
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!

Adams Farm-"The Little Farmhouse"
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.

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

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

Hollywood Bungalow in the Berkshires #C0191633410
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

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

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!

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.

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!

Mountain View Getaway
My partner and I were craving a weekend getaway to unwind and escape our hectic schedules. Nicole’s place was the perfect fit! It was exactly as depicted in the listing - quiet, private, and with a breathtaking view of Mt Tabor. Manchester, VT, was just a short drive away, offering a delightful mix of shopping and dining options. This place exceeded our expectations and was exactly what we needed!

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

VT Cabin sitting above the West River and Village
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
Private house rentals

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

Ludlow Lake & Ski Cottage - Adventure Awaits!
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.

Lakeview | Family-friendly | Stargaze | Relax
Absolutely beautiful stay! The place was spotless, with an amazing lake view that made for a perfect, peaceful getaway. The beds were all very comfortable, and the amenities provided truly made it feel like being at home. There were plenty of towels, toilet paper, and paper towels, which was a thoughtful touch. Communication with the host was smooth, and check-in and check-out were super easy. A great spot to decompress and relax. I highly recommend!

Luxury VT Retreat. Breathtaking Views & Sunsets
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!

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

Large Riverfront Home | Minutes to Stratton!
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.

Beautiful 3-4 BR, 2 Ba, Sleeps 9
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.

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.
Quick stats about house rentals in Jamaica
Total rentals
130 properties
Nightly prices starting at
$139 AUD 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
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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
- Dorset Field Club
- Autumn Mountain Winery
- 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