
Holiday rentals with a pool in Jamaica
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Top-rated rentals with a pool in Jamaica
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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!

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!

Ranch at Mendon Mt Orchards
Perfect location for skiing, and cosy home that we all enjoyed (including our pup). We appreciated the thoughtful touches provided by the host, and the apple orchard was a beautiful setting. Would definitely stay again!

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.

Ski and tennis house by Stratton Ski Resort.
We spent our winter break at Adam's condo. This condo experience had all the important Cs: Clean Condo - it was very clean upon arrival. Convenient Condo - the Stratton shuttle stops right outside the door. Communicative Condo Owner - any questions we had were answered in a timely manner. Cost effective Condo - great value Okay I went overboard with the Cs but honestly it was such a great experience. Adam is great host and the condo worked out perfect for us! Hopefully we get a chance to stay here again!

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)
Condo rentals with a pool

Mount Snow Ski Chalet
Great place to stay. There are no Ubers the week we stayed there and we should have rented a car. But the place was great.

Seasons on Mt Snow Condo - Ski/Hike/Bike/Swim
We stayed at Julia's vacation rental for a 3-day weekend with our four children under the age of 12. The things that were great: 1) the unit is 150 foot walk in ski boots from a ski trail that will take you to the Mount Snow lift, which was great because we didn't have to shlep 4 kids ski gear, 2) the four kids loved the bunk bed room and were comfortable, 3) there are two large shelves of board games the kids enjoyed, 4) the access to the Sports Center which has a heated indoor pool and hot tubs were a great way to end the day after skiing, 5) the outdoor locker was a great place to dump all the ski gear (much better storage location than inside the car or inside the unit) and 6) very nice fluffy towels and bed sheeting was comfortable. A combined liquid shampoo and body soap is provided in each bathroom, which is the same that we use to bath our kids at home.

Location + Spa! - Cozy 2BR Condo - Mountain Side
We had an amazing stay at this place! The location was perfect—just a short walk to all the incredible relaxation amenities like the pool, steam room, and sauna, which made our trip feel like a true escape. Going for a walk while taking in the views of the mountains were absolutely stunning and made every morning feel special. The unit itself was spotless and had everything we needed for a comfortable, short stay. The kitchen was well-stocked, the bed was cozy, and everything felt thoughtfully arranged. It was the perfect home base for exploring Killington and unwinding after a day of adventure. Would absolutely recommend and may come back during the Peak of the Snow Sport Season!

Killington Mnt Escape Ski/Golf/Bike/Hike/Pool
It was a pleasure staying at Shirley's place for our last trip to Killington this season. The place was nice and clean, the kitchen had everything we needed to cook our meals, and the amenities in the building were great!

Skier's Retreat 2bed/1.5 bath condo w/ Amenities
This condo has a great location, and the unit itself is extremely pleasant. If you're going to Killington I highly recommend it

3BR Whiffletree Condo!
Jeff and Melissa’s place was the perfect getaway with shuttles to take you to and from the mountain and a trail to ski back to the house. Would definitely stay here again!

Stratton Duplex Condo Steps to Lifts, Village!
Great walkable location. Loft space granted nice privacy for 2 couples or extended family. Fireplace and living room were cozy.

Luxury Condo*Walk to Ski Lifts*Hot Tub*Pool*Sauna!
I can’t say enough good things about my stay The condo was amazing My hosts were absolutely amazing people Every amenity and little extras were abundant and well thought out My hosts clearly thought of everything Pool and hot tub was awesome Staff at lodging were very friendly I would absolutely recommend this for anyone who wants to stay in Stratton
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- Stratton Mountain
- Okemo Mountain Resort
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Monadnock State Park
- Pats Peak Ski Area
- Saratoga Race Course
- West Mountain Ski Resort
- Berkshire East Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Mount Snow Ski Resort
- Mount Sugarloaf State Reservation
- Mount Greylock Ski Club
- Pineridge Cross Country Ski Area
- Ekwanok Country Club
- Hooper Golf Course
- The Shattuck Golf Club
- Baker Hill Golf Club
- Stump Sprouts Ski Touring Center
- Northern Cross Vineyard
- Clarksburg State Park
- Hildene, The Lincoln Family Home