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.
Vacation rentals for every style
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Popular amenities for West Windsor rentals with a pool
House rentals with a pool
Home in Killington
4.91 out of 5 average rating, 190 reviewsLuxury Condo Tucked in the Heart of Killington
Matt’s condo had everything we needed for a comfortable weekend ski trip. Its location was convenient & we loved the view of the stream in the backyard. Everything was clean and functioned as expected. Nice for couples traveling together because there are two private bedrooms with large beds.
Home in Mendon
4.88 out of 5 average rating, 231 reviewsRanch at Mendon Mt Orchards
Great location and property! Close to Killington (~20 min) with plenty of grocery stores and restaurants nearby. But the best part of our stay was the fantastic apple pie!!
Home in Landgrove
4.75 out of 5 average rating, 28 reviewsPrivate 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!
Home in Dorset
4.95 out of 5 average rating, 20 reviewsIdyllic Dorset Home: Serene Escape w/amazing views
We had an amazing experience staying at the house hosted by Johns! The home was exactly as described (if not better), and everything was clean, comfortable, and well-maintained. The location was perfect, private yet close to civilization. Even if you don't want to step out, the house is picture perfect to see fall colors all around you, We however, also loved the access to hiking trails nearby. The check-in process was seamless, with clear instructions provided to us. The host/manager was incredibly responsive and helpful throughout the stay, making sure we had everything we needed. They even went the extra mile by leaving a welcome note, a lovely local pie and some maple syrup. The cozy living room, spacious kitchen, hot tub, outdoor grill, and the indoor pizza grill made it feel like a home away from home. I especially loved the space, layout and design of the house which comfortably accommodated us seven adults and had room for more. We would definitely return for another visit!
Home in Hartford
4.91 out of 5 average rating, 33 reviewsBright & Modern Quechee Town House - Self Check-In
My husband and I have stayed in several condos in the Quechee area and Michael's is one of the best. It was really clean and well stocked. Very nice lower level with lots of room for hanging out. The living room is cozy with a nice fireplace. We would definitely return.
Home in Hartland
5 out of 5 average rating, 10 reviewsPrivate Farmhouse with 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!
Home in Ludlow
4.77 out of 5 average rating, 43 reviewsBeautiful Okemo Farmhouse 0.7 mile from base lodge
Sue's place was perfect for our group of 10. It slept everyone well, and was a great ground base for our ski trip to Okemo. the home is just 0.5 miles from Clocktower, and barely 4 minutes to town. The hot tub was perfect for a cold evening dip. we are already planning our return.
Home in Springfield
4.99 out of 5 average rating, 74 reviewsLuxury Mid-Century Modern Vermont Home, Okemo View
Nice surrounding and clean home. Living room and fireplace is the best part of the house. Couple of Bathroom’s lock wasn’t working but apart from that pleasant stay.
Condo rentals with a pool
Condo in Killington
4.84 out of 5 average rating, 75 reviewsMountain Oasis
Gail and Steve's place was great if your priority is being super-close to the mountain and having a pleasant place to stay. It's smallish--cozy or a bit cramped, depending on your perspective-- for the price, but the trade-off in proximity made it well worth it for us. The ski rental place in the condo building is top-notch. Super-clean. The photos were accurate, though the living room is a little smaller than I realized. And, if you choose to make dinner in their very well equipped and updated kitchen, expect the downstairs to smell like it--at least in the winter, when you can't open the sliding glass doors for long. The two bedrooms are completely adequate--again, on the small side, but good mattresses and way-above typical pillows (I find that Airbnbs tend to have crummy-at-best pillows), adequate slightly dated upstairs bathroom--there's another downstairs. No in-unit washer-dryer, but easy to access and use laundry room in the building. Pluses: the health club, Gail and Steve!
Condo in Killington
4.92 out of 5 average rating, 111 reviewsLocation + Spa! - Cozy 2BR Condo - Mountain Side
Everything was exactly as described. We would definitely rent here again!
Condo in Killington
4.9 out of 5 average rating, 135 reviews2 bed-2 bath (6 max): walk to lifts and lodges
We just have enjoyed another nice stay at Bonnie and Craig’s place. They are very friendly and accommodating by walking over to lend us their snow shuffle! Highly recommend this place and its wonderful hosts. Thank you!
Condo in Killington
4.88 out of 5 average rating, 41 reviewsKillington Mnt 2Br/2Ba Ski/Golf/Bike/Hike/Pool
Thank you very much. Everything was wonderful
Condo in Killington
4.82 out of 5 average rating, 154 reviewsSkier's Retreat 2bed/1.5 bath condo w/ Amenities
The condo was beautifully set up and as described, there is construction going on at the building during the off-season though Scott was great at communicating this and the impact was minimal. overall it was a great stay for the weekend and we would love to come back and see how the condo is after the building renovations are complete.
Condo in Killington
4.82 out of 5 average rating, 251 reviewsSki, Ride, Walk On/Off Condo On Pico at Killington
We enjoyed this condo! It fit our group of 5 adults and a baby with no problem. The kitchen has a big table we all sat at for dinners and games. It was convenient to Killington, Woodstock and Rutland. Jonathan was great at communicating quickly, and sharing recommendations (Sugar & Spice was great!). Check-in and out was easy and Jonathan was accommodating with our early arrival/late check out requests. It felt clean and well taken care of. Would recommend!
Condo in Killington
4.82 out of 5 average rating, 17 reviews3 BR Ski-Home Condo!
Had a great stay at Jeff and Melissa's place. It was easy to find and communication was clear throughout the stay.
Condo in Killington
4.93 out of 5 average rating, 420 reviewsSlopeside Pico 1 bedroom 1 nite Ok free shuttle
Great stay for us since we wanted a convenient location to get to killington for skiing (10 minutes). Loved the fireplace and that there were TVs in both the living room and bedroom. Host was very responsive. One thing to note though was the address sometimes directed us to the wrong place when we put it in google maps, not sure why!
Quick stats about vacation rentals with a pool in West Windsor
Total rentals
20 properties
Nightly prices starting at
$160 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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