
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
The place was amazing. Probably one of the best Airbnb’s I’ve rented in terms of value for money. Very responsive host. The location is private, had pretty much all the amenities one needs and everything was well organized. The only downside is the check in is at 3pm but the checkout is at 10am. Which is pretty much unheard of. I’ve asked for one hour extension but was immediately sent a 25$ surcharge request for 1 hour. Apart from that everything was good.

Epic Views of the Green Mountains
Great place to take your family if you like to escape from humanity! Very remote setting and plenty of places to hike. The house is as described and the kitchen if fully stocked to make full dinners. My daughters, our German Shepard and I had a wonderful time. Suggestions - bring groceries as Granville is in the middle of nowhere. Closest store is in Rochester, 12 miles South. William was very commun icative and the value for the money was phenominal. Hope I can return next year!

Hilltop 9-BR Mountain Retreat 5-min to Okemo
Great communication, even with two days of snow excellent clearance. Definitely recommend 4WD as noted in the listing. Otherwise great place/location for large family gathering! GO BIRDS!

Ranch at Mendon Mt Orchards
Perfect location for skiing, and cosy home that we all enjoyed (including our pup). We appreciated the thoughtful touches provided by the host, and the apple orchard was a beautiful setting. Would definitely stay again!

6 BR Perfect Private Retreat in Vermont!
Large house in a very remote area. Approximately 70 acres. It was very relaxing and was nice to enjoy the pool which was professionally cleaned before arrival. The master bath has an incredible view of the mountains and an enormous shower. Pool table was fun and well taken care of. We stayed on probably one of the hotter weekends and the house cooled down at night pretty well just by opening the windows. Most rooms had ceiling fans if no other fans were provided. I can imagine this house would be amazing in the winter or fall too. With the screened in fireplace room and additional fire place inside the main house. You’re also close to 2 ski mountains each about 18 miles away. I could see myself renting again in the future. Thanks again

Brand New 4 Bedroom Listing with private hot tub!
We had the best ski trip staying at Todd’s place with our kids and family. The house has a great layout and is spacious, beautifully decorated, cozy, and well equipped with games. Location is great, 5 minutes from the slopes, and the shuttle can even pick you up from the driveway. Kids enjoyed the jacuzzi on the deck and the indoor swimming pool at the amenities center. Todd is super responsive and takes very good care of his guests. We highly recommend his place, thank you for everything!

The Brick House on Washington Street
We had a great stay in Keene. Ruth is a fantastic hostess. Her house is just close enough to Main Street to keep it a walkable distance to multiple restaurants and shopping. The house is a nice cozy spot that was big to accommodate my whole family meeting up for a fun winter weekend in Keene. I would stay there again without hesitation

Ski and tennis house by Stratton Ski Resort.
We spent our winter break at Adam's condo. This condo experience had all the important Cs: Clean Condo - it was very clean upon arrival. Convenient Condo - the Stratton shuttle stops right outside the door. Communicative Condo Owner - any questions we had were answered in a timely manner. Cost effective Condo - great value Okay I went overboard with the Cs but honestly it was such a great experience. Adam is great host and the condo worked out perfect for us! Hopefully we get a chance to stay here again!
Weekly house rentals

Clean, Captivating VT Farmhouse near Stratton!
Great house, amazing location near Stratton, and Matthew was just great. He was super communicative, and went above and beyond to make sure we were happy with our stay. We'd love to return again.

Sunapee Four Season Getaway with a Mountain View
We had an amazing family ski weekend at this house! With four young children, finding a place that accommodates everyone can be challenging, but this house was perfect. It had two cribs, which was a huge bonus for us. The open floor plan made it easy to keep an eye on the kids while still enjoying time together as a family. The hot tub was a great way to relax after a day on the slopes, and there was plenty of space for our entire group to spread out and feel comfortable. The location was also fantastic—just a short drive to Mount Sunapee, making it so easy to hit the slopes. We couldn't have asked for a better place for our weekend getaway!

Hot Tub & Game Room - Ski Mt. Snow/Stratton
We truly enjoyed staying here!! The hosts were amazing! They gave us plenty of local recommendations that made our stay so enjoyable. The home was wonderful. Plenty of this to do if you don’t want to leave. Game room was a great bonus!! We can’t wait to return!

