Windham Vacation Rentals

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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Windham vacation rentals

Exterior

Owl's Nest Treehouse

Owl's Nest Treehouse
Alstead
10.0 out of 10, Exceptional, (18 reviews)
"10/10 across the board! The cabin was a great experience. The hot tub was amazing. They have their own store near by with lots of goodies. They were very helpful with any questions we had. Would come here again!"
United States
Adriana
$312 nightly
The price is $339
Feb 23 - Feb 24
Total with taxes and fees
Owl's Nest Treehouse
TV, books

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
$231 nightly
The price is $250
Feb 17 - Feb 18
Total with taxes and fees
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Exterior

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, (166 reviews)
"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "
United States
Philip
$324 nightly
The price is $363
Feb 23 - Feb 24
Total with taxes and fees
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Private kitchen

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

The Studio with a View. Bring your dog, too!
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"
United States
James M.
$234 nightly
The price is $262
Mar 15 - Mar 16
Total with taxes and fees
The Studio with a View. Bring your dog, too!
Interior

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Cavendish
10.0 out of 10, Exceptional, (11 reviews)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
$366 nightly
The price is $401
Mar 9 - Mar 10
Total with taxes and fees
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Terrace/patio

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Walpole
10.0 out of 10, Exceptional, (50 reviews)
"We had a very lovely stay. "
United States
mary c.
$558 nightly
The price is $605
Feb 23 - Feb 24
Total with taxes and fees
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Interior

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.
$246 nightly
The price is $277
Feb 16 - Feb 17
Total with taxes and fees
Cozy cabin in charming Londonderry
Exterior

Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK

Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK
Jamaica
10.0 out of 10, Exceptional, (6 reviews)
"Great stay"
United States
Chelsea D.
$342 nightly
The price is $386
Feb 19 - Feb 20
Total with taxes and fees
Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK
Property grounds

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (59 reviews)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
United States
Louis T.
$259 nightly
The price is $290
Mar 2 - Mar 3
Total with taxes and fees
Family Friendly Hilltop House In Putney Vermont
Exterior

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Plymouth
10.0 out of 10, Exceptional, (14 reviews)
"We had a great stay! Beautiful spot tucked in the woods. Great host communication!"
United States
Julie-Anne B.
$639 nightly
The price is $716
Feb 24 - Feb 25
Total with taxes and fees
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Exterior

Romantic Riverbed Treehouse - hot tub & new sauna!

Romantic Riverbed Treehouse - hot tub & new sauna!
londonderry
9.6 out of 10, Exceptional, (5 reviews)
"Great little space"
United States
John
$567 nightly
The price is $641
Feb 23 - Feb 24
Total with taxes and fees
Romantic Riverbed Treehouse - hot tub & new sauna!
Interior

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
7.4 out of 10, Good, (55 reviews)
"Irish Bar nearby was a plus on St. Patrick’s Day !"
United States
Warren
$314 nightly
The price is $355
Feb 24 - Feb 25
Total with taxes and fees
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Interior

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Dover
9.8 out of 10, Exceptional, (10 reviews)
"We enjoyed our stay."
United States
Anonymous traveler
$459 nightly
The price is $519
Feb 23 - Feb 24
Total with taxes and fees
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Exterior

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.
$781 nightly
The price is $883
Feb 17 - Feb 18
Total with taxes and fees
Insanely romantic treehouse perched next to a stream and rolling hills.
Property grounds

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
9.0 out of 10, Wonderful, (78 reviews)
"Perfect location for a quick ski trip. "
United States
Michael D.
$295 nightly
The price is $334
Mar 11 - Mar 12
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Exterior

8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly

8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly
West Dover
10.0 out of 10, Exceptional, (23 reviews)
"Wonderful time..the home was very spacious and comfortable..great location!"
United States
Ellen P.
$734 nightly
The price is $829
Feb 22 - Feb 23
Total with taxes and fees
8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly
Exterior

Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo
Chester
10.0 out of 10, Exceptional, (3 reviews)
"We really enjoyed our stay at this home. It had everything we needed and was very comfortable. The countryside around this part of Vermont is beautiful. We found lots of great museums and restaurants. "
United States
Donald M.
$992 nightly
The price is $1,111
Feb 22 - Feb 23
Total with taxes and fees
Cozy Vermont Cabin · Mountain Views · Near Okemo
Interior

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Cozy little spot that had everything we needed. Peaceful, quiet, and once the rain let up on our stay we walked out to the gorgeous little pond on the property. So serene. Catherine was great!"
United States
Erica H.
$183 nightly
The price is $207
Feb 28 - Mar 1
Total with taxes and fees
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Outdoor pool, a heated pool

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.2 out of 10, Wonderful, (21 reviews)
"So cute and in such a great area! It was a perfect stay"
United States
Jaden F.
$267 nightly
The price is $301
Mar 10 - Mar 11
Total with taxes and fees
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Fridge, oven, stovetop, dishwasher

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Londonderry
8.0 out of 10, Very Good, (1 review)
"I was "sold" & excited when I saw the pictures online bc the barn looked really neat. Although the barn was a neat concept, the pictures ARE NOT accurate, it is not as updated as pictured & it was VERY DISAPPOINTING. I now understand the non-refundable policy bc what you see online is definitely NOT what you walked into when you opened the door & they don't want to have to give people their back. Although we had fun, the accommodations were VERY misleading & disappointing. "
United States
Christine M.
$434 nightly
The price is $490
Mar 16 - Mar 17
Total with taxes and fees
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
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

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent
"The room was very comfortable and clean. The staff ( front end clerk) was extremely friendly. "
Rebecca 1-night trip
Posted 2 days ago
Comfort Inn & Suites Brattleboro I-91

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 $254 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 12 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 popular places like Stratton Mountain Resort and Okemo Mountain Resort.

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.