Search Vacation Homes in Jamaica

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Jamaica vacation homes

Family-friendly A-Frame near Stratton, Bromley & Magic — hot tub retreat in the quiet, peaceful woods

Family-friendly A-Frame near Stratton, Bromley & Magic — hot tub retreat in the quiet, peaceful woods
Jamaica
9.0 out of 10, Wonderful, (6 reviews)
"Great location. House was recently updated but has some older charm in parts. Fun and cozy. Hot tub was great the first day but smell seemed off the next day. Perhaps more chlorine was needed. Great time , great trip. Pet friendly is a bonus and the house looks never used so the cleaning crew is doing great work. Will rent again next year perhaps !"
United States
Michael C.
Family-friendly A-Frame near Stratton, Bromley & Magic — hot tub retreat in the quiet, peaceful woods

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (59 reviews)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
United States
Louis T.
The price is ¥28,493
¥50,571 total
includes taxes & fees
Jan 27 - Jan 28
Family Friendly Hilltop House In Putney Vermont

The Dorothy-10 minutes from Okemo- freshly renovated

The Dorothy-10 minutes from Okemo- freshly renovated
Cavendish
9.2 out of 10, Wonderful, (5 reviews)
"We had an enjoyable stay! Our hosts were very communicative and thought of the details for our stay!"
United States
Maya T.
The Dorothy-10 minutes from Okemo- freshly renovated

Luxury Condo Stratton Mountain

Luxury Condo Stratton Mountain
Stratton
10.0 out of 10, Exceptional, (1 review)
"Katherine was a perfect host. The house is beautiful and had everything we needed for our family vacation. Thank you so much! "
United States
Katryn B.
The price is ¥311,400
¥410,892 total
includes taxes & fees
Jan 26 - Jan 27
Luxury Condo Stratton Mountain

Chester Farmhouse Ski Retreat near Slopes

Chester Farmhouse Ski Retreat near Slopes
Chester Depot
9.6 out of 10, Exceptional, (18 reviews)
"This was my second time staying at this property. Everything was great just like last year. I highly recommend it if you are staying in Chester, VT. "
United States
Lori N.
The price is ¥29,427
¥62,080 total
includes taxes & fees
Jan 28 - Jan 29
Chester Farmhouse Ski Retreat near Slopes

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Londonderry
8.0 out of 10, Very Good, (1 review)
"I was "sold" & excited when I saw the pictures online bc the barn looked really neat. Although the barn was a neat concept, the pictures ARE NOT accurate, it is not as updated as pictured & it was VERY DISAPPOINTING. I now understand the non-refundable policy bc what you see online is definitely NOT what you walked into when you opened the door & they don't want to have to give people their back. Although we had fun, the accommodations were VERY misleading & disappointing. "
United States
Christine M.
The price is ¥39,517
¥77,730 total
includes taxes & fees
Jan 28 - Jan 29
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Walpole
10.0 out of 10, Exceptional, (50 reviews)
"We had a very lovely stay. "
United States
mary c.
The price is ¥43,580
¥90,869 total
includes taxes & fees
Jan 26 - Jan 27
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Secluded Vermont Chalet w/ Sweeping Mountain Views

Secluded Vermont Chalet w/ Sweeping Mountain Views
Dover
The price is ¥22,265
¥80,536 total
includes taxes & fees
Jan 26 - Jan 27
Secluded Vermont Chalet w/ Sweeping Mountain Views

Stratton Woods · Secluded Vermont Cabin Retreat

Stratton Woods · Secluded Vermont Cabin Retreat
Wardsboro
The price is ¥26,002
¥69,730 total
includes taxes & fees
Feb 3 - Feb 4
Stratton Woods · Secluded Vermont Cabin Retreat

