Search Vacation Homes in Windham

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Vacation Homes in Windham

Interior
Whimsical Room & Private Bathroom in Historic Inn

Whimsical Room & Private Bathroom in Historic Inn

Chester Depot
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!"
United States
Paul S.
$130 nightly
The price is $146
Nov 18 - Nov 19
Total with taxes and fees
Whimsical Room & Private Bathroom in Historic Inn
Smart TV, fireplace, table tennis
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

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

Dover
10.0 out of 10, Exceptional, (5)
"We enjoyed our stay."
United States
Anonymous traveler
$385 nightly
The price is $435
Nov 18 - Nov 19
Total with taxes and fees
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Property grounds
Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont

Putney
9.4 out of 10, Exceptional, (56)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
United States
Louis T.
$214 nightly
The price is $239
Nov 23 - Nov 24
Total with taxes and fees
Family Friendly Hilltop House In Putney Vermont
Interior
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

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

Stratton
7.8 out of 10, Good, (52)
"Location was great, pool, hot tubs and sauna were great"
United States
Lin M.
$244 nightly
The price is $276
Nov 23 - Nov 24
Total with taxes and fees
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Interior
Charming Cavendish Guesthouse

Charming Cavendish Guesthouse

Cavendish
9.8 out of 10, Exceptional, (7)
"Just as described with Everything we needed. Very comfy and roomy. Loved the private feeling and backyard. Would highly recommend to anyone wanting to stay in this area of Vermont."
United States
deborah m.
$248 nightly
The price is $277
Nov 18 - Nov 19
Total with taxes and fees
Charming Cavendish Guesthouse
Outdoor spa tub
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Jamaica
9.6 out of 10, Exceptional, (21)
"House was perfect and just what we were looking for! Very clean, great hot tub, loved the fire pit!Cassie was incredibly helpful with local recommendations and going above and beyond!Highly recommend!"
United States
Neal T.
$588 nightly
The price is $664
Nov 19 - Nov 20
Total with taxes and fees
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Fridge, microwave, oven, stovetop
The Carol - 10 minutes to Okemo & Newly Renovated

The Carol - 10 minutes to Okemo & Newly Renovated

Cavendish
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"
United States
Esther K.
$264 nightly
The price is $295
Nov 18 - Nov 19
Total with taxes and fees
The Carol - 10 minutes to Okemo & Newly Renovated
Fridge, microwave, oven, stovetop
Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming

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

South Londonderry
9.6 out of 10, Exceptional, (4)
"Host was accommodating with responses."
United States
Michael S.
$367 nightly
The price is $415
Nov 18 - Nov 19
Total with taxes and fees
Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming
Outdoor dining
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Walpole
10.0 out of 10, Exceptional, (50)
"Worked out perfectly for us!"
United States
Andrew P.
$513 nightly
The price is $557
Nov 18 - Nov 19
Total with taxes and fees
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
2 bedrooms, WiFi, bed sheets
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

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

2.0 star property
Londonderry
8.0 out of 10, Very Good, (1)
"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.
$439 nightly
The price is $496
Nov 18 - Nov 19
Total with taxes and fees
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Outdoor spa tub
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

Jamaica
9.8 out of 10, Exceptional, (27)
"EXCELLENT location managed by an amazing host who was very communicative and helpful!Hottub was perfect, plenty of sleeping and activities available at the house and in the immediate area (local food was AWESOME)."
United States
s w.
$590 nightly
The price is $667
Nov 18 - Nov 19
Total with taxes and fees
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Outdoor spa tub
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Winhall
9.6 out of 10, Exceptional, (30)
"It was exactly what we wanted. Fireplace , hot tub, and ample sleeping arrangements "
United States
Craig F.
$562 nightly
The price is $630
Nov 18 - Nov 19
Total with taxes and fees
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
House, 3 Bedrooms | Exterior
Bear Pass - Mountain View 4 Bedroom Home by RedAwning

