Condo Rentals in Cheshire County

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Our top choices for Cheshire County condo rentals

Ski-in/ski-out condo w/ wood-burning fireplace, patio, shared bbq, w/d, wifi

Ski-in/ski-out condo w/ wood-burning fireplace, patio, shared bbq, w/d, wifi
West Dover
8.0 out of 10, Very Good, (1 review)
"Ski lifts would be easily accessible when the carpet is operating. If not the lift is an uphill walk approx. 250 yards. Unfortunately it was not running through the week when we were there. Other than that the place fit our basic needs."
United States
jenn t.
Ski-in/ski-out condo w/ wood-burning fireplace, patio, shared bbq, w/d, wifi

NEW Ski in/out condo with Mt views, hot tub, porch, gym & wifi!

NEW Ski in/out condo with Mt views, hot tub, porch, gym & wifi!
Dover
9.4 out of 10, Exceptional, (9 reviews)
"rented for a ski trip, was nice clean and accommodating. "
United States
yehuda t.
NEW Ski in/out condo with Mt views, hot tub, porch, gym & wifi!

Convenient 3BR condo, close to Okemo, wifi, TV, village dining & walking

Convenient 3BR condo, close to Okemo, wifi, TV, village dining & walking
Proctorsville
9.0 out of 10, Wonderful, (8 reviews)
"Clean. Great location."
United States
joe h.
Convenient 3BR condo, close to Okemo, wifi, TV, village dining & walking

Seasons On Mount Snow - Ski-in/Ski-out

Seasons On Mount Snow - Ski-in/Ski-out
Dover
9.8 out of 10, Exceptional, (188 reviews)
"Wonderful host, excellent property and amenities! Had a fantastic stay!"
United States
Eric W.
Seasons On Mount Snow - Ski-in/Ski-out

Comfortable condo with fireplace, pool, and sauna access - near slopes

Comfortable condo with fireplace, pool, and sauna access - near slopes
Dover
7.6 out of 10, Good, (23 reviews)
"Clean, great proximity to mount snow"
United States
Melodi C.
Comfortable condo with fireplace, pool, and sauna access - near slopes

Slopeside condo with nearby skiing, balcony, fireplace, & washer/dryer

Slopeside condo with nearby skiing, balcony, fireplace, & washer/dryer
Dover
8.8 out of 10, Excellent, (21 reviews)
"The condo was very clean and comfortable. The host checked in on occasion and was accessible when we had a question. It was a great stay."
United States
Craig S.
Slopeside condo with nearby skiing, balcony, fireplace, & washer/dryer

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, (23 reviews)
"Great communication without host. The property is clean, well stocked and well maintained. Would definitely stay again! Thanks for letting us share your space."
United States
Steve G.
The price is AED 1,102
AED 1,970 total
includes taxes & fees
14 May - 15 May
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Spacious Mount Snow condo near slopes with private hot tub, sauna & fireplace

Spacious Mount Snow condo near slopes with private hot tub, sauna & fireplace
Dover
8.6 out of 10, Excellent, (14 reviews)
"We had a great time In this home.. we hope return soon. Everything was great."
United States
Thaina P.
Spacious Mount Snow condo near slopes with private hot tub, sauna & fireplace

The Slope Side Lodge, Ski off w/ Fireplace!

The Slope Side Lodge, Ski off w/ Fireplace!
Dover
10.0 out of 10, Exceptional, (5 reviews)
"Greg was very helpful, his condo was clean and well stocked with utensil, pots & pans for cooking. Easy to hit the trails for skiing! Great trip!"
United States
Sonia W.
The Slope Side Lodge, Ski off w/ Fireplace!

Walk to Mount Snow, Cozy, Clean and Comfortable!

Walk to Mount Snow, Cozy, Clean and Comfortable!
West Dover
9.6 out of 10, Exceptional, (44 reviews)
"Great place! Host is very friendly and responsive! Will definitely stay again! "
United States
Halyna
Walk to Mount Snow, Cozy, Clean and Comfortable!

Timber Creek Getaway w/ Fireplace,Sauna&Mtn Views!

Timber Creek Getaway w/ Fireplace,Sauna&Mtn Views!
Dover
10.0 out of 10, Exceptional, (5 reviews)
"Great property and perfect family getaway for a weekend in VT!"
United States
Bryan B.
Timber Creek Getaway w/ Fireplace,Sauna&Mtn Views!

