Holiday Rentals in Windham County

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Top Cities in Windham County

Holiday RentalsHoliday Rentals

Stratton

Stratton

Featured Holiday Rentals in Windham County

Seasons On Mount Snow - Ski-in/Ski-out
Indoor pool, a heated pool

Seasons On Mount Snow - Ski-in/Ski-out

9.8 out of 10, Exceptional, (174)
"Wonderful host / fantastic location "
Seasons On Mount Snow - Ski-in/Ski-out
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
Interior

Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!

10.0 out of 10, Exceptional, (4)
"We had a wonderful stay."
The price is €493
includes taxes & fees
24 Sept - 25 Sept
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
Long Trail House at Stratton Mountain Resort
Condo, 2 Bedrooms | Pool

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 €364
includes taxes & fees
1 Oct - 2 Oct
Long Trail House at Stratton Mountain Resort
★No Cleaning Fee★10% OFF★Walk To Mountain★Amenities+
Fridge, microwave, oven, stovetop

★No Cleaning Fee★10% OFF★Walk To Mountain★Amenities+

10.0 out of 10, Exceptional, (55)
"From beginning to end, a great experience:the owners are very responsive throughout the process, check-in and parking was a breeze, condo is great, location is perfect -- right across the street from the village -- we had a wonderful time -- thank you Brandon!!"
★No Cleaning Fee★10% OFF★Walk To Mountain★Amenities+
Long Trail House Studio at Stratton Mountain Resort
Property grounds

Long Trail House Studio at Stratton Mountain Resort

10.0 out of 10, Exceptional, (64)
"Incredible stay in the perfect location! Walking distance to everything at Stratton and amenities that are perfect after a long ski day. Highly recommend and would stay again!"
Long Trail House Studio at Stratton Mountain Resort
Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.
Smart TV, fireplace, table football, ping pong

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

10.0 out of 10, Exceptional, (52)
"Consistently great time at this place (3rd time there)"
Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.
Charming 1-bedroom condo in delightful Dover
Fridge, microwave, oven, stovetop

Charming 1-bedroom condo in delightful Dover

10.0 out of 10, Exceptional, (1)
"The place was nice. It was clean, lots of supplies were provided, and it was in a great location. The host contacted me the day before, letting me know that the wifi was out, and the technician was unavailable until the next week. I was appreciative of the heads up. Unfortunately, the TV was unusable without wifi, no option to watch local channels. Cellular (Verizon) data was non-existent throughout the majority of daytime hours. Despite this smallish issue, I would stay here again! "
The price is €176
includes taxes & fees
22 Sept - 23 Sept
Charming 1-bedroom condo in delightful Dover
Treetop townhouse with Hot Tub and plenty of space for the whole family!
Smart TV, fireplace, books

Treetop townhouse with Hot Tub and plenty of space for the whole family!

3.0 out of 10, (2)
"We arrived at our rental at 4:05pm (check-in was at 4pm) and were met by the management company. They just started to clean the rental, due to cleaners canceling. They did not contact us to let us know the rental would not be ready. They allowed us to settled in. They finished cleaning about 30 minutes later. I specially asked if they were finished with everything and they replied yes. The next morning I woke up and had an asthma attack. I realized there was dog hair everywhere. I...
Treetop townhouse with Hot Tub and plenty of space for the whole family!
Beautiful house w/ mountain views, fireplace, balcony, bbq, gameroom, w/d, a/c
Fridge, microwave, oven, stovetop

Beautiful house w/ mountain views, fireplace, balcony, bbq, gameroom, w/d, a/c

10.0 out of 10, Exceptional, (2)
"Great family space. Comfortable furniture, well-stocked kitchen, close to restaurants. A/C units worked well."
Beautiful house w/ mountain views, fireplace, balcony, bbq, gameroom, w/d, a/c
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Interior

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

10.0 out of 10, Exceptional, (7)
"Great house, great location, Great communication with Todd. Will be back for sure!!!! Thanks for everything Todd. "
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Beautiful, private log cabin with huge, relaxing screened porch
Outdoor dining

Beautiful, private log cabin with huge, relaxing screened porch

10.0 out of 10, Exceptional, (39)
"The spot was amazing and everything was exactly what we wanted. "
Beautiful, private log cabin with huge, relaxing screened porch
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Fridge, microwave, oven, stovetop

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

10.0 out of 10, Exceptional, (59)
"We had so much fun between swimming and having a fire . The place is beautiful and private and yet not to far from everything."
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Beautiful Modern A-Frame in Southern Vermont is The Place To BE!
Interior

Beautiful Modern A-Frame in Southern Vermont is The Place To BE!

