Windham Vacation Rentals

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Vacation Rentals in Windham

Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.

10.0 out of 10, Exceptional, (49)
"Consistently great time at this place (3rd time there)"
Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.

Long Trail House at Stratton Mountain Resort

3.0 star property
8.6 out of 10, Excellent, (74)
"Nice, clean room in prime location"
The price is CA $441
CA $549 total
includes taxes & fees
Jul 13 - Jul 14
Long Trail House at Stratton Mountain Resort

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (209)
"Location was perfect. Cabin cute and comfortable. Pond was an amazing bonus with lots of cool birds. We had the best vacation there ever!"
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

9.0 out of 10, Wonderful, (25)
"Had a great stay, cozy log cabin, beds were very comfortable. So nice to have a few garbage bags, paper towels, soaps and toiletries!! Also some coffee filters:) Hot tub was great too! "
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (221)
"Cabin was beautiful! Love the little stream outside. Very close to restaurants, shopping, and hiking trails. "
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond

10.0 out of 10, Exceptional, (20)
"Beautiful location and so many cozy touches throughout home!"
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond

8 min to Stratton, 6 min to golf, 15 min to Manchester. Pet friendly!

8.0 out of 10, Very good, (1)
8 min to Stratton, 6 min to golf, 15 min to Manchester. Pet friendly!

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (157)
"Thank you for a peaceful weekend away in a charming cottage!"
The price is CA $231
CA $498 total
includes taxes & fees
Jul 7 - Jul 8
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

10.0 out of 10, Exceptional, (17)
"Loved this property. Was clean, well maintained, and cozy. My partner loved the size and the full kitchen. Was a good distance from Ludlow downtown, not too far. "
The price is CA $238
CA $423 total
includes taxes & fees
Jul 29 - Jul 30
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

The Mountain Escape!

9.8 out of 10, Exceptional, (17)
"It was a perfect house and great location! Would definitely stay again!"
The price is CA $151
CA $1,033 total
includes taxes & fees
Jul 7 - Jul 8
The Mountain Escape!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

9.8 out of 10, Exceptional, (21)
"Family ski weekend. Our stay was very comfortable. Communication with host was phenomenal, always prompt and courteous Location is nice , very close to the ski resorts "
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

8-bedroom vacation home just 16 minutes from Golf Club at Equinox

9.6 out of 10, Exceptional, (15)
"Happy experience and plenty of room. Everyone enjoyed the lake and sounding places."
8-bedroom vacation home just 16 minutes from Golf Club at Equinox

Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

9.6 out of 10, Exceptional, (14)
"We loved the house and especially the location. The views are beautiful and the proximity to town, the mountain and parks make it a fantastic spot to stay."
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

8.0 out of 10, Very good, (38)
"Had a business retreat with 6 associates. The cabin was great and operated as one would expect for a ski cabin. Nice fire place and hot tub. The TVs are older so they have a hard time connecting to the WIFI for Netflix, Prime, etc. I recommend bringing agame console aor "
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Quaint lakefront home with a private deck, firepit, and dock

9.4 out of 10, Exceptional, (95)
"We had a great time staying at this cabin. It’s really well located and was perfect for our stay."
Quaint lakefront home with a private deck, firepit, and dock

Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults

10.0 out of 10, Exceptional, (24)
"A terrific place. Highly recommended. We had a great family ski vacation."
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

9.4 out of 10, Exceptional, (22)
"ideal for a large group of adult friends "
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Solitude Village at Okemo

4.0 star property
8.0 out of 10, Very good, (26)
"Beautiful Area. "
Solitude Village at Okemo

Home with View of Mount Snow!! Indoor-pool, spa, sauna Gym & more Sleeps 23+

6.0 out of 10, (1)
"Inside property was great - house was very fun and spacious and clean . HOWEVER..the driveway clearly hadn’t been plowed for a long time when we got there and so once we pulled in our cars were stuck. We were trapped at the house for 3 days. The plow driver came to plow the neighbor and told us he hadn’t been paid by the owners so hadn’t been plowing for some time The owners finally arranged for a different plow to come but not being able to leave for 3 days really affected our ability to...
Home with View of Mount Snow!! Indoor-pool, spa, sauna Gym & more Sleeps 23+

Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

10.0 out of 10, Exceptional, (52)
"Would recommend if anyone wants a quiet, peaceful getaway."
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
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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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?

Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.: 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 9 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 Ball Mountain Dam.

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.