Jamaica Holiday Rentals

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Holiday Rentals in Jamaica

Long Trail House at Stratton Mountain Resort

3.0 star property
8.6 out of 10, Excellent, (74)
"Nice, clean room in prime location"
The price is AU$589
includes taxes & fees
19 Aug - 20 Aug
Long Trail House at Stratton Mountain Resort

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

8.8 out of 10, Excellent, (50)
"really enjoyed our stay. Place would be much better if there was a microwave."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

8.0 out of 10, Very good, (38)
"Had a business retreat with 6 associates. The cabin was great and operated as one would expect for a ski cabin. Nice fire place and hot tub. The TVs are older so they have a hard time connecting to the WIFI for Netflix, Prime, etc. I recommend bringing agame console aor "
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (223)
"Cabin was beautiful! Love the little stream outside. Very close to restaurants, shopping, and hiking trails. "
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond

9.6 out of 10, Exceptional, (25)
"Beautiful location and so many cozy touches throughout home!"
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

9.0 out of 10, Wonderful, (26)
"Had a great stay, cozy log cabin, beds were very comfortable. So nice to have a few garbage bags, paper towels, soaps and toiletries!! Also some coffee filters:) Hot tub was great too! "
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

8 min to Stratton, 6 min to golf, 15 min to Manchester. Pet friendly!

8.0 out of 10, Very good, (1)
8 min to Stratton, 6 min to golf, 15 min to Manchester. Pet friendly!

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (157)
"Thank you for a peaceful weekend away in a charming cottage!"
The price is AU$564
includes taxes & fees
19 Aug - 20 Aug
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Solitude Village at Okemo

4.0 star property
8.0 out of 10, Very good, (26)
"Beautiful Area. "
Solitude Village at Okemo

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

10.0 out of 10, Exceptional, (43)
"We enjoyed our stay at the tiny home!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

9.8 out of 10, Exceptional, (21)
"This place was very enjoyable, it was just 3 of us so there was more than enough room. It is a very comfortable home and we enjoyed the easy trip into Manchester for some meals and a wonderful day of hiking some great nearby trails."
The price is AU$998
includes taxes & fees
17 Aug - 18 Aug
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

The Mountain Escape!

9.8 out of 10, Exceptional, (17)
"Good spot for catching up with friends for the weekend. Hot tub was perfect and everything was comfortable."
The price is AU$1,180
includes taxes & fees
7 Aug - 8 Aug
The Mountain Escape!

Home with a spring-fed pond and mountain view.

10.0 out of 10, Exceptional, (117)
"Cute cottage with a lot of charm. The kiddos loved the concept of staying next to a pond. Convenient location to Manchester center and also to Bromley. Jeremy was quick to respond to all to all pf our questions."
Home with a spring-fed pond and mountain view.

Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.

10.0 out of 10, Exceptional, (49)
"Consistently great time at this place (3rd time there)"
Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.

Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults

10.0 out of 10, Exceptional, (24)
"A terrific place. Highly recommended. We had a great family ski vacation."
The price is AU$3,096
includes taxes & fees
10 Aug - 11 Aug
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults

Bright three-level home with water views, jetted tub, firepit, and pool table

8.4 out of 10, Very good, (29)
"Had a fantastic weekend at this cabin. Beautifully maintained, sparking clean and beautiful cabin. Everything was exactly as pictured and is even better in person. Would stay here again x100"
Bright three-level home with water views, jetted tub, firepit, and pool table

Beautiful Custom Built Timber Frame Home, Sleeps 11

10.0 out of 10, Exceptional, (103)
"Home was big, clean, and close to mt snow. We had a great stay. Thanks!"
Beautiful Custom Built Timber Frame Home, Sleeps 11

Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont

10.0 out of 10, Exceptional, (201)
"This location is awesome. Close to town and skiing but we felt like we were secluded in the forest when sitting in the hot tub. We had a great time!"
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont

Home with View of Mount Snow!! Indoor-pool, spa, sauna Gym & more Sleeps 23+

6.0 out of 10, (1)
"Inside property was great - house was very fun and spacious and clean . HOWEVER..the driveway clearly hadn’t been plowed for a long time when we got there and so once we pulled in our cars were stuck. We were trapped at the house for 3 days. The plow driver came to plow the neighbor and told us he hadn’t been paid by the owners so hadn’t been plowing for some time The owners finally arranged for a different plow to come but not being able to leave for 3 days really affected our ability to...
Home with View of Mount Snow!! Indoor-pool, spa, sauna Gym & more Sleeps 23+

Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

10.0 out of 10, Exceptional, (52)
"Would recommend if anyone wants a quiet, peaceful getaway."
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Jamaica Hotel Reviews

Frequently asked questions

Can I find holiday rentals in Jamaica?

Yes, there are holiday rentals close to the most popular sights in Jamaica, or you can select a more secluded option if you're looking for a relaxing stay. Jamaica is known for its mountain views and art. Make sure you have time to check out the monuments while you're in the area.

What are some of the best holiday rentals that Jamaica has to offer?

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable: This holiday home rental outside of Jamaica is located in the city centre, and has a fireplace, a patio and laundry facilities to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

How many holiday rentals are there in Jamaica?

With 35 Expedia holiday rentals, you're guaranteed to find just the right place for your Jamaica stay.

What can I see and do in Jamaica?

Cultural attractions include Hot Glass Works and Margie's Muse Handweaving & Gallery, whereas Green Mountain National Forest and Winhall River are a couple of picturesque spots to enjoy the outdoors. Jamaica State Park and Ball Mountain Dam are other places to visit while you're in town.

What are holiday rentals like in Jamaica?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Jamaica. Holiday rentals offer extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for family gatherings.