Vacation rentals in West Windsor

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Top-rated vacation rentals in West Windsor

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Guest favorite

Farm stay in Plainfield

4.97 out of 5 average rating, 175 reviews

Renovated 1817 Hobby Farm Close to Dartmouth

Come stay at our hobby farm in Plainfield Village! Experience country living with a 20-minute proximity to Dartmouth University. It is a daily work in progress, gardening and taking care of the chickens and sheep, so it is not perfect, but it is lively and ever-changing. You can see gorgeous views of Mount Ascutney from your window, hike to the French Ledges, visit St. Gaudens Park, or J.D. Sallingers farm. Every season is beautiful here! Or learn how to make macarons :) if you are brave enough.

Nov 11 – 18

$130 per night

Guest favorite

Home in West Windsor

4.98 out of 5 average rating, 127 reviews

Firewheel Hill: Private, contemporary house

Firewheel Hill House is nestled on a private road in the mountains of West Windsor Vermont. With modern amenities and a breathtaking view of Mount Ascutney; This house is the perfect getaway for you and your family to enjoy all this area has to offer. A network of bike and horse trails abuts the property. The house is ten minutes to GMHA, 20 minutes to Woodstock 30-40 minutes from Suicide Six and Okemo and less than an hour to Killington. You must have 4WD to stay here between December-April.

Sep 15 – 22

$213 per night

Guest favorite

Cottage in Hartland

4.97 out of 5 average rating, 419 reviews

Breeze Hill Cottage

This cozy two bedroom home sits on a rural dirt road overlooking fields, woods, and the NH mountains. Watch birds from the window, relax on the patio, and enjoy the flower gardens. The cottage boasts modern amenities mixed with antiques. Please note: if we don’t respond to an Airbnb message and you need to speak with us, call us on our phones day or night!!! We have had people message us when we were asleep and so we have not been aware and have not responded. Call us! We will hear the phone!

Dec 4 – 11

$106 per night

Guest favorite

Guesthouse in Springfield

4.86 out of 5 average rating, 321 reviews

Connecticut River-Cozy Cottage

This cozy cottage is located on the beautiful Connecticut River, nestled between fertile farmland and Skitchewaug Mountain with views abound. The cottage design utilizes a small footprint while offering functionality and basic comforts, including a small kitchen. Great for all seasons, close to Okemo, Sunapee, Ascutney and other worthy attractions. Hiking and snowshoeing options at your front door. Secrete fishing and swimming holes located on the property. Boat dock available upon request.

Mar 6 – 13

$80 per night

Guest favorite

Barn in Chester

4.99 out of 5 average rating, 492 reviews

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. We are as close or as far away as you would like us to be with our house right next door.

Sep 22 – 29

$89 per night

Guest favorite

Apartment in Weathersfield

4.99 out of 5 average rating, 157 reviews

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.

Nov 26 – Dec 3

$106 per night

Guest favorite

Cabin in West Windsor

4.98 out of 5 average rating, 205 reviews

Sunset Cabin - your private romantic hideaway

Your private woodlands retreat awaits. Nestled atop a beautiful 10 acre meadow with 25 acres of woods for you to enjoy; this rustic, pet friendly cabin is a perfect romantic hideaway. Two trout ponds are steps from your door for fishing and swimming. Just a few minutes from Mt. Ascutney's hiking and mountain-biking trails and in the middle of fantastic cycling country. WiFi now available! Sunset Cabin is a marvelous spot for enjoying fall foliage and exploring Vermont.

Jul 2 – 9

$135 per night

Guest favorite

Guest suite in Brownsville/West Windsor

4.99 out of 5 average rating, 161 reviews

Cozy Guest Suite in Charming Farmhouse

Your two story guest suite is attached to the (main house) with a private FRONT DOOR entry. Sorry there are no cooking elements available. Please take note that the antique stairs to the second floor are steep. You will find your very own first floor library/eating area with WiFi, mini fridge, coffee maker and 1/2 bath. Upstairs is a comfy bedroom suite with a private modern bathroom that includes a shower and Jacuzzi tub. None of these area are shared. It’s all yours!

Jul 8 – 15

$143 per night

Guest favorite

Cottage in Windsor

4.97 out of 5 average rating, 316 reviews

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.

Nov 20 – 27

$118 per night

Guest favorite

Condo in Ludlow

4.92 out of 5 average rating, 122 reviews

Okemo Ski-in/Ski-out, Steps to lift Condo

Just steps of walk to the amazing Okemo slopes, C Building is the closest property to the A-Quad/B-Quad lift and this building offers convenient parking right downstairs and free wi-fi (dedicated Xfinity modem, no issue video conference). You’ll love this cozy place with hardwood floor and private balcony and sunshine after skiing. Great sun exposure. Fireplace has been updated to electric fireplace starting from 2023-2024 season.

