Cheshire County Holidays

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Your Cheshire County Holiday

Book a holiday package to Cheshire County and make travel planning easy. With all the logistics arranged before you leave, you can focus on enjoying every minute in this destination. With so much to see on a trip to Cheshire County, it can be tricky to know where to begin. Kick off your journey in Jaffrey at Laurel Lake and Friendly Farm — two popular attractions here. Another top city worth adding to your itinerary is Walpole. Be sure not to miss Vermont Country Store and Bellows Falls Opera House. Expedia is your one-stop shop when it comes to planning your Cheshire County holiday. From flights and hotels, to activities and more, we know how to curate a travel experience like no other.

Cheshire County Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Manchester-Boston Regional Airport (MHT)
Top Sights
Monadnock State Park, Friendly Farm and Pitcher Mountain

Our pick of the best Cheshire County Hotel Deals

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St, Keene, NH
Fully refundableReserve now, pay when you stay
The price is AU$247 per night from 2 Nov to 3 Nov
AU$247
2 Nov - 3 Nov
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
Checking in was a little confusing as I called Best Western before I booked through Expedia to see if I could get my AARP discount and he said yes. When I got there, they said no discount but were kind enough to apply the discount. Plus I booked a room with a balcony and sleep sofa and got a different ...

Reviewed on 27 Oct 2025

Best Western Plus Keene Hotel
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd, Keene, NH
Fully refundable
The price is AU$207 per night from 9 Nov to 10 Nov
AU$207
9 Nov - 10 Nov
includes taxes & fees
8.4/10 Very Good! (936 reviews)
Best value in New England! Staff is supportive and site is super clean. Decor is nice. Comfy beds. Subpar breakfast but who cares?! Free coffee, and the food is a bonus... and again, you can't beat the value!

Reviewed on 27 Oct 2025

Keene Elm City Hotel, an Ascend Collection Hotel
Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

2.5 out of 5
20 Riverside Drive, West Chesterfield, NH
Fully refundable
The price is AU$252 per night from 3 Nov to 4 Nov
AU$252
3 Nov - 4 Nov
includes taxes & fees
9.6/10 Exceptional! (621 reviews)
Perfect and peaceful! It surpassed my expectations. Would love to come back and stay again.

Reviewed on 26 Oct 2025

Riverside Hotel, an Ascend Collection Hotel
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.