
House vacation rentals in West Windsor
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Top-rated house rentals in West Windsor
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Vacation rentals for every style
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Popular amenities for West Windsor house rentals
House rentals with a pool

Luxury Condo Tucked in the Heart of Killington
Very nice place easy access to routes 4 and 100 with plenty of things to do

Golf, Bike, Fish, or Hike!
Had a wonderful weekend at Ashley's place! The condo is located just a few minutes from the K-1 base (and skiable too, but we came late in the season) and had everything we needed. Fireplace and sauna/hot tub (in an adjacent building) was a great bonus. Ashley was incredibly helpful and friendly, I'd love to come back!

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
Can I say it? The word is: PERFECT. Perfect house. Perfect location (calm, beautiful, convenient). Perfect aesthetics. Perfect hosts (honestly, I feel Denise and Josh are true friends). BOOK NOW!!!!

The Brick House on Washington Street
Beautiful, historic home in a lovely neighborhood close to downtown Keene. Charming and cozy inside and out. Comfortable beds and furniture. Wonderful artwork by Ruth throughout her home. Large bright kitchen with everything you’d need to stay. Enjoyed the architecture and restaurants in Keene. Highly recommend Ruth’s home to stay in this area!

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!
Weekly house rentals

19th Century Bohemian Barn House
We loved our stay at Stacy’s pretty little cottage. It was really spacious. We liked the creativity and quirkiness of the space and we had everything we needed for a family of four. Woodstock and Quechee are nearby and we enjoyed the fall foliage, delicious local food, apple orchards and the amazing local pies. We would definitely stay there again.

Charming New England Cape
Really nice peaceful place to stay. Was super clean and a most interesting house with many antiques, brought back many memories from childhood. Host was very responsive and very friendly. Would definitely stay there again!

Quaint Cottage
David was very friendly and responsive. We enjoyed the location and the peaceful atmosphere. I was with my sister. The stay was a great experience and felt well worth it. Just a note—one bedroom is accessed via a spiral staircase, another by a ladder, and there’s a sleeper couch in the living room. Would definitely recommend!

VT Cabin near Okemo & Killington
We had a wonderful stay at Matthew‘s place. The house is beautifully decorated and well appointed – perfect for a family ski weekend. There were a total of 10 of us that stayed in the house and we fit comfortably. The house was perfect for gathering for meals and game night, but large enough that we can spread out if needed. We hope to return again next year!

Tranquility Farm 3
Beautiful, seemingly brand new home. Everything was spotless. Large space overall; the "bedroom" is a second floor loft, which was beautiful, but be aware no sound control from the first floor. Host was super helpful and responsive. Would stay there again in a heartbeat!!!

The Cornish Cottage
I rented Eliza‘s place for my mother and in-laws to attend my daughters graduation. It was just perfect for them and they couldn’t have been happier. The location is beautiful and Eliza's communication and flexibility was so appreciated. She even stocked the fridge with farm fresh eggs, milk and coffee for them to start their day. A cozy home away from home. We will certainly be back.

Cozy 1 bedroom home with private hot tub
Great place to relax and unwind with friends! We had an amazing time and the hot tub was a great touch!

Private & Cozy Farmhouse in New Hampshire
Lindsay and Wes' place is a beautifully modernized traditional farmhouse. It is spacious, with comfortable living areas and one of the best stocked kitchens I've seen. The bed was comfortable and the towels are LARGE and fluffy. Out every window are peaceful farmland views. Lindsay and Wes were perfect hosts, giving us privacy but letting me know that they were there to help with anything. Loved our stay and would love to come back if we are in the area again.
Private house rentals

Ludlow Lake & Ski Cottage - Adventure Awaits!
Exceptional experience! This is one of the relaxing place I have ever been! Large windows give you sense of experience living in nature. The stunning view gives you awesome feeling in any weather conditions.The house is nice, clean and equipped with pretty much everything. They have all the utensils for cooking and lots of toys for kids both indoor and outdoor. They also have paddles boat and kayak to use at anytime ! In addition, Brian is very respectful, responsible and quick to respond for any questions. All together Feel like you live in your own house. Great vacation spot without any doubt.