10.0 out of 10, Exceptional, (84)
"A beautiful cabin in the woods. Very clean and a perfect stay."
Beautiful Modern A-Frame in Southern Vermont is The Place To BE!
The Jelly Mill-A Peaceful River Retreat
Exterior

The Jelly Mill-A Peaceful River Retreat

10.0 out of 10, Exceptional, (58)
"Very much off the beaten path, but lets you experience the beauty of Vermont. Quiet and peaceful. A beautiful little property that served our needs perfectly. Would definitely come back."
The Jelly Mill-A Peaceful River Retreat
Comfortable condo with fireplace, pool, and sauna access - near slopes
Sauna

Comfortable condo with fireplace, pool, and sauna access - near slopes

8.0 out of 10, Very good, (16)
"Perfect location. On the MOOver line. Plenty of space for my family of four. "
Comfortable condo with fireplace, pool, and sauna access - near slopes
The Green Mountain Chapel // Old Church repositioned into 3 BR
Interior

The Green Mountain Chapel // Old Church repositioned into 3 BR

2.0 star property
10.0 out of 10, Exceptional, (18)
"This is a really beautiful place to stay. The kitchen has pretty much very your would need for a stay, and the host leaves little extras for you. Absolutely would stay here again."
The Green Mountain Chapel // Old Church repositioned into 3 BR
Waterfalls-View-Pond. Secluded Vermont Log Cabin at Mount Snow. EV Outlet
Fridge, microwave, oven, stovetop

Waterfalls-View-Pond. Secluded Vermont Log Cabin at Mount Snow. EV Outlet

10.0 out of 10, Exceptional, (81)
"Perfectly clean and welcoming cabin. Comfy beds, great location. Would definitely return. "
Waterfalls-View-Pond. Secluded Vermont Log Cabin at Mount Snow. EV Outlet
Stratton Mountain Resort Solstice Luxury 5 bedroom Ski-In/Out Vacation Home
Outdoor pool, a heated pool

Stratton Mountain Resort Solstice Luxury 5 bedroom Ski-In/Out Vacation Home

9.8 out of 10, Exceptional, (52)
"Greatly enjoyed it"
Stratton Mountain Resort Solstice Luxury 5 bedroom Ski-In/Out Vacation Home
Mountain Views•Summer Sunsets•Private Hiking Tail•Gameroom•Minimalist
Outdoor dining

Mountain Views•Summer Sunsets•Private Hiking Tail•Gameroom•Minimalist

10.0 out of 10, Exceptional, (38)
"Absolutely gorgeous mountain view, beautiful cabin, fully stocked kitchen, loved the hiking trails! Owners thought of every little detail to make it feel like home away from home. "
Mountain Views•Summer Sunsets•Private Hiking Tail•Gameroom•Minimalist
Spacious Riverfront Home 7 Minutes to Stratton!
Fridge, microwave, oven, stovetop

Spacious Riverfront Home 7 Minutes to Stratton!

10.0 out of 10, Exceptional, (32)
"Perfect house for a few families to gather and have fun. "
Spacious Riverfront Home 7 Minutes to Stratton!
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 County Hotel Reviews

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

10/10 Excellent
"Our stay was exceptional from the moment we arrived. The hotel was spotless, beautifully designed, and very comfortable. The service was outstanding—every staff member we interacted with was friendly, attentive, and went above and beyond to make our stay enjoyable. A truly wonderful experience that we highly recommend!Ñ"
Carmen 1-night trip
Posted 3 days ago
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Find out more about Windham County

Find out more about Windham County

Holiday Homes in Windham County

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