Photo by Rachel Samanyi

Search and Rent Windsor County Condos

Compare and save

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jan 23 - Jan 25
In two months
Mar 6 - Mar 8
In three months
Apr 3 - Apr 5
In four months
May 1 - May 3

Top Cities in Windsor County

Woodstock featuring a house
Condo RentalsCondo Rentals

Woodstock

Woodstock

Our top choices for Windsor County condo rentals

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

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, (75)
"Perfect location for a quick ski trip. "
United States
Michael D.
$276 nightly
The price is $312
Jan 11 - Jan 12
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Indoor pool, outdoor pool
Ski on/off Solitude Village 3 bedroom condo directly on Okemo Mt ski trail

Ski on/off Solitude Village 3 bedroom condo directly on Okemo Mt ski trail

Ski on/off Solitude Village 3 bedroom condo directly on Okemo Mt ski trail
3.0 star property
Ludlow
10.0 out of 10, Exceptional, (3)
"Great Ski-in/out Unit. Very clean and spacious. nice kitchen and proximity fort he Solitude lift was good. "
United States
Svetlana K.
Ski on/off Solitude Village 3 bedroom condo directly on Okemo Mt ski trail
Exterior detail
Ski-in/out condo with pool, 2 hot tubs, sauna - short walk to Solitude clubhouse

Ski-in/out condo with pool, 2 hot tubs, sauna - short walk to Solitude clubhouse

Ski-in/out condo with pool, 2 hot tubs, sauna - short walk to Solitude clubhouse
Ludlow
9.4 out of 10, Exceptional, (33)
"Nice location steps off of Moonshadow trail. "
United States
Abby P.
Ski-in/out condo with pool, 2 hot tubs, sauna - short walk to Solitude clubhouse
TV, fireplace
Ski-in/out condo with water & mountain views, private sauna & fireplace

Ski-in/out condo with water & mountain views, private sauna & fireplace

Ski-in/out condo with water & mountain views, private sauna & fireplace
Ludlow
9.8 out of 10, Exceptional, (51)
"Great place, clean and exactly as advertised. "
United States
Beth h.
Ski-in/out condo with water & mountain views, private sauna & fireplace
Indoor pool, a heated pool
Okemo Ski in-Ski out @ Winterplace, 3 bdr, 2 ba Condo with Pool, Hot Tub, W/D

Okemo Ski in-Ski out @ Winterplace, 3 bdr, 2 ba Condo with Pool, Hot Tub, W/D

Okemo Ski in-Ski out @ Winterplace, 3 bdr, 2 ba Condo with Pool, Hot Tub, W/D
Okemo Village
10.0 out of 10, Exceptional, (27)
"The location was great and the condo was just what we needed and very clean!"
United States
Jane G.
Okemo Ski in-Ski out @ Winterplace, 3 bdr, 2 ba Condo with Pool, Hot Tub, W/D
Property grounds
Convenience & location! Direct ski access-1 BR/2BA fully stocked condo at Okemo

Convenience & location! Direct ski access-1 BR/2BA fully stocked condo at Okemo

Convenience & location! Direct ski access-1 BR/2BA fully stocked condo at Okemo
3.5 star property
Jackson Gore Base Area
10.0 out of 10, Exceptional, (3)
"Great location. Comfortable stay. Proximity to the mountain is terrific. "
United States
Dari K.
Convenience & location! Direct ski access-1 BR/2BA fully stocked condo at Okemo
Smart TV, fireplace
Mountainside Luxury 2-Level Condo at Okemo. Ski-In/Out.

Mountainside Luxury 2-Level Condo at Okemo. Ski-In/Out.

Mountainside Luxury 2-Level Condo at Okemo. Ski-In/Out.
Ludlow
10.0 out of 10, Exceptional, (36)
"The condo is beautiful, the beds were comfortable, and the community is quiet. We loved having the pool and gym to use during our stay. The proximity to downtown Ludlow, Okemo Clocktower and Jackson Gore, Camp Plymouth, and the Green Mountain Sugar House is ideal. We very much enjoyed our time here and would come back again. "
United States
Beth L.
Mountainside Luxury 2-Level Condo at Okemo. Ski-In/Out.
Property grounds
Okemo's Jackson Gore-1 Bedroom Condo /Direct Ski Access. Walk to Pool & hot tubs

Okemo's Jackson Gore-1 Bedroom Condo /Direct Ski Access. Walk to Pool & hot tubs

Okemo's Jackson Gore-1 Bedroom Condo /Direct Ski Access. Walk to Pool & hot tubs
Jackson Gore Base Area
9.8 out of 10, Exceptional, (25)
"The property was very clean and spacious and right on the slope. It was a great weekend getaway."
United States
Wendy S.
Okemo's Jackson Gore-1 Bedroom Condo /Direct Ski Access. Walk to Pool & hot tubs
Indoor pool
Ski-in/out condo near lifts with a fireplace, pool, hot tub, & tennis

Ski-in/out condo near lifts with a fireplace, pool, hot tub, & tennis

Ski-in/out condo near lifts with a fireplace, pool, hot tub, & tennis
Okemo Village
9.2 out of 10, Wonderful, (73)
"Everything was excellent "
United States
andy f.
Ski-in/out condo near lifts with a fireplace, pool, hot tub, & tennis
TV, fireplace, offices
Highland Golf, Walk to Club - Lakeland Village 2D

Highland Golf, Walk to Club - Lakeland Village 2D

Highland Golf, Walk to Club - Lakeland Village 2D
Quechee
10.0 out of 10, Exceptional, (2)
"Golf was incredible. Place was in great location. Very nice condo."
United States
Zach A.
Highland Golf, Walk to Club - Lakeland Village 2D
Indoor pool
Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!

Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!

Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
Okemo Village
10.0 out of 10, Exceptional, (58)
"We had a great time at the wonderful Winterplace condo. The host was very responsive . "
United States
Ivania R.
Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
Smart TV, fireplace, video games, DVD player
Slopeside 3-level 4BR Townhouse at the Top of Trailside Village -Okemo Mountain

Slopeside 3-level 4BR Townhouse at the Top of Trailside Village -Okemo Mountain

Slopeside 3-level 4BR Townhouse at the Top of Trailside Village -Okemo Mountain
Ludlow
9.6 out of 10, Exceptional, (4)
"Great condo in excellent location with easy access to the slopes. Owner excellent with communication and very hospitable. Our family had a great time. "
United States
William F.
Slopeside 3-level 4BR Townhouse at the Top of Trailside Village -Okemo Mountain
Terrace/patio
Dog-friendly & riverfront condo one mile from Okemo with wood fireplace

Dog-friendly & riverfront condo one mile from Okemo with wood fireplace

Dog-friendly & riverfront condo one mile from Okemo with wood fireplace
Ludlow
8.6 out of 10, Excellent, (21)
"Great Location. Inside of place was great. "
United States
Dan D.
Dog-friendly & riverfront condo one mile from Okemo with wood fireplace
TV, fireplace, DVD player
Recently Renovated Ski-In/Out Condo w/Fireplace, Shared Pool, Hot Tub, Sauna

Recently Renovated Ski-In/Out Condo w/Fireplace, Shared Pool, Hot Tub, Sauna

Recently Renovated Ski-In/Out Condo w/Fireplace, Shared Pool, Hot Tub, Sauna
Ludlow
9.8 out of 10, Exceptional, (29)
"Clean and comfortable"
United States
Lynn D.
Recently Renovated Ski-In/Out Condo w/Fireplace, Shared Pool, Hot Tub, Sauna
Indoor pool, a heated pool
3BR/2BA, Ski in/out from A/B lift, pool & hot tub

3BR/2BA, Ski in/out from A/B lift, pool & hot tub

3BR/2BA, Ski in/out from A/B lift, pool & hot tub
Okemo Village
10.0 out of 10, Exceptional, (3)
"The property was beautiful. Everything was modern and in excellent working condition. David and Shannon provided all of the little items to support our stay. Parking was easy and the walk to the lifts wasn't too far. "
United States
Robin R.
3BR/2BA, Ski in/out from A/B lift, pool & hot tub
Indoor pool
Ski-in/out condo with mountain and lift views, hot tub, & pool

Ski-in/out condo with mountain and lift views, hot tub, & pool

Ski-in/out condo with mountain and lift views, hot tub, & pool
Okemo Village
9.4 out of 10, Exceptional, (71)
"The location can't be beat, walk right out the back door onto the slopes! Nicely updated condo too."
United States
Jeff H.
Ski-in/out condo with mountain and lift views, hot tub, & pool
Fridge, microwave, oven, stovetop
OKEMO WINTERPLACE Best Location, Ski-In/Ski-Out 4BR/3BATH + LOFT. Spacious.

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

OKEMO WINTERPLACE Best Location, Ski-In/Ski-Out 4BR/3BATH + LOFT. Spacious.
Okemo Village
10.0 out of 10, Exceptional, (15)
"The condo is great for ski in ski out"
United States
Nanette P.
$1,341 nightly
The price is $1,515
Jan 19 - Jan 20
Total with taxes and fees
OKEMO WINTERPLACE Best Location, Ski-In/Ski-Out 4BR/3BATH + LOFT. Spacious.
Exterior
Ski-in/ski-out condo with WiFi, washer/dryer, mountain views & golf nearby

Ski-in/ski-out condo with WiFi, washer/dryer, mountain views & golf nearby

Ski-in/ski-out condo with WiFi, washer/dryer, mountain views & golf nearby
Clock Tower Base Area
9.0 out of 10, Wonderful, (17)
"Great stay"
United States
Esther K.
Ski-in/ski-out condo with WiFi, washer/dryer, mountain views & golf nearby
TV, books
Three-level ski-in/out condo with sauna, washer/dryer & mountain view

Three-level ski-in/out condo with sauna, washer/dryer & mountain view

Three-level ski-in/out condo with sauna, washer/dryer & mountain view
Ludlow
9.0 out of 10, Wonderful, (12)
"Loved skiing out our back door. This place was the perfect vacation getaway for our group!"
United States
Elaine C.
Three-level ski-in/out condo with sauna, washer/dryer & mountain view
Property grounds
Renovated Luxury 4 Bedroom 3.5 Bath Okemo Trailside

Renovated Luxury 4 Bedroom 3.5 Bath Okemo Trailside

Renovated Luxury 4 Bedroom 3.5 Bath Okemo Trailside
Ludlow
10.0 out of 10, Exceptional, (29)
"Very nicely maintained and detailed. Great for families"
United States
Xavier V.
Renovated Luxury 4 Bedroom 3.5 Bath Okemo Trailside
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor County Hotel Reviews

Align Inn Vermont

Align Inn Vermont

10/10 Excellent
"Awesome 👌 "
Mariusz 3-night trip
Posted 2 days ago
Align Inn Vermont

Find out more about Windsor County

Windsor County Condo Rentals information

Number of reviews
350
Accommodation
348 Condo Rentals
Lowest Price
$312
Highest Price
$1,515

Explore a world of travel with Expedia