House holiday rentals in Jamaica

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Popular amenities for house rentals in Jamaica

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 stars1 month 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!
Superhost
Home in Wilmington
4.87 out of 5 average rating, 171 reviews

Adams Farm-"The Little Farmhouse"

Catherine (Lou)Rating, 5 stars4 months ago
We had an amazing stay! The house is lovely and very comfortable, perfect for going skiing at mount snow and cross country skiing and prospect mountain. We were really glad to have picked it. The house is spacious, we all had a lot of room to ourselves, and the kitchen had everything we needed. The farm is gorgeous. Great grocery stores nearby. Sharon was amazing - so helpful when a winter storm threatened to make it hard for us to drive home. She offered us extra time or even another night discounted, which was really generous. She also communicated with friends to help us determine if the road back to NYC had been cleared. We are so grateful for her help! We hope to return in warmer weather to enjoy the farm even more.
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!
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!! 🤩
Top guest favourite
Home in Dover
4.98 out of 5 average rating, 52 reviews

Spring Getaway @ Mt Snow! Hike, Bike, Sleeps 8.

JessicaRating, 5 stars3 months ago
We had such a great time staying here! The house was so cozy and clean and was perfect! Felt like being at home and not staying in an Airbnb. Super close to the mountain, especially if you park in carinthia! Loved the guest book that they have in the kitchen, a fun added touch! Robert was extremely responsive to any messages and super accommodating with us and our needs! Absolutely would recommend staying here!!
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
Guest favourite
Home in Williamstown
4.89 out of 5 average rating, 218 reviews

Hollywood Bungalow in the Berkshires #C0191633410

JohnRating, 5 stars4 months ago
We had a great stay at the Hollywood Bungalow. House was described accurately and had so many thoughtful touches to make us feel welcome. Diana met us upon arrival and walked us around the property and the house. Such a great host! She had generously provided snacks, treats and gave a thorough overview for our stay. We were primarily focused on skiing at Jiminy Peak which was a short 20 minute drive. We also brought our 5 year-old rescue who had the best vacation of her life. She was able to use the fenced-in backyard to run around off leash and even meet a new friend when Jackson's dog visited. Diana even shoveled walking paths in the yard throughout our stay so we could get around in the high snow. The Screening Room is awesome and provided hours of entertainment. Quiet street and picturesque location. We will definitely return.

Weekly house rentals

Guest favourite
Home in Jamaica
5 out of 5 average rating, 5 reviews

Stratton; 6 min. King beds. Game rm. Dog friendly

PaulaRating, 5 stars3 weeks ago
Fantastic home in such a beautiful area. The waterfall nearby is beautiful. The house is comfortable and has all amenities needed. We had a great time with family and friends
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.
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.
Top guest favourite
Home in Londonderry
5 out of 5 average rating, 12 reviews

Modern Chalet: Magic Mountain

RileyRating, 5 stars3 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!
Superhost
Home in Dover
4.91 out of 5 average rating, 82 reviews

FULLY renovated 1 bed/1 bath ski in-out condo!

AnastasiaRating, 5 stars2 months ago
My husband and I spent a long last winter weekend here. The condo was perfect for ski on/off and we enjoyed a day on the mountain. Though the weather wasn’t great the whole time, Brittany & Jen were quick to send recommendations for things to do, trails to hike and their favorite restaurants. So close to lots of great spots in this little mountain town. We would absolutely stay here again
Guest favourite
Home in Londonderry
4.92 out of 5 average rating, 73 reviews

VT Cabin sitting above the West River and Village

JoshuaRating, 5 stars3 months ago
great small cabin nested in a small VT town! Rachel was great and we were within 20 minutes of Stratton which was perfect for our quick weekend
Guest favourite
Home in Grafton
4.93 out of 5 average rating, 75 reviews

Artist Forest Retreat

MiraRating, 5 stars3 months ago
Really lovely cabin with beautiful open design and decor. Reasonable drive to Magic Mountain and the surrounding area for skiing and other winter sport activities, and a great bathtub for your sore muscles afterward. Heat was super effective, hot water didn't run out even with four of us showering back-to-back, kitchen was well-supplied and there's a nice big driveway with plenty of room to park and turn around. There was even a closet full of boardgames; we played a lot of Scrabble. Of note — like much of Vermont, this is on a gravel/dirt road and it would be a bit sketchy to get there without good tires and four wheel drive. It also snowed a couple times while we were there and the stairs up to the house get very icy. So generally, if you're going in winter, be prepared.

