
House vacation rentals in Jamaica
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Top-rated house rentals in Jamaica
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Vacation rentals for every style
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Popular amenities for Jamaica house rentals
House rentals with a pool

Country hideaway
Second visit and it was just as nice as the first. We like this house inside and out. The pool and walking trail through the woods are great, and the living room is super comfy for family hanging out at night or on a rainy morning. Highly recommend!

Magical Farm Getaway - a must visit!
A fun winter break/birthday getaway! Sarah’s house had plenty of bedrooms for all guests. The game room, pool table, and wood stove/fireplace were great to have on these cold February days. Everyone enjoyed the sunroom and large dining table. The hot tub and outdoor sleds were used as well. The history of the house and beautiful views from the property were an interest to all. I bet this house is a lovely spot in the summer as well!

The 1770 House
Another great weekend at Ed’s! It was our group’s second time staying here, and we loved it just as much as the first, which is to say—a lot! Ed is very considerate and responsive, and there’s plenty to do for everyone. We are already looking forward to next year!

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
We had a great stay in Keene. Ruth is a fantastic hostess. Her house is just close enough to Main Street to keep it a walkable distance to multiple restaurants and shopping. The house is a nice cozy spot that was big to accommodate my whole family meeting up for a fun winter weekend in Keene. I would stay there again without hesitation

Private Farmhouse with in ground pool!
My family and I truly enjoyed our time spent at the farmhouse. Everything was as expected from the listing. The pictures do not do justice for the property. It's beautiful and well maintained. The pool was nice, warm, and clean. There are yard games readily available and a nice fire pit area. Brin and Maria are super responsive and left very detailed instructions on the property for you. Everything you need is there minus food, which is a 12-minute drive towards a few different grocery stores. The hill is so fun to roll down, too! Thank you so much!

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.

Historic 1850’s Renovated Farmhouse w/ Pool!
Beautiful home. Pictures don’t do this location justice. Booked for our daughters wedding being held close by for relatives traveling and ourselves to be close to wedding. Would highly recommend for anyone looking in that area. They have thought of everything you could possibly need. We were out at events more than at the home and I honestly with we had done another day to enjoy some down time in the beautiful home. Owners and local property manager were wonderful at communicating and making sure everything was cared for (we had no concerns, but having contacts if there were any)
Weekly house rentals

Clean, Captivating VT Farmhouse near Stratton!
Great house, amazing location near Stratton, and Matthew was just great. He was super communicative, and went above and beyond to make sure we were happy with our stay. We'd love to return again.

Sunapee Four Season Getaway with a Mountain View
We had an amazing family ski weekend at this house! With four young children, finding a place that accommodates everyone can be challenging, but this house was perfect. It had two cribs, which was a huge bonus for us. The open floor plan made it easy to keep an eye on the kids while still enjoying time together as a family. The hot tub was a great way to relax after a day on the slopes, and there was plenty of space for our entire group to spread out and feel comfortable. The location was also fantastic—just a short drive to Mount Sunapee, making it so easy to hit the slopes. We couldn't have asked for a better place for our weekend getaway!

Hot Tub & Game Room - Ski Mt. Snow/Stratton
We truly enjoyed staying here!! The hosts were amazing! They gave us plenty of local recommendations that made our stay so enjoyable. The home was wonderful. Plenty of this to do if you don’t want to leave. Game room was a great bonus!! We can’t wait to return!

Spring/Summer Fun Treasures Waiting
Great place. Was a bit further from Stratton but close to Manchester and Rutland for food options. It is check in with the hosts - clearly in the instructions - which I overlooked upon booking. The place was just as described and the event brought over blueberry muffins which was a nice touch.

Charming 6 BR home 8 min walk to MassMoca
Nancy was a great host. She was responsive and proactive providing us instructions for accessing the property. The house had lots of space for our group of 9 and it was nice to have a full kitchen to cook in while we stayed. The walk to MOCA was around 15 minutes with our group, which included five kids. It was nice being so close to town. We hope to be back again!

Downtown Hot Tub Escape
This place is great! Exactly as described inside, clean & well-appointed home. Everything is labeled very helpfully and all amenities were available and clean. Hot tub is inside a sweet little screen tent that allows for extra privacy which is much needed as the next door neighbors are very visible/present next to the outdoor space. The washer and dryer were new, the fridge was very new and had an awesome ice dispenser with 2 types of ice it automatically created. Don't let the house rules shy you away. This host is through but very kind and professional. The only downside of the entire place is a rather complex air conditioning/heating system that I found diddicult to understand but also made it uncomfortably hot throughout the night and there are signs everywhere instructing not to open the windows at all which was odd. Overall this place is so worth it, if you're staying in Keene and need a larger space, this place is perfect.

