Top Resorts in Cheshire County in 2026

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Our top choices for Cheshire County resorts

A water play area with children and adults.

1. Great Wolf Lodge Boston / Fitchburg, MA

Fitchburg

michael

5.416.651 ₫ total

includes taxes & fees

14 Oct - 15 Oct

A red building with a stone fire pit and outdoor seating.

2. Grand Summit Resort, A Vail Resorts Property

West Dover

Eben

4.653.301 ₫ total

includes taxes & fees

11 Nov - 12 Nov

A stone-clad building entrance with a covered patio and benches.

3. Mountain Edge Suites at Sunapee, an Ascend Collection Hotel

Newbury

Jen

5.026.102 ₫ total

includes taxes & fees

11 Nov - 12 Nov

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Top Cheshire County Hotel Reviews

Pointe at Castle Hill Resort

10/10 Excellent

"My sister and I needed a very last minute place to stay after our VRBO rental was not what we thought. The ladies at the front desk were really nice and very help. The beds and pillows were very comfortable and the room was very clean. The only issue is the area, it’s a bit of a drive if you want to shop however, one minute up the road is Murdoch’s restaurant and they had delicious food. We ate there twice. Just make sure to make a reservation. All in all it was a nice stay and we definitely suggest staying there."

Great Wolf Lodge Boston / Fitchburg, MA

10/10 Excellent

"The facility is great. I was able to get handicapped parking this time which is always a plus. The room was great, very clean. The waterpark was fun. The food was delicious. Specifically at the Fireside restaurant. The staff at the restaurant was fast and efficient. We definitely will be going back."

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent

"It is a charming inn with very lovely staff & family attending the guests. I highly recommend staying here if you appreciate history & charm! The building was built in 1788 I believe they said. We stayed inPikes Suite and were comfortable and happy. Yes, the beautiful old floors creak, but it’s all part of the charm of this lovely still family owned hideaway! I hope to return again!"

The White House Inn

8/10 Good

"It was a beautiful property with friendly staff. The room was very pretty but the mattress was very soft and the pillows were tiny. We loved the fireplace as well but when you lay down you can't see the fire and it was uncomfortable to sit at the end of the bed. A cozy area should be in front of the fire place. However I would still stay there again."

Motel 6 Leominster, MA

10/10 Excellent

"There are few things to be concerned about. You can here your next door neighbor when they speaking loud and there were some cigarettes smoke in the room eventhough we had a non smoking room. It wasn't strong. Overall, the property surprised me how clean it is and how white the sheets and towels are. Very convenient locati I need to shopping area and to the soccer tournament location."

Find out more about Cheshire County

Cheshire County Resorts information

Number of reviews	1,772
Accommodation	3 Resorts
Lowest Price	4.653.301 ₫
Highest Price	5.416.651 ₫

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Check prices for these dates

Our top choices for Cheshire County resorts

1. Great Wolf Lodge Boston / Fitchburg, MA

2. Grand Summit Resort, A Vail Resorts Property

3. Mountain Edge Suites at Sunapee, an Ascend Collection Hotel

Top Cheshire County Hotel Reviews

Pointe at Castle Hill Resort

Grand Summit Resort, A Vail Resorts Property

Great Wolf Lodge Boston / Fitchburg, MA

Keene Elm City Hotel, an Ascend Collection Hotel

Fairfield Inn & Suites by Marriott Keene Downtown

The White House Inn

Motel 6 Leominster, MA

Days Inn by Wyndham Keene NH

Hideaway Inn Mt. Snow

Find out more about Cheshire County

Cheshire County Resorts information