Windham County Condo Rentals from CA $399

A wooden covered bridge over a river with stone walls on either side.

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Top Cities in Windham County

A snow-covered road winding through a forested area with buildings and mountains in the background.

Our top choices for Windham County condo rentals

A rustic cabin with a large window and a wooden exterior, surrounded by snow and trees.

1. Stratton 1 Bedroom Long Trail Condo, Walk to Village and Lifts

Stratton

Lisa D.

An indoor swimming pool with a wooden ceiling and skylights, surrounded by lounge chairs and a sign reading "SEASONS ON MONTLIT SNOW".

2. Seasons On Mount Snow - Ski-in/Ski-out

Dover

Noah E.

A modern kitchen with white cabinetry, granite countertops, a dining area with a round table and chairs, and a large window providing natural light.

3. Remodeled Vantage Point condo with wood fireplace, walk to the village

Stratton

Jason G.

A group of people performing a yoga session outdoors on a wooden deck with a scenic view of trees and mountains in the background.

4. Cozy Fireside Retreat for Two — Hot Tubs, Pool & Stratton Village Steps Away

Stratton

Lauren S.

A multi-story hotel with a prominent entrance, a covered outdoor area, and a parking lot.

5. Founders Lodge condo at Stratton Mountain with gas fireplace

Stratton

CA $565 total

includes taxes & fees

Nov 11 - Nov 12

A modern kitchen with a central island, a stone fireplace, and a dining area with chairs.

6. Ski on ski off condo

Stratton

Brian L.

An outdoor patio area with Adirondack chairs, a stone fire pit, and a grill station.

7. Clean Ski in ski out condo located at Seasons on Mt. Snow.

Dover

Shayne

A modern kitchen with white cabinetry, a microwave, a toaster, and a dishwasher.

8. Third-floor slopeside condo with balcony and fireplace, walk to Mount Snow

Dover

Mark A.

A large building with multiple balconies and windows, surrounded by snow.

9. Mountain & sunset views from balcony! Heated pool/spas, walk to lifts & village!

Stratton

Theodore D.

A calm lake with a wooden boat on the shore.

10. Cozy 3 bedroom condo 2.5 miles to Mount Snow

West Dover

Scott S.

CA $399 total

includes taxes & fees

Nov 17 - Nov 18

A large indoor swimming pool with a wooden ceiling and large windows.

11. Mount snow ski on ski off at Seasons

Dover

Mark L.

A living room with a fireplace, a sofa, a coffee table, and a television.

12. Beautifully renovated 2 bedroom condo in Stratton VT - walk to Village/Lifts!

Stratton

John S.

13. ★No Cleaning Fee★10% OFF★Walk To Mountain★Amenities+

Stratton

Shanon L.

A dining area with a dark wooden table, chairs, and a chandelier. There is a fireplace and a sofa in the background.

14. RENOVATIONS ALMOST COMPLETE- NEW PHOTOS SOON! Ski-In Ski-Out OberTal F Building!

Stratton

Jen M.

A wooden sauna with benches and frosted glass panels.

15. Mount Snow Resort condo with indoor pool, under a half mile to Timber Creek

Dover

Unspecified U.

A bedroom with a large bed, two bedside tables, a window with curtains, a wall clock, and a piece of wall art.

16. Styles Brook townhome with loft, wood fireplace and shuttle route access

Stratton

Christine H.

A modern kitchen with dark cabinetry, stainless steel appliances, and a bar area with stools.

17. Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub

Stratton Mountain

Susan F.

CA $725 total

includes taxes & fees

Nov 11 - Nov 12

A snow-covered town with a prominent clock tower, colorful buildings, and a visible street with snow-covered trees.

18. Steps to Stratton Village, Lifts! Duplex Condo!

Stratton

Adam K.

A well-maintained outdoor area with a paved walkway, a gazebo, and a stone fire pit.

19. Cozy ski-in/ski-out condo on Mount Snow w/fireplace

Dover

Robert H.

A two-story house with a covered porch, a garage, and a well-maintained lawn.

20. East-side Stratton condo with gas fireplace, by the rec center and shuttle

Stratton

Valerie B.

