Windham Vacation Rentals from $244: Search Short-Term Rentals

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Our top choices for Windham vacation rentals

A cozy cabin interior with a wooden ceiling, a round table with chairs, a fireplace, and a large window overlooking a snowy landscape.

1. Beautiful country cabin with hot tub and outdoor shower in Londonderry

Londonderry

Michael D.

$309 nightly

Nov 16 - Nov 17

Total with taxes and fees

A living room with a sofa, a television, a fireplace, and a dining area with chairs and a table.

2. Stratton ski-in/ski-out condo steps from the lift with valley-view balcony

Stratton

eric m.

$283 nightly

Nov 14 - Nov 15

Total with taxes and fees

A multi-story building with a stone facade, a central courtyard with a hot tub, and a stone pathway.

3. Founders Lodge condo at Stratton Mountain with gas fireplace

Stratton

$367 nightly

Nov 14 - Nov 15

Total with taxes and fees

A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

4. Long Trail House 368 condo in Stratton Village, walk to the lifts

Stratton

$232 nightly

Nov 16 - Nov 17

Total with taxes and fees

A cozy cabin interior with a wooden ceiling, a sofa, a red armchair, a small table with magazines, and a window with curtains.

5. Cozy Vermont Cabin at Trail End Ranch! The Best of VT is all around you!

Andover

Betsy S.

$381 nightly

Nov 14 - Nov 15

Total with taxes and fees

A red house with a covered porch and a chimney.

6. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Grafton

Neil S.

$332 nightly

Nov 16 - Nov 17

Total with taxes and fees

A building with a sign reading 'Fire Tower Restaurant & Tavern.'

7. Fourth-floor Stratton Village studio with valley-view balcony

Stratton

$217 nightly

Nov 15 - Nov 16

Total with taxes and fees

A wooden cabin with a balcony and a staircase leading to a second level.

8. Romantic Riverbed Treehouse - hot tub & new sauna!

londonderry

Tracey V.

$521 nightly

Nov 16 - Nov 17

Total with taxes and fees

A swimming pool with a stone border, surrounded by a snow-covered landscape and a wooden fence.

9. Long Trail House at Stratton Mountain Resort

Stratton

Michael

$391 nightly

Nov 15 - Nov 16

Total with taxes and fees

A spacious living room with a stone fireplace, wooden beams, and a large sofa.

10. Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester

Londonderry

Meghan R.

$490 nightly

Nov 17 - Nov 18

Total with taxes and fees

A view through a window with a wooden frame, revealing a forested area with snow on the ground.

11. Cozy cabin in charming Londonderry

Londonderry

Eric H.

$232 nightly

Nov 16 - Nov 17

Total with taxes and fees

A modern kitchen with stainless steel appliances, a wooden dining table set for four, and a seating area with a sofa and chairs.

12. Cozy Village Condo-Okemo Shuttle

Ludlow

walter s.

$217 nightly

Nov 15 - Nov 16

Total with taxes and fees

A cozy living room with a stone fireplace, large windows, and a wooden ceiling.

13. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

Andover

Lorraine C.

$603 nightly

Nov 14 - Nov 15

Total with taxes and fees

A playground with slides and climbing structures surrounded by trees.

14. Cozy Bromley Retreat — Ski-In, Ski-Out

Bromley Mountain

Andrew P.

$387 nightly

Nov 15 - Nov 16

Total with taxes and fees

A cozy cabin interior with a sofa, dining table, chairs, wooden cabinets, and a kitchen area.

15. Condo a short walk to the Sachem trail with seasonal pool and tennis

Ludlow

$262 nightly

Nov 17 - Nov 18

Total with taxes and fees

16. Insanely romantic treehouse perched next to a stream and rolling hills.

Londonderry

Beth H.

$716 nightly

Nov 16 - Nov 17

Total with taxes and fees

A living room with a sofa, a bench, a fireplace, a TV, and a large window.

17. Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge

Clock Tower Base Area

tiliger01

$229 nightly

Nov 16 - Nov 17

Total with taxes and fees

A view of a grassy area with a ski lift and a building in the background.

18. Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts

Clock Tower Base Area

Danna K.

$239 nightly

Nov 17 - Nov 18

Total with taxes and fees

A modern, compact cabin with large windows, a wooden exterior, and a small porch with outdoor seating.

19. Wellness Getaway with a Personal Sauna, and Private River Beach!

Newfane

Joseph P.

$248 nightly

Nov 17 - Nov 18

Total with taxes and fees

A wooden deck with a table set for a meal, featuring a plate of food, glasses of wine, and a bowl of dip.

20. The MountainTop | Stratton & Mt Snow | Fire Pit

Stratton

Brenna G.

$427 nightly

Nov 14 - Nov 15

Total with taxes and fees

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Find vacation rentals that suit your style

Top Windham Hotel Reviews

A snow-covered cabin with a large window, surrounded by trees and a mountain in the background.

Blue Gentian Lodge at Magic Mountain

Londonderry

10/10 Excellent

Anonymous traveler

A restaurant with wooden tables and chairs, a central table with a sign reading "The Red Slate Restaurant", and large windows with views of the outside.

The Upper Pass Lodge at Magic Mountain

Londonderry

10/10 Excellent

Five stars for ambience, comfort, cleanliness. Very cozy common area and bar. Location is beautiful. Staff friendly. I rated medium for condition as the place is old and clearly gets well used during ski season. HOWEVER, this is not ugly or bad as in a gross motel with broken stuff and dirt. The room was clean and nice and smelled fine, but the carpets were well worn and there is a lot of wear to the place in general. I did not want to leave too many stars on condition and have folks...

Anonymous traveler

A large two-story house with a front porch and a well-maintained lawn.

The Landgrove

Londonderry

10/10 Excellent

The Inn is in a beautiful setting. The staff were very friendly and helpful. My room was spacious and a comfortable arm chair and good lamp provided a cozy place for R&R. The spacious common area & well kept grounds would be a very pleasant place to spend time with family and friends. I was advised in advance that the restaurant was not serving dinner, but the staff provided a list of eateries in the local area. I had a very good meal at the New American Grill. The breakfast menu at the...

Rita

A triangular wooden structure with a bench and a table, surrounded by lush greenery and a building in the background.

Otherland Hotel

Newfane

10/10 Excellent

The property is very well maintained and decorated. The room and bathroom are very clean. It has two very nice common area with 2 big windows that made them bright and sunny and cozy. It's also along a major highway so it's easy to find. The owners/operators of this hotel are very kind, thoughtful and accomodating to the needs of their guests. I especially and directly experienced their wonderful hospitality as a disabled person in a wheelchair. When I inquired about the accessibility of...

Rosalie

A hotel entrance with a wooden porch, a sign reading 'Ascend Collection Hotel,' and potted plants.

Sun Lodge near Manchester VT, Ascend Collection Hotel

Bromley Mountain

10/10 Excellent

Anonymous traveler

A large, snow-covered house with multiple windows and a well-lit porch.

The Inn at Manchester

Manchester Village Historic District

10/10 Excellent

Mary

A room with a large window overlooking a lake and forested hills. There are two wooden chairs on a balcony.

Harvest Barn Inn

Bellows Falls

10/10 Excellent

Virginia

A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

Four Columns Inn

Newfane

10/10 Excellent

Nettie

A white two-story house with a front porch, a covered patio, and a well-maintained garden.

The Weston

Weston

10/10 Excellent

astrid

A spacious living area with a high ceiling, a wooden staircase, and a built-in kitchen visible through an open door.

Brittany Motel

Manchester Center

10/10 Excellent

Heaven

A restaurant with tables set for dining, chairs, and a fireplace in the background.

