
Vacation 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
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!

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!

Comfortable, relaxing large country home
Great spot for a week of skiing! Danielle was very helpful and communicative throughout

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!
Condo rentals with a pool

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
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

New - walk to Mt Snow w/ Tub & Gym
We loved the proximity to Mount snow, and the layout of the place was cozy and comfortable. We loved the newly renovated kitchen and all kitchen supplies were new. We didn’t get to use the amenities but we loved the sauna and hot tub offerings!

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.

Pico discounted 1 bedroom 1 nght Ok shuttle
Great place !
Quick stats about vacation rentals with a pool in West Windsor
Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ477 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
- Monadnock State Park
- Owl's Nest Resort
- Ragged Mountain Resort
- Mount Snow Ski Resort
- Tenney Mountain Resort
- Bretwood Golf Course
- Hooper Golf Course
- Baker Hill Golf Club
- Veterans Memorial Recreation Area Ski Hill
- Northeast Slopes Ski Tow
- Dartmouth Skiway
- Mount Sunapee Resort
- Hildene, The Lincoln Family Home
- Ekwanok Country Club
- Dorset Field Club
- Bromley Mountain Ski Resort
- The Shattuck Golf Club
- Crotched Mountain Ski and Ride