House holiday rentals in Jamaica

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Popular amenities for Jamaica house rentals

House rentals with a pool

Guest favourite
Home in Salem
4.98 out of 5 average rating, 192 reviews

Magical Farm Getaway - a must visit!

BriannaRating, 5 stars2 weeks ago
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!
Guest favourite
Home in Colrain
4.9 out of 5 average rating, 129 reviews

The 1770 House

CatherineRating, 5 stars4 weeks ago
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!
Guest favourite
Home in Dover
5 out of 5 average rating, 15 reviews

Private chalet tucked in the green mountains

CarolineRating, 5 stars1 month ago
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.
Guest favourite
Home in Keene
4.93 out of 5 average rating, 211 reviews

The Brick House on Washington Street

PaulRating, 5 stars1 week ago
Great stay and was exactly what we needed for our entire family for a weekend wedding!
Top Guest favourite
Home in Wilmington
4.96 out of 5 average rating, 27 reviews

Family/Dog Friendly Mountain Home w/ Amenities

ReutRating, 5 stars3 weeks ago
The house was just outstanding!! Beyond our expectations. We had so much fun at the house with such great facilities and wonderful location.
Guest favourite
Home in Plainfield
4.89 out of 5 average rating, 139 reviews

Historic Home on 17 acres of land. Go escape!

BrandieRating, 5 stars3 months ago
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!! 🤩
Guest favourite
Home in Wardsboro
5 out of 5 average rating, 8 reviews

Wander In | Close to Mount Snow & Stratton

KatherineRating, 5 stars3 months ago
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.
Guest favourite
Home in Granville
4.94 out of 5 average rating, 105 reviews

Historic 1850’s Renovated Farmhouse w/ Pool!

KimberlyRating, 5 stars3 weeks ago
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

Top Guest favourite
Home in Peru
5 out of 5 average rating, 11 reviews

Highland Haus: stunning ski getaway with hot tub

AbigailRating, 5 stars3 weeks ago
The home and location are great, but the hosts are what make this place. They go above and beyond to make your stay special.
Superhost
Home in Jamaica
4.93 out of 5 average rating, 15 reviews

The Mountain Escape

DanRating, 5 stars3 months ago
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.
Guest favourite
Home in Jamaica
5 out of 5 average rating, 13 reviews

Magic Cottage in Jamaica Vermont

SamRating, 5 stars3 months ago
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
Top Guest favourite
Home in Jamaica
5 out of 5 average rating, 42 reviews

Mountain Log Cabin near Stratton

MichaelRating, 5 stars3 months ago
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.
Superhost
Home in Winhall
4.78 out of 5 average rating, 9 reviews

Stratton; 8 min! Swimming, 2 min. Pet friendly

AlisonRating, 5 stars10 months ago
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!!!
Guest favourite
Home in Jamaica
4.73 out of 5 average rating, 11 reviews

Cozy Cottage at Cold Moon Farm!

VictoriaRating, 5 stars2 months ago
Very cozy cottage for a short ski trip. It was nice and clean, and it was in a very convenient location near Stratton.
Guest favourite
Home in Jamaica
4.91 out of 5 average rating, 23 reviews

Minutes from Stratton Mountain

NehaRating, 5 stars3 weeks ago
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.
Guest favourite
Home in Dover
4.93 out of 5 average rating, 91 reviews

New Hot Tub! Gas Fireplace! 2 min to Mt Snow

Stacie LynnRating, 5 stars3 months ago
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

Top Guest favourite
Home in Argyle
5 out of 5 average rating, 18 reviews

Lakefront gem

RebeccaRating, 5 stars1 month ago
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!
Top Guest favourite
Home in Londonderry
5 out of 5 average rating, 21 reviews

Magical Retreat in Londonderry, 3 bd, EV charger

TsvetelinaRating, 5 stars3 months ago
Beautiful, spacious house, just as described. Clear instructions and responsive hosts.
Top Guest favourite
Home in Springfield
5 out of 5 average rating, 26 reviews

Scandinavian Serenity Close to Okemo

ColleenRating, 5 stars2 days ago
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!
Superhost
Home in Jamaica
4.93 out of 5 average rating, 59 reviews

Large Riverfront Home | Minutes to Stratton!

KirstieRating, 5 stars2 weeks ago
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!
Top Guest favourite
Home in Londonderry
5 out of 5 average rating, 12 reviews

Modern Chalet: Magic Mountain

RileyRating, 5 stars2 months ago
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!
Guest favourite
Home in Townshend
4.94 out of 5 average rating, 86 reviews

Cozy, Comfy Country Home in Southern VT Village

MarkRating, 5 stars3 months ago
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.
Guest favourite
Home in Dorset
4.9 out of 5 average rating, 51 reviews

Mountain View Getaway

OliviaRating, 5 stars2 weeks ago
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!
Top Guest favourite
Home in Londonderry
4.95 out of 5 average rating, 21 reviews

Come Enjoy Summer at Vermontany!

FrankRating, 5 stars3 months ago
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

  1. Airbnb
  2. United States
  3. Vermont
  4. Windham County
  5. Jamaica
  6. House rentals