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Top Windham County Hotel Reviews

Holiday Inn Express Hotel & Suites Brattleboro by IHG

10/10 Excellent

"Easy check in, clean room and nice location"

Grand Summit Resort, A Vail Resorts Property

8/10 Good

"The room and atmosphere of the hotel was amazing. But we came on the off season and a lot of things were closed. The restaurant and spa were closed but also a bunch of the restaurants in the area were closed on a Saturday night for dinner. But again this was an off season so I get it."

Hideaway Inn Mt. Snow

10/10 Excellent

"The room was small and simple, but nicely decorated, including a record player with a vinyl album (cover, at least; didn't check for actual vinyl). The room was warm and the place was quiet when I stayed, which was off-season. I've been pulling into the parking lot of this place for five years now (MOOver), so staying there was interesting for me. I stayed there during a HAZMAT spill that closed Woodford Mtn for a couple days. Of special note, this is the ONLY hotel I've ever stayed at that had a sleep/sound machine in the room. I ALWAYS take one with me when traveling, but this was a last minute decision, so I would've had to pull up something on my phone, but there was a nice sound machine on the nightstand and I used it. Those are so helpful when staying in hotels/inns."

Find out more about Windham County

Windham County Condo Rentals information

Number of reviews	754
Accommodation	148 Condo Rentals
Lowest Price	CA $399
Highest Price	CA $725

Frequently asked questions

How much do condos in Windham County cost?

Condos in Windham County range from CA $399 to CA $725 per night. This means lots of room for the entire family at a price that's easy on your wallet. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

How many condos are there in Windham County?

Browse through our 148 condos in Windham County and then book your favorite. Whether you're organizing a vacation with the fam or kicking it with your pals, with Expedia, your perfect stay is just clicks away.

Why book your condo in Windham County with Expedia?

Reserving a condo in Windham County is as simple as entering your travel dates and picking a place that checks your boxes. On the search for something affordable or luxurious, or a stay that also has a laundry and kitchen? Use Expedia's search filters to further narrow your search results and find the perfect fit.

How can I find cheap condos in Windham County?

The easiest way to compare cheap condos in Windham County is with Expedia's easy-to-use filter tool. Fine-tune your search results by star rating, amenities and budget to access awesome rates in just a few clicks.

What is there to do in Windham County near my condo?

Whatever you're into, there are many ways to spend your time in Windham County. If you're off to Wilmington, be sure to look around The Hermitage Golf Club, Jim McGrath Gallery and Studio and Lake Raponda. Escaping to Londonderry? Taylor Farm, Viking Nordic Center and Lowell Lake State Park are among the top attractions here.

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Search Condos Rentals in Windham County from CA $399

Change your mind

Treat yourself

Be picky

Check prices for these dates

Top Cities in Windham County

West Dover

Our top choices for Windham County condo rentals

1. Stratton 1 Bedroom Long Trail Condo, Walk to Village and Lifts

2. Seasons On Mount Snow - Ski-in/Ski-out

3. Remodeled Vantage Point condo with wood fireplace, walk to the village

4. Cozy Fireside Retreat for Two — Hot Tubs, Pool & Stratton Village Steps Away

5. Founders Lodge condo at Stratton Mountain with gas fireplace

6. Ski on ski off condo

7. Clean Ski in ski out condo located at Seasons on Mt. Snow.

8. Third-floor slopeside condo with balcony and fireplace, walk to Mount Snow

9. Mountain & sunset views from balcony! Heated pool/spas, walk to lifts & village!

10. Cozy 3 bedroom condo 2.5 miles to Mount Snow

11. Mount snow ski on ski off at Seasons

12. Beautifully renovated 2 bedroom condo in Stratton VT - walk to Village/Lifts!

13. ★No Cleaning Fee★10% OFF★Walk To Mountain★Amenities+

14. RENOVATIONS ALMOST COMPLETE- NEW PHOTOS SOON! Ski-In Ski-Out OberTal F Building!

15. Mount Snow Resort condo with indoor pool, under a half mile to Timber Creek

16. Styles Brook townhome with loft, wood fireplace and shuttle route access

17. Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub

18. Steps to Stratton Village, Lifts! Duplex Condo!

19. Cozy ski-in/ski-out condo on Mount Snow w/fireplace

20. East-side Stratton condo with gas fireplace, by the rec center and shuttle

Find vacation rentals that suit your style

Top Windham County Hotel Reviews

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Find out more about Windham County

Windham County Condo Rentals information

Frequently asked questions

Explore a world of travel with Expedia