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Dover
9.8 out of 10, Exceptional, (6 reviews)
"We enjoyed our stay."
United States
Anonymous traveler
The price is ¥34,892
¥89,747 total
includes taxes & fees
Jan 27 - Jan 28
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Stratton
7.6 out of 10, Good, (54 reviews)
"Location was great, pool, hot tubs and sauna were great"
United States
Lin M.
The price is ¥19,774
¥57,332 total
includes taxes & fees
Jan 28 - Jan 29
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Dover
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful neighborhood to take walks. Home was very clean, as you see in the photo. Very spacious and relaxing. Pretty home overall."
United States
Stephen G.
The price is ¥111,403
¥226,526 total
includes taxes & fees
Jan 26 - Jan 27
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (104 reviews)
"Had a wonderful stay. Clean,well kept and cozy."
United States
Edwin G.
The price is ¥35,453
¥71,185 total
includes taxes & fees
Jan 28 - Jan 29
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Wilmington
10.0 out of 10, Exceptional, (18 reviews)
"Very pet friendly place! We enjoyed our stay"
United States
Kurt K.
The price is ¥56,052
¥120,583 total
includes taxes & fees
Feb 25 - Feb 26
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

Bear Pass - Mountain View 4 Bedroom Home by RedAwning

Bear Pass - Mountain View 4 Bedroom Home by RedAwning
3.0 star property
Arlington
8.0 out of 10, Very Good, (1 review)
"Cozy cottage. Very clean and everything you need is there. Nice kitchen and fireplace. Lots of room and 3 bathrooms as well. Reasonably close to the ski mountains. "
United States
Manish
The price is ¥38,076
¥105,101 total
includes taxes & fees
Feb 2 - Feb 3
Bear Pass - Mountain View 4 Bedroom Home by RedAwning

Bear Pass - Mountain View by RedAwning

Bear Pass - Mountain View by RedAwning
Sunderland
9.6 out of 10, Exceptional, (5 reviews)
"We loved our stay at Bear Pass! The kitchen was more than adequately stocked. The hous was great for our extended family and our 3 dogs"
United States
Megan G.
The price is ¥39,154
¥105,513 total
includes taxes & fees
Jan 26 - Jan 27
Bear Pass - Mountain View by RedAwning

Stratton + Mt. Snow family getaway with Hot Tub, Fire Pit, Game Room, and AC!

Stratton + Mt. Snow family getaway with Hot Tub, Fire Pit, Game Room, and AC!
Wardsboro
10.0 out of 10, Exceptional, (16 reviews)
"The house was beautiful and had everything we needed. We would definitely stay again"
United States
Bonnie P.
The price is ¥68,664
¥147,087 total
includes taxes & fees
Feb 5 - Feb 6
Stratton + Mt. Snow family getaway with Hot Tub, Fire Pit, Game Room, and AC!

3 min to Mt Snow & FREE Shuttle! Family-Size fun, Wood Fireplace, Arcades.

3 min to Mt Snow & FREE Shuttle! Family-Size fun, Wood Fireplace, Arcades.
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Great place! There was plenty of room for our family of five and absolutely loved the 5 min drive to the slopes. The check in and out process was seamless. "
United States
Jason K.
The price is ¥58,193
¥143,524 total
includes taxes & fees
Jan 26 - Jan 27
3 min to Mt Snow & FREE Shuttle! Family-Size fun, Wood Fireplace, Arcades.

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (84 reviews)
"We had a great stay at this home for a long weekend skiing at Okemo. "
United States
Lisa W.
The price is ¥33,211
¥68,300 total
includes taxes & fees
Jan 27 - Jan 28
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VT

6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VT
Manchester Center
10.0 out of 10, Exceptional, (51 reviews)
"Had a great time."
United States
Neetesh B.
The price is ¥149,939
¥321,092 total
includes taxes & fees
Feb 3 - Feb 4
6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester 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.
Save an average of 15% on thousands of hotels when you're signed in

Top Jamaica Hotel Reviews

Find out more about Jamaica

Jamaica Vacation Homes information

Number of reviews
454
Accommodation
815 Vacation Homes
Lowest Price
¥50,571
Highest Price
¥410,892