Windham Vacation Rentals

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Vacation Rentals in Windham

Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
Interior
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
10.0 out of 10, Exceptional, (30)
"Awesome home on a beautiful piece of land. Suki was a great host and the house was well stocked with everything we needed!"
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Fridge, microwave, oven, stovetop
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, (32)
"Lovely property and great location to outdoor activities."
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Long Trail House at Stratton Mountain Resort
Condo, 2 Bedrooms | Pool
Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very good, (70)
"The unit was perfect for our ski race weekend. Very accessible, underground parking included (ski boxes on top of SUVs will not fit - thankfully we left ours at home), really nice place with everything we needed!"
The price is CA $425
CA $515 total
includes taxes & fees
Jul 3 - Jul 4
Long Trail House at Stratton Mountain Resort
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Exterior
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, (176)
"This property was beautiful and literally had everything we needed to cook family meals including spices and all necessary pots/pans. I was impressed by how much this hike had available form our convenience. My only issue is that the home is advertised as a 2 bedroom but it is a loft space with 3 beds and no doors. We were not expecting this but made it work. Other than that this place is a slice of heaven!"
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Exterior
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
9.6 out of 10, Exceptional, (179)
"My husband and I loved this little cottage , we will definitely be back."
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Cabin in So. Vt enjoy the Mtns.
Exterior
Cabin in So. Vt enjoy the Mtns.
10.0 out of 10, Exceptional, (97)
"Everything was lovely. Owners were extremely pleasant. Muffins in the morning was a great touch. We will be back."
Cabin in So. Vt enjoy the Mtns.
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
Interior
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
9.4 out of 10, Exceptional, (47)
"We loved our stay at the chalet. It's perfectly situated in the cutest little neighborhood, while also feeling very secluded. The chalet had everything we needed for our stay. While visiting we walked a few of the trails nearby, part of the Valley Trail and the Hoot, Toot and Whistle. They were both perfect for our pups, especially during hunting season. We gave our pups an extra squeeze in honor of Scarlet. Thank you for sharing your place with us! We would love to stay again!!"
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
Summer Deals Free Gym Pool Pass- Luxury Log Home, 6 BR/4BA, Pool Table, Hot Tub
Exterior
Summer Deals Free Gym Pool Pass- Luxury Log Home, 6 BR/4BA, Pool Table, Hot Tub
9.8 out of 10, Exceptional, (157)
"The place is beautiful and the stay was fantastic. It is up a couple mile hill/road from the center of town, just long enough to make you feel you are out of the hustle. The property presents very well. The rooms are large for private space with 2 common rooms that are just as large for group time. The one suggestion would be to add a check in book of information, including necessary passwords (WIFI) and local attractions/restaurants. We had much of this in the interaction with the host through...
Summer Deals Free Gym Pool Pass- Luxury Log Home, 6 BR/4BA, Pool Table, Hot Tub
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Exterior
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
9.6 out of 10, Exceptional, (140)
"Great little house to enjoy spending time with family and all that VT has to offer. Wonderful host, we will be back."
The price is CA $233
CA $492 total
includes taxes & fees
Jul 11 - Jul 12
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
VT Cabin overlooking the West River and Village
Fridge, oven, stovetop, dishwasher
VT Cabin overlooking the West River and Village
10.0 out of 10, Exceptional, (19)
"The cabin was perfect for a getaway! Felt secluded however walkable to small village, and within 20 minutes to Stratton. Perfectly stocked to stay in for meals!"
The price is CA $272
CA $521 total
includes taxes & fees
Jun 28 - Jun 29
VT Cabin overlooking the West River and Village
Idyllic Lakefront House Suited Two Families
Property grounds
Idyllic Lakefront House Suited Two Families
9.8 out of 10, Exceptional, (144)
"Really enjoyed our stay! The view of the lake from the living room was so peaceful and pretty. The flowers were just starting to bloom, which added a nice splash of color to the view. The house is fully equipped with everything you need both inside and out. There were kayaks available (as well as a canoe) and we were out on the lake a couple times. The lake is long enough to really experience a very scenic paddle. There is also a little country store down a ways a bit where you can stop and get...
Idyllic Lakefront House Suited Two Families
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
Exterior
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
10.0 out of 10, Exceptional, (39)
"My husband and I wanted a relaxing few days to get away from our hectic lives. This small cabin was perfect, comfortable, and nicely appointed. Reading a book on the screened in porch with a cup of coffee was my favorite part. It is a quiet place in the woods but close to many small and quaint towns to visit in Vermont. The Newfane Store a few miles down the road was a great place to grab a coffee and meal. I also really appreciate that I could bring my dog. Many thanks for a warm and cozy...
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
Quaint mountain retreat with a gas fireplace, balcony, central AC - dog-friendly
TV, fireplace
Quaint mountain retreat with a gas fireplace, balcony, central AC - dog-friendly
9.4 out of 10, Exceptional, (18)
"We enjoyed the small cabin and the view. The loft was a bit difficult to climb to. Kitchen had all supplies and we enjoyed cooking our meals and eating them with a view."
Quaint mountain retreat with a gas fireplace, balcony, central AC - dog-friendly
Dog-friendly, lakefront home with large yard, firepit, canoe, and fireplace
Dining
Dog-friendly, lakefront home with large yard, firepit, canoe, and fireplace
9.6 out of 10, Exceptional, (4)
"Really enjoyed our stay. Beautiful location and truly relaxing"
Dog-friendly, lakefront home with large yard, firepit, canoe, and fireplace
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
Lake
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
10.0 out of 10, Exceptional, (116)
"Great place to stay for an early spring ski trip and eclipse viewing (we drove north after checking out). Clean, cozy place and pet friendly for our small dog. Located on a quiet dirt road but close to Ludlow town center and Okemo for skiing. Not too far from Killington either (which is where we went to ski). Minor issue for me was the bed was a bit too soft for my liking but otherwise, great place and would consider again in future."
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
Fridge, microwave, oven, stovetop
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
9.8 out of 10, Exceptional, (15)
"Great location to restaurant and ski mountain"
The price is CA $134
CA $401 total
includes taxes & fees
Jun 23 - Jun 24
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Property grounds
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
9.8 out of 10, Exceptional, (189)
"Our family enjoyed the dock and decks most of all, and my children spent as much time as they could playing in the water. The cottage is small but fit our family of four nicely. It had everything we needed for our 4-night getaway!"
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
Exterior
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
10.0 out of 10, Exceptional, (27)
"This was one of the best locations we have stayed at! We came up for a fundraiser at Stratton Mountain. Tommy was so helpful and provided great information from booking up until checkout. There is a great virtual guide that answers all important questions. The house and outdoors were exactly what we were looking for. Our dog loved running around and we enjoyed the hot tub. The house was very clean and had all the necessities we needed. Our favorite part was being cozy on the coach watching...
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
9 bedrooms, desk, iron/ironing board, free WiFi
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
9.4 out of 10, Exceptional, (17)
"Definitely recommend this place for large groups. Very clean, so much to do, and great communication with host. Very private location"
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
3 bedrooms, internet, bed sheets
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
8.8 out of 10, Excellent, (18)
"This is a great cabin with stunning views!"
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
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See all available properties in Windham
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.

