Search and Rent Windham Condos

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Jan 16 - Jan 18
In two months
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In three months
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In four months
Apr 24 - Apr 26

Our top choices for Windham condo rentals

Property grounds
Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi

Condo in Clock Tower Base Area

Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi
8.6 out of 10, Excellent, (14)
"Excellent Location.. "
United States
Juan Carlos L.
$300 nightly
The price is $339
Jan 4 - Jan 5, 2026
Total with taxes and fees
Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi
Property grounds
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Condo in Clock Tower Base Area

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
9.0 out of 10, Wonderful, (74)
"Perfect location for a quick ski trip. "
United States
Michael D.
$283 nightly
The price is $320
Jan 11 - Jan 12, 2026
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Property grounds
Cozy 3 bedroom condo 2.5 miles to Mount Snow

Condo in West Dover

Cozy 3 bedroom condo 2.5 miles to Mount Snow
9.0 out of 10, Wonderful, (46)
"Great quiet location, kitchen had enough essentials for basic cooking to be easy. The king bed was comfortable and the living room is a great hangout spot."
United States
Franklin C.
$261 nightly
The price is $295
Jan 14 - Jan 15, 2026
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Fridge, microwave, oven, stovetop
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Condo in Ludlow

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
7.6 out of 10, Good, (53)
"Irish Bar nearby was a plus on St. Patrick’s Day !"
United States
Warren
$328 nightly
The price is $370
Jan 12 - Jan 13, 2026
Total with taxes and fees
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Exterior
2nd-floor downtown Ludlow studio condo with kitchenette, streaming

Condo in Ludlow

2nd-floor downtown Ludlow studio condo with kitchenette, streaming
8.6 out of 10, Excellent, (4)
"Great location and convenient to all local businesses. I enjoyed it very much. Would stay here anytime and plan to again. "
United States
Kevin C.
$268 nightly
The price is $303
Jan 5 - Jan 6, 2026
Total with taxes and fees
2nd-floor downtown Ludlow studio condo with kitchenette, streaming
Property grounds
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Condo in Dover

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
8.8 out of 10, Excellent, (32)
"Very nice accommodations and location!"
United States
Michael M.
$403 nightly
The price is $455
Jan 20 - Jan 21, 2026
Total with taxes and fees
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
TV, fireplace
Lovely ski-in/out condo steps from ski lift with trails and amazing views

Condo in Stratton

Lovely ski-in/out condo steps from ski lift with trails and amazing views
8.6 out of 10, Excellent, (27)
"We loved staying at the townhome. It was a welcome place to stay while we traveled around, enjoying fall. It was very comfortable and the village amenities were great."
United States
John N.
$370 nightly
The price is $418
Jan 6 - Jan 7, 2026
Total with taxes and fees
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Interior
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Condo in Ludlow

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
9.0 out of 10, Wonderful, (22)
"Great rate for a place with all the basics!"
United States
Macgregor
$268 nightly
The price is $303
Jan 5 - Jan 6, 2026
Total with taxes and fees
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Microwave, oven, stovetop, coffee/tea maker
Condo in the heart of town near skiing - less than a mile to Okemo Mountain

Condo in Ludlow

Condo in the heart of town near skiing - less than a mile to Okemo Mountain
9.0 out of 10, Wonderful, (14)
"Great location and very comfortable."
United States
Richard J.
$313 nightly
The price is $353
Jan 13 - Jan 14, 2026
Total with taxes and fees
Condo in the heart of town near skiing - less than a mile to Okemo Mountain
Property grounds
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi

Condo in Clock Tower Base Area

Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
9.4 out of 10, Exceptional, (22)
"Enjoy our stay !!!!! Awesome in and out right on the slope feet away for deck."
United States
Dan G.
$390 nightly
The price is $441
Jan 8 - Jan 9, 2026
Total with taxes and fees
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
Exterior
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Condo in Cavendish

