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Our top choices for Windsor condo rentals

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
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

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Cavendish
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

2nd-floor downtown Ludlow studio condo with kitchenette, streaming

2nd-floor downtown Ludlow studio condo with kitchenette, streaming
Ludlow
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

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

Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi
Clock Tower Base Area
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

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Ludlow
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.
$324 nightly
The price is $354
Jan 12 - Jan 13, 2026
Total with taxes and fees
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (26)
"Loved the location"
United States
Steven W.
$302 nightly
The price is $341
Jan 8 - Jan 9, 2026
Total with taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
7.6 out of 10, Good, (53)
"Irish Bar nearby was a plus on St. Patrick’s Day !"
United States
Warren
$338 nightly
The price is $382
Jan 12 - Jan 13, 2026
Total with taxes and fees
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Condo in the heart of town near skiing - less than a mile to Okemo Mountain

Condo in the heart of town near skiing - less than a mile to Okemo Mountain
Ludlow
9.0 out of 10, Wonderful, (14)
"Great location and very comfortable."
United States
Richard J.
$321 nightly
The price is $363
Jan 12 - Jan 13, 2026
Total with taxes and fees
Condo in the heart of town near skiing - less than a mile to Okemo Mountain

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Ludlow
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

Ground Floor ski-in/out condo, full kitchen & high-speed WiFi

Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
Clock Tower Base Area
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

Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
2.0 star property
Killington
10.0 out of 10, Exceptional, (1)
"8 mins drive from ski lodge"
United States
YUXIANG
$280 nightly
The price is $317
Jan 19 - Jan 20, 2026
Total with taxes and fees
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

Killington Ground-Level 2BR/2BA Condo Walk-Out Patio, Easy Access

Killington Ground-Level 2BR/2BA Condo Walk-Out Patio, Easy Access
2.0 star property
Killington
$340 nightly
The price is $384
Jan 13 - Jan 14, 2026
Total with taxes and fees
Killington Ground-Level 2BR/2BA Condo Walk-Out Patio, Easy Access

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
Killington
9.4 out of 10, Exceptional, (9)
"Great property, as advertised."
United States
Chris A.
$298 nightly
The price is $336
Jan 8 - Jan 9, 2026
Total with taxes and fees
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
$418 nightly
The price is $459
Jan 14 - Jan 15, 2026
Total with taxes and fees
The Suites at Killington Center

Killington Ski Resort VT Vacation Condos

Killington Ski Resort VT Vacation Condos
3.5 star property
Killington
$375 nightly
The price is $421
Jan 21 - Jan 22, 2026
Total with taxes and fees
Killington Ski Resort VT Vacation Condos

Trail Creek Killington Condos #18: Ski Home Trail. Bus. Hot Tub. Pool.

Trail Creek Killington Condos #18: Ski Home Trail. Bus. Hot Tub. Pool.
2.5 star property
Killington
10.0 out of 10, Exceptional, (2)
"Roomy, excellant property. I would rent again, loved it"
United States
Mickey E.
$651 nightly
The price is $736
Jan 19 - Jan 20, 2026
Total with taxes and fees
Trail Creek Killington Condos #18: Ski Home Trail. Bus. Hot Tub. Pool.

Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service

Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
Killington
9.4 out of 10, Exceptional, (64)
"Condo well equipped- hosts very responsive-pool area great! "
United States
gail m.
$277 nightly
The price is $313
Jan 6 - Jan 7, 2026
Total with taxes and fees
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service

Resort condo with balcony & shared seasonal amenities - close to skiing

Resort condo with balcony & shared seasonal amenities - close to skiing
Killington
8.2 out of 10, Very Good, (35)
"Perfect accommodations. Clean, modern, comfortable, plenty of space, walking distance from the entire resort. The queen bed is incredibly comfortable! 10/10!"
United States
Ryan L.
$322 nightly
The price is $364
Jan 26 - Jan 27, 2026
Total with taxes and fees
Resort condo with balcony & shared seasonal amenities - close to skiing

Welcoming condo near the slopes with free WiFi and full kitchen

Welcoming condo near the slopes with free WiFi and full kitchen
Killington
7.2 out of 10, Good, (30)
"beds were comfortable"
United States
Juan T.
$328 nightly
The price is $371
Jan 4 - Jan 5, 2026
Total with taxes and fees
Welcoming condo near the slopes with free WiFi and full kitchen

Whiffletree Cozy Condo: 2-Bedroom Condo in Killington, VT with Garden View and Ski Rental Deals

Whiffletree Cozy Condo: 2-Bedroom Condo in Killington, VT with Garden View and Ski Rental Deals
2.0 star property
Killington
$357 nightly
The price is $403
Jan 12 - Jan 13, 2026
Total with taxes and fees
Whiffletree Cozy Condo: 2-Bedroom Condo in Killington, VT with Garden View and Ski Rental Deals
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 Windsor Hotel Reviews

Find out more about Windsor

Windsor Condo Rentals information

Number of reviews
340
Accommodation
948 Condo Rentals
Lowest Price
$303
Highest Price
$736

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