Fabulous Log Home in the Woods
The log cabin is very comfortable with great flow. Loved the sunroom and upstairs den. Heated floors in bathrooms and sunroom were great touches. Not conventional decor: maximally furnished with an interesting blend of western, contemporary abstract art and figurative paintings and knick- knacks. We thought it fun and loved our stay.

Ski Sunapee or Pat’s Peak Look To The Mountain
Absolutely incredible experience! From the moment we arrived, it was clear that this place was something special. The property was immaculate—clean, beautifully decorated, and thoughtfully stocked with everything we could possibly need for a comfortable stay. Every detail, from the cozy bedding to the pristine kitchen, was perfection and made our trip unforgettable. Judith went above and beyond in every way, and clearly thought of everything a guest would need to feel right at home. She is also very responsive and easy to communicate with Without question, this property sets the gold standard for all Airbnb rentals. If every Airbnb were like this one, hotel chains would be out of business. We can’t recommend it highly enough and will absolutely be back. Mahalo you for an exceptional stay and A Hui Hou!

Private, Large 4BR home | Pet friendly | 10 Acres
The house was perfect for a large family getaway. And the hosts were so kind and flexible with checkout time so we could maximize our last day together.

The Brook House
I can't say enough great things about Jeff and this beautiful rental. The house is gorgeous with every amenity we could have wished for. The property was breathtaking with manicured gardens, fire pit area and the roaring brook right outside the windows. The water was pretty high when we were there due to all the rain, but it made for the most peaceful background sound. Linens were high end, beds were comfortable, the house was spotless, Jeff was super responsive and accommodating to our large group. I could go on. Would love to rent again in the future! Thank you Jeff!

Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain
Great stay! The Chalet is nice and secluded. A Great way to getaway with friends and/or family. The size of the stay is great for those looking to spend time intimately. Everything you see is what you get. There were no complaints with our stay and that is why it deserves a 5 ⭐️. The hosts are kind enough to have had firewood available for use of the fire pit. The hosts were both hospitable and responsive. I hope to stay there again maybe in the winter to go skiing or snowboarding. The towns of Ludlow and Springfield are roughly 15 minutes away in their respective directions with tons of dining options and activities. New England Cider donuts is right on Main St. in Ludlow which is a great spot for breakfast sandwiches and pastries. Okemo Mountain is a great hiking experience also found in Ludlow. If you find yourself looking for a quiet and peaceful getaway, don’t give it a second thought and just book this place you won’t regret it!

Vermont Mountain Escape
The house is fantastic and I highly recommend it to anyone who’s planning a trip to the area. Austin’s place is very stylish, comfortable and has everything that’ll make your stay an enjoying experience. You’ll find nice touches and well-thought details throughout the house the moment you step in. Location is also amazing to have a safe and peaceful stay with beautiful surroundings while being close to all nearby actions. We had a great ski trip overall and already planning to be back.

The Weatherbee 🖤 Country Home with a view!!
We really enjoyed our stay here. We have three children under seven and this house was such an easy place to be: high chair, covered outlets, not a ton of super breakable knickknacks to try and keep our one year old from….it actually felt like a vacation!! The view was beautiful and the neighborhood was really quiet. Such a nice spot to unwind. Our boys enjoyed exploring the yard, and the sunsets were spectacular from the deck. Wish we could have stayed longer!
Quick stats about house rentals in West Windsor
Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ441 before taxes and fees
Total number of reviews
760 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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- Rentals with a washer and dryer West Windsor
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- Stratton Mountain
- Sugarbush Resort
- Okemo Mountain Resort
- Monadnock State Park
- Owl's Nest Resort
- Pico Mountain Ski Resort
- Pats Peak Ski Area
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Dartmouth Skiway
- Ragged Mountain Resort
- Dorset Field Club
- Tenney Mountain Resort
- Hildene, The Lincoln Family Home
- The Shattuck Golf Club
- Bromley Mountain Ski Resort
- Autumn Mountain Winery
- Fox Run Golf Club
- Northeast Slopes Ski Tow
- Baker Hill Golf Club
- Ekwanok Country Club
- Bretwood Golf Course
- Hooper Golf Course