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
10.0 out of 10, Exceptional, (19)
"Amazing place! "
United States
Tara
$481 nightly
The price is $539
Jan 4 - Jan 5, 2026
Total with taxes and fees
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Microwave, oven, stovetop, dishwasher
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

Condo in Ludlow

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
10.0 out of 10, Exceptional, (102)
"Convenient 2 BR space with comfy beds right in the heart of Ludlow. Would definitely stay there again."
United States
Andrew L.
$326 nightly
The price is $356
Jan 12 - Jan 13, 2026
Total with taxes and fees
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Microwave, oven, stovetop, dishwasher
NEW Ski in/out condo with Mt views, hot tub, porch, gym & wifi!

Condo in Dover

NEW Ski in/out condo with Mt views, hot tub, porch, gym & wifi!
10.0 out of 10, Exceptional, (1)
"Excellent stay super close to the mtn. "
United States
Matt B.
$401 nightly
The price is $453
Jan 7 - Jan 8, 2026
Total with taxes and fees
NEW Ski in/out condo with Mt views, hot tub, porch, gym & wifi!
TV, DVD player
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Condo in Clock Tower Base Area

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
9.2 out of 10, Wonderful, (26)
"Loved the location"
United States
Steven W.
$367 nightly
The price is $414
Jan 28 - Jan 29, 2026
Total with taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Terrace/patio
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

Condo in Stratton

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
7.4 out of 10, Good, (20)
"A great weekend. The property was clean and comfortable."
United States
Joan P.
$385 nightly
The price is $435
Jan 12 - Jan 13, 2026
Total with taxes and fees
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Dining
Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Condo in Ludlow

Ski-In/Out Condo with Mountain Views, and Washer/Dryer
9.8 out of 10, Exceptional, (16)
"Perfect spot to jump onto the mountain and ski. Two adults and 4 kids, and we had plenty of space for a long weekend."
United States
Allison T.
$855 nightly
The price is $966
Jan 4 - Jan 5, 2026
Total with taxes and fees
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Property grounds
Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)

Condo in Dover

Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)
9.4 out of 10, Exceptional, (18)
"Property was perfect for proximity to the mountain, restaurants and stores. Perfect family spot for a ski vacay!"
United States
amy
$724 nightly
The price is $818
Jan 4 - Jan 5, 2026
Total with taxes and fees
Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)
Interior
Perfect location for your next Vermont Getaway!

Condo in Stratton

Perfect location for your next Vermont Getaway!
9.2 out of 10, Wonderful, (5)
"Perfect location and nice condo"
United States
Doug M.
$884 nightly
The price is $976
Jan 12 - Jan 13, 2026
Total with taxes and fees
Perfect location for your next Vermont Getaway!
Exterior
Okemo | 1BR + Loft Condo + Close to All Amenities

Condo in Jackson Gore Base Area

Okemo | 1BR + Loft Condo + Close to All Amenities
$894 nightly
The price is $987
Jan 13 - Jan 14, 2026
Total with taxes and fees
Okemo | 1BR + Loft Condo + Close to All Amenities
Interior
Stratton Mtn Studio | Renovated | Walk to Lifts

Condo in Stratton Mountain

Stratton Mtn Studio | Renovated | Walk to Lifts
10.0 out of 10, Exceptional, (30)
"Great location."
United States
Jeffrey
$563 nightly
The price is $636
Jan 5 - Jan 6, 2026
Total with taxes and fees
Stratton Mtn Studio | Renovated | Walk to Lifts
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

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"The suite has everything what we need it ,this place is great for stay ,everyone is so polite ,location is great .Highly recommend!!!"
bozena 3-night trip
Posted 1 day ago
Pointe at Castle Hill Resort

Find out more about Windham

Windham Condo Rentals information

Number of reviews
12,431
Accommodation
415 Condo Rentals
Lowest Price
$85
Highest Price
$206

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