
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.
Vacation rentals for every style
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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
So close to many houses king spots.

Pond, Pool, Mountain Views | Au Bout du Chemin
This is a beautiful property tucked away in the hills of farmland above Norwich. It was perfect for an extended family getaway. Kids loved the pool, ping-pong table and pool table and we loved cooking in the well-appointed kitchen. Great little hike with outstanding views about 20 minutes away on Gile Mountain.

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!

Private Tavern, Hot Tub, 8-Fireplaces, Spa Baths!
Beautiful home and cottage with stunning surrounding scenery. Came here on a getaway from NYC and it was exactly what we needed. The jumbo jet bathtubs and fireplaces give this cozy space a luxurious feel, and the kitchen was downright impressive (brought a chef friend for us who was very impressed). Had to call the host with some questions when I arrived but they were answered immediately. Very clear check in instructions from the host and once we pulled up to the property it was very seamless to get inside and begin unpacking. We had an stress-free stay and checkout thanks to the intention with which these hosts set up their space and rental process. We will be coming back next year!

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
Condo rentals with a pool

Mountain Oasis
Cozy, clean, well appointed condo with great amenities within walking distance of the mountain, wonderful!

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

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.

Stratton two bedroom condo on a shuttle
Megan’s place was great for a weekend of skiing at Stratton. Right on a shuttle route that picks you up at the front door and is very reliable. Clean and comfortable. Megan was extremely helpful and responsive throughout the whole process from booking to check in and check out.

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!

Pico discounted 1 bedroom 1 nght Ok shuttle
Always a great quiet place to stay
Quick stats about vacation rentals with a pool in West Windsor
Total rentals
20 properties
Nightly prices starting at
$181 CAD 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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- Stratton Mountain
- Okemo Mountain Resort
- Sugarbush Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Monadnock State Park
- Owl's Nest Resort
- Pats Peak Ski Area
- Ragged Mountain Resort
- Mount Snow Ski Resort
- Tenney Mountain Resort
- Northeast Slopes Ski Tow
- Ekwanok Country Club
- Hooper Golf Course
- The Shattuck Golf Club
- Veterans Memorial Recreation Area Ski Hill
- Dartmouth Skiway
- Baker Hill Golf Club
- Dorset Field Club
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Crotched Mountain Ski and Ride
- Bretwood Golf Course