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Windham Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Windham vacation rentals

A red house with a covered porch and a chimney.

1. 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, (171 reviews)
"We had a very lovely stay. The kitchen was well-equipped and the whole home was very cozy. There was wood for the wood stove and lots of games and puzzles to do. Check-in and check-out was simple. Just what we were looking for! "
United States
Eleanor D.
The price is ￥27,164
￥58,521 total
includes taxes & fees
Sep 10 - Sep 11
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A spacious living room with a stone fireplace, wooden beams, and a large sofa.

2. 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, (24 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.
The price is ￥40,555
￥103,968 total
includes taxes & fees
Sep 8 - Sep 9
Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

3. Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Stratton
The price is ￥11,912
￥41,460 total
includes taxes & fees
Sep 8 - Sep 9
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A building with a sign reading 'Fire Tower Restaurant & Tavern.'

4. Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna

Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Stratton
The price is ￥11,935
￥36,293 total
includes taxes & fees
Sep 2 - Sep 3
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
A playground with slides and climbing structures surrounded by trees.

5. Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (19 reviews)
"This is an amazing location. The home is exceptionally clean and well equipped. The pool was amazing and so was our experience. We were centrally located to everything we wanted to do. I would highly recommend this home and Management company to anyone visiting the Bromley area. Exceptional."
United States
Jaime
The price is ￥16,159
￥54,955 total
includes taxes & fees
Sep 2 - Sep 3
Cozy Bromley Retreat
A modern kitchen with dark cabinetry, stainless steel appliances, and a bar area with stools.

6. 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, (33 reviews)
"Great space, great location!"
United States
Jason S.
The price is ￥25,214
￥63,588 total
includes taxes & fees
Sep 2 - Sep 3
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
A modern two-story house with a front porch, a staircase, and a driveway.

7. Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Jamaica
9.6 out of 10, Exceptional, (30 reviews)
"House was perfect for a guys trip for skiing. Just as expected. Would stay again. "
United States
Michael A.
The price is ￥33,379
￥135,046 total
includes taxes & fees
Sep 2 - Sep 3
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
A living room with a sofa, a television, a fireplace, and a dining area with chairs and a table.

8. Lovely ski-in/out condo steps from ski lift with trails and amazing views

Lovely ski-in/out condo steps from ski lift with trails and amazing views
Stratton
8.4 out of 10, Very Good, (36 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.
The price is ￥11,935
￥50,765 total
includes taxes & fees
Sep 7 - Sep 8
Lovely ski-in/out condo steps from ski lift with trails and amazing views
A multi-story building with a stone facade, a central courtyard with a hot tub, and a stone pathway.

9. Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Stratton
8.0 out of 10, Very Good, (1 review)
The price is ￥22,357
￥65,037 total
includes taxes & fees
Sep 2 - Sep 3
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
A swimming pool with a stone border, surrounded by a snow-covered landscape and a wooden fence.

10. 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, (83 reviews)
"Nice place and great location!!!"
United States
William
The price is ￥45,506
￥56,566 total
includes taxes & fees
Sep 6 - Sep 7
Long Trail House at Stratton Mountain Resort
A cozy cabin interior with a sofa, dining table, chairs, wooden cabinets, and a kitchen area.

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

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
The price is ￥10,235
￥48,156 total
includes taxes & fees
Oct 1 - Oct 2
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
A cabin with a large, curved roof and a smaller adjacent structure, surrounded by dense forest and mountains in the background.

12. Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.

Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
Ludlow
9.8 out of 10, Exceptional, (16 reviews)
"Great stay, house is clean and has everything you’de ever need. Perfect location to explore the ludlow area. Thanks Bob, we enjoyed ourselves "
United States
Tyler
The price is ￥28,762
￥50,557 total
includes taxes & fees
Sep 3 - Sep 4
Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
A hallway with a bench, a wall-mounted towel rack, and a door leading to an outdoor area.

13. The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Wardsboro
9.8 out of 10, Exceptional, (10 reviews)
"Loved this place so much! Adorable spot, quaint but has everything you need. Loved the luxury details. "
United States
Carly L.
The price is ￥25,614
￥74,531 total
includes taxes & fees
Sep 14 - Sep 15
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
A living room with a sofa, a bench, a fireplace, a TV, and a large window.

14. Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"The slope side condo was wonderful, warm and had everything we needed. Thank you, Amy"
United States
AMY K.
The price is ￥8,221
￥37,087 total
includes taxes & fees
Sep 2 - Sep 3
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
A spacious living area with a gray sofa, a coffee table, and a kitchen area with a bar counter and stools.

15. 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.
The price is ￥64,836
￥135,495 total
includes taxes & fees
Sep 13 - Sep 14
Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!
A spacious living room with a high ceiling, wooden beams, a large sofa, a dining table, and a view of the outdoors through large windows.

16. Vermont A-Frame | Sleeps10, Hot Tub, Sauna, EV, AC

Vermont A-Frame | Sleeps10, Hot Tub, Sauna, EV, AC
Jamaica
10.0 out of 10, Exceptional, (3 reviews)
"Great peaceful stay. Hosts were always in communication with us. Close to Stratton. Hot tube & sauna were a great top off to a day of skiing. "
United States
fran g.
Vermont A-Frame | Sleeps10, Hot Tub, Sauna, EV, AC
A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

17. 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
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is ￥7,766
￥48,319 total
includes taxes & fees
Sep 2 - Sep 3
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A wooden house with a porch lit by string lights, surrounded by snow.

18. Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (14 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is ￥21,021
￥73,641 total
includes taxes & fees
Sep 14 - Sep 15
Chalet Mount Snow/Stratton Skiing/hiking
A wooden deck with a black Adirondack chair and a small table, surrounded by trees.

19. Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Wardsboro
10.0 out of 10, Exceptional, (20 reviews)
"Cute place, very pet-friendly."
United States
Jeff H.
The price is ￥31,218
￥73,447 total
includes taxes & fees
Sep 15 - Sep 16
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

20. Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.4 out of 10, Exceptional, (22 reviews)
"Beautiful classic farmhouse in lovely neighbourhood."
United States
Kimberly B.
The price is ￥33,459
￥68,493 total
includes taxes & fees
Sep 2 - Sep 3
Charming Chester Farmhouse near Near VT Slopes
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
"exellent"
kevin 1-night trip
Posted 3 hours ago
Comfort Inn & Suites Brattleboro I-91

Find out more about Windham

Search for holiday rentals in Windham on Expedia! You can easily find your home rentals, villas, holiday apartments in Windham using one of the methods below:

  • View our selection of featured holiday rentals in Windham
  • Use the map to find apartments and other holiday homes in the Windham neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windham while they last

Look no further and take a look at our great range of rental properties in Windham!

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 11 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.