The Reluctant Panther Inn and Restaurant

Manchester Village Historic District

10/10 Excellent

Anonymous traveler

A hotel with a covered entrance, stone facade, and a sign indicating it is part of the Best Western chain.

Best Western Springfield Hotel

Springfield

10/10 Excellent

JULIA

A red barn with a white door and shutters, surrounded by a garden with various plants and flowers.

Stone Hearth Inn and Eatery

Chester

10/10 Excellent

William

A cozy indoor space with a chalkboard sign advertising free fire entertainment from 7pm to 9pm.

Toll Road Inn

Manchester Center

10/10 Excellent

I had an incredible stay at this renovated 1960s motel! They've done an amazing job of preserving the vintage character while adding tasteful, modern updates. The retro decor instantly transports you back in time, with original furnishings that feel straight out of the ‘60s—quirky lamps, classic wood paneling, and a color palette that’s delightfully retro. Despite the vintage aesthetic, the amenities are modern and comfortable: fast Wi-Fi and cozy, plush beds that offer a great night’s sleep....

Abby

Find out more about Windham

Everything you need to know about Windham vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windham vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windham vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windham vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windham. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windham in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $244 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windham rentals

At Expedia, we put the best Windham vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windham vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Are there vacation rentals in Windham?

Yes, we give you a choice of vacation rentals near the most popular points of interest in Windham, or you can select a secluded option if you want a relaxing place to stay.

What's the top vacation rental that Windham has to offer?

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna: Visitors give good reviews to this Windham vacation home rental, which is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 11 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Windham?

With 10 Expedia vacation rentals, you're sure to find just the right place for your Windham stay.

What’s there to see and do in Windham?

Explore the area and family-friendly sights such as Vermont Country Store, or get out into nature at a spot like Lowell Lake State Park. In the larger area, you’ll find Magic Mountain Ski Resort and Jamaica State Park.

What’s a vacation rental in Windham like?

Vacation rentals are private properties where you can stay for several days or longer in Windham. Vacation rentals feature amenities such as hot tubs, fire pits, and patios to help you enjoy your stay. If you're concerned about cleanliness, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.

Windham Vacation Rentals

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Check prices for these dates

Our top choices for Windham vacation rentals

1. Beautiful country cabin with hot tub and outdoor shower in Londonderry

2. Stratton ski-in/ski-out condo steps from the lift with valley-view balcony

3. Founders Lodge condo at Stratton Mountain with gas fireplace

4. Long Trail House 368 condo in Stratton Village, walk to the lifts

5. Cozy Vermont Cabin at Trail End Ranch! The Best of VT is all around you!

6. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

7. Fourth-floor Stratton Village studio with valley-view balcony

8. Romantic Riverbed Treehouse - hot tub & new sauna!

9. Long Trail House at Stratton Mountain Resort

10. Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester

11. Cozy cabin in charming Londonderry

12. Cozy Village Condo-Okemo Shuttle

13. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

14. Cozy Bromley Retreat — Ski-In, Ski-Out

15. Condo a short walk to the Sachem trail with seasonal pool and tennis

16. Insanely romantic treehouse perched next to a stream and rolling hills.

17. Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge

18. Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts

19. Wellness Getaway with a Personal Sauna, and Private River Beach!

20. The MountainTop | Stratton & Mt Snow | Fire Pit

Find vacation rentals that suit your style

Top Windham Hotel Reviews

Blue Gentian Lodge at Magic Mountain

10/10 Excellent

Find out more about Windham

Everything you need to know about Windham vacation rentals

Windham vacation rentals: An excellent choice for every season

How to find incredible deals on Windham rentals

Frequently Asked Questions

Are there vacation rentals in Windham?

What's the top vacation rental that Windham has to offer?

How many vacation rentals are there in Windham?

What’s there to see and do in Windham?

What’s a vacation rental in Windham like?

Explore a world of travel with Expedia