Vacation rentals in Windham

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Top-rated vacation rentals in Windham

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Guest favorite

Cabin in Londonderry

4.93 out of 5 average rating, 308 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond in S Londonderry, VT. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery and hiking right outside your front door. The Cabin has an open floor plan with a galley kitchen, dining/living area with pullout futon couch & 1 full bathroom. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

Nov 5 – 12

R1,992 ZAR per night

Guest favorite

Cottage in Jamaica

4.82 out of 5 average rating, 464 reviews

Forest Cottage ~ 7min to Stratton, Private, Views

Authentic Vermont post & beam cottage with privacy. 3 miles to Stratton's Sun Bowl, a 7-minute drive. Nearby swimming hole at the brook on the property. Dogs welcome, $30 fee per dog. No cats due to allergies. Vinyl record player, VCR/DVD player, board games, Starlink Satellite Internet 20-100 mbps. Heat options: 2 gas wall furnaces & wood stove. Front porch, propane BBQ, fire pit, picnic table & spectacular views of Stratton Mountain. Back deck surrounded by woods with hammock, table & chairs.

May 8 – 15

R2,139 ZAR per night

Guest favorite

Cottage in Londonderry

4.97 out of 5 average rating, 200 reviews

Vermont Treehouse - Romantic Private Elegant

SPECIAL 2 night minimum, self checkin. Work remotely. Enjoy this romantic, elegant, private getaway for two (or one) in our "Treehouse" with sleeping loft, full kitchen & bathroom, screened porch, deck, sauna, WiFi, BBQ grill, etc. Overlooking pasture & mountains. Enjoy the property with 3 miles hiking/snowshoe trails on property. Guest house on 160 acre private horse farm. Lots to do at nearby ski areas, shopping, hiking, biking, theater in summer. Or just relax. Discount for longer stays.

Sep 21 – 28

R6,548 ZAR per night

Guest favorite

Home in Putney

4.94 out of 5 average rating, 337 reviews

Vermont Botanical Studio Apartment

This room is one half of a floor in our studio building (35 sq m). It is the only occupied space in the building, which is separated from the main house by a yard. There is a queen-sized bed, full bath (no-curb shower), and an outdoor shower (not available in the winter) Small kitchen with a sink, fridge, 2-burner induction hob, microwave/convection oven, toaster, coffee pot, and cookware. Arched ceiling, with ceiling fan, large windows, deck, and Maggie's botanical art lining the walls.

Oct 23 – 30

R1,965 ZAR 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.

Feb 26 – Mar 5

R1,774 ZAR per night

Guest favorite

Cabin in Jamaica

4.99 out of 5 average rating, 185 reviews

New Cabin in Jamaica

Recently constructed 500sq ft passive solar cabin, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

Jul 11 – 18

R2,850 ZAR per night

Guest favorite

Tiny home in Athens

4.95 out of 5 average rating, 148 reviews

Luxury “Tiny” House, Immersed In Nature (Timbery)

The Timbery: This is a brand new, fully handmade, timber frame "tiny" house. The house is nestled in the forest, accessible by foot. With 17 vertical ft. of floor to ceiling windows, this property represents a unique experience to fully immerse yourself into nature. It is like lying down on the forest floor and looking out the front of your tent. Except instead of wet sleeping bags and dirty hair, you enjoy a queen sized bed, in home theater, full kitchen and 71in soaking tub. NO SMOKING

Aug 2 – 9

R4,881 ZAR per night

Guest favorite

Cabin in Londonderry

4.96 out of 5 average rating, 99 reviews

Summit view cottage: Secluded cabin with hot tub

Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 6 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.

Mar 18 – 25

R15,067 ZAR per night

Guest favorite

Barn in Chester

4.99 out of 5 average rating, 493 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 4 – 11

R1,996 ZAR per night

Guest favorite

Apartment in Townshend

4.94 out of 5 average rating, 203 reviews

Private Apt. on Farm, great views and Hot tub,

Self-contained apt with fantastic views, outside deck & private entrance with keypad lock. Two queen bedrooms and queen sleeping loft, kitchen and open plan living room. Located on a historic 38-acre working farm. If you need more space we have an adjoining apartment that sleeps 5. Apartment is above garage and attached to the main farmhouse. Pls note pricing is based on up to four guests; add'l $25/person/night up to max 6 guests added automatically.

