
House holiday rentals in West Windsor
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Top-rated house rentals in West Windsor
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday 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

Pond, Pool, Mountain Views | Au Bout du Chemin
This is a beautiful property tucked away in the hills of farmland above Norwich. It was perfect for an extended family getaway. Kids loved the pool, ping-pong table and pool table and we loved cooking in the well-appointed kitchen. Great little hike with outstanding views about 20 minutes away on Gile Mountain.

Golf, Bike, Fish, or Hike!
Ashley was super friendly and responsive and her place was as described with everything I need and more to make me feel right at home. Would love to stay here again. Thank you so much for letting us stay at your beautiful place!

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!

Beautiful & Bright Eastman Home
Beautiful and spacious home. Everything was clean and at any point I would message Denise she would respond right away. The area was beautiful as well. I would definitely book her home again.

The Brick House on Washington Street
Great stay and was exactly what we needed for our entire family for a weekend wedding!

The Fairway House - Premier Golf Course 3 BR Home
Jenna' place was great! Nice open and comfy feel to the living room and dining room. The kitchen was well stocked and really clean. The beds were comfortable and the bedrooms were cozy. I would definitely recommend Jenna's home.
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.

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!

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.

Cozy 1BR Hilltop Getaway minutes from Okemo
Great experience - perfect size for our group of 4 and super close to Okemo. Very clean and cozy.

BEST OF LAKE FRONT LIVING, HOT TUB & FIREPIT !!
Absolutely loved staying here for our anniversary. It had everything we needed to unwind and relax. The views were beautiful from just about every spot on the property and every detail was included to make the stay feel more at home.

Private, Large 4BR home | Pet friendly | 10 Acres
The place was in a wonderful quiet setting and the owners had left a thoughtful gift bag. They were great about communicating throughout and would definitely recommend the place

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

Twin Mountain River House
Had a very nice stay. Was worried about being snowed in but someone came to plow the driveway multiple times during our stay. Would definitely recommend !

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!

Luxury VT Retreat. Breathtaking Views & Sunsets
First and foremost, Julia is one of the most accommodating and most responsive hosts I’ve ever had. She was very friendly and proactively looked for ways to help me and my group feel welcome. Beautiful space scenically located on a Vermont mountainside - would absolutely recommend!

Highland Haus: stunning ski getaway with hot tub
The home and location are great, but the hosts are what make this place. They go above and beyond to make your stay special.

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!

Valhalla
Great house with plenty of amenities - perfect for a ski weekend with friends! Very clean and well stocked. Would rent again!

Magical Retreat Cottage - Waterfalls Everywhere
Gene’s house is a place of peaceful quiet and beauty. It’s well appointed and comfortable, with wireless and all the various conveniences, but it’s far more than that. The separation between the interior and the beautiful meadow and forest outside dissolves through Gene’s use of windows and glass doors, and the calming sound of falling water can be heard in every room. His use of color and symmetry create an environment that allows you to decompress, and as a result, you can’t help but to connect with the beauty of the forest. The waterfalls are wonderful to sit by; it was too early in the season for a swim in a cold mountain stream, but that’s just me. The design and setting of the home is a reflection of Gene. If you visit, I recommend that you get to know him a bit. His kind attentiveness makes him a first-rate host, but it’s part and parcel of his uncommon connection to the world around him. Gene was more than a host to us- he became a true friend. We will be back.

Modern VT Farmhouse w/Hot Tub & Fire Pit
This place was truly me & my husband’s ultimate favorite place to have a peaceful vacation thus far. We loved how spacious and together everything felt, from having so many windows and the theming through the whole house was truly unique and thoughtful. Sure there is a camera looking dead at you while in the hot tub, but most likely it’s because there’s an entrance right there. Outdoors is nature central: river close by, all types of birds chirping and surrounded by trees. Kitchen was equipped with seasonings & stocked with pots and utensils. Host was super helpful & responsive for sure. Overall: 10/10! Don’t hesitate to book! Really wonderful stay!!
Quick stats about house rentals in West Windsor
Total rentals
20 properties
Nightly prices starting at
$186 AUD before taxes and fees
Total number of reviews
760 reviews
Family-friendly rentals
10 properties are a good fit for families
Wi-Fi availability
20 properties include access to Wi-Fi
Popular amenities
Kitchen, Wi-Fi and Pool
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- Stratton Mountain
- Sugarbush Resort
- Okemo Mountain Resort
- Monadnock State Park
- Owl's Nest Resort
- Pats Peak Ski Area
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Dartmouth Skiway
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- The Shattuck Golf Club
- Ragged Mountain Resort
- Dorset Field Club
- Autumn Mountain Winery
- Tenney Mountain Resort
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Northeast Slopes Ski Tow
- Baker Hill Golf Club
- Ekwanok Country Club
- Hooper Golf Course
- Brattleboro Ski Hill
- Bretwood Golf Course