Vacation rentals with a pool in West Windsor

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Popular amenities for West Windsor rentals with a pool

House rentals with a pool

Guest favorite

Home in Killington

4.9 out of 5 average rating, 195 reviews

Luxury Condo Tucked in the Heart of Killington

NelsonRating, 5 stars1 week ago
My family and I had a wonderful and quiet stay at Matt’s place. The location is very peaceful yet still close to everything. Perfect for relaxing after a long day of skiing!
Guest favorite

Home in Mendon

4.88 out of 5 average rating, 236 reviews

Ranch at Mendon Mt Orchards

LilyRating, 5 stars1 week ago
Jonathan’s place was fantastic! The home is incredibly charming and sits in a beautiful orchard rich with history. The location is perfect close to both Rutland and Killington, making it convenient for exploring the area. Upon arrival, we were warmly welcomed with a delicious apple pie and thoughtful treats for our dogs, which was such a kind gesture. The hospitality and attention to detail made our stay extra special. I highly recommend this wonderful spot and hope to return soon!
Superhost

Home in Landgrove

4.75 out of 5 average rating, 28 reviews

Private Tavern, Hot Tub, 8-Fireplaces, Spa Baths!

JadeRating, 5 stars5 months ago
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!
Guest favorite

Home in Dorset

4.95 out of 5 average rating, 21 reviews

Idyllic Dorset Home: Serene Escape w/amazing views

KatherineRating, 5 stars1 week ago
Modern, clean home with great views. Home has somewhat of an unusual layout but it accommodated our group just fine. Nice proximity to Bromley ski resort (15 min). John and Lisa were very responsive when we were having issues with the heat. We loved having the hot tub to soak after a day of skiing! We appreciated the great hospitality.
Guest favorite

Home in Hartford

4.91 out of 5 average rating, 35 reviews

Bright & Modern Quechee Town House - Self Check-In

AustinRating, 5 stars1 month ago
Terrific place and Michael is a great host. Would definitely come back again!!
Guest favorite

Home in Hartland

5 out of 5 average rating, 10 reviews

Private Farmhouse with Pool

ChrisRating, 5 stars5 months ago
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!
Superhost

Home in Hartford

4.81 out of 5 average rating, 54 reviews

Quechee Mountain Home w/Jacuzzi, Gym and Game Room

KevinRating, 5 stars4 weeks ago
My family and I stayed here for new years and had a great stay. Was perfect for our 2 kids. House was very clean and exactly as pictured. Location is great, with the Quechee Club ski hill being great for kids that are learning. Hot tub and game room were nice amenities. Kitchen was well stocked with all of the essentials. Would stay at again.
Guest favorite

Home in Ludlow

4.78 out of 5 average rating, 46 reviews

Beautiful Okemo Farmhouse 0.7 mile from base lodge

SherylRating, 5 stars3 weeks ago
Lovely farmhouse close to okemo. Tons of space for two families with college age kids to spread out. The hot tub was fantastic after a day of skiing. Would stay again.

Condo rentals with a pool

Guest favorite

Condo in Killington

4.85 out of 5 average rating, 79 reviews

Mountain Oasis

ChristianRating, 5 stars4 days ago
Steve and Gail were very accommodating and gracious hosts! They provided very clear instructions and helpful tips to navigate the condo complex and local area. Their condo is newly renovated and immaculate!! Everything we needed for a comfortable stay was provided and the kitchen contained everything necessary to cook gourmet meals (even a spice rack!!). There is a great health club right in the same building as their condo with a hot tub, pool, steam room and saunas (this was much needed after vigorous days on the slopes.) The Snowshed lodge and slopes are directly across the parking lot from their building and a shuttle runs regularly. I would highly recommended these great hosts and their amazing two-bedroom condo! -Christian
Superhost

Condo in Killington

4.86 out of 5 average rating, 85 reviews

1 BR Best Location w/ Pools/Massage Chair/Hottub!

CooperRating, 5 stars1 month ago
My family and I have stayed at Mt. Green condos a few times in the past and this was definitely a nicer unit. Had lots of kitchenware which is very helpful and fresh linens available for pull out. Will be keeping in my saves for future trips.
Guest favorite

Condo in Killington

4.91 out of 5 average rating, 117 reviews

Location + Spa! - Cozy 2BR Condo - Mountain Side

TerrenceRating, 5 stars1 week ago
Clean and convenient to the mountain, we would stay again. Great place.
Guest favorite

Condo in Killington

4.89 out of 5 average rating, 44 reviews

Killington Mnt 2Br/2Ba Ski/Golf/Bike/Hike/Pool

PatrickRating, 5 stars1 week ago
We stayed at Shirley's condo in January 2025 and we were there to ski at Killington. It was very convenient to the mountain, the ski lockers were well-located, and the pool/hot tub was great for post-ski. The lodge has a great gym (new equipment, clean) and there were free EV chargers in the main Killington lot across the street. I would highly recommend it for families skiing at K.
Guest favorite

Condo in Killington

4.83 out of 5 average rating, 160 reviews

Skier's Retreat 2bed/1.5 bath condo w/ Amenities

EricRating, 5 stars2 weeks ago
Scott is super responsive and friendly. Amazing location with a convenient shuttle to the mtn if you dint want to walk. Would definitely stay here again.
Guest favorite

Condo in Stratton

4.92 out of 5 average rating, 12 reviews

Stratton two bedroom condo on a shuttle

JeffRating, 5 stars4 weeks ago
Megan was an excellent host and this condo is spacious and very cozy! We loved every minute of our trip and will absolutely be back! 1st floor was a huge plus!
Superhost

Condo in Killington

4.83 out of 5 average rating, 18 reviews

Renovated 3BR Ski-Home Condo!

SamRating, 5 stars1 month ago
This was a perfect location for skiing at killington. The ski base was likely 10 minutes walk away. The condo was extremely roomy and in good shape. It had all we needed and then some. We have already discussed our return. We loved this stay.
Guest favorite

Condo in Killington

4.93 out of 5 average rating, 430 reviews

Ski in n out Pico 1 bedroom 1 nite Ok free shuttle

BurcinRating, 5 stars1 week ago
This is our second season staying at Gabe’s place. We keep coming back. The location is great especially for Pico and the apt and building is clean and cozy. There is an elevator and locker downstairs which makes your life easier. Highly recommended!

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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