
Vacation rentals with a pool in West Windsor
Find and book unique homes with a pool on Airbnb
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
Matt's luxury Condo was excellent! It was very clean, roomy, and felt modern. I especially loved the kitchen. Being only a quick 10 minute drive from the K1 Gondola at Killington, the location is great! It's in a nice quiet spot but it only takes a few minutes to get to the mountain and local shops/restaurants. I will definitely be back!

Ranch at Mendon Mt Orchards
The house was great. Very comfortable and the house was spacious. It was nice that they had board games there. The apple pie they left for us was delicious. The orchard is beautiful. It was close to Killington for skiing. Highly recommend!

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!

Bright & Modern Quechee Town House - Self Check-In
Michael was very responsive and helpful during our stay! We would rent from him 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!

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 . . .).
Condo rentals with a pool

Mountain Oasis
Everything was as described. Great location. Shuttle to resort was super convenient. Very clean. Nicely renovated. Would stay again!

1 BR Best Location w/ Pools/Massage Chair/Hottub!
Andre was very communicative and had clear instructions. The Airbnb was very convenient if you’re skiing at Killington ski resort, would recommend!

Location + Spa! - Cozy 2BR Condo - Mountain Side
We had a great long ski weekend. Host is very communicative and helpful - with quick answers to any questions we had. Great spot for our family of 5. Easy to get to mountain. Very clean and comfortable rental! This was our second stay and we’d be happy to stay again.

Killington Mnt 2Br/2Ba Ski/Golf/Bike/Hike/Pool
Accommodations were as pictured, nicely updated. The unit was very clean, kitchen was well appointed and k-cups available. Plenty of blankets and extra pillows available. The building was clean and quiet. Host was very responsive and helpful.

Skier's Retreat 2bed/1.5 bath condo w/ Amenities
This is the second time we lived in the host’s unit. Well located and easy to go to lift. Unit is clean and has everything we need for ski trip. Five stars!

Stratton two bedroom condo on a shuttle
We enjoyed staying with our kids for a ski weekend! The condo was well stocked with sheets and towels and it was easy to access. The mudroom makes it especially easy for a place to put ski clothing and we appreciated that! I'm always curious about the coffee set up in the places we stay: this place has a Keurig and a standard Mr. Coffee, make sure you bring your own coffee and (round basket) filters. The kitchen had everything we needed to heat up food. It is well set up with pots, pans and dishes. Easy internet access. Comfortable furnishings. The shuttle picks up right outside the building in the morning and drops off in the same place in the afternoon. (As a note, we've stayed at other ski mountains where the shuttles run as a loop all day: this one does not. It goes only to the base in until 12 and only from the base starting at 1, so you'll want to plan accordingly.) We lucked out with 8" of powder one of the mornings we were there and had a fantastic stay overall!

Ski-Home Condo! Renovated 3BR
We enjoyed our stay! The condo was perfect for our needs.

Pico April discounts 1 bedroom 1 nite Ok shuttle
Gabe’s condo was perfect for me and my kids on our ski trip. Very clean, quiet, and cozy. We loved the fireplace, plus the extra hand and toe warmers left out on the counter were a nice touch. We would definitely stay here again on future trips!
Quick stats about vacation rentals with a pool in West Windsor
Total rentals
20 properties
Nightly prices starting at
$140 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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