
Vacation rentals in West Windsor
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in West Windsor
Guests agree: these stays are highly rated for location, cleanliness, and more.

Cozy - Killington 40 min. Woodstock-Hanover-Piano!
Luxurious, well appointed cottage - Beautiful sunrise view located between Woodstock VT and Hanover NH. Inspiring treat for musician’s getaway is a fully restored 1929 Steinway Full kitchen, custom cabinets, gas fireplace, energy efficient heat pump, washer, dryer. VERY comfortable queen bed. Romantic getaway in the woods, relax, work in peace, explore the beauty and history of the area. Hiking, biking, fishing, hot air balloon rides and shopping are all close by. Long (90 day) or weekend rental

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba
Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn.Very close proximity to the town of Manchester, which has great shops and restaurants

Adorable one bedroom studio in 1844 farmhouse.
Keep it simple at this peaceful and centrally-located place. We have a beautiful 1844 farm house located in Quechee, that has been in our family for over a hundred years. It is located less than a 1/4 mile from the Quechee Gorge and Antique Mall. The farm includes fifty acres of land and trails with wonderful views of Mt. Ascutney, Killington and more. We also abut the state park which has twelve hundred acres of land. All perfect for hiking, snowshoeing, snowshoeing, biking or just relaxing.

Sugar River Treehouse
Welcome to Sugar River Treehouse! If you’re looking for serenity, peace and quiet, in the most unique, breathtaking, beautiful setting, you have found it. On top of the trees, overlooking the Sugar River in the quaint town of Newport, NH you will find plenty of year round activities including swimming, floating, fishing on the beautiful, clear Sugar River, right outside the back door. You will find the treehouse sits up in between 2 beautiful northern hemlocks and is fully equipped inside.

Ogden's Mill Farm
Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

Inviting studio apartment above barn in Vermont
This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. I am as close or as far away as you would like me to be with my house right next door.

Birdie's Nest Guesthouse
Welcome to our newly renovated studio apartment, nestled among the trees in the serene hills of West Windsor, Vermont. Elevated on the second floor, this separate structure offers a tranquil escape with breathtaking views of Mount Ascutney and our own private pond. Immerse yourself in the comforts of this thoughtfully designed studio apartment, surrounded by the natural beauty of the Vermont landscape. Every detail has been curated to ensure your utmost comfort and enjoyment.

The Loft at Weathersfield
Close to Okemo, The Loft at Weathersfield, is just 1/2 hour south of Woodstock / Hanover area and 22 minutes from Okemo Mountain. The Loft, is located in a private agricultural setting with easy access to Vermont's best biking, hiking, fly fishing, skiing, and many equine trails. The loft is 900 square feet with a kitchen/dining room, living room, full bath, one bedroom with a queen bed and one twin bed. There is a spacious deck off the kitchen and a car port underneath.

Meadow View. 35 acres outside your door!
Meadow View - pet friendly home away from home. 35 acres- including 2 trout ponds and 25 acres of wooded trails (perfect for hiking, cross country skiing/snow shoeing!). Featuring a newly remodeled kitchen and bathroom. Minutes from Mt. Ascutney (trails galore, rope tow in the winter). The unit is perfect spot for couples craving time in rural Vermont or for families/outdoor enthusiasts who want to go mountain biking, skiing, hiking. (Okemo 30 min Killington 45 min)

Cozy Little Spot (Self Check-in)
Contactless check-in. Cozy guest house, cabin-studio-getaway; enjoy the sounds of a stream outside the window (next to the bed). Views of a larger brook below. The"Cabin"is nestled in the trees giving a feeling of floating above the brook below. The interior is decorated w/family heirlooms gathered from around the country. Nothing fancy, just a cozy simple getaway. 3.25 mi from town. Choose from a variety of activities in town or hop on nearby trails. NO PETS ALLOWED.