Other types of properties in Windham you may be interested in

Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
Interior
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
10.0 out of 10, Exceptional, (30)
"Awesome home on a beautiful piece of land. Suki was a great host and the house was well stocked with everything we needed!"
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
Colonial Motel And Spa
Exterior
Colonial Motel And Spa
3.0 star property
6.8 out of 10, (1005)
"Great spot"
The price is CA $121
CA $133 total
includes taxes & fees
Jul 4 - Jul 5
Colonial Motel And Spa
The Covered Bridge Inn
Concierge desk
The Covered Bridge Inn
2.5 star property
8.2 out of 10, Very good, (1005)
"Clean, quiet and comfortable. An enjoyable stay."
The Covered Bridge Inn
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.

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windham vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windham vacation rentals we have selected for you start as low as CA $134 per night. Entering your travel dates in the search wizard 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. 

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?

Secluded Escape in Rural Vermont! Sauna Pool, 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 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.

Recent reviews of Windham properties
Expedia verified reviews

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

5/5 Excellent
Spacious, clean suite...wonderful staff!
"Suite was spacious, clean, well-equipped. Even had washer/dryer! Staff was accommodating and so very friendly. Thank you!"
A verified traveller stayed at Pointe at Castle Hill Resort
Posted 10 hours ago
Pointe at Castle Hill Resort