Private house rentals

Top guest favourite
Home in Ludlow
5 out of 5 average rating, 32 reviews

Ludlow Lake & Ski Cottage - Adventure Awaits!

MdRating, 5 stars1 week ago
Exceptional experience! This is one of the relaxing place I have ever been! Large windows give you sense of experience living in nature. The stunning view gives you awesome feeling in any weather conditions.The house is nice, clean and equipped with pretty much everything. They have all the utensils for cooking and lots of toys for kids both indoor and outdoor. They also have paddles boat and kayak to use at anytime ! In addition, Brian is very respectful, responsible and quick to respond for any questions. All together Feel like you live in your own house. Great vacation spot without any doubt.
Superhost
Home in Newfane
4.94 out of 5 average rating, 99 reviews

Clark Farm-2 Master-Suites, Great kitchen, views!

WarrenRating, 5 stars1 week ago
A really terrific, historic Farm House in a beautiful setting...quiet and peaceful, yet only about 10 minutes to Newfane village. Lots of room to spread out, comfortable furnishings. Host and manager were easy to communicate with, fast responses. Would definitely repeat when in the area.
Top guest favourite
Home in Andover
5 out of 5 average rating, 53 reviews

Luxury VT Retreat. Breathtaking Views & Sunsets

ZackRating, 5 stars3 months ago
First and foremost, Julia is one of the most accommodating and most responsive hosts I’ve ever had. She was very friendly and proactively looked for ways to help me and my group feel welcome. Beautiful space scenically located on a Vermont mountainside - would absolutely recommend!
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 Windsor
4.99 out of 5 average rating, 94 reviews

Stylish Ascutney Cabin •View •Chef’s Kitchen •Pets

AmandaRating, 5 stars1 week ago
We had a great stay! The house was well-appointed and comfortable. We especially loved the covered porch and beautiful view. It was a great home base for exploring the area, including several nearby hiking trails, Woodstock and Quechee (about a half hour away), and Brattleboro (less than an hour away). Ab was a fantastic host. He was proactive with communication and even checked in with us to make sure we had power after some strong thunderstorms that had moved through the area.
Guest favourite
Home in Jamaica
4.93 out of 5 average rating, 60 reviews

Large Riverfront Home | Minutes to Stratton!

ElizabethRating, 5 stars6 days ago
We couldn’t be happier with our stay! The property was beautiful and we even saw a baby moose come through the yard one evening. The house was amazing and every room held a new delightful surprise from the pool table, to the oversized comfy couches, and the well equipped game room. Beds were super comfortable and each bedroom had its own bathroom. We hope to get back for a winter ski trip. Hosts were super responsive and proactive to ensure we got in easily and had everything we needed.
Top guest favourite
Home in Stratton
5 out of 5 average rating, 15 reviews

Beautiful 3-4 BR, 2 Ba, Sleeps 9

CathyRating, 5 stars4 months ago
Patrick’s place was all we needed for out family skiing weekend. Once coming from the mountain we were able to relax, play pool, listen to music, just relax. The house is so beautiful, we felt pretty much at home. Patrick took care of every detail to make it the perfect place to stay when in the area, easy to drive to Stratton Mountain. I will stay here again for sure.
Guest favourite
Home in Jamaica
4.92 out of 5 average rating, 24 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.

Quick stats about house rentals in Jamaica

  • Total rentals

    130 properties

  • Nightly prices starting at

    ₹7,791 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