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Condo Rentals in Cheshire County

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Cheshire County condo rentals

Indoor pool, a heated pool

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

Seasons On Mount Snow - Ski-in/Ski-out
Dover
9.8 out of 10, Exceptional, (191 reviews)
"Wonderful host, excellent property and amenities! Had a fantastic stay!"
United States
Eric W.
Seasons On Mount Snow - Ski-in/Ski-out
Microwave, oven, stovetop, dishwasher

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)
"The host is so helpful and responsive. The location is excellent for access to Mount Snow, you can walk right to the main lodge. I definitely recommend staying here for a ski weekend!"
United States
Jillian A.
NEW Ski in/out condo with Mt views, hot tub, porch, gym & wifi!
Outdoor dining

Ski in Ski out Condo at Seasons on Mount Snow Hosted by Dean and Tina

Ski in Ski out Condo at Seasons on Mount Snow Hosted by Dean and Tina
Dover
10.0 out of 10, Exceptional, (53 reviews)
"Comfortable condo that had everything we needed for our ski vacation. I loved the decor!"
United States
Elizabeth H.
Ski in Ski out Condo at Seasons on Mount Snow Hosted by Dean and Tina
Smart TV, fireplace

Charming 1-bedroom condo in delightful Dover

Charming 1-bedroom condo in delightful Dover
Dover
9.4 out of 10, Exceptional, (10 reviews)
"Great little place! Bed was super comfy and heated bathroom floor was really nice!"
United States
Michelle T.
Charming 1-bedroom condo in delightful Dover
Indoor pool, a heated pool

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

Condo < 1mi. from Mt. Snow / Free Shuttle
West Dover
9.8 out of 10, Exceptional, (15 reviews)
"Ron has a great condo, very well kept unbelievably convenient to the mountain and great communication from the host. Would definitely stay again."
United States
Adam F.
Condo < 1mi. from Mt. Snow / Free Shuttle
Outdoor pool, a heated pool

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 location, and comfortable for the whole family. Everyone in the enjoyed the open living room and dining room, plus the privacy of their own bedroom space. "
United States
Ania H.
The price is AEDĀ 1,102
AEDĀ 1,995 total
includes taxes & fees
29 Jun - 30 Jun
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Indoor pool, a heated pool

Perfect for family getaway, across from Mount Snow Mountain- Sleeps up to 12!

Perfect for family getaway, across from Mount Snow Mountain- Sleeps up to 12!
Dover
9.4 out of 10, Exceptional, (11 reviews)
"Great location. Plenty of room. And clean. Had a blast. "
United States
Gregory L.
Perfect for family getaway, across from Mount Snow Mountain- Sleeps up to 12!
Pool

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!
Interior

3 bedroom Chic condo - Community pool and tennis - 1 Mile to Mount Snow

3 bedroom Chic condo - Community pool and tennis - 1 Mile to Mount Snow
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.
3 bedroom Chic condo - Community pool and tennis - 1 Mile to Mount Snow
Interior

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)
"We loved the fireplace and the proximity to the resort"
United States
Micah P.
Cozy 1-bedroom condo in Dover, VT steps away from Mount Snow
Interior

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)
"Host was great and gave all of the information that we needed well in advance. Condo was very nice and amenities were fantastic. "
United States
Jason G.
Seasons on Mount Snow | Walk Out / Ski Home!
Interior

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!
TV

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!
TV, fireplace

Par Paradise | On Haystack Golf Course w/Fireplace

Par Paradise | On Haystack Golf Course w/Fireplace
Wilmington
10.0 out of 10, Exceptional, (3 reviews)
"We had a great stay! The instructions from the host were very easy to follow. The house is a short drive to Mt. Snow. The house was well stocked with items, making our stay a breeze and enjoyable. The beds were also very comfortable. "
United States
Jamie M.
Par Paradise | On Haystack Golf Course w/Fireplace
TV, fireplace

Snow Tree Lodge @ Base of Mount Snow w/ Fireplace!

Snow Tree Lodge @ Base of Mount Snow w/ Fireplace!
Dover
9.8 out of 10, Exceptional, (11 reviews)
"Great location close to the slopes"
United States
John T.
Snow Tree Lodge @ Base of Mount Snow w/ Fireplace!
TV, fireplace, DVD player, books

Ski-In/Ski-Out Magic Mountain Condo w/ Deck!

Ski-In/Ski-Out Magic Mountain Condo w/ Deck!
Londonderry
10.0 out of 10, Exceptional, (2 reviews)
"Cozy condo, great views and the Black Line pub had great atmosphere and food."
United States
Teresa P.
Ski-In/Ski-Out Magic Mountain Condo w/ Deck!
Property grounds

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
Exterior

Walk to Mt Snow: Cozy West Dover Condo

Walk to Mt Snow: Cozy West Dover Condo
West Dover
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, great communication and was super easy to deal with, looking forward to staying again"
United States
joseph g.
Walk to Mt Snow: Cozy West Dover Condo
Interior

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
TV, fireplace

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!
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

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

8/10 Good
"Really helpful staff. Fresh cooked breakfast. Spotless property. Comfortable bed. Large room."
Katherine 1-night trip
Posted less than an hour ago
Keene Elm City Hotel, an Ascend Collection Hotel