Holiday Homes in Jamaica

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Featured Holiday Homes in Jamaica

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

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

8.2 out of 10, Very good, (39)
"This place was great for my family and I. It is very close to Okemo and town "
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Breaktime - Quiet and Private on dead end street

10.0 out of 10, Exceptional, (30)
"I like the location close to mountain walking trails and fine dining options. "
Breaktime - Quiet and Private on dead end street

Ski-in/out home with a hot tub, fireplace, cable & golf nearby

9.4 out of 10, Exceptional, (23)
"Nice and roomy. Plenty of room throughout the entire house. Kitchen area LARGE. back deck was nice with the hot tub. Ski run steps from the house. Really nice place."
Ski-in/out home with a hot tub, fireplace, cable & golf nearby

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

10.0 out of 10, Exceptional, (44)
"We enjoyed our stay at the tiny home!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

Cozy 3 bedroom house on 16 quiet acres, Mtn views, Close to Manchester

9.0 out of 10, Wonderful, (22)
"Property out and peaceful and quiet. View is great thanks."
Cozy 3 bedroom house on 16 quiet acres, Mtn views, Close to Manchester

Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!

10.0 out of 10, Exceptional, (5)
"In town for funeral, the place was great. Very roomy and comfy."
Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!

Timeless Red Sox Retreat w/ Scenic Mountain Views!

10.0 out of 10, Exceptional, (23)
"Beautiful property "
Timeless Red Sox Retreat w/ Scenic Mountain Views!

NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays

10.0 out of 10, Exceptional, (36)
"Our annual trip was great! The house was fantastic and the owners were very friendly and responsive. Would definitely recommend this awesome house!"
NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays

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$1,010
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)
"Easy booking, clean home, great location and the owner very easy to get in touch with."
The price is AU$1,076
includes taxes & fees
1 Sept - 2 Sept
The Mountain Escape!

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

Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

10.0 out of 10, Exceptional, (24)
"Great location close to the slopes. Clean and comfortable. Loved the fireplace. "
Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

10.0 out of 10, Exceptional, (54)
"Clean, ideal location, great communication."
Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

Sleep 20. Pool. Tennis. Dogs loved. Private home on #1 resort on TripAdvisor.

9.8 out of 10, Exceptional, (16)
"Spacious house and beautiful grounds."
Sleep 20. Pool. Tennis. Dogs loved. Private home on #1 resort on TripAdvisor.

Spacious Riverfront Home 7 Minutes to Stratton!

10.0 out of 10, Exceptional, (30)
"Perfect house for a few families to gather and have fun. "
Spacious Riverfront Home 7 Minutes to Stratton!

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

10.0 out of 10, Exceptional, (6)
"Great house, great location, Great communication with Todd. Will be back for sure!!!! Thanks for everything Todd. "
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

The S T A C K HAUS on golf course/10 mins to Lake Witingham <br>

9.8 out of 10, Exceptional, (6)
The S T A C K HAUS on golf course/10 mins to Lake Witingham <br>

My Abode: Heated Pool - Hot Tub, Tennis court, Firepit, Sauna, Gym, Hot Tub

My Abode: Heated Pool - Hot Tub, Tennis court, Firepit, Sauna, Gym, Hot Tub
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.
Save an average of 15% on thousands of hotels when you're signed in