
House holiday rentals in West Windsor
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Top-rated house rentals in West Windsor
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Popular amenities for house rentals in West Windsor
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

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!

SugarBear- Pool, AC, Sauna, Gym, Tennis!
Dan & Holly are amazing hosts. They provided everything needed to make our week great. They left dining recommendations and all of the information we needed for the property. It was the perfect space for our family. The on-site amenities were great. The pool space was super clean and the staff was amazing. The property is well maintained and we had everything we needed to feel at home. We would definitely recommend this property to friends and family. Downtown Rutland was a short drive, and there was so much to see just minutes from the property. Dan & Holly are extremely responsive and truly think of everything. We had no questions and checking in and out was a breeze because they are so thorough. It was a wonderful experience from start to finish.

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!!!!

“Big Red” @ New London/Sunapee | Lake-Ski-Wellness
We thoroughly enjoyed our stay at the Big Red house in New London! The host, Chris, was so helpful in working with our dates. We traveled to New London for my mother-in-law's celebration of life, and I could not think of a better place to stay with my family and close family friends. The children (and adults!) enjoyed the game room and other amenities such as the screened porch and hot tub. We would have used the sauna/cold plunge if we had more time. The house was spacious, comfortable, and very private but easy access and close to downtown New London which was perfect for us. Again, I must highlight how gracious and helpful the host was - it was one of the best experiences I had so far with Airbnb. Please consider staying here - you will love it!

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

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.

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!

Sunflower Burrow Cottage
We enjoyed staying at Sunflower Burrow! It had all the things we needed. Highly recommend to anyone visiting the area.

The Cornish Cottage
As advertised and super comfortable stay. Power was unfortunately out the first night because of weather but the host had a generator set up for us so we had power and lights. Super responsive and super accommodating. We would definitely revisit!

Private & Cozy Farmhouse in New Hampshire
This was our second stay at the farmhouse. We love this place! Wes and Lindsey are so nice and welcoming. The house is roomy, clean, and the property is beautiful. We most enjoyed walking our dog on the path out back, and spending time with family we have in the area. Hope to stay many more times!

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.

Four Season River Retreat: Private beaches & more!
We had a great stay. Everyone really loved the farmhouse feel. Check in was easy and Jarad was very responsive and accommodating. We would have loved to use the outdoor space and bar but it was just too cold this visit, we will be back to give that all a shot when the weather warms up. There was a great local grocer not to far away and the ski mountain was just a short drive. This was a great place to stay and it had the first indoor toilet in cavadish (at least according to the previous owner)

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!
Private house rentals

Pet-friendly escape to hike, bike, golf, swim
This house is perfect for a family ski weekend getaway! Beautifully tucked away on a quiet road yet a super short drive from lots to do, skiing, etc. Beautiful and comfortable interior, our son and dogs were right at home too. Jeanne really thought of everything with the welcome basket! We have added this one to our favorites 😊👏🏻

Lakeview | Family-friendly | Stargaze | Relax
We had a wonderful stay and would be excited to come back again! This cottage was incredibly peaceful and comfortable with great views of the lake! Danielle is very responsive and everything went very smoothly.

Cornish-Windsor Bridge Retreat with Amazing Views
We had a lovely stay at Jonathan's place at a pretty much perfect time of year. The views were incredible! The home had a ton of character, and somehow managed to be cozy despite being huge. The view from the shower/bath did not get old! We would definitely recommend to friends and family looking for a getaway.

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!

BEST OF LAKE FRONT LIVING, HOT TUB & FIREPIT !!
Incredible home and host! This place was lake house cabin meets modern. The views are incredible, we had an amazing time. The hot tub was worth the additional purchase. The home is spacious and clean. It’s private enough but still close to local towns for good food and fun. I would highly recommend this place :)

Secluded/Hot Tub/views! Minutes to Everything!
The space was just as described. The view of the mountains is beautiful, and the house sits far enough above the road that there's no sounds of traffic. It felt secluded and peaceful, with all the amenities one would need.

Eastman Luxury Retreat Dartmouth College /Sunapee
I had a fantastic stay! The place was clean, comfortable, and exactly as described. The host was a great communicator and made the whole process easy. Highly recommend
Quick stats about house rentals in West Windsor
Total rentals
20 properties
Nightly prices starting at
$154 SGD 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
Destinations to explore
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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
- Autumn Mountain Winery
- Bromley Mountain Ski Resort
- Fox Run Golf Club
- Northeast Slopes Ski Tow
- Baker Hill Golf Club
- Ekwanok Country Club
- Brattleboro Ski Hill
- Hooper Golf Course