
House holiday rentals in Jamaica
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Top-rated house rentals in Jamaica
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Popular amenities for Jamaica house rentals
House rentals with a pool

Magical Farm Getaway - a must visit!
We had a wonderful & relaxing weekend here with a large group for my sister's lowkey bachelorette party. Even with a day of non-stop pouring rain, we were perfectly content with staying in and enjoying the coziness of the house. We had a blast watching the chickens roam around and hanging out with the overly-friendly barn cats while we sat outside. The goats & pigs were happy to greet us at the fence every time. The hot tub and pool were perfect! Highly recommend staying here if you're looking for a beautifully scenic and peaceful getaway. Thanks, Sarah & BBVF team!

The 1770 House
Historic house on a beautiful property. Kitchen had all the equipment you could need along with top of the line stove and oven. Make cooking for a large group easy and enjoyable!

Private chalet tucked in the green mountains
We had a wonderful weekend at Liz’s cabin. Everything was clean. Hot tub was awesome. Would recommend to anyone looking for a beautiful cabin getaway.

The Brick House on Washington Street
Great stay and was exactly what we needed for our entire family for a weekend wedding!

Family/Dog Friendly Mountain Home w/ Amenities
The house was just outstanding!! Beyond our expectations. We had so much fun at the house with such great facilities and wonderful location.

Historic Home on 17 acres of land. Go escape!
Staying here is always a joy for the entire family! It has become an annual tradition that we all look forward to in winter. Thank you for being so accommodating with our schedule and a special thanks to Mitchell for going the extra mile to snow blow a waking path for me and the dogs to keep our daily routine of visiting the horses, after the last storm brought over 13” of snow. P.S. the new stove/oven is amazing!! 🤩

Wander In | Close to Mount Snow & Stratton
This place was a dream for families. We traveled with 4 children and an infant. The house was roomy for the whole crew to hang out and eat together. We loved how clean and organized it was. We enjoyed hours at the pool, which was a huge hit with the littles. VRM was very helpful with any questions that came up. The location was great for skiing at Mt. Snow. We wish we had stayed one more night but our infant became very sick and had to head back a day early. To be honest, the place is more beautiful in person than in the pictures and we feel so lucky to have been able to stay there. Big plus to have laundry on site. Kitchen has everything you need to cook all your meals.

Historic 1850’s Renovated Farmhouse w/ Pool!
9 adults and 3 children all met up for a family weekend! We came from NY, NH and Maine! The house was perfect! Plenty of room to gather or separate! Even tho it was a chilly rainy weekend the kids managed to get in plenty of pool time! Tanya was very responsive and Melvin was the greatest! Our first morning he came right over to fix a slow drain. Highly recommend!! Kim and family
Weekly house rentals

Highland Haus: stunning ski getaway with hot tub
The home and location are great, but the hosts are what make this place. They go above and beyond to make your stay special.

The Mountain Escape
Great space! We were comfortable with a big group here, and loved being so close to the slopes. Hot tub seems new and is in great condition.

Magic Cottage in Jamaica Vermont
Melanie’s place was terrific! It is a great comfortable place, plenty of size for the whole family. We cooked great family meals in the evening and enjoyed the board games in the house. Approximately equal distance to Stratton, Magic or Mt Snow- 25min

Mountain Log Cabin near Stratton
Daniel's cabin in the woods was comfortable and cozy, and only a 5 minute drive from the Sunbowl lot at Stratton Mountain. It was perfect for me and my kids for a weekend ski vacation, and the icing on the cake was the the sauna which was so relaxing each afternoon after skiing.

Stratton; 8 min! Swimming, 2 min. Pet friendly
Kelly was very responsive and helpful. She went out of her way to get us a last minute booking and it didn’t disappoint! It was clean, well stocked and very comfortable! I will definitely book this again when its available!!!

Cozy Cottage at Cold Moon Farm!
Very cozy cottage for a short ski trip. It was nice and clean, and it was in a very convenient location near Stratton.

