
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

Ski-In/Ski-Out Hike Okemo Mountain Condo
Words can’t describe the experience we had this weekend. Linda was the best host we have ever worked with and the place was extraordinary to say the least! Extremely clean, comfortable and well located! Kid friendly and close to downtown! We will highly recommend it to friends and family and if we could leave more stars than a 5-star review we would! Looking forward to booking this place again in the near future! Thank you Linda for your amazing hospitality!

Ranch at Mendon Mt Orchards
We enjoyed our stay. we felt at home. very spacious and cozy. this house has everything you need for your stay. Very close to Rutland. The fresh baked apple pie was a bonus. It was so delicious. Everything was perfect for us! Thank you! We will definitely be back again!

Private! Sauna, 3BR/2Ba, Pet-Friendly | Twin Peaks
Perfect place for a family ski trip. The only negative feedback I heard was that the house was so nice, my father in law had nothing to complain about.

Beautiful & Bright Eastman Home
Beautiful and spacious home. Everything was clean and at any point I would message Denise she would respond right away. The area was beautiful as well. I would definitely book her home again.

The Fairway House - Premier Golf Course 3 BR Home
Jenna' place was great! Nice open and comfy feel to the living room and dining room. The kitchen was well stocked and really clean. The beds were comfortable and the bedrooms were cozy. I would definitely recommend Jenna's home.

Bright & Modern Quechee Town House - Self Check-In
We stayed at Michael’s place for 5 nights for our son’s graduation at Dartmouth. It’s a very comfortable house in a nice quiet location in cul-de-sac so there were no outside noises. The beds were comfortable, we slept well, there was enough room to spread out for everyone. We loved the proximity to Woodstock and Quchee gorge. And getting to Hanover to campus was an easy 20 minute drive. Michael is a great host! Very responsive and helpful. Thank you !

Dana Road House Sunlit VT Country Home w/HotTub
Kat’s house on Dana road was the perfect place for our vacation to Vermont. Our family appreciated the clear instructions, helpful hints, and well thought out amenities. We really liked the Whisper Hill products in the bathrooms and made sure we went to the store in Quechee to buy some of the lotion before we left. We have stayed at a lot of AirBnB’s, but the house on Dana road was the most well equipped out of all of our stays!

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!
Condo rentals with a pool

Comfy ski in/out studio at base of Pico-Killington
Apartment was clean including the bathroom, just as described by the listing. The place was very comfortable to stay at.

Renovated unit, prime location! Shuttle on/Ski off
This was our second time staying at Caitlyn’s condo in Killington, we chose it again for a reason !! The vibe of the condo is super relaxing, the decor is thoughtful and cool. The fire place makes coming back after a day on the slopes so cozy! We love coming to Killington and this condo is so close to the snowshed lot, it’s perfect!

¤5-15 Mins to Ski Slopes | Fast WiFi | Fireplace¤
Jared was very helpful and responsive, seemed like he was waiting for us to check in to make sure everything was ok. The place was very clean, spacious and got everything we needed. Highly recommend!

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!

Walk/Bike to Snowshed Lift 2BR @ Mt. Green Resort!
Amazing experience! Will be back soon!!

Winterplace - Steps away from Slopes
A short walk to the ski slopes. The host was very helpful and proactive recommending where to go to ski based on your skill level. The place is functional and spacious. my favorite two things was proximity to the ski lifts/slopes and very comfortable mattresses/beds. When I ski, I need a nice rest and this place is a great for that. I would recommend this place and I would stay at Andrew's place again. Thank you Andrew for a great vacation!

Renovated 1BR, Walk to Lifts, Covered parking
I took my 13 yo son for a weekend visit to ski Killington for the first time and Gregory’s condo made our stay worthwhile! It was easy to access, clean, and equipped with all necessities. We will be sure to return!!

Newly renovated ski retreat at Killington
Wayne is super nice, friendly, and responsive. He gave me heads up note on check-in day when the main road (Killington Access Road) was closed due to downed trees&wires. He also helped me confirm the parking spot in late night when I arrived late. The place is cozy and clean. There’s a number of good restaurants and taverns nearby.
Quick stats about vacation rentals with a pool in West Windsor
Total rentals
20 properties
Nightly prices starting at
G$27,188 GYD 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
- Sugarbush Resort
- Okemo Mountain Resort
- Monadnock State Park
- Owl's Nest Resort
- Pats Peak Ski Area
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Dartmouth Skiway
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- The Shattuck Golf Club
- Ragged Mountain Resort
- Autumn Mountain Winery
- Dorset Field Club
- Tenney Mountain Resort
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Baker Hill Golf Club
- Northeast Slopes Ski Tow
- Ekwanok Country Club
- Bretwood Golf Course
- Hooper Golf Course
- Brattleboro Ski Hill