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Check prices for these dates

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Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
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Oct 10 - Oct 12

Condo Rentals in Windsor

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Microwave, oven, stovetop, dishwasher

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

10.0 out of 10, Exceptional, (97)
"Wonderful two bedroom condo, fantastic communication from the manager, easy everything, parking, accessing the beautiful unit, checking out, just perfect!"
$248 nightly
The price is $268
Aug 18 - Aug 19
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
Fridge, microwave, oven, stovetop

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."
$199 nightly
The price is $225
Aug 24 - Aug 25
Total includes taxes and fees
Condo in the heart of town near skiing - less than a mile to Okemo Mountain
2nd-floor downtown Ludlow studio condo with kitchenette, streaming
Exterior detail

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

8.8 out of 10, Excellent, (3)
"Great location and convenient to all local businesses. I enjoyed it very much. Would stay here anytime and plan to again. "
$199 nightly
The price is $225
Aug 17 - Aug 18
Total includes taxes and fees
2nd-floor downtown Ludlow studio condo with kitchenette, streaming
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Interior

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!"
$199 nightly
The price is $225
Aug 25 - Aug 26
Total includes taxes and fees
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Property grounds

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

9.0 out of 10, Wonderful, (72)
"Perfect location for a quick ski trip. "
$225 nightly
The price is $254
Aug 17 - Aug 18
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
TV, DVD player

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. "
$194 nightly
The price is $219
Aug 17 - Aug 18
Total includes taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Ski Haven: 1-Bed Ski-in/out Condo, Okemo Base Area
Smart TV, fireplace

Ski Haven: 1-Bed Ski-in/out Condo, Okemo Base Area

9.8 out of 10, Exceptional, (10)
"Great communication, ski in/out location"
$339 nightly
The price is $383
Aug 17 - Aug 18
Total includes taxes and fees
Ski Haven: 1-Bed Ski-in/out Condo, Okemo Base Area
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
Property grounds

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."
$328 nightly
The price is $371
Aug 17 - Aug 18
Total includes taxes and fees
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
Okemo | Charming 1BR Condo + Close to Amenities
Exterior

Okemo | Charming 1BR Condo + Close to Amenities

$305 nightly
The price is $337
Aug 21 - Aug 22
Total includes taxes and fees
Okemo | Charming 1BR Condo + Close to Amenities
Okemo | 1BR + Loft Condo + Close to All Amenities
Exterior

Okemo | 1BR + Loft Condo + Close to All Amenities

$344 nightly
The price is $380
Aug 21 - Aug 22
Total includes taxes and fees
Okemo | 1BR + Loft Condo + Close to All Amenities
Cozy Slopeside Escape - Ski-In/Out Condo at Okemo
Sport court

Cozy Slopeside Escape - Ski-In/Out Condo at Okemo

3.0 star property
10.0 out of 10, Exceptional, (5)
"Location was perfect for skiing. Hosts were responsive and the stay was pleasant. Would book again."
$374 nightly
The price is $422
Sep 1 - Sep 2
Total includes taxes and fees
Cozy Slopeside Escape - Ski-In/Out Condo at Okemo
Ultimate Ski Retreat - Ski in/out at Okemo
Interior

Ultimate Ski Retreat - Ski in/out at Okemo

9.8 out of 10, Exceptional, (12)
"Ahmad was great, and was very responsive! The condo location was amazing, and convenient to all amenities. "
$374 nightly
The price is $422
Sep 1 - Sep 2
Total includes taxes and fees
Ultimate Ski Retreat - Ski in/out at Okemo
OKEMO WINTERPLACE Best Location, Ski-In/Ski-Out 4BR/3BATH + LOFT. Spacious.
Property grounds

OKEMO WINTERPLACE Best Location, Ski-In/Ski-Out 4BR/3BATH + LOFT. Spacious.

10.0 out of 10, Exceptional, (12)
"The condo is great for ski in ski out"
$656 nightly
The price is $741
Sep 10 - Sep 11
Total includes taxes and fees
OKEMO WINTERPLACE Best Location, Ski-In/Ski-Out 4BR/3BATH + LOFT. Spacious.
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Fridge, microwave, oven, stovetop

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

7.6 out of 10, Good, (53)
"Great location! Small walk to the trails but easy to get to! Definitely needed some improvements with the amount of sheets and cleanliness but other than that a great stay for an affordable rate!"
$232 nightly
The price is $262
Aug 17 - Aug 18
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
Dining

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

9.8 out of 10, Exceptional, (16)
"Location location location!"
$338 nightly
The price is $382
Aug 17 - Aug 18
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
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (23)
"convenient to okemo"
$516 nightly
The price is $578
Aug 17 - Aug 18
Total includes taxes and fees
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Experience the ultimate Vermont getaway at our cozy 1BR/1BA ski-in/ski-out condo in Killington
Exterior

Experience the ultimate Vermont getaway at our cozy 1BR/1BA ski-in/ski-out condo in Killington

$387 nightly
The price is $438
Aug 18 - Aug 19
Total includes taxes and fees
Experience the ultimate Vermont getaway at our cozy 1BR/1BA ski-in/ski-out condo in Killington
Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Fridge, microwave, oven, stovetop

Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

7.0 out of 10, Good, (2)
"Overall we had a nice stay. Location is perfect on the Great Eastern ski trail and discounted lift tickets a plus. Appreciate that it's dog friendly. Hot tub and sauna were awesome. Wood burning stove was great. That said, place is a bit dated and finishings definitely on the cheaper side. Formica (not granite) counters were starting to peel. Several burners on the stove wouldn't light without using the lighter from the fireplace. Coffee maker was missing a piece or a bad design and leaked 20%...
$491 nightly
The price is $555
Aug 17 - Aug 18
Total includes taxes and fees
Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Trailside Village #5: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Outdoor spa tub

Trailside Village #5: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

$465 nightly
The price is $525
Aug 17 - Aug 18
Total includes taxes and fees
Trailside Village #5: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Trailside Village #7: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Interior

Trailside Village #7: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

$465 nightly
The price is $525
Aug 17 - Aug 18
Total includes taxes and fees
Trailside Village #7: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
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

The Shire Woodstock

The Shire Woodstock

10/10 Excellent
"Nice get away spit in the country. Very clean and bed was comfortable. Fire pits were lite each night to sit out and enjoy. Short walk into town for shopping and eating. A market across the road was very convenient."
Cheryl 2-night trip
Posted 2 days ago
The Shire Woodstock