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Windham Vacation Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Windham vacation rentals

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

1. 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 AED 274
AED 824 total
includes taxes & fees
12 Oct - 13 Oct
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
A red house with a covered porch and a chimney.

2. 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, (173 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 AED 624
AED 1,362 total
includes taxes & fees
12 Oct - 13 Oct
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A living room with a sofa, a television, a fireplace, and a dining area with chairs and a table.

3. 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 AED 274
AED 1,161 total
includes taxes & fees
14 Oct - 15 Oct
Lovely ski-in/out condo steps from ski lift with trails and amazing views
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

4. 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 AED 274
AED 941 total
includes taxes & fees
13 Oct - 14 Oct
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
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, (21 reviews)
"Nice place "
United States
Janja L.
The price is AED 473
AED 1,382 total
includes taxes & fees
26 Oct - 27 Oct
Cozy Bromley Retreat
Exterior

6. 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, (1 review)
"Very nice stay. Owners were very gracious. House was clean & comfortable."
United States
Lorraine C.
The price is AED 1,028
AED 2,604 total
includes taxes & fees
12 Oct - 13 Oct
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
A spacious living room with a stone fireplace, wooden beams, and a large sofa.

7. 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.
The price is AED 1,158
AED 2,683 total
includes taxes & fees
3 Nov - 4 Nov
Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
A swimming pool with a stone border, surrounded by a snow-covered landscape and a wooden fence.

8. 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, (84 reviews)
"Nice place and great location!!!"
United States
William
The price is AED 1,304
AED 1,621 total
includes taxes & fees
12 Oct - 13 Oct
Long Trail House at Stratton Mountain Resort
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 AED 513
AED 1,488 total
includes taxes & fees
12 Oct - 13 Oct
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
A cozy cabin interior with a sofa, dining table, chairs, wooden cabinets, and a kitchen area.

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

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
The price is AED 204
AED 1,088 total
includes taxes & fees
12 Oct - 13 Oct
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
A living room with a sofa, a bench, a fireplace, a TV, and a large window.

11. 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)
"Great property, clean and close to the slope"
United States
tiliger01
The price is AED 189
AED 853 total
includes taxes & fees
13 Oct - 14 Oct
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
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.

12. Ski Stratton A-Frame | Sleeps 10, Hot Tub, Sauna

Ski Stratton A-Frame | Sleeps 10, Hot Tub, Sauna
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.
The price is AED 1,271
AED 3,768 total
includes taxes & fees
19 Oct - 20 Oct
Ski Stratton A-Frame | Sleeps 10, Hot Tub, Sauna
A two-story house with a porch, a staircase, and a front door.

13. Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Ludlow
8.8 out of 10, Excellent, (27 reviews)
"You better ask for one of the rear units because the front one is practically in the middle of the road. It’s noisy. It’s dingy, the owner refused to let us check in an hour early, which actually worked out in our favor since we didn’t want to stay there after we saw the place. We asked to move to a rear unit. The answer was no. We didn’t ask for a refund. We just went and booked another room and left this place empty for the night. There are so many other nice places to stay in this area. I...
United States
William
The price is AED 386
AED 997 total
includes taxes & fees
13 Oct - 14 Oct
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
A spacious living area with a gray sofa, a coffee table, and a kitchen area with a bar counter and stools.

14. 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 AED 1,488
AED 3,109 total
includes taxes & fees
19 Oct - 20 Oct
Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!
A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

15. 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 AED 226
AED 1,123 total
includes taxes & fees
27 Oct - 28 Oct
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A view of a grassy area with a ski lift and a building in the background.

16. 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
8.8 out of 10, Excellent, (81 reviews)
"It was a perfect location and had everything we needed for a great stay."
United States
Danna K.
The price is AED 274
AED 978 total
includes taxes & fees
13 Oct - 14 Oct
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
A wooden cabin with a snow-covered roof and a large cylindrical structure, surrounded by a snowy forest.

17. Cozy A-Frame Cabin with Hot Tub & Sauna near Stratton Mountain, Vermont

Cozy A-Frame Cabin with Hot Tub & Sauna near Stratton Mountain, Vermont
Jamaica
The price is AED 3,317
AED 4,284 total
includes taxes & fees
3 Nov - 4 Nov
Cozy A-Frame Cabin with Hot Tub & Sauna near Stratton Mountain, Vermont
A modern kitchen with dark cabinetry, stainless steel appliances, and a bar area with stools.

18. 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, (36 reviews)
"Great space, great location!"
United States
Jason S.
The price is AED 749
AED 1,909 total
includes taxes & fees
19 Oct - 20 Oct
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
A golf course with a winding path, trees, and a hilly landscape.

19. Well-appointed studio right downtown - less than a mile to Okemo Mountain

Well-appointed studio right downtown - less than a mile to Okemo Mountain
Ludlow
8.8 out of 10, Excellent, (13 reviews)
"This place was so close to Okemo, and walking distance to the local pub and restaurants."
United States
Brian
The price is AED 366
AED 1,134 total
includes taxes & fees
21 Oct - 22 Oct
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Dining

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 AED 768
AED 1,551 total
includes taxes & fees
1 Nov - 2 Nov
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

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent
"Beautiful place for getaway!!!😊"
Esther 2-night trip
Posted 5 hours ago
The Black Bear Lodge at Stratton Mountain Resort

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.