Luxury Cabin#1 Hot Tub Fire Pit Kayak Paddle Board
Escape in a beautiful light-filled upscale cabin deep in the woods at Sugar Maple Mountain Retreat. Relax at the end of the day in our hot tub which is shared between our 3 cabins. Steps away from two picturesque lakes, enjoy complimentary seasonal use of our kayaks, paddle boards and snow shoes. Go fishing, biking, hike country roads or trails on the 1275 acres of surrounding preserved land. In winter hop on the VAST trail nearby. 4 WD Required Dec 1- April 15th

Yurt In The Woods - Come to the Yurt.
The Yurt In The Woods is 30 ft in diameter - 700 spacious sq. ft. It's surrounded by trees and has a yard. 2 night stays required for Weekends. October 6th and 12th are currently vacant if you want a fall foliage trip. There is a "one" night stay fee of $50 Allowed 2 dogs with the agreement to my animal policy & $50 fee WiFi 1,000 megabits per second a fiber network Outdoor Gas Grill , Outdoor Fire Circle, and Outdoor Shower available May - October
Popular amenities for West Windsor vacation rentals
Other great vacation rentals in West Windsor

Cute, clean and comfy 2 BR studio

Cozy 1 bedroom home with private hot tub

Cozy historic hilltop cottage

The Westerdale | Woodstock Retreat | Pet Friendly

3BR Farmhouse-Long Trail Brewery

Quiet Country Retreat

Mountain Edge Living

Chuck's Place
When is the best time to visit West Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$43,910 GYD | G$43,910 GYD | G$43,910 GYD | G$42,656 GYD | G$41,819 GYD | G$42,865 GYD | G$44,956 GYD | G$43,701 GYD | G$44,956 GYD | G$45,792 GYD | G$44,537 GYD | G$49,556 GYD |
| Avg. temp | -5°C | -4°C | 1°C | 7°C | 14°C | 19°C | 22°C | 21°C | 16°C | 10°C | 4°C | -2°C |
Frequently Asked Questions
Are there family-friendly apartment rentals in West Windsor?
West Windsor has more than 10 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in apartment rentals in West Windsor?
Experience the best of West Windsor with our apartment rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly cabin rentals in West Windsor?
Four-legged friends are welcome in West Windsor. Choose from more than 10 cabin rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in West Windsor?
Yes! Work meets play with ease at over 30 vacation rentals in West Windsor featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there West Windsor vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in West Windsor, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in West Windsor have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in West Windsor. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in West Windsor have a kitchen?
Absolutely! We offer over 10 apartment rentals with a kitchen in West Windsor. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in West Windsor have wifi?
Absolutely! We offer over 10 cabin rentals with wifi in West Windsor. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in West Windsor have free parking?
Absolutely! We offer over 10 cabin rentals with free parking in West Windsor. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in West Windsor?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with a kitchen, over 20 homes with free parking, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about vacation rentals in West Windsor

Total vacation rentals
Explore 70 vacation rentals in West Windsor

Nightly prices starting at
West Windsor vacation rentals start at G$18,819 GYD per night before taxes and fees

Verified guest reviews
Over 2,770 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Vacation rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
70 of West Windsor vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across West Windsor rentals

4.9 Average rating
West Windsor stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Tuckahoe Vacation rentals
- Long Island Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- Pocono Mountains Vacation rentals
- Québec City Vacation rentals
- The Hamptons Vacation rentals
- Pet-friendly rentals West Windsor
- Rentals with a washer and dryer West Windsor
- House rentals West Windsor
- Rentals with a fireplace West Windsor
- Family-friendly rentals West Windsor
- Fitness-friendly rentals West Windsor
- Rentals with a patio West Windsor
- Apartment rentals West Windsor
- Rentals with pools West Windsor
- Rentals with a fire pit West Windsor
- Rentals with outdoor seating West Windsor
- Okemo Mountain Resort
- Stratton Mountain
- Sugarbush Resort
- Killington Resort
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Monadnock State Park
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- Tenney Mountain Resort
- Ragged Mountain Resort
- Fox Run Golf Club
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Crotched Mountain Ski and Ride
- Montshire Museum of Science
- Dartmouth College
- Mount Sunapee Resort
- Squam Lakes Natural Science Center
- Emerald Lake State Park
- Middlebury College
- Stinson Lake
- Plymouth State University