Dec 11 – 18

R3,029 ZAR per night

Guest favorite

Apartment in Andover

4.98 out of 5 average rating, 386 reviews

Private Hilltop farm apartment

Our cozy apartment is located on a beautiful hilltop farm with views out from the porch across horse pasture and to the mountains as far away as New Hampshire. There are over 100 acres of field to walk through as well as a mile long trail running down through our property. We are 15 minutes from Chester, Ludlow and Weston. We also have very fast internet!

Sep 22 – 29

R2,179 ZAR per night

Guest favorite

Apartment in Londonderry

4.94 out of 5 average rating, 333 reviews

Cozy Suite in a Historic Building Near Ski Resorts

Located on the second floor of a historical building in the Village of South Londonderry, Vermont, this renovated studio suite features unique touches of modern amenities but with a Vermont feel. Your room will include a 65 inch Smart TV, WiFi, electric fireplace, lush queen bed, full renovated bathroom, small kitchenette, as well as on site parking.

May 8 – 15

R2,170 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Windham vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Windham's top sights

Magic Mountain Ski Area136 locals recommend

The Upper Pass Lodge3 locals recommend

Hamilton Falls27 locals recommend

The Red Slate Restaurant4 locals recommend

West River Dam3 locals recommend

Tater Hill Golf Course8 locals recommend

Other great vacation rentals in Windham

Superhost

Cabin in Wardsboro

4.8 out of 5 average rating, 202 reviews

Log Cabin Near Stratton/Mt Snow

May 14 – 21

R1,907 ZAR per night

Guest favorite

Home in Putney

4.95 out of 5 average rating, 307 reviews

Cozy Train Depot in Putney Vermont

May 13 – 20

R1,967 ZAR per night

Guest favorite

Apartment in Jamaica

4.84 out of 5 average rating, 199 reviews

The Getaway

Mar 19 – 26

R2,627 ZAR per night

Guest favorite

Barn in Marlboro

4.95 out of 5 average rating, 263 reviews

The Studio With a View. Bring your dog, too!

Aug 26 – Sep 2

R2,728 ZAR per night

Guest favorite

Guesthouse in Wallingford

4.98 out of 5 average rating, 588 reviews

Vermont Home Central to Ski Areas-No Cleaning Fees

Oct 26 – Nov 2

R2,628 ZAR per night

Guest favorite

Apartment in Manchester

4.99 out of 5 average rating, 147 reviews

Private two-bedroom suite within a two-story house

May 5 – 12

R1,686 ZAR per night

Guest favorite

Condo in Londonderry

4.95 out of 5 average rating, 43 reviews

Magical Ski-In/Ski-Out Condo at Magic w/ game room

Sep 17 – 24

R1,981 ZAR per night

Guest favorite

Home in Windham

4.95 out of 5 average rating, 77 reviews

Artistic Southern Vt Countryside Home at Windham

Aug 28 – Sep 4

R5,183 ZAR per night

Show all

Quick stats about vacation rentals in Windham

Total rentals
60 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
1.9K reviews
Nightly prices starting at
R1,713 ZAR before taxes and fees

Frequently Asked Questions

Are there pet-friendly vacation rentals in Windham?
Four-legged friends are welcome in Windham. Choose from more than 20 vacation rentals for guests traveling with pets.
Do house rentals in Windham have a kitchen?
Absolutely! We offer over 30 house rentals with a kitchen in Windham. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Windham?
Experience the best of Windham with our house rentals, starting at about $160 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Windham have wifi?
Absolutely! We offer over 30 house rentals with wifi in Windham. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Windham?
Windham 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 House Rentals in Windham?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with wifi, over 30 homes with a kitchen, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Windham have free parking?
Absolutely! We offer over 20 house rentals with free parking in Windham. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Windham?
Yes! Work meets play with ease at over 30 vacation rentals in Windham featuring dedicated workspaces. Stay connected and productive in your home away from home.

Vacation rentals in Windham

Top-rated vacation rentals in Windham

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Windham vacation rentals

Stay near Windham's top sights

Other great vacation rentals in Windham

Cabin in Wardsboro

Home in Putney

Apartment in Jamaica

Barn in Marlboro

Guesthouse in Wallingford

Apartment in Manchester

Condo in Londonderry

Home in Windham

Quick stats about vacation rentals in Windham

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there pet-friendly vacation rentals in Windham?

Do house rentals in Windham have a kitchen?

How much does it cost to stay in house rentals in Windham?

Do house rentals in Windham have wifi?

Are there family-friendly vacation rentals in Windham?

What are the most popular amenities for House Rentals in Windham?

Do house rentals in Windham have free parking?

Are there vacation rentals with a dedicated workspace in Windham?

Destinations to explore