MT SNOW Chalet + HOT TUB + new upgrades for 2024!
We had a great weekend at Lisa's house! Lisa was easy to get in touch with and when she knew she might be out of touch she gave us an alternate person to contact. It's snowed overnight during our stay and we were plowed out early to get on the mountain for first tracks. The house is exactly as pictured on the listing, we were very comfortable, and the hot tub was key for relaxing after a day on the mountain. The house has a 80's feel to it, and the wood panelling gives mountain vibes. We had everything we needed for our stay and really enjoyed the time we spent together!

Spring/Summer Fun Treasures Waiting
Great place. Was a bit further from Stratton but close to Manchester and Rutland for food options. It is check in with the hosts - clearly in the instructions - which I overlooked upon booking. The place was just as described and the event brought over blueberry muffins which was a nice touch.

OKEMO MT HOUSE - OKEMO-LUDLOW-JACKSON GORE
House fit our need was a good location for skiing at Okemo

Luxury Barn Home w/Hot Tub, Sauna, Gardens MtnView
This is my second time staying at Hilary’s home, and for good reason! My family loved gathering by the fireplace everyday, using the hot tub and sauna, and cooking dinners for our group of 8 in the well equipped kitchen every night! Plenty of room for us to spread out. Also love how close it is to the town of Woodstock (adorable with great shopping!) Hilary is very responsive and I am sure we will be back for a 3rd time at some point.

Relaxing Hot Tub Getaway
The perfect place for a few days getaway will definitely be back someday
Private house rentals

Charming Vacation Home in Manchester Center
Steal of a deal for this place. Perfect for any couple or family looking to do a vermont ski vacation. Has all the amenities you need, it’s super spacious, it’s right by town, and it’s a short drive to stratton or bromley. Easy 5 stars.

2 Units, 1 Home | Perfect for Multiple Families
The overall experience is good. Just a reminder: the 1st and 2nd floors use separate doors and are not internally connected. However, the location is very close to Okemo and Killington, and the interior decoration is quite good for the price.

Cozy Private House on Killington Mtn - Hottub
This airbnb was even better than we expected! It is just minutes away from all the Killington lodges and the restaurants/bars in town. The house was extremely clean, easy to find, and perfect for a group of skiers. I highly recommend it for anyone looking for a beautiful, easy place to stay at Killington. Would love to stay here again next time we visit! Highly recommend.

Pete's Place Cabin Okemo/Killington (whole house)
Pete's Place was fantastic. Our family of 6 (with 4 boys) really enjoyed it. Great place to get away from the crowds, yet super convenient location to OKEMO (particularly the Gore Area) and very short drive into town for groceries/restaurants.

New Hot Tub! Gas Fireplace! 2 min to Mt Snow
We loved staying in your home. It was close to Mount Snow where we went skiing and we especially loved the fireplace and hot tub. The kitchen was so big and had everything we needed. Thanks so much for leaving the binder of instructions because it is important for us to treat your home like our own home and we want to do things right. We will be back next year. Tom and Stacie

Cozy Riverfront Home in beautiful Jamaica
Great place. Very isolated and a beautiful location but still has all the creature comforts. The deck, view, and space are amazing. Fast WiFi, 2 bathrooms, and a dishwasher with garbage disposal are really cool in a rustic location like this. The wood fires hot tub was obviously the star of the show. Clear instructions and good communication for everything. The gas grill and gas fire pit were nice. Every thing was comfortable and great. Stress free. Hope to stay here again, thanks for everything.

Large Mount Snow Ski House with Hot Tub
Big group of friends and I stayed at Michele's place for a ski-weekend at Mount Snow. House was comfortable and fun with lots of games in the basement and space for us to hang out as a group in the main living area. Hot tub was 🧑🍳 perfection. Michele was responsive and helpful via messages.

Comfy and Cozy House on 67 acres
Surrounding area was very peaceful and the wrap around porch was a great way to see the nature. We loved the wood burning stove. Eccentric details and the space felt lived in.
Quick stats about house rentals in West Windsor
Total rentals
20 properties
Nightly prices starting at
£90 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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- Stratton Mountain
- Okemo Mountain Resort
- Sugarbush Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Monadnock State Park
- Pats Peak Ski Area
- Owl's Nest Resort
- Ragged Mountain Resort
- Mount Snow Ski Resort
- Tenney Mountain Resort
- Northeast Slopes Ski Tow
- Ekwanok Country Club
- Hooper Golf Course
- Bretwood Golf Course
- Baker Hill Golf Club
- Veterans Memorial Recreation Area Ski Hill
- Dartmouth Skiway
- Dorset Field Club
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Santa's Land USA
- Brattleboro Ski Hill