
Holiday rentals with a pool in West Windsor
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Top-rated rentals with a pool in West Windsor
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
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Popular amenities for West Windsor rentals with a pool
House rentals with a pool

Luxury Condo Tucked in the Heart of Killington
Comfortable and convenient location. Everything we needed was in the kitchen. We had most of our meals in and took advantage of the kitchen. The sleeping accommodations were very comfortable. It is only a short drive to Killington, where my family skied. We would definitely stay there again.

Ranch at Mendon Mt Orchards
I had a great time with some friends here on a ski trip. The house had everything we needed to cook breakfasts and dinners, with a surprisingly spacious living room area. Great location and lovely welcome when we arrived. I’m looking forward to coming back again!

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!

Idyllic Dorset Home: Serene Escape w/amazing views
My group of 9 had a wonderful stay here! The house was very spacious, clean, and modern and accurately represented in the posting. John was extremely responsive during our process and proactively checked in with us to ensure we were able to check-in to the property smoothly. We had a small issue with one of the stove top burners and when we reached out to John, he followed up immediately to resolve the issue. I highly recommend staying here!

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!

Beautiful Okemo Farmhouse 0.7 mile from base lodge
Sue’s place was amazing! So close to Okemo and the hot tub was amazing after a cold day of skiing. Plenty of room for 9 of us. We especially liked hanging out in the living room with the wood stove going. Very comfortable and great value! Would recommend and would come back!

Luxury Mid-Century Modern Vermont Home, Okemo View
Wonderful Stay with Family – Highly Recommended! We had an amazing stay at this property with our family. The house was spacious, clean, and had all the amenities we needed for a comfortable stay. The host was fantastic – very responsive and always available to help with any questions we had. Communication was seamless, and he made sure we had everything we needed for a smooth experience. We really appreciated his hospitality. I highly recommend this place for anyone looking for a great place to stay. We had a memorable time and would definitely return!

Your country home awaits! Pool, tennis, Dogs loved
Great place to stay if you plan to ski or snowboard at Stratton. Close to the center of Manchester (grocery store, shops, etc . . .).
Apartment rentals with a pool

1 BR Best Location w/ Pools/Massage Chair/Hottub!
The Condo Unit: The one bedroom was exactly what I needed. Great wifi and plenty of space. The Complex: Mountain Green is a gem. 10 minute walk to the slopes. Free shuttle. Amazing spa and fitness area- hot tub, steam room, sauna a& heated pool. Plus a very safe area. The Host: Andres was extremely easy to work with and very fast to respond. If anything came up, he was very quick to resolve the issue. What more can you ask?

Location + Spa! - Cozy 2BR Condo - Mountain Side
Very clean and great location. It was about an 8 minute walk to the Ramshead lodge and we ate at two restaurants within a 5 minute walk. The shuttle was also easy and ran frequently. Would recommend!

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

Ski, Ride, Walk On/Off Condo On Pico at Killington
Great location for pico mountain. The ski on ski off was pretty easy to find and nicely located. The location is slightly less ideal for killington, as you need to take a shuttle that has multiple stops. We also ended up on a bigger bus to take us back from Killington and the drop off was on the main road, which was a bit difficult to walk on in our snow gear. Overall, nice apartment and perfect for my group of friends.

Ski-Home Condo! Renovated 3BR
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 condo duplex in the BEST location for Stratton Village. Situated just across the street from the entrance. Five-minute walk to main base lodge and ski lifts. Easy access to restaurants in village. Underground secure indoor parking. Great complex. Fully stocked kitchen with all you need to cook. Cable TV. Can't think of anything missing! Terrific option all around for a family.

Pico discounted 1 bedroom 1 nght Ok shuttle
The place was very clean. Lovely place. Would stay there again. Quiet.
Quick stats about holiday rentals with a pool in West Windsor
Total rentals
20 properties
Nightly prices starting at
£98 before taxes and fees
Total number of reviews
110 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
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- Okemo Mountain Resort
- Sugarbush Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Pats Peak Ski Area
- Ragged Mountain Resort
- Owl's Nest Resort
- Monadnock State Park
- Tenney Mountain Resort
- Mount Snow Ski Resort
- Veterans Memorial Recreation Area Ski Hill
- Hooper Golf Course
- Mount Sunapee Resort
- Hildene, The Lincoln Family Home
- Ekwanok Country Club
- Dorset Field Club
- Bromley Mountain Ski Resort
- Brattleboro Ski Hill
- Storrs Hill Ski Area
- Whaleback Mountain
- Fox Run Golf Club
- Santa's Land USA
- Lake Sunapee Country Club