Windham Vacation Rentals

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Browse Select Windham Vacation Homes

Our top choices for Windham vacation homes

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

7.8 out of 10, Good, (50)
"Great condo in great location. Easy walk to restaurants and lifts."
The price is CA $98
CA $333 total
includes taxes & fees
Aug 24 - Aug 25
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

10.0 out of 10, Exceptional, (4)
"Great location to Mt Snow and its surroundings. Easy, pleasant and accommodating communications with the host. Comfortable accommodations. "
The price is CA $161
CA $609 total
includes taxes & fees
Aug 26 - Aug 27
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

Ski in Ski out Condo! Pool access

9.0 out of 10, Wonderful, (2)
"Great location with plenty of space for the whole family. Highly recommend!"
The price is CA $241
CA $737 total
includes taxes & fees
Aug 25 - Aug 26
Ski in Ski out Condo! Pool access

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 CA $148
CA $280 total
includes taxes & fees
Sep 3 - Sep 4
Charming 1-bedroom condo in delightful Dover

Family Friendly Hilltop House In Putney Vermont

9.4 out of 10, Exceptional, (56)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
The price is CA $270
CA $475 total
includes taxes & fees
Aug 24 - Aug 25
Family Friendly Hilltop House In Putney Vermont

Charming Cavendish Guesthouse NEW SAUNA SEPT 2025!

9.8 out of 10, Exceptional, (7)
"Very cozy and had all the essentials we needed for our trip! Check in and check out were easy, and it was perfect for our winter trip. It's a short drive to Okemo, which is super convenient - would definitely stay here again!"
The price is CA $222
CA $390 total
includes taxes & fees
Aug 25 - Aug 26
Charming Cavendish Guesthouse NEW SAUNA SEPT 2025!

Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming

9.0 out of 10, Wonderful, (2)
"Our family had the best time staying here. The home was spacious and gave our two young children plenty of room to roam and explore. It was also close enough to the main road where everything was accessible but also isolated enough where you feel like you're getting away. Erin was great about answering any questions and making sure our stay was comfortable. We'd definitely return here!"
The price is CA $207
CA $600 total
includes taxes & fees
Sep 1 - Sep 2
Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming

The Mountain Escape!

9.8 out of 10, Exceptional, (18)
"Easy booking, clean home, great location and the owner very easy to get in touch with."
The price is CA $169
CA $788 total
includes taxes & fees
Sep 1 - Sep 2
The Mountain Escape!

Mountain Oasis - Hot Tub, Sauna, Fire Pit, & MORE!

9.8 out of 10, Exceptional, (26)
"Amazing stay. Perfect weekend friend getaway"
The price is CA $170
CA $792 total
includes taxes & fees
Sep 11 - Sep 12
Mountain Oasis - Hot Tub, Sauna, Fire Pit, & MORE!

Bear Pass - Mountain View 4 Bedroom Home by RedAwning

3.0 star property
8.0 out of 10, Very good, (1)
"Cozy cottage. Very clean and everything you need is there. Nice kitchen and fireplace. Lots of room and 3 bathrooms as well. Reasonably close to the ski mountains. "
The price is CA $332
CA $867 total
includes taxes & fees
Aug 25 - Aug 26
Bear Pass - Mountain View 4 Bedroom Home by RedAwning

Modern Chic Cabin near Mount Snow

The price is CA $188
CA $645 total
includes taxes & fees
Sep 4 - Sep 5
Modern Chic Cabin near Mount Snow

Brook Bound Inn - Main Lodge - Deluxe King w/ Pullout Couch - Room 203

10.0 out of 10, Exceptional, (1)
"We stayed here for one night to ski at Mount Snow and it was amazing! Very comfortable, cozy, well kept, clean with well stocked kitchen. It was perfect for our purpose and would definitely come back!! "
The price is CA $380
CA $492 total
includes taxes & fees
Aug 27 - Aug 28
Brook Bound Inn - Main Lodge - Deluxe King w/ Pullout Couch - Room 203

Mt Snow/Stratton Ski Cottage w/ scenic water views

The price is CA $512
CA $656 total
includes taxes & fees
Aug 26 - Aug 27
Mt Snow/Stratton Ski Cottage w/ scenic water views

The Carol - 10 minutes to Okemo & Newly Renovated- NEW SAUNA SEPT 2025!

10.0 out of 10, Exceptional, (6)
"Check in and check out were incredibly easy, house decor was eclectic upscale, beds were super comfortable. Thank you Chris! Would definitely stay here again"
The price is CA $218
CA $411 total
includes taxes & fees
Sep 2 - Sep 3
The Carol - 10 minutes to Okemo & Newly Renovated- NEW SAUNA SEPT 2025!

Whimsical Room & Private Bathroom in Historic Inn

8.8 out of 10, Excellent, (9)
"After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!"
The price is CA $123
CA $215 total
includes taxes & fees
Sep 1 - Sep 2
Whimsical Room & Private Bathroom in Historic Inn

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

2.0 star property
The price is CA $351
CA $686 total
includes taxes & fees
Sep 1 - Sep 2
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

The price is CA $270
CA $879 total
includes taxes & fees
Aug 25 - Aug 26
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

10.0 out of 10, Exceptional, (4)
"Great location, large space for family, good amenities, love the fireplace and coffee set up."
The price is CA $373
CA $992 total
includes taxes & fees
Sep 2 - Sep 3
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Room 4 - Prickly Pear double room

The price is CA $146
CA $215 total
includes taxes & fees
Aug 24 - Aug 25
Room 4 - Prickly Pear double room

Alpine 5, cozy Vermont retreat

The price is CA $145
CA $214 total
includes taxes & fees
Aug 27 - Aug 28
Alpine 5, cozy Vermont retreat
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