265 reviews

A charming VT chalet

Nov 11 – 18

G$32,115 GYD per night

Guest favorite

Cottage in Dover

4.95 out of 5 average rating, 216 reviews

Cozy summer cottage in the woods of southern VT

Aug 7 – 14

G$24,682 GYD per night

Guest favorite

Tiny home in Wilmington

4.99 out of 5 average rating, 140 reviews

Beautiful Timber Frame Retreat

Sep 13 – 20

G$45,778 GYD per night

Guest favorite

Apartment in Townshend

4.94 out of 5 average rating, 203 reviews

Private Apt. on Farm, great views and Hot tub,

Nov 5 – 12

G$32,362 GYD per night

Guest favorite

Guest suite in Brattleboro

4.94 out of 5 average rating, 518 reviews

Charming studio in renovated 19th century church.

Dec 17 – 24

G$19,439 GYD per night

Superhost

Home in Jamaica

4.84 out of 5 average rating, 232 reviews

Historic 1832 Parker House ~ Sleeps 10, Pool Table

Oct 5 – 12

G$38,103 GYD per night

Guest favorite

Cottage in Newfane

4.99 out of 5 average rating, 175 reviews

Cozy Vermont Antique Sugar House with Fireplace

Aug 31 – Sep 7

G$32,329 GYD per night

Guest favorite

Cottage in Newfane

4.89 out of 5 average rating, 216 reviews

Ridgeview: Cozy Cottage with a View

Dec 5 – 12

G$29,311 GYD per night

Show all

Other great vacation rentals in Jamaica

Guest favorite

Apartment in Bennington

4.93 out of 5 average rating, 527 reviews

The Octopus's Garden

Sep 26 – Oct 3

G$20,315 GYD per night

Guest favorite

Apartment in Manchester

4.99 out of 5 average rating, 147 reviews

Private two-bedroom suite within a two-story house

G$14,594 GYD per night

Guest favorite

Guest suite in Newfane

4.93 out of 5 average rating, 177 reviews

Cute studio apt on lovely historic VT farm

May 20 – 27

G$21,413 GYD per night

Guest favorite

Cabin in Newfane

4.99 out of 5 average rating, 238 reviews

Log Cabin: Amazing Views, River Frontage, Hot Tub

Feb 19 – 26

G$56,272 GYD per night

Guest favorite

Apartment in Dummerston

4.96 out of 5 average rating, 160 reviews

HeART Barn Retreat

Oct 13 – 20

G$18,390 GYD per night

Guest favorite

Apartment in Londonderry

4.97 out of 5 average rating, 554 reviews

Vermont Getaway Apartment

Aug 6 – 13

G$37,788 GYD per night

Guest favorite

Home in Jamaica

5.0 out of 5 average rating, 26 reviews

2-Bedroom Home, 7 Minutes From Stratton Mountain

Jan 25 – Feb 1

G$33,411 GYD per night

Guest favorite

Condo in Londonderry

4.95 out of 5 average rating, 43 reviews

Magical Ski-In/Ski-Out Condo at Magic w/ game room

Jul 21 – 28

G$22,275 GYD per night

Show all

Quick stats about vacation rentals in Jamaica

Total rentals
230 properties
Rentals with a pool
20 properties have a pool
Pet-friendly rentals
100 properties allow pets
Family-friendly rentals
190 properties are a good fit for families
Total number of reviews
13K reviews
Nightly prices starting at
G$4,170 GYD before taxes and fees

Frequently Asked Questions

Are there pet-friendly vacation rentals in Jamaica?
Four-legged friends are welcome in Jamaica. Choose from more than 100 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Jamaica?
Yes! Work meets play with ease at over 130 vacation rentals in Jamaica featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in Jamaica?
Experience the best of Jamaica with our house rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Jamaica have wifi?
Absolutely! We offer over 130 house rentals with wifi in Jamaica. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Jamaica have a bbq area?
Absolutely! We offer over 50 cabin rentals with a bbq area in Jamaica. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Jamaica have a gym?
Absolutely! We offer over 10 house rentals with a gym in Jamaica. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Jamaica have air conditioning?
Absolutely! We offer over 40 house rentals with air conditioning in Jamaica. Enjoy a tailored experience with all the comforts you desire.
Are there Jamaica house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 house rentals with pools in Jamaica, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly cabin rentals in Jamaica?
Jamaica has more than 20 family-friendly cabin rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Cabin Rentals in Jamaica?
Enhance your stay in our Cabin Rentals with the most popular amenities: over 30 homes with wifi, over 50 homes with a bbq area, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Jamaica vacation rentals

Top-rated vacation rentals in Jamaica

Vacation rentals for every style

Houses

Cabins

Hotels

Popular amenities for Jamaica vacation rentals

Stay near Jamaica's top sights

Other great vacation rentals in Jamaica

Chalet in Dover

Cottage in Dover

Tiny home in Wilmington

Apartment in Townshend

Guest suite in Brattleboro

Home in Jamaica

Cottage in Newfane

Cottage in Newfane

Other great vacation rentals in Jamaica

Apartment in Bennington

Apartment in Manchester

Guest suite in Newfane

Cabin in Newfane

Apartment in Dummerston

Apartment in Londonderry

Home in Jamaica

Condo in Londonderry

Quick stats about vacation rentals in Jamaica

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there pet-friendly vacation rentals in Jamaica?

Are there vacation rentals with a dedicated workspace in Jamaica?

How much does it cost to stay in house rentals in Jamaica?

Do house rentals in Jamaica have wifi?

Do cabin rentals in Jamaica have a bbq area?

Do house rentals in Jamaica have a gym?

Do house rentals in Jamaica have air conditioning?

Are there Jamaica house rentals on Airbnb with pools?

Are there family-friendly cabin rentals in Jamaica?

What are the most popular amenities for Cabin Rentals in Jamaica?

Destinations to explore