Bear Pass - Mountain View 4 Bedroom Home by RedAwning

3.0 star property
Arlington
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. "
United States
Manish
$588 nightly
The price is $647
Nov 24 - Nov 25
Total with taxes and fees
Bear Pass - Mountain View 4 Bedroom Home by RedAwning
Terrace/patio
Chester Farmhouse Ski Retreat near Slopes

Chester Farmhouse Ski Retreat near Slopes

Chester Depot
9.6 out of 10, Exceptional, (16)
"This was my second time staying at this property. Everything was great just like last year. I highly recommend it if you are staying in Chester, VT. "
United States
Lori N.
$311 nightly
The price is $348
Nov 23 - Nov 24
Total with taxes and fees
Chester Farmhouse Ski Retreat near Slopes
Fridge, microwave, oven, stovetop
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, (103)
"A lovely time enjoying the off-season in a ski town. "
United States
Ed C.
$383 nightly
The price is $415
Nov 18 - Nov 19
Total with taxes and fees
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Terrace/patio
Ski in Ski out Condo! Pool access

Ski in Ski out Condo! Pool access

Stratton
8.8 out of 10, Excellent, (3)
"Great location with plenty of space for the whole family. Highly recommend!"
United States
Joseph S.
$466 nightly
The price is $526
Nov 18 - Nov 19
Total with taxes and fees
Ski in Ski out Condo! Pool access
TV
Must-See Okemo Mountain Resort, 18 Miles Away, Beautiful Place. Visit Now.

Must-See Okemo Mountain Resort, 18 Miles Away, Beautiful Place. Visit Now.

Springfield
$356 nightly
The price is $398
Nov 23 - Nov 24
Total with taxes and fees
Must-See Okemo Mountain Resort, 18 Miles Away, Beautiful Place. Visit Now.
Fridge, microwave, oven, stovetop
Family-friendly A-Frame near Stratton, Bromley & Magic — hot tub retreat in the quiet, peaceful woods

Family-friendly A-Frame near Stratton, Bromley & Magic — hot tub retreat in the quiet, peaceful woods

Jamaica
9.0 out of 10, Wonderful, (6)
"Great location. House was recently updated but has some older charm in parts. Fun and cozy. Hot tub was great the first day but smell seemed off the next day. Perhaps more chlorine was needed. Great time , great trip. Pet friendly is a bonus and the house looks never used so the cleaning crew is doing great work. Will rent again next year perhaps !"
United States
Michael C.
$677 nightly
The price is $716
Nov 18 - Nov 19
Total with taxes and fees
Family-friendly A-Frame near Stratton, Bromley & Magic — hot tub retreat in the quiet, peaceful woods
Interior
MT Holly Ski/lake house hideaway(Avail. Daily, weekends & seasonally Dec-April)

MT Holly Ski/lake house hideaway(Avail. Daily, weekends & seasonally Dec-April)

Mount Holly
9.8 out of 10, Exceptional, (20)
"Everything was as expected. Very clean, great location. Would stay again!"
United States
Jenna K.
$473 nightly
The price is $530
Dec 1 - Dec 2
Total with taxes and fees
MT Holly Ski/lake house hideaway(Avail. Daily, weekends & seasonally Dec-April)
Fridge, microwave, oven, stovetop
8mins Mount Snow - NEW Cabin 3600SF - Game Room - 20%OFF

8mins Mount Snow - NEW Cabin 3600SF - Game Room - 20%OFF

2.0 star property
Wardsboro
$1,759 nightly
The price is $1,988
Nov 18 - Nov 19
Total with taxes and fees
8mins Mount Snow - NEW Cabin 3600SF - Game Room - 20%OFF
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

10/10 Excellent
"Room was clean, spacious. The hotel was close to the outlets which was a plus. We liked the convenience of being provided with our room number and code to our room, which was helpful, as we didnt have to arrive at the hotel by a certain time to be able to check in."
Sarah 3-night trip
Posted 4 days ago
Aspen At Manchester

Find out more about Windham

Windham Vacation Homes information

Number of reviews
374
Accommodation
830 Vacation Homes
Lowest Price
$146
Highest Price
$1,988

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