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Windham Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Windham vacation homes

A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

1. Long Trail House 368 condo in Stratton Village, walk to the lifts

Long Trail House 368 condo in Stratton Village, walk to the lifts
Stratton
The price is CA $104
CA $363 total
includes taxes & fees
Nov 2 - Nov 3
Long Trail House 368 condo in Stratton Village, walk to the lifts
A rustic kitchen with wooden beams, a large island, and a hanging light fixture.

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

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Londonderry
7.0 out of 10, Good, (2 reviews)
"I was "sold" & excited when I saw the pictures online bc the barn looked really neat. Although the barn was a neat concept, the pictures ARE NOT accurate, it is not as updated as pictured & it was VERY DISAPPOINTING. I now understand the non-refundable policy bc what you see online is definitely NOT what you walked into when you opened the door & they don't want to have to give people their back. Although we had fun, the accommodations were VERY misleading & disappointing. "
United States
Christine M.
The price is CA $355
CA $701 total
includes taxes & fees
Oct 27 - Oct 28
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
A cozy living room with a stone fireplace, large windows, and a wooden ceiling.

3. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
Andover
10.0 out of 10, Exceptional, (2 reviews)
"Very nice stay. Owners were very gracious. House was clean & comfortable."
United States
Lorraine C.
The price is CA $392
CA $991 total
includes taxes & fees
Oct 26 - Oct 27
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
A lodge with a large fireplace, a covered porch, and a staircase leading to the upper level.

4. Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.

Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.
Jamaica
8.8 out of 10, Excellent, (8 reviews)
"Beautiful home, we enjoyed our stay!"
United States
Luke B.
The price is CA $581
CA $845 total
includes taxes & fees
Oct 27 - Oct 28
Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.
Dining

5. Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.4 out of 10, Exceptional, (22 reviews)
"Beautiful classic farmhouse in lovely neighbourhood."
United States
Kimberly B.
The price is CA $293
CA $591 total
includes taxes & fees
Nov 1 - Nov 2
Charming Chester Farmhouse near Near VT Slopes
A spacious room with wooden beams, large windows, and a cozy seating area with white furniture.

6. Gorgeous couples barn with WiFi & hot tub in lovely Londonderry

Gorgeous couples barn with WiFi & hot tub in lovely Londonderry
Londonderry
10.0 out of 10, Exceptional, (2 reviews)
"The converted barn was absolutely stunning. Kitchen was well appointed and the family room spacious and comfortible."
United States
Tim M.
The price is CA $994
CA $1,556 total
includes taxes & fees
Oct 26 - Oct 27
Gorgeous couples barn with WiFi & hot tub in lovely Londonderry
A living room with a brick fireplace, a sofa, a chair, and a coffee table.

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

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Winhall
10.0 out of 10, Exceptional, (15 reviews)
"Clean, lots of room, easy access to Stratton, responsive host."
United States
Mark H.
The price is CA $427
CA $1,125 total
includes taxes & fees
Oct 28 - Oct 29
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
A cozy cabin interior with a dining table, chairs, a sofa, a fireplace, and a ceiling fan.

8. Peaceful Stay w/ Pond & Massage Chair | Near Okemo

Peaceful Stay w/ Pond & Massage Chair | Near Okemo
Ludlow
The price is CA $161
CA $620 total
includes taxes & fees
Oct 26 - Oct 27
Peaceful Stay w/ Pond & Massage Chair | Near Okemo
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

9. Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Winhall
9.2 out of 10, Wonderful, (44 reviews)
"Our family had a wonderful vacation. The house and location were great. We will come back."
United States
Victoria L.
The price is CA $276
CA $916 total
includes taxes & fees
Oct 26 - Oct 27
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
A cozy living room with a fireplace, comfortable seating, and a television.

10. Bear`s Den in Ludlow, Okemo Views + Epic Game Room

Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Ludlow
The price is CA $253
CA $569 total
includes taxes & fees
Oct 26 - Oct 27
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
A deck with two wicker chairs and a string of lights against a backdrop of trees and a sunset.

11. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.8 out of 10, Exceptional, (6 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is CA $216
CA $275 total
includes taxes & fees
Oct 26 - Oct 27
The Eagles Wing at The CHM - Private Apartment
A garden with a wooden pergola, purple flowers, and a river view.

12. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (65 reviews)
"The house was all we expected. Very comfortable and ready for us when we arrived. It’s a bit out of the way, at the end of a private road, but quiet and secluded. Our host was attentive without being intrusive. She clearly wanted to make sure our stay met our expectations and was pleasant. All in all, a delightful way to visit Vermont!"
United States
Susan G.
The price is CA $202
CA $394 total
includes taxes & fees
Oct 26 - Oct 27
Family Friendly Hilltop House In Putney Vermont
A two-story house with a deck, surrounded by dense forest.

13. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
Chester
10.0 out of 10, Exceptional, (6 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is CA $755
CA $1,409 total
includes taxes & fees
Oct 26 - Oct 27
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

14. Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (114 reviews)
"Wendi was very responsive when I had questions. We enjoyed our weekend getaway. Great location we walked into town to the Farmers Market Sunday."
United States
Tina l.
The price is CA $309
CA $707 total
includes taxes & fees
Nov 18 - Nov 19
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
A spacious indoor area with multiple wooden tables and green chairs, large windows offering a view of a snowy mountain, and a stone fireplace with a fire.

15. Modern Mount Snow Gnarvana - Steps to Carinthia

Modern Mount Snow Gnarvana - Steps to Carinthia
Dover
10.0 out of 10, Exceptional, (26 reviews)
"Perfect for our getaway, convenient for getting to the slopes and a beautiful area to visit"
United States
Lynn B.
The price is CA $170
CA $574 total
includes taxes & fees
Oct 26 - Oct 27
Modern Mount Snow Gnarvana - Steps to Carinthia
A cozy cabin interior with a stone fireplace, leather sofas, and large windows offering a view of the forest.

16. Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Mt Holly
9.8 out of 10, Exceptional, (42 reviews)
"This house has great hang out space and plenty of space for a big family!"
United States
Cheri V.
The price is CA $189
CA $687 total
includes taxes & fees
Oct 26 - Oct 27
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
A modern kitchen with a central island, built-in appliances, and a dining area with a wooden table and chairs.

17. New Ludlow Village Home with Stunning Okemo Mountain View

New Ludlow Village Home with Stunning Okemo Mountain View
Ludlow
10.0 out of 10, Exceptional, (22 reviews)
"The perfect stop on the way to UVM. Super clean! Walkable eateries & a beautiful view. Thank you!"
United States
Tara
The price is CA $376
CA $837 total
includes taxes & fees
Oct 27 - Oct 28
New Ludlow Village Home with Stunning Okemo Mountain View
A room with a large window, a wooden table, two chairs, and a woven basket on the table.

18. Cozy 3 Bedroom Condo in the Heart of Manchester VT

Cozy 3 Bedroom Condo in the Heart of Manchester VT
Manchester
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful accommodations. Great communication with host."
United States
Peggy S.
The price is CA $378
CA $858 total
includes taxes & fees
Oct 26 - Oct 27
Cozy 3 Bedroom Condo in the Heart of Manchester VT
A wooden barrel structure with a staircase and railing, surrounded by a forest.

19. Dover Mountain Retreat with Hot Tub Near Mt. Snow

Dover Mountain Retreat with Hot Tub Near Mt. Snow
Dover
10.0 out of 10, Exceptional, (11 reviews)
"Awesome place, fantastic amenities and easy to get to. Looking forward to coming back."
United States
Connor S.
The price is CA $374
CA $922 total
includes taxes & fees
Nov 1 - Nov 2
Dover Mountain Retreat with Hot Tub Near Mt. Snow
A spacious kitchen with a large island, wooden ceiling beams, and a view to the outside.

20. 5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton

5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton
Stratton
10.0 out of 10, Exceptional, (20 reviews)
"Great spot for a large group. "
United States
Brian G.
The price is CA $681
CA $1,561 total
includes taxes & fees
Oct 30 - Oct 31
5BR Retreat w/ Hot Tub - Sleeps 12 in 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 Hotel Reviews

Aspen At Manchester

Aspen At Manchester

8/10 Good
"I loved having two bedrooms and two bathrooms all to ourselves. The only problem we had was the water pressure in one of the bathrooms. It was so low of a pressure my husband came out and went to the other one."
Shara 2-night trip
Posted 4 hours ago
Aspen At Manchester

Find out more about Windham

Windham Vacation Homes information

Number of reviews
295
Accommodation
843 Vacation Homes
Lowest Price
CA $275
Highest Price
CA $1,561

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