Jul 27 – Aug 3

$87 per night

Guest favorite

Guesthouse in Hartland

4.95 out of 5 average rating, 912 reviews

Yurt In The Woods - Private Refuge

The Yurt In The Woods is 30 ft in diameter which offers 700 spacious sq. ft. It's surrounded by trees and has a yard. 2 night stays required for all Weekends. I require atleast a two night stay for the whole month of October. There is a "one" night stay fee of $40 Allowed 2 dogs with the agreement to my animal policy & $50 fee WiFi 1,000 megabits per second a fiber network Outdoor Gas grill available May - October

Dec 7 – 14

$133 per night

Guest favorite

Guest suite in West Windsor

4.9 out of 5 average rating, 102 reviews

Newly renovated private space on Ascutney Trails

Newly renovated space on Ascutney trails--walking distance Ascutney Outdoors Center, hotel, restaurant, skiing, and Brownsville Butcher & Pantry. Trail access in back yard with miles of hiking, mountain biking, running and skiing. Parking for 2 cars. Close to Woodstock shops and Okemo adventure center. Private keycode entrance with self-check in. Microwave, refrigerator, Keurig, coffee and tea provided. Fast wifi.

Dec 8 – 15

$86 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for West Windsor vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in West Windsor

Guest favorite

Apartment in Andover

4.98 out of 5 average rating, 386 reviews

Private Hilltop farm apartment

Sep 10 – 17

$98 per night

Guest favorite

Guesthouse in Woodstock

4.98 out of 5 average rating, 205 reviews

Cozy Little Spot (Self Check-in)

Jan 22 – 29

$137 per night

Guest favorite

Guest suite in Hartford

4.92 out of 5 average rating, 315 reviews

Sunny Side Airbnb (dog friendly)

May 17 – 24

$97 per night

Guest favorite

Home in West Windsor

4.96 out of 5 average rating, 54 reviews

Birdie's Nest Guesthouse

Feb 1 – 8

$118 per night

Guest favorite

Townhouse in West Windsor

5.0 out of 5 average rating, 44 reviews

Lovely Trailside 2 Bedroom Townhouse

Nov 21 – 28

$210 per night

Guest favorite

Cabin in West Windsor

5.0 out of 5 average rating, 18 reviews

Cozy Log Cabin w/ Incredible Mountain View

Aug 9 – 16

$549 per night

Guest favorite

Tiny home in West Windsor

5.0 out of 5 average rating, 13 reviews

Red Barn Cabin

Nov 19 – 26

$132 per night

Guest favorite

Apartment in Hartland

5.0 out of 5 average rating, 9 reviews

Lovely Upper Valley 1 Bedroom

Dec 5 – 12

$74 per night

Show all

Quick stats about vacation rentals in West Windsor

Total rentals
60 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
2K reviews
Nightly prices starting at
$90 before taxes and fees

Frequently Asked Questions

Do house rentals in West Windsor have a kitchen?
Absolutely! We offer over 20 house rentals with a kitchen in West Windsor. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in West Windsor?
West Windsor has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Apartment Rentals in West Windsor?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with free parking, over 10 homes with a kitchen, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there pet-friendly vacation rentals in West Windsor?
Four-legged friends are welcome in West Windsor. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there West Windsor vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in West Windsor, available on Airbnb. Make a splash and soak up the sun in style!
Are there vacation rentals with a dedicated workspace in West Windsor?
Yes! Work meets play with ease at over 20 vacation rentals in West Windsor featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in West Windsor?
Experience the best of West Windsor with our house rentals, starting at about $140 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in West Windsor have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in West Windsor. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in West Windsor have wifi?
Absolutely! We offer over 20 house rentals with wifi in West Windsor. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in West Windsor have free parking?
Absolutely! We offer over 10 apartment rentals with free parking in West Windsor. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in West Windsor

Top-rated vacation rentals in West Windsor

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for West Windsor vacation rentals

Other great vacation rentals in West Windsor

Apartment in Andover

Guesthouse in Woodstock

Guest suite in Hartford

Home in West Windsor

Townhouse in West Windsor

Cabin in West Windsor

Tiny home in West Windsor

Apartment in Hartland

Quick stats about vacation rentals in West Windsor

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in West Windsor have a kitchen?

Are there family-friendly vacation rentals in West Windsor?

What are the most popular amenities for Apartment Rentals in West Windsor?

Are there pet-friendly vacation rentals in West Windsor?

Are there West Windsor vacation rentals on Airbnb with pools?

Are there vacation rentals with a dedicated workspace in West Windsor?

How much does it cost to stay in house rentals in West Windsor?

Do apartment rentals in West Windsor have air conditioning?

Do house rentals in West Windsor have wifi?

Do apartment rentals in West Windsor have free parking?

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