Mt Snow Getaway - 3 bedroom Chic condo - Community pool and tennis

Mt Snow Getaway - 3 bedroom Chic condo - Community pool and tennis
Dover
10.0 out of 10, Exceptional, (6 reviews)
"Great condo, very close to Mount Snow! Good heating and Wi-Fi. Would stay again!"
United States
Aaron A.
Mt Snow Getaway - 3 bedroom Chic condo - Community pool and tennis

Condo < 1mi. from Mt. Snow / Free Shuttle

Condo < 1mi. from Mt. Snow / Free Shuttle
West Dover
9.8 out of 10, Exceptional, (14 reviews)
"Everything was great!"
United States
Tracey S.
Condo < 1mi. from Mt. Snow / Free Shuttle

Redecorated! Great Location at Mount Snow, Free Shuttle, Pool/Hot Tub

Redecorated! Great Location at Mount Snow, Free Shuttle, Pool/Hot Tub
West Dover
8.8 out of 10, Excellent, (10 reviews)
"The condo is very cute and comfortable. Check in and check out are very easy. The shuttle takes you to and from the ski resort. Was a perfect getaway."
United States
Suzanne M.
Redecorated! Great Location at Mount Snow, Free Shuttle, Pool/Hot Tub

SnowTree Retreat: Large 2-Bedroom Condo 5 Minute Walk from The Mount Snow Base!

SnowTree Retreat: Large 2-Bedroom Condo 5 Minute Walk from The Mount Snow Base!
West Dover
9.4 out of 10, Exceptional, (3 reviews)
"Host was very kind. Great location to walk to resort! "
United States
Brook T.
SnowTree Retreat: Large 2-Bedroom Condo 5 Minute Walk from The Mount Snow Base!

Cozy 1-bedroom condo in Dover, VT steps away from Mount Snow

Cozy 1-bedroom condo in Dover, VT steps away from Mount Snow
Dover
10.0 out of 10, Exceptional, (8 reviews)
"The place was super clean and cozy and also close to ski resorts and many restaurants "
United States
Jason G.
Cozy 1-bedroom condo in Dover, VT steps away from Mount Snow

Trailside Tranquility, new renovations 2025 | Slope-Side at Mount Snow

Trailside Tranquility, new renovations 2025 | Slope-Side at Mount Snow
Dover
10.0 out of 10, Exceptional, (2 reviews)
"We keep coming back to the condos at Seasons for ski weekends, and had another terrific experience. Condo was perfect in terms of layout/amenities/location, and owners are highly responsive. Highly recommend!"
United States
Sean R.
Trailside Tranquility, new renovations 2025 | Slope-Side at Mount Snow

Updated Condo at Base of Mt Snow w Fireplace

Updated Condo at Base of Mt Snow w Fireplace
Dover
9.6 out of 10, Exceptional, (16 reviews)
"Just as listed. Had a great time."
United States
Jerry P.
Updated Condo at Base of Mt Snow w Fireplace

Seasons on Mount Snow | Walk Out / Ski Home!

Seasons on Mount Snow | Walk Out / Ski Home!
Dover
9.6 out of 10, Exceptional, (5 reviews)
"My family had a wonderful time staying at the townhouse. It was very spacious, had everything we needed, great amenities like the indoor pool and hot tub, and walking distance to the Sundance Lift. We would definitely recommend this property to our family and friends. Thank you."
United States
Gregory W.
Seasons on Mount Snow | Walk Out / Ski Home!

Multi-level resort home near ski resorts with balcony, streaming, W/D

Multi-level resort home near ski resorts with balcony, streaming, W/D
Wilmington
9.6 out of 10, Exceptional, (5 reviews)
"This wasn't our first time staying at this house and it definitely won't be the last! Once again, everything was perfect. The home is clean, cozy, and beautifully maintained, with all the comforts we needed to relax and enjoy. You can really feel the care the hosts put into every detail – they’ve been amazing every single time. The whole process is always easy and smooth. We highly recommend it and can't wait to come back. Thanks again for another perfect stay!"
United States
Camila D.
Multi-level resort home near ski resorts with balcony, streaming, W/D
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 Cheshire County Hotel Reviews