Stone n' Sky Lodge
I genuinely don't know what to say other than the fact that this may be one of the greatest places I've had the honor to lodge at. I did a lot of vetting across New England to find a wonderful place that could sleep a decent amount of people, provide a scenic and comfortable escape, and keep us entertained. Sarah's wonderful Stone and Sky Lodge exceeded every expectation I just listed. It's cozy, warm, and feels like a hidden nook! The scenery and nature couldn't be more beautiful. I never got the pleasure to meet Sarah, though I wish I did. Over messages and from what my friends told me, I just know that Sarah is the most hospitable and kind host that I've talked with in a while, and I hope that next time I can thank her personally. From my friends and I, we thank you for sharing your home with us. If you think that the excellent reviews are too good to be true, don't. This IS the truth, and I can't wait to have another reason to come back to this wonderful treasure of a place.

Wilmington A-Frame- Cozy and Convenient
This spot is absolutely perfect to be on a quite spot to enjoy nature but still right within walking distance of the center of Wilmington. The cabin itself is beautifully appointed, gorgeous, and super comfortable. Due to rain we ended up spending most of our time inside relaxing and watching movies, and have zero regrets about it. The host was also extremely friendly, helpful and responsive. I'll definitely be coming back again and recommend this for a Wilmington get away weekend!
Private house rentals

Charming Vacation Home in Manchester Center
Steal of a deal for this place. Perfect for any couple or family looking to do a vermont ski vacation. Has all the amenities you need, it’s super spacious, it’s right by town, and it’s a short drive to stratton or bromley. Easy 5 stars.

Little House with Lots to Offer
I stayed at the Tiny House with my significant other and our dog for a small, private getaway during our anniversary. It was a nice, cozy little home for us which we all enjoyed. It was also great to be right next to a grocery store and near downtown Keene for food and activities.

2 Units, 1 Home | Perfect for Multiple Families
The overall experience is good. Just a reminder: the 1st and 2nd floors use separate doors and are not internally connected. However, the location is very close to Okemo and Killington, and the interior decoration is quite good for the price.

Spacious Brattleboro home on river, walk to town
Absolutely incredible place! Tons of room, bathrooms for each bedroom was a big hit. Amazing location. Views were magnificent after 8 inches of snow and some freezing rain. Perfect excuse to not leave the house and enjoy the peaceful serenity over a nice margarita. Fall views must be totally awesome. Don’t need to bring anything except you, your friends and some food. The home has everything you need, all set and ready to go, and I mean everything you’ll need. The house manager Teri was an absolute peach. Her connection to the house and knowledge of the local history was amazing. 5 STARS doesn’t do this place justice. Already planning a return visit.

6 BR Perfect Private Retreat in Vermont!
Large house in a very remote area. Approximately 70 acres. It was very relaxing and was nice to enjoy the pool which was professionally cleaned before arrival. The master bath has an incredible view of the mountains and an enormous shower. Pool table was fun and well taken care of. We stayed on probably one of the hotter weekends and the house cooled down at night pretty well just by opening the windows. Most rooms had ceiling fans if no other fans were provided. I can imagine this house would be amazing in the winter or fall too. With the screened in fireplace room and additional fire place inside the main house. You’re also close to 2 ski mountains each about 18 miles away. I could see myself renting again in the future. Thanks again

Cozy Riverfront Home in beautiful Jamaica
Great place. Very isolated and a beautiful location but still has all the creature comforts. The deck, view, and space are amazing. Fast WiFi, 2 bathrooms, and a dishwasher with garbage disposal are really cool in a rustic location like this. The wood fires hot tub was obviously the star of the show. Clear instructions and good communication for everything. The gas grill and gas fire pit were nice. Every thing was comfortable and great. Stress free. Hope to stay here again, thanks for everything.

Green Mountains Lake Retreat - Hidden Gem
Great little house close to trails. Was perfect for our visit to the Mt Prospect Nordic center. The house was very comfortable and we enjoyed the games and books in our downtime. Would recommend a stay here!

Private Field House - Spacious 4 Bedroom Home
Absolutely pristine and gorgeous home. We were constantly talking about how perfect it was the entire time we were there. Would definitely stay again!
Quick stats about house rentals in Jamaica
Total rentals
130 properties
Nightly prices starting at
$90 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
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- Okemo Mountain Resort
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Pats Peak Ski Area
- Monadnock State Park
- Berkshire East Mountain Resort
- West Mountain Ski Resort
- Saratoga Race Course
- Six Flags Great Escape Lodge & Indoor Water park
- Mount Sugarloaf State Reservation
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Hooper Golf Course
- Baker Hill Golf Club
- Mount Sunapee Resort
- Northern Cross Vineyard
- Pineridge Cross Country Ski Area
- Willard Mountain
- Stump Sprouts Ski Touring Center
- Clarksburg State Park
- Dorset Field Club
- Hildene, The Lincoln Family Home
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