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Windham Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Windham vacation rentals

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

1. Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
8.6 out of 10, Excellent, (85 reviews)
"Clean well, equipped room. Great amenities, wonderful proximity to all the action in the village,easy parking and access throughout the facility."
United States
Michael
$391 nightly
The price is $441
Nov 3 - Nov 4
Total with taxes and fees
Long Trail House at Stratton Mountain Resort
A cozy living room with a stone fireplace, large windows, and a wooden ceiling.

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

Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
Andover
10.0 out of 10, Exceptional, (2 reviews)
"Very nice stay. Owners were very gracious. House was clean & comfortable."
United States
Lorraine C.
$599 nightly
The price is $671
Nov 3 - Nov 4
Total with taxes and fees
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
A red house with a covered porch and a chimney.

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

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (175 reviews)
"We had such a great time! Those is a well taken care of, clean, cozy property. We would absolutely visit again!!"
United States
Kathy H.
$326 nightly
The price is $365
Nov 3 - Nov 4
Total with taxes and fees
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A wooden cabin with a balcony and a staircase leading to a second level.

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

Romantic Riverbed Treehouse - hot tub & new sauna!
londonderry
9.0 out of 10, Wonderful, (7 reviews)
"Beautiful location and place. Could have been a bit cleaner (windows, TV, shower curtain) and the hot tub worked well but definitely needed to be cleaner."
United States
Tracey V.
$546 nightly
The price is $617
Nov 3 - Nov 4
Total with taxes and fees
Romantic Riverbed Treehouse - hot tub & new sauna!
A spacious living area with a gray sofa, a coffee table, and a kitchen area with a bar counter and stools.

5. Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!

Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!
Londonderry
10.0 out of 10, Exceptional, (11 reviews)
"Great location, well-designed house, and a beautiful view."
United States
Marcel P.
$711 nightly
The price is $803
Nov 3 - Nov 4
Total with taxes and fees
Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!
A wooden cabin with a balcony and a staircase leading to a second level.

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

Insanely romantic treehouse perched next to a stream and rolling hills.
Londonderry
10.0 out of 10, Exceptional, (2 reviews)
"Very nice secluded treehouse. We would definitely recommend!"
United States
Beth H.
$750 nightly
The price is $848
Nov 3 - Nov 4
Total with taxes and fees
Insanely romantic treehouse perched next to a stream and rolling hills.
A view through a window with a wooden frame, revealing a forested area with snow on the ground.

7. Cozy cabin in charming Londonderry

Cozy cabin in charming Londonderry
Londonderry
8.4 out of 10, Very good, (5 reviews)
"Very cozy and quiet. "
United States
Eric H.
$232 nightly
The price is $262
Nov 3 - Nov 4
Total with taxes and fees
Cozy cabin in charming Londonderry
A spacious room with wooden beams, large windows, and a cozy seating area with white furniture.

8. Gorgeous couples barn with WiFi & hot tub in lovely Londonderry

Gorgeous couples barn with WiFi & hot tub in lovely Londonderry
Londonderry
10.0 out of 10, Exceptional, (2 reviews)
"The converted barn was absolutely stunning. Kitchen was well appointed and the family room spacious and comfortible."
United States
Tim M.
$962 nightly
The price is $1,087
Nov 3 - Nov 4
Total with taxes and fees
Gorgeous couples barn with WiFi & hot tub in lovely Londonderry
A spacious living room with a stone fireplace, wooden beams, and a large sofa.

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

Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
Londonderry
9.6 out of 10, Exceptional, (25 reviews)
"Super attentive and accommodating host! It was a perfect cozy getaway on a frigid weekend, and the fireplace and hot tub were just the ticket. "
United States
Meghan R.
$487 nightly
The price is $550
Nov 3 - Nov 4
Total with taxes and fees
Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
A modern kitchen with dark cabinetry, stainless steel appliances, and a bar area with stools.

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

Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
Stratton Mountain
10.0 out of 10, Exceptional, (37 reviews)
"Excellent place! Impeccable!"
United States
Susan F.
$476 nightly
The price is $537
Nov 4 - Nov 5
Total with taxes and fees
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
A building with a sign reading 'Landmark' and a large spherical sculpture in the center.

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

Fourth-floor Stratton Village studio with valley-view balcony
Stratton
$201 nightly
The price is $227
Nov 3 - Nov 4
Total with taxes and fees
Fourth-floor Stratton Village studio with valley-view balcony
A lodge with a large fireplace, a covered porch, and a staircase leading to the upper level.

12. Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.

Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.
Jamaica
8.8 out of 10, Excellent, (8 reviews)
"Beautiful home, we enjoyed our stay!"
United States
Luke B.
$537 nightly
The price is $580
Nov 3 - Nov 4
Total with taxes and fees
Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

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

Long Trail House 368 condo in Stratton Village, walk to the lifts
Stratton
$228 nightly
The price is $258
Nov 3 - Nov 4
Total with taxes and fees
Long Trail House 368 condo in Stratton Village, walk to the lifts
A living room with a television, sofa, and coffee table.

14. Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
10.0 out of 10, Exceptional, (8 reviews)
"Very clean 2br 2ba condo in excellent location. Host provided detailed important information that helped us find property and how to access unit. I would definitely recommend staying here."
United States
Eileen R.
$389 nightly
The price is $440
Nov 9 - Nov 10
Total with taxes and fees
Long Trail House South Wing 2B2B Condo
A living room with a sofa, a television, a fireplace, and a dining area with chairs and a table.

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

Stratton ski-in/ski-out condo steps from the lift with valley-view balcony
Stratton
8.4 out of 10, Very good, (37 reviews)
"I have stayed in this condo a few times now, and for my needs it is a great value; affordable, comfortable and ideal location. "
United States
eric m.
$278 nightly
The price is $314
Nov 3 - Nov 4
Total with taxes and fees
Stratton ski-in/ski-out condo steps from the lift with valley-view balcony
A cozy living room with a sofa, coffee table, and dining area. A ceiling fan is visible, and there are skis leaning against the wall.

16. Two bedroom Condo With Mountain View And Fireplace

Two bedroom Condo With Mountain View And Fireplace
Stratton
9.2 out of 10, Wonderful, (5 reviews)
"Very comfortable stay for four adults. The kitchen is well appointed, great beds and showers. Easy, prompt communication with owner. "
United States
Marie B.
$617 nightly
The price is $697
Nov 3 - Nov 4
Total with taxes and fees
Two bedroom Condo With Mountain View And Fireplace
A cozy cabin interior with a wooden ceiling, a round table with chairs, a fireplace, and a large window overlooking a snowy landscape.

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

Beautiful country cabin with hot tub and outdoor shower in Londonderry
Londonderry
10.0 out of 10, Exceptional, (3 reviews)
"Stay is very cozy and rustic. Be prepared for house to be cold when you show up. Host is very responsive and accommodating."
United States
Michael D.
$309 nightly
The price is $349
Nov 3 - Nov 4
Total with taxes and fees
Beautiful country cabin with hot tub and outdoor shower in Londonderry
A living room with a brick fireplace, a sofa, a chair, and a coffee table.

18. Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Winhall
10.0 out of 10, Exceptional, (15 reviews)
"Clean, lots of room, easy access to Stratton, responsive host."
United States
Mark H.
$679 nightly
The price is $767
Nov 9 - Nov 10
Total with taxes and fees
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A fire pit with logs, surrounded by Adirondack chairs and a table with a mug.

19. Tranquil Brookside Retreat with Hot Tub & Firepit

Tranquil Brookside Retreat with Hot Tub & Firepit
Peru
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful place. Comfortable and well furnished. "
United States
Michael B.
$655 nightly
The price is $734
Nov 10 - Nov 11
Total with taxes and fees
Tranquil Brookside Retreat with Hot Tub & Firepit
A multi-story building with a stone facade, a central courtyard with a hot tub, and a stone pathway.

20. Founders Lodge condo at Stratton Mountain with gas fireplace

Founders Lodge condo at Stratton Mountain with gas fireplace
Stratton
8.0 out of 10, Very good, (1 review)
$363 nightly
The price is $410
Nov 3 - Nov 4
Total with taxes and fees
Founders Lodge condo at Stratton Mountain with gas fireplace
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windham Hotel Reviews

The Putney Inn

The Putney Inn

10/10 Excellent
"GREAT VALUE, QUIET, TRAIN WHISTLE SEVERAL TIMES A DAY, BUT NOT THE MOTELS FAULT....SECOND FLOOR SQUEAKS, I DID NOT MIND....BUT WAS AFRAID I WAS DISTURBING THE PEOPLE BELOW....OTHERWISE EVERYTHING ELSE WAS GOOD...."
Jonathan 3-night trip
Posted 9 hours ago
The Putney Inn

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 $365 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.

Explore a world of travel with Expedia

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.