Top Condo Rentals in Cheshire County in 2026

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Top Cities in Cheshire County

A group of hikers on rocky terrain with dense forest in the background.

Our top choices for Cheshire County condo rentals

An indoor swimming pool with a wooden ceiling and skylights, surrounded by lounge chairs and a sign reading "SEASONS ON MONTLIT SNOW".

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

Dover

Dean W.

An outdoor patio area with Adirondack chairs, a stone fire pit, and a grill station.

2. Clean Ski in ski out condo located at Seasons on Mt. Snow.

Dover

Shayne

A modern kitchen with white cabinetry, a microwave, a toaster, and a dishwasher.

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

Dover

Mark A.

A calm lake with a wooden boat on the shore.

4. Cozy 3 bedroom condo 2.5 miles to Mount Snow

West Dover

Scott S.

SAR 1,102 total

includes taxes & fees

2 Nov - 3 Nov

A large indoor swimming pool with a wooden ceiling and large windows.

5. Mount snow ski on ski off at Seasons

Dover

Mark L.

A wooden sauna with benches and frosted glass panels.

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

Dover

Unspecified U.

A swimming pool with lounge chairs and umbrellas, surrounded by trees and stone walls.

7. Two-story townhome with forest/mountain view, gas fireplace, pool, gym & saunas

Proctorsville

Anonymous traveler

A well-maintained outdoor area with a paved walkway, a gazebo, and a stone fire pit.

8. Cozy ski-in/ski-out condo on Mount Snow w/fireplace

Dover

Robert H.

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Top Cheshire County Hotel Reviews

Keene Elm City Hotel, an Ascend Collection Hotel

8/10 Good

"Good location. Well appointed room. Clean, updated. Comp breakfast was okay. TV was outdated but WiFi was strong."

Hideaway Inn Mt.Sunapee

10/10 Excellent

"The Hideaway Inn at Mt. Sunapee is an absolute hidden gem! We loved the fun, unique rooms and the retro vibe that makes this place feel so special. It’s unlike your typical hotel and has so much character and charm. The pool was amazing, and the game room was incredible — there was so much to enjoy! We had such a great experience that we’re already planning a future trip specifically to stay here again. If you’re looking for a fun, unique, and memorable place to stay in New Hampshire, I couldn’t recommend The Hideaway Inn enough. We can’t wait to come back!"

Latchis Hotel

8/10 Good

"It’s located with restaurants within walking distance. It is well maintained for a historic hotel with probably about 15 steps in the lobby before you get to the elevator. It was noisy some nights due to being in the city and having residents living life. Staff was wonderful. Again location was great to see Buffalo—Niagara is 20 min away, Botanic Garden and Eternal Flame about the same. We enjoyed our stay."

Days Inn by Wyndham Keene NH

8/10 Good

"Clean comfortable room with a comfortable bed. I didn’t like the smell of whatever cleaning product they used, it was a bit bit strong let the kind you used to cover up something. Was this recently a smoking hotel? Also I missed an cycle in the fitness center, although the machines that were there seemed to work well. All in all it’s about what you would expect for a moderately priced hotel in New Hampshire during leaf peeper season."

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Top Cities in Cheshire County

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Our top choices for Cheshire County condo rentals

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

2. Clean Ski in ski out condo located at Seasons on Mt. Snow.

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

4. Cozy 3 bedroom condo 2.5 miles to Mount Snow

5. Mount snow ski on ski off at Seasons

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

7. Two-story townhome with forest/mountain view, gas fireplace, pool, gym & saunas

8. Cozy ski-in/ski-out condo on Mount Snow w/fireplace

9. 9 Mi to Wachusett Mtn! Family Base w/ Porch

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

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

12. Charming 2-bedroom ski in/ski out condo on Mt. Snow with fitness, pool, WiFi

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

14. Mountain view condo w/ fireplace, shared hot tub, pool, sauna, tennis & shuttle

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

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

17. The Slope Side Lodge, Ski off w/ Fireplace!

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

19. 1 Mile to Mount Snow - Moover Stop - 3 Bedroom Chic Condo

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

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Top Cheshire County Hotel Reviews

Keene Elm City Hotel, an Ascend Collection Hotel

The Colonial Hotel

Hideaway Inn Mt.Sunapee

Great Wolf Lodge Boston / Fitchburg, MA

Latchis Hotel

Riverside Hotel, an Ascend Collection Hotel

Days Inn by Wyndham Keene NH

Colonial Motel

Best Western Plus Keene Hotel