Minutes from Stratton Mountain
Theresa's place is a hidden gem off of Vermont's scenic route 100. My husband and I with another couple of friends stayed there for a weekend as we came to explore the green mountain forest area. The property is conveniently located at 5-10 min driving distance from local restaurants and cafes. There is also a grocery store and gas station nearby. The house itself has a cozy, rustic charm and is stocked with various books, board games, DVD classics, etc for entertainment. The kitchen has all the cutlery, pots and pans, required to cook a meal or two. The bedrooms are cozy each with a window opening onto lush green forested surroundings. Theresa was very responsive and accommodated our request for a slightly early check-in as one of us was travelling with a hip issue. Overall, I would highly recommend staying at Theresa's idyllic home.

New Hot Tub! Gas Fireplace! 2 min to Mt Snow
We loved staying in your home. It was close to Mount Snow where we went skiing and we especially loved the fireplace and hot tub. The kitchen was so big and had everything we needed. Thanks so much for leaving the binder of instructions because it is important for us to treat your home like our own home and we want to do things right. We will be back next year. Tom and Stacie
Private house rentals

Lakefront gem
Our stay at the lake was truly amazing! The house was impeccably clean and well-maintained, and the location was perfect for enjoying the lake. Lisa was incredibly responsive and helpful throughout our stay. Highly recommended!

Magical Retreat in Londonderry, 3 bd, EV charger
Beautiful, spacious house, just as described. Clear instructions and responsive hosts.

Scandinavian Serenity Close to Okemo
We adore this perfectly peaceful getaway in VT! This was our third stay at the Scandanadian oasis and for anyone visiting VT, you have to see it in June! So many beautiful flowers in bloom decorating the property. Yulia and Mark were absolutely wonderful and responsive. The house is always immaculate! Highly recommended!

Large Riverfront Home | Minutes to Stratton!
Been back here three years in a row! Can’t recommend enough, beautiful peaceful place, responsive hosts, lovely home! The river is magical and it’s perfect for spending a sweet time with friends or family! The new game room was really fun on a rainy day!

Modern Chalet: Magic Mountain
Tyler’s place exceeded expectations! The home was exactly as advertised—beautiful, spotless, and in a fantastic location. Check-in and check-out were seamless, making our stay even more enjoyable. Tyler was an outstanding host, incredibly responsive, and went above and beyond by providing detailed information and fantastic restaurant recommendations. I’d highly recommend staying here to anyone looking for a top-notch experience!

Cozy, Comfy Country Home in Southern VT Village
All the conveniences that we needed! Very cozy and comfortable! Beautifully neat and clean and totally loved instructions for each room. Very thorough in extreme details on how to utilize the her home. Looking forward to coming back again.

Mountain View Getaway
We loved our stay at Nicole’s place. It was very peaceful and private- just what we needed! Our dog also felt right at home thanks to her welcoming touches. We would definitely stay there again!

Come Enjoy Summer at Vermontany!
Diana's home was well furnished and equipped with everything we needed for a quick ski getaway. We had a couple questions throughout the stay, and each time Diana was super responsive and accommodating. Could not recommend this place enough.
Quick stats about house rentals in Jamaica
Total rentals
130 properties
Nightly prices starting at
$150 NZD before taxes and fees
Total number of reviews
4.6K reviews
Family-friendly rentals
120 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Destinations to explore
- Hudson Valley Holiday rentals
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- Rentals with a fireplace Jamaica
- Chalet rentals Jamaica
- Waterfront rentals Jamaica
- Fitness-friendly rentals Jamaica
- Cabin rentals Jamaica
- Rentals with a hot tub Jamaica
- Pet-friendly rentals Jamaica
- Rentals with an EV charger Jamaica
- Rentals with a patio Jamaica
- Rentals with a washing machine and dryer Jamaica
- Rentals with a fire pit Jamaica
- Kid-friendly rentals Jamaica
- Family-friendly rentals Jamaica
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- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Six Flags Great Escape Lodge & Indoor Water park
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Pico Mountain Ski Resort
- West Mountain Ski Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- The Shattuck Golf Club
- Autumn Mountain Winery
- Dorset Field Club
- Mount Sugarloaf State Reservation
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Baker Hill Golf Club
- Pineridge Cross Country Ski Area
- Clarksburg State Park
- Ekwanok Country Club