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Holiday rentals in West Windsor

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Top-rated holiday rentals in West Windsor

Guests agree: these stays are highly rated for location, cleanliness and more.

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Cabin

4.9 out of 5 average rating, 93 reviews

100 Acres Views & Creek near Woodstock/Killington

You will leave the demands of your busy lifestyle behind when you vacation on our 100+ acre 4 BR 2 BA cabin property with a babbling crystal clear mountain creek. Place your beach chair in the creek, relax with your favorite book for Best Spa Experience Ever! Large open covered porch with porch swing seating to enjoy the expansive mountain views, listen to the leaves rustle and the stream running in the distance. Miles of hiking & biking trails, skiing, restaurants and more nearby.

Guest favourite

Home

4.95 out of 5 average rating, 19 reviews

Upper Valley Shaker-Style Home, close to Dartmouth

Located within minutes to Dartmouth Health Medical Center and Dartmouth College, this home offers a comfortable, warm place to gather with friends and family during your visit to the Upper Valley. Just off Route 4, this home offers easy access to I-89 and I-91. This home is unique in its location and proximity to Mascoma Lake. A common right of way and short walk will lead you to the lakefront park and rail trail, where the views are breathtaking. Snowmobile access to rail trail

Guest favourite

Cabin

4.96 out of 5 average rating, 24 reviews

Luxury Ski Cabin, 2 bedrooms, den & 3 bathrooms

This luxury residence on Killington Mountain is merely a 400-yard walk to the closest ski trail or a short 5-minute drive to the principal ski bases, along with the resort's array of bars, eateries, and retail outlets. It features an indoor jacuzzi, a spacious living/kitchen area bathed in natural light. A variety of summer pursuits, including golf, hiking, mountain biking, and canoeing, are conveniently accessible within minutes from the home. Plus, the property welcomes pets.

Guest favourite

Apartment

5 out of 5 average rating, 10 reviews

Top Flr Duplex 3BR 4BA - Walk to All @ Stratton Mt

Rising Bear Duplex 411 at Stratton Mt-Seasonal Rental Available Spacious 3Br/4Bth Lodge on The Commons w/ Ice Skating Pond, Heated Pool, 2 Min Walk To Ski Family Friendly Spacious Lodge With Mountain Views, Excellent Location. Inspired by the great lodges, Rising Bear is located on the Commons, with ice skating, firepits and family activities. Convenient heated underground parking space and generous living spaces make Rising Bear ideal for bigger families and group gatherings.

Guest favourite

Home

4.95 out of 5 average rating, 44 reviews

Modern 3-bedroom home walkable downtown location

Enjoy our open concept home with a modern flair while being centrally-located to many amenities including skiing, swimming, snowmobiling, fishing, hiking, golfing, and much more! This property offers two clean, bright, and spacious bedrooms with lots of natural light and high ceilings. The third bedroom is an intimate room with a propane fireplace and private sunroom. (Additional attached bedrooms and living space available for rent. Reach out for more information.)

Guest favourite

Flat

4.96 out of 5 average rating, 26 reviews

Norm's Place

Located in historic Pittsford Vermont, come stay in our newly renovated private unit. Close to Killington and Pico for skiing, the Mountain Top Inn , The Brandon Inn and Lilac Inn for weddings and events. Walking distance to the Pittsford Recreation center and walking trails. Convenient to swimming at the Chittenden reservoir or State Parks. Lots of opportunities for hiking and experiencing local breweries. Come see what our beautiful state has to offer!

Guest favourite

Home

4.95 out of 5 average rating, 20 reviews

Charming 3BR 1Bth New England Cape- Experience VT!

Relax with the whole family, or friends at this peaceful place to stay. Close to many local ski resorts, hiking trails, trophy fishing in the Black River off Route 131! Close to Ludlow And Historic Windsor and Woodstock VT! Only a 10 minute drive to Okemo Mountain and Jackson Gore! 30 Minutes to Killington Mountain and Magic Mountain 40 Minutes to Bromley Mountain Accessible to the natural beauty of Vermont!

