Top Cheshire County Hotels: 2026 Best Hotels in Cheshire County

Top Cities in Cheshire County

A street with a clock, red brick buildings, and autumn leaves.

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Cheshire County hotels

A hotel reception area with two counters labeled 'Choice Hotels' and 'Ascend Hotel Collection'. There are vending machines and a refrigerator with beverages.

1. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

Lisa

$133 nightly

Nov 16 - Nov 17

Total with taxes and fees

A bar area with a high ceiling and stained glass windows, bar stools, and a checkered floor.

2. Best Western Plus Keene Hotel

Keene

Ruddy

$142 nightly

Nov 15 - Nov 16

Total with taxes and fees

A hotel room with two beds, a TV, a desk, and a window with curtains.

3. Days Inn by Wyndham Keene NH

Keene

Latisha

$95 nightly

Nov 15 - Nov 16

Total with taxes and fees

A dock extending into a lake with a grassy area in the foreground and trees in the background.

4. Riverside Hotel, an Ascend Collection Hotel

West Chesterfield

Steve

$145 nightly

Dec 6 - Dec 7

Total with taxes and fees

A modern dining area with a central seating area, a kitchen in the background, and large windows providing natural light.

5. Hampton Inn & Suites Keene

Keene

Dayle

$157 nightly

Dec 5 - Dec 6

Total with taxes and fees

6. Fairfield Inn & Suites by Marriott Keene Downtown

Keene

Christopher

$194 nightly

Nov 18 - Nov 19

Total with taxes and fees

A historic brick building with a porch and a sign reading "Burrell House."

7. The Burrell House

Keene

Carol

$135 nightly

Dec 13 - Dec 14

Total with taxes and fees

A bar area with a dark tiled backsplash, multiple stools, and a variety of bottles and glasses on the counter.

8. Courtyard by Marriott Keene Downtown

Keene

Madeline

$169 nightly

Nov 29 - Nov 30

Total with taxes and fees

A two-story building with a white facade and green shutters, a covered front porch, and a sign for the "M" Inn.

9. Monadnock Inn

Jaffrey

Jim

$122 nightly

Nov 15 - Nov 16

Total with taxes and fees

A wooden table set with plates, cutlery, and a folded napkin.

10. The Carriage Barn Inn

Keene

Richard

$138 nightly

Nov 30 - Dec 1

Total with taxes and fees

A lakeside park with picnic tables and a concrete walkway.

11. 2 private mountain RV pads for rent. Full hook ups

Winchester

A large, two-story house with a snow-covered driveway and surrounding trees.

12. Chesterfield Inn

West Chesterfield

Wayne

$301 nightly

Nov 15 - Nov 16

Total with taxes and fees

A spacious room with large windows, wicker furniture, and a sign reading "Valley Farms".

13. Inn at Valley Farms

Walpole

Ronald

A yurt with a deck, two Adirondack chairs, and a stone fire pit in a forest setting.

14. Yurt Oasis in the woods of Hinsdale, NH

Hinsdale

Ian C.

$138 nightly

Nov 18 - Nov 19

Total with taxes and fees

A wooden cabin with a red roof, a balcony, and a staircase leading to the upper level.

15. Handcrafted NH Treehouse · 2hr Boston · Fire Pit, Lake, Stargazing

Munsonville

Sara H.

$296 nightly

Nov 15 - Nov 16

Total with taxes and fees

A yurt interior with a bed, wooden lattice walls, and a door leading to an outdoor balcony.

16. RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

Hinsdale

Adrienne

$137 nightly

Nov 17 - Nov 18

Total with taxes and fees

A lake surrounded by trees, with a wooden deck leading to a white railing.

17. "Pondlife" - Waterfront home in a peaceful, wooded setting.

Fitzwilliam

Margaret

$260 nightly

Nov 13 - Nov 14

Total with taxes and fees

A house by a lake with a dock and a boat.

18. Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Rindge

clifford t.

$253 nightly

Nov 15 - Nov 16

Total with taxes and fees

An outdoor deck with a table and chairs, a barbecue grill, and a large umbrella.

19. Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.

Fitzwilliam

Patrick R.

A rustic cabin with a dirt path leading to it, surrounded by leafless trees.

20. Cozy Updated Log Cabin with Mountain Views close to Monadnock

Fitzwilliam

SAJU C.

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 Cheshire County Hotel Reviews

Doubletree by Hilton Hotel Leominster

10/10 Excellent

"Staff was very courteous and helpful. Room was very nice, bed was very comfortable. Hotel was quiet. Bar had our MNF game on; NE Clam Chowder, House Salad, Beer and a Glass of wine came to $50 with tip. Only negative is our bathroom had handicap amenities; the bathtub didn’t seem to be handicap friendly. Tall walls and narrow space; water would flow off of the seat onto the floor. We would stay here again."

Hideaway Inn Mt.Sunapee

10/10 Excellent

"As someone who travels up to New Hampshire frequently, finding a reliable and welcoming place to stay is essential, and the Hideaway Inn at Mt Sunapee absolutely delivered. I stayed here with my two sons, and we had an incredible time. Our room was comfortable and flawlessly clean, and the whole facility feels like a super retro cabin. The property strikes the perfect balance, as it is incredibly family-oriented with endless entertainment for kids, yet maintains a relaxed, well-kept atmosphere that is genuinely great for adults trying to unwind. There was never a dull moment during our stay. The boys spent hours swimming and smiling in the indoor pool, challenging each other to ping pong and chess, and trying to beat the high score on the classic Pac-Man arcade game. The dedicated play area, complete with a pretend ice cream stand and the adorable Hideaway Inns teepee, was a massive hit. It is a fantastic, joyful retreat with something for everyone. We will definitely be back on our next trip north!"

Riverside Hotel, an Ascend Collection Hotel

10/10 Excellent

"We loved the size of the room and bathroom. Well-maintained property, very friendly staff. They have an under-utilized dining room on the ground floor with nice views of the river but no offered breakfast, just coffee. Some type of offered breakfast would make this a five star review."

Grand Summit Resort, A Vail Resorts Property

8/10 Good

"The room and atmosphere of the hotel was amazing. But we came on the off season and a lot of things were closed. The restaurant and spa were closed but also a bunch of the restaurants in the area were closed on a Saturday night for dinner. But again this was an off season so I get it."

Search Hotels in Cheshire County

Upfront pricing

Treat yourself

Be picky

Top Cities in Cheshire County

Keene

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Cheshire County hotels

1. Keene Elm City Hotel, an Ascend Collection Hotel

2. Best Western Plus Keene Hotel

3. Days Inn by Wyndham Keene NH

4. Riverside Hotel, an Ascend Collection Hotel

5. Hampton Inn & Suites Keene

6. Fairfield Inn & Suites by Marriott Keene Downtown

7. The Burrell House

8. Courtyard by Marriott Keene Downtown

9. Monadnock Inn

10. The Carriage Barn Inn

11. 2 private mountain RV pads for rent. Full hook ups

12. Chesterfield Inn

13. Inn at Valley Farms

14. Yurt Oasis in the woods of Hinsdale, NH

15. Handcrafted NH Treehouse · 2hr Boston · Fire Pit, Lake, Stargazing

16. RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

17. "Pondlife" - Waterfront home in a peaceful, wooded setting.

18. Cabin & Sauna on Lake Monomonac near Mt. Monadnock

19. Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.

20. Cozy Updated Log Cabin with Mountain Views close to Monadnock

Top Cheshire County Hotel Reviews

Doubletree by Hilton Hotel Leominster

Explore a world of travel with Expedia

Go further with the Expedia app