Photo by William E Berry Jr.

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Condo Rentals in Windsor

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

10.0 out of 10, Exceptional, (18)
"Lovely large property, everything was clean and well maintained! Will happily stay there again!"
$482 nightly
The price is $540
Jun 19 - Jun 20
Total includes taxes and fees
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

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

10.0 out of 10, Exceptional, (95)
"We loved Wendy's place. It was clean, updated and had everything we needed. Its in the center of town so convenient to shops and restaurants and close to the mountain. We will be booking again. "
$239 nightly
The price is $257
Jun 22 - Jun 23
Total includes taxes and fees
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

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

9.0 out of 10, Wonderful, (13)
"Great location and very comfortable."
$223 nightly
The price is $252
Jul 15 - Jul 16
Total includes taxes and fees
Condo in the heart of town near skiing - less than a mile to Okemo Mountain

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

9.0 out of 10, Wonderful, (72)
"Dated but well appointed and comfortable condo. Be prepared for lots of stairs but great location directly slopeside."
$238 nightly
The price is $266
Jun 19 - Jun 20
Total includes taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

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

9.4 out of 10, Exceptional, (24)
"Great location for ski in ski out unit on 1st floor. Steps away from clock tower base and lift. Easy access to post ski fun for drink/dining super close The Loft or The Bull both 2 mins walk from condo. "
$205 nightly
The price is $230
Jun 22 - Jun 23
Total includes taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

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

9.4 out of 10, Exceptional, (20)
"Enjoy our stay !!!!! Awesome in and out right on the slope feet away for deck."
$348 nightly
The price is $390
Jun 19 - Jun 20
Total includes taxes and fees
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi

Okemo Westwood Condo 3 Bedroom Condo by RedAwning

3.5 star property
Okemo Westwood Condo 3 Bedroom Condo by RedAwning

Mountain Bliss: Hot Tub, Shuttle to Okemo, Quiet Ludlow Retreat

9.6 out of 10, Exceptional, (19)
"Just as described. A great place with hot tubEverything you need and more "
$604 nightly
The price is $676
Jun 19 - Jun 20
Total includes taxes and fees
Mountain Bliss: Hot Tub, Shuttle to Okemo, Quiet Ludlow Retreat

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

7.6 out of 10, Good, (53)
"This cozy cabin was perfect for a ski weekend with friends. We really enjoyed gathering by the stone fireplace after a couple long days out on the slopes."
$245 nightly
The price is $275
Jun 22 - Jun 23
Total includes taxes and fees
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Ski-In/Out Condo with Mountain Views, and Washer/Dryer

9.8 out of 10, Exceptional, (16)
"Location location location!"
$357 nightly
The price is $400
Jun 19 - Jun 20
Total includes taxes and fees
Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

9.8 out of 10, Exceptional, (23)
"convenient to okemo"
$558 nightly
The price is $625
Jun 19 - Jun 20
Total includes taxes and fees
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

Cozy 2 BR Ski On Ski Off Condo in Killington's Sunrise Mountain Village. Pool. Hot Tub.

2.0 star property
9.4 out of 10, Exceptional, (3)
"Absolutely perfect spot. Kids and parents loved it. Everything you’re looking for in an on mountain condo. Pool and hot tub are a short drive away but we still used it. "
$482 nightly
The price is $545
Jun 19 - Jun 20
Total includes taxes and fees
Cozy 2 BR Ski On Ski Off Condo in Killington's Sunrise Mountain Village. Pool. Hot Tub.

Sunrise Timberline: 3br, 2ba Ski In/ski Out Condo 3 Bedroom Condo

3.0 star property
$599 nightly
The price is $667
Jun 22 - Jun 23
Total includes taxes and fees
Sunrise Timberline: 3br, 2ba Ski In/ski Out Condo 3 Bedroom Condo

Sunrise Timberline: 3BR, 2BA Ski In/Ski Out Condo

9.2 out of 10, Wonderful, (20)
"Ski in Ski out using the sunrise village lift. "
$454 nightly
The price is $513
Jun 19 - Jun 20
Total includes taxes and fees
Sunrise Timberline: 3BR, 2BA Ski In/Ski Out Condo

Sunrise West Glade: 3br, 3ba Ski In/ski Out Condo 3 Bedroom Condo

3.0 star property
$563 nightly
The price is $625
Jun 23 - Jun 24
Total includes taxes and fees
Sunrise West Glade: 3br, 3ba Ski In/ski Out Condo 3 Bedroom Condo

Sunrise West Glade: 3BR, 3BA Ski In/Ski Out Condo

9.4 out of 10, Exceptional, (16)
"We've stayed in a number of condos in the area and appreciiate easy access to the lifts when snow permits. This is a pretty typical ski rental, ticking the boxes of what we needed."
$439 nightly
The price is $496
Jun 25 - Jun 26
Total includes taxes and fees
Sunrise West Glade: 3BR, 3BA Ski In/Ski Out Condo

SunBear- AC, Pool, Game Room, Fireplace, Hiking!

10.0 out of 10, Exceptional, (26)
"Lovely proactive hosts, covered every detail for a convenient and welcoming stay. Accommodations were clean, well organized, family friendly, and close to the mountains. Highly recommend. "
$498 nightly
The price is $563
Jun 22 - Jun 23
Total includes taxes and fees
SunBear- AC, Pool, Game Room, Fireplace, Hiking!

Sunrise Bear Ridge C4 4 Bedroom Condo

3.0 star property
$641 nightly
The price is $705
Jun 19 - Jun 20
Total includes taxes and fees
Sunrise Bear Ridge C4 4 Bedroom Condo

Fall Line Condo D1 1 Bedroom Condo

3.5 star property
$354 nightly
The price is $394
Jun 19 - Jun 20
Total includes taxes and fees
Fall Line Condo D1 1 Bedroom Condo

Fall Line Condo D6 3 Bedroom Condo

3.5 star property
$721 nightly
The price is $793
Jun 19 - Jun 20
Total includes taxes and fees
Fall Line Condo D6 3 Bedroom Condo
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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