Guest favourite

Home

5 out of 5 average rating, 13 reviews

Killington Retreat

The whole group will enjoy easy access to everything from this bright, spacious and airy 5 bedroom, 5 bath (3 full & 2 half) vacation rental! Less than 1 mile to shopping and restaurants, and less than 3 miles to Snowshed and Rams Head, yet nestled in a quiet wooded neighborhood. This home features all the space, amenities, and conveniences for a peaceful and fun time away with friends and family!

Guest favourite

Chalet

5 out of 5 average rating, 53 reviews

Cozy chalet mins from Okemo & VAST.

Come enjoy some time in our cozy & relaxing 3-bedroom, 2-bath home. If you prefer a winter or summer getaway, all the options are available. Minutes from all activities and restaurants. Enjoy the nearby hiking and biking trails, Buttermilk Falls, Jackson Gore and Okemo SP. Property located opposite mountain traffic. Hang a left on 103 when leaving JG/ Okemo Main Rd.

Guest favourite

Home

5 out of 5 average rating, 13 reviews

Nature, comfort, & large tiled hot tub

Sitting at 1,100 feet above sea level, on 32 acres, bask in the fresh mountain air at this unique and family-friendly place. Relax with an oversized stone and tile hot tub with a waterfall. 7 minute drive to skiing at Mt. Sunapee. Minutes to various trailheads. Wilderness and wildlife abound. Bring your family and friends to this unforgettable location.

Guest favourite

Home

5 out of 5 average rating, 10 reviews

Comfortable Vermont Getaway. Three bedroom home.

Your family will be close to many venues when you stay at this centrally-located place. You will be 15 minutes to Pico Ski Area and 20 minutes to Killington Ski Area. Mountain Top ski area and wedding venue is a 15 minute drive. Downtown Rutland is five minutes to enjoy the many shops, restaurants and the Paramount Theatre.

Guest favourite

Campervan/Motorhome

4.93 out of 5 average rating, 41 reviews

Lake front hideaway!

This picturesque location has private dock, located across from public boat launch, access to kayaks and is on the Northern Rail-trail biking and walking path. Enjoy the fire pit and play some outdoor yard games. We would love to make your experience special and are located next door to address your needs.

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Flats

Convenient locations with everyday essentials

Hotels

Stylish accommodation and amenities

Popular amenities for West Windsor holiday rentals

Free parking on premises

Air conditioning

Stay near West Windsor's top sights

Brownsville Butcher & Pantry32 locals recommend

Hall Art Foundation15 locals recommend

Ascutney Trails15 locals recommend

Other great holiday rentals in West Windsor

Guest favourite

Townhouse

5 out of 5 average rating, 21 reviews

New! Vermont Getaway! Stratton - close to skiing!

Apartment

4.74 out of 5 average rating, 85 reviews

2 Bedroom 2 Bath Condo at the Base of Killington

Home

4.83 out of 5 average rating, 84 reviews

Killington Racquetball House

Guest favourite

Home

5 out of 5 average rating, 20 reviews

Great Maples

Home

4.85 out of 5 average rating, 34 reviews

Your VT Ski House: Fireplace, Indoor Pool, Dogs

Guest favourite

Home

5 out of 5 average rating, 7 reviews

Modern, secluded new build near Okemo & Killington

Guest favourite

Home

4.92 out of 5 average rating, 50 reviews

Crescent Lake retreat near Golf and Hiking trails

Guest favourite

Apartment

5 out of 5 average rating, 8 reviews

Modern Comfort in The Woods – 2BD/2BA Dog-Friendly

Quick stats about holiday rentals in West Windsor

Total rentals
70 properties
Nightly prices starting at
£71 before taxes and fees
Total number of reviews
2.1K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
20 properties have a pool

Destinations to explore