Jamaica Vacation Homes

Jamaica Vacation Homes
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A beautiful 3 mile hike to the Hamilton Falls in Jamaica State Park is well worth the trip. Such a peaceful experience and great camping in the campground. Other hiking options close by also.

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Our top choices for Jamaica holiday homes

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)

9.0/10

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 !"

Michael C.

The price is HK$2,684

HK$2,684

HK$5,688 total

includes taxes & fees

4 Feb - 5 Feb

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

Family Friendly Hilltop House In Putney Vermont

Putney

9.4 out of 10, Exceptional, (59 reviews)

9.4/10

Exceptional

(59 reviews)

"The property was beautiful--great views, super peaceful, and fabulous hosts. "

Louis T.

The price is HK$1,428

HK$1,428

HK$2,542 total

includes taxes & fees

4 Feb - 5 Feb

Family Friendly Hilltop House In Putney Vermont

Luxury Condo Stratton Mountain

Stratton

10.0 out of 10, Exceptional, (1 review)

10/10

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! "

Katryn B.

The price is HK$15,601

HK$15,601

HK$20,145 total

includes taxes & fees

3 Feb - 4 Feb

Luxury Condo Stratton Mountain

Secluded Vermont Chalet w/ Sweeping Mountain Views

Dover

Secluded Vermont Chalet w/ Sweeping Mountain Views

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

Ludlow

9.8 out of 10, Exceptional, (104 reviews)

9.8/10

Exceptional

(104 reviews)

"Had a wonderful stay. Clean,well kept and cozy."

Edwin G.

The price is HK$1,874

HK$1,874

HK$3,695 total

includes taxes & fees

2 Feb - 3 Feb

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

1 bedroom, Internet, bed sheets, wheelchair access

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

Stratton

7.6 out of 10, Good, (54 reviews)

7.6/10

Good

(54 reviews)

"Location was great, pool, hot tubs and sauna were great"

Lin M.

The price is HK$920

HK$920

HK$2,768 total

includes taxes & fees

11 Feb - 12 Feb

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

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

Walpole

10.0 out of 10, Exceptional, (50 reviews)

10/10

Exceptional

(50 reviews)

"We had a very lovely stay. "

mary c.

The price is HK$2,275

HK$2,275

HK$4,661 total

includes taxes & fees

2 Feb - 3 Feb

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

Chester Farmhouse Ski Retreat near Slopes

Chester Depot

9.6 out of 10, Exceptional, (18 reviews)

9.6/10

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. "

Lori N.

The price is HK$1,623

HK$1,623

HK$3,268 total

includes taxes & fees

10 Feb - 11 Feb

Chester Farmhouse Ski Retreat near Slopes

2 bedrooms, desk, iron/ironing board, WiFi

Stratton Woods · Secluded Vermont Cabin Retreat

Wardsboro

The price is HK$1,303

HK$1,303

HK$3,503 total

includes taxes & fees

3 Feb - 4 Feb

Stratton Woods · Secluded Vermont Cabin Retreat

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

Dover

10.0 out of 10, Exceptional, (11 reviews)

10/10

Exceptional

(11 reviews)

"Beautiful neighborhood to take walks. Home was very clean, as you see in the photo. Very spacious and relaxing. Pretty home overall."

Stephen G.

The price is HK$5,582

HK$5,582

HK$11,351 total

includes taxes & fees

2 Feb - 3 Feb

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

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

Dover

9.8 out of 10, Exceptional, (6 reviews)

9.8/10

Exceptional

(6 reviews)

"We enjoyed our stay."

Anonymous traveller

The price is HK$1,748

HK$1,748

HK$4,444 total

includes taxes & fees

5 Feb - 6 Feb

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

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

Londonderry

8.0 out of 10, Very good, (1 review)

8.0/10

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. "

Christine M.

The price is HK$1,980

HK$1,980

HK$3,868 total

includes taxes & fees

4 Feb - 5 Feb

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

Bear Pass - Mountain View 4 Bedroom Home by RedAwning

3.0 star property

Arlington

8.0 out of 10, Very good, (1 review)

8.0/10

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. "

Manish

The price is HK$1,908

HK$1,908

HK$5,267 total

includes taxes & fees

10 Feb - 11 Feb

Bear Pass - Mountain View 4 Bedroom Home by RedAwning

Smart TV, fireplace, video games, offices

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)

10/10

Exceptional

(18 reviews)

"Very pet friendly place! We enjoyed our stay"

Kurt K.

The price is HK$2,356

HK$2,356

HK$5,459 total

includes taxes & fees

3 Feb - 4 Feb

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

Fridge, microwave, oven, coffee/tea maker

Bear Pass - Mountain View by RedAwning

Sunderland

9.6 out of 10, Exceptional, (5 reviews)

9.6/10

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"

Megan G.

The price is HK$3,090

HK$3,090

HK$6,809 total

includes taxes & fees

16 Feb - 17 Feb

Bear Pass - Mountain View by RedAwning

Cozy Vermont Cabin · Mountain Views · Near Okemo

Chester

10.0 out of 10, Exceptional, (3 reviews)

10/10

Exceptional

(3 reviews)

"We really enjoyed our stay at this home. It had everything we needed and was very comfortable. The countryside around this part of Vermont is beautiful. We found lots of great museums and restaurants. "

Donald M.

The price is HK$4,907

HK$4,907

HK$8,659 total

includes taxes & fees

1 Feb - 2 Feb

Cozy Vermont Cabin · Mountain Views · Near Okemo

Smart TV, fireplace, video games, stereo

4 bedrooms, desk, iron/ironing board, travel cot

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

Dover

10.0 out of 10, Exceptional, (4 reviews)

10/10

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. "

Jason K.

The price is HK$2,915

HK$2,915

HK$7,191 total

includes taxes & fees

11 Feb - 12 Feb

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

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)

10/10

Exceptional

(51 reviews)

"Had a great time."

Neetesh B.

The price is HK$7,506

HK$7,506

HK$16,222 total

includes taxes & fees

9 Feb - 10 Feb

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

MtSnow* HotTub* Pool * AirHockeyPingPong Darts

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

Wilmington

The price is HK$1,863

HK$1,863

HK$5,184 total

includes taxes & fees

1 Feb - 2 Feb

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

3 bedrooms, desk, iron/ironing board, travel cot

New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly

Wilmington

The price is HK$1,950

HK$1,950

HK$4,451 total

includes taxes & fees

2 Feb - 3 Feb

New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet 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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