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Compare 950 Vacation Homes in Jamaica with updated reviews, rates, and availability.

Secluded home with game room, private hot tub, golf, river & mtn views, firepit

9.6 out of 10, Exceptional, (7)
"The property is secluded but close enough to shops and restaurants. The deck is amazing with a jacuzzi and lounge chairs overlooking the golf course and mountains! Would definitely stay at again!"
Secluded home with game room, private hot tub, golf, river & mtn views, firepit

Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer

8.6 out of 10, Excellent, (4)
"House was great. We were able to walk up the road with our skis and drop right in. I’d definitely stay here again."
Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer

Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

10.0 out of 10, Exceptional, (167)
"Our second time staying here and it was just as great as the first. A wonderful home and excellent hosts."
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

Potter's Place | House in Jamaica with mountain views

9.6 out of 10, Exceptional, (4)
"Stayed at this lovely home for a short weekend trip in the winter. Very convenient location, clean and well kept. Be sure to have AWD and proper tires if you visit in the winter!"
Potter's Place | House in Jamaica with mountain views

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

8.0 out of 10, Very Good, (38)
"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

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

10.0 out of 10, Exceptional, (6)
"We had an absolute amazing stay at Toddā€˜s place. Communication was extremely responsive. This was a last-minute trip with the family during the holiday and we had an absolute blast. The kids had so much fun in the bunk bedroom. The house is extremely spacious and absolutely beautiful. To be able to ski to the backyard was such a luxury. This was a special house with an unreal location. We will be coming back in February. Thank you so much for the memories."
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Cozy retreat near slopes

5.0 out of 10, (8)
"Unit is a little outdated but nice.Not truly a ski in - out since you have to walk on the road about 200 yards to get to the Sachem trail.Condo does need ice cube trays since the ice maker is not working.Also the down stairs bath room heater does not work and would be nice since this is where the bath tub is located"
Cozy retreat near slopes

GAMERS HAVEN, River Wine Inn!

2.0 star property
10.0 out of 10, Exceptional, (11)
"The property is very large. Lots of sleeping area. Many activities within the rental to keep everyone off all ages busy, kept finding new things in nooks and crannies. Lots of property got our dog to run. "
GAMERS HAVEN, River Wine Inn!

Walk to Okemo Ski Lift - Private Classic VT Ski Chalet w/ Fire Pit & Pool Table

10.0 out of 10, Exceptional, (107)
"Great house for our family of 7. Plenty of room in the house to spread out. Enjoyed the fireplace - plenty of wood provided."
Walk to Okemo Ski Lift - Private Classic VT Ski Chalet w/ Fire Pit & Pool Table

Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

10.0 out of 10, Exceptional, (57)
"The barn is beautiful and much more spacious than it looks in the photos. The property the barn is on is also beautiful, a short drive from the town center, and also close to cool sites to visit like the Lincoln House and many amazing hiking trains."
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

Family Friendly Hilltop House In Putney Vermont

9.6 out of 10, Exceptional, (54)
"We were caught in the winter storm, and the host was so kind in helping us navigate our car situation. Our kids had such a great time playing in the snow, exploring the books and games they had. "
The price is AEDĀ 716
AEDĀ 1,251 total
includes taxes & fees
9 May - 10 May
Family Friendly Hilltop House In Putney Vermont

Ground-floor apartment with pool, hot tub, tennis & gym access - near skiing

9.2 out of 10, Wonderful, (5)
"Close to skiing"
Ground-floor apartment with pool, hot tub, tennis & gym access - near skiing

7200 sf Villa & Barn on 4 Acre Manchester Estate

9.6 out of 10, Exceptional, (8)
"This rental was stunning! Such a cool property with so many different spaces for a large group to spend time. Everything was labeled for ease of access (very grateful for this!), we enjoyed many of the amenities, and communication with the host was fast! Wonderful stay with no issues!H"
7200 sf Villa & Barn on 4 Acre Manchester Estate

Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen

10.0 out of 10, Exceptional, (2)
"Beautiful house well stocked with spices and everything you need. The only thing they are missing is there’s no hairdryer and I called a few times to the property manager for a blanket because the master upstairs has no blanket and I never received one."
Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen

Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Indoor Pool, Golf, Hike, Relax!

10.0 out of 10, Exceptional, (1)
"We had such a lovely time in this well loved cabin. Super quiet location and well stocked with everything we needed for our end of year ski trip in Stratton. The owner was very friendly and helpful. We hope we will be back soon!"
Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Indoor Pool, Golf, Hike, Relax!

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

10.0 out of 10, Exceptional, (36)
"Great space for our 3 families. Would book again."
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, (18)
"Family ski weekend. Our stay was very comfortable. Communication with host was phenomenal, always prompt and courteous Location is nice , very close to the ski resorts "
The price is AEDĀ 744
AEDĀ 2,365 total
includes taxes & fees
12 May - 13 May
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Okemo Mountain Lodging

3.5 star property
7.8 out of 10, Good, (27)
"We are so impressed with the lodging. We will definitely be back. "
Okemo Mountain Lodging

Wilmington Vacation Rental Near Hiking and Skiing!

9.4 out of 10, Exceptional, (19)
"Perfect weekend house close to mt snow"
Wilmington Vacation Rental Near Hiking and Skiing!

Mountain-view home near the slopes with at-home entertainment - dog-friendly

7.8 out of 10, Good, (68)
"Several items, microwave and dishwasher, were not working. House was somewhat clean. Great location, but very dated and in need of a upgrade."
Mountain-view home near the slopes with at-home entertainment - dog-friendly
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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Other property types in Jamaica

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

9.8 out of 10, Exceptional, (18)
"Family ski weekend. Our stay was very comfortable. Communication with host was phenomenal, always prompt and courteous Location is nice , very close to the ski resorts "
The price is AEDĀ 744
AEDĀ 2,365 total
includes taxes & fees
12 May - 13 May
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

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

9.6 out of 10, Exceptional, (209)
"Perfect get away. "
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

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 AEDĀ 624
AEDĀ 1,345 total
includes taxes & fees
8 May - 9 May
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
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.