Holiday Rentals in Windham

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Holiday Rentals in Windham

Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
Smart TV, fireplace, table football, ping pong
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
10.0 out of 10, Exceptional, (37)
"Recently held a staff retreat here, and it was amazing. The space is clean, and has everything you need for a great stay. Host was super responsive. Thank you!"
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
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, (189)
"Cabin was beautiful, wife loved the decor of the cabin. They had everything we needed onsite for a wonderful stay."
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
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, (72)
"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!"
Long Trail House at Stratton Mountain Resort
Dog-friendly chalet cabin with valley view, deck, and private hot tub
TV
Dog-friendly chalet cabin with valley view, deck, and private hot tub
7.2 out of 10, Good, (14)
"We had a great weekend staying here. The projector and hot tub were awesome amenities. There was a snow storm right before we arrived and the roads were clear and the driveway was plowed. We had a great experience and would stay here again!"
Dog-friendly chalet cabin with valley view, deck, and private hot tub
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Outdoor dining
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, (190)
"The cabin was super cute and cozy! It was very clean and well kept. It was a little bit off the main road, but far enough back so the noise from the traffic wasn't too bad. There's also train tracks behind. We only saw one train, but it wasn't long and not too noisy. The loft space was a little tight, especially if you're on the taller side, but the bed was super comfy! There were many appliances and utensils in the kitchen and the hot tub was just awesome after a long day of hiking! Thank you...
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
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, (198)
"We had a great and restful stay. The house was exactly as listed. Views were great with ducks, beaver and a family of deer. Good fishing from the dock. This is in my top 3 of all places at which we have stayed! Definitely recommended!!!"
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
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, (33)
"Lovely property and great location to outdoor activities."
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Walk to Mount Snow, Cozy, Clean and Comfortable!
Pool
Walk to Mount Snow, Cozy, Clean and Comfortable!
9.6 out of 10, Exceptional, (29)
"Upon reserving the property, I sent an email to the owner and requested an early checkin, he responded very quickly and accomodated my request. The check in process was very easy, and the property was very clean. The only issue was the hot tub was not installed and functioning dury my stay, which I specifically asked for. The inside of the condo was very clean and the owner provided everything you needed. The only downside was the outside of the property was a little run down and needed some...
Walk to Mount Snow, Cozy, Clean and Comfortable!
Idyllic Lakefront House Suited Two Families
Property grounds
Idyllic Lakefront House Suited Two Families
9.8 out of 10, Exceptional, (151)
"Beautiful lake, kayaking, backyard firepit, hiking , such a fun area with a lot to explore.nearby, "
Idyllic Lakefront House Suited Two Families
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, (144)
"My friend and I had a very nice stay. The place was clean and very comfortable. We had trouble locking the door when we left, but other than that it was a great stay! Thank you"
The price is €338
includes taxes & fees
28 Oct - 29 Oct
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Air Conditioning
Exterior
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Air Conditioning
9.8 out of 10, Exceptional, (162)
"Our Golf group enjoyed everything about our stay. From the hot tub, outdoor grill, pool table, jetted tub to the kitchen was great. Plenty of space to spread out or congregate. 5 Stars all day. Hosts we great. Property was great. Weather was great. Golf Courses Were great (scores we acceptable)! Convenient to restaurants and stores but house is in the woods. Perfect."
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Air Conditioning
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
TV, fireplace, DVD player, books
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
9.4 out of 10, Exceptional, (52)
"We had a fabulous time. "
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
Mount Snow's Best View - Sleeps 8-10
Fridge, microwave, oven, stovetop
Mount Snow's Best View - Sleeps 8-10
10.0 out of 10, Exceptional, (43)
"The property has great views of the mountain, the place was clean and offered plenty of space. It is located near plenty of restaurant's and across the street from Mt. Snow. The clubhouse is new and was a nice bonus to use. "
Mount Snow's Best View - Sleeps 8-10
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Property grounds
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
8.6 out of 10, Excellent, (20)
"Good Condo in a great location"
The price is €252
includes taxes & fees
1 Oct - 2 Oct
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
TRAILSIDE, Huge, Newly Renovated, 6 bedroom condo ski-on ski-off, sleeps 18
6 bedrooms, WiFi, bed sheets
TRAILSIDE, Huge, Newly Renovated, 6 bedroom condo ski-on ski-off, sleeps 18
9.6 out of 10, Exceptional, (71)
"We had a great time here. The property was very big with lots of bedrooms for everyone to spread out. The loft was perfect for kids. Plenty to do in the nearby area, even when it is off season for skiing."
TRAILSIDE, Huge, Newly Renovated, 6 bedroom condo ski-on ski-off, sleeps 18
Countryside, lakefront cabin with kayaks, stone fireplace, balcony, & fast WiFi
Property grounds
Countryside, lakefront cabin with kayaks, stone fireplace, balcony, & fast WiFi
9.0 out of 10, Wonderful, (16)
"Wonderful location on Lake Rescue. House is spacious with great views. High end finishes. Beds and linens were very comfortable. Kitchen has plenty of dishes, pots and pans. No keurig but we brought our own. Management was pretty responsive when we realized there was no remote for the firestick and they dropped one off the next day. There is only one tv for the entire house and it's in the basement.For a house that size, this is odd. But, we were there to fish, kyack and spend time together so...
Countryside, lakefront cabin with kayaks, stone fireplace, balcony, & fast WiFi
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Fridge, microwave, oven, stovetop
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
8.2 out of 10, Very good, (32)
"This place was great for my family and I. It is very close to Okemo and town "
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Beautiful Manchester VT Mountain Retreat w/Hot Tub
Fridge, microwave, oven, stovetop
Beautiful Manchester VT Mountain Retreat w/Hot Tub
10.0 out of 10, Exceptional, (27)
"We really enjoyed our stay at this house. All the rooms were beautiful, clean and nicely decorated. The beds were very comfortable. Our dog loved the porch on the main floor. We will definitely book this house again, it is one of our favorites."
Beautiful Manchester VT Mountain Retreat w/Hot Tub
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Interior
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
10.0 out of 10, Exceptional, (194)
"The place was beautiful and immaculate "
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!
Interior
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!
10.0 out of 10, Exceptional, (53)
"Lovely"
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!
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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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Other types of properties in Windham you may be interested in

Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
Smart TV, fireplace, table football, ping pong
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
10.0 out of 10, Exceptional, (37)
"Recently held a staff retreat here, and it was amazing. The space is clean, and has everything you need for a great stay. Host was super responsive. Thank you!"
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, (1003)
"Fantastic for this regular swimmer to have these lap pools on the property. The place is a bit long in the tooth (worn) but for the price it was a great deal. "
The price is €104
includes taxes & fees
1 Oct - 2 Oct
Colonial Motel And Spa
The Black Bear Lodge at Stratton Mountain Resort
10 restaurants, lunch, dinner served; American cuisine
The Black Bear Lodge at Stratton Mountain Resort
3.0 star property
7.6 out of 10, Good, (849)
"Liked your staff. Very helpful "
The price is €130
includes taxes & fees
1 Oct - 2 Oct
The Black Bear Lodge at Stratton Mountain Resort
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.

Frequently asked questions

Are there holiday rentals in Windham?

Yes, there are holiday rentals close to the most popular sights in Windham, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Windham has to offer?

Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.: This highly rated holiday home rental in Windham is located on a lake, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Windham?

With 9 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find Magic Mountain Ski Resort and Jamaica State Park.

What’s a holiday rental in Windham like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Windham. Holiday rentals feature extras such as patios, hot tubs and fire pits to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for a family trip.