
Cheshire County Vacations & Trips from $515
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Your Cheshire County Vacation
Book a vacation 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 vacation. From flights and hotels, to activities and more, we know how to curate a travel experience like no other.
Top destinations in Cheshire County

Keene
The Latest Cheshire County Vacation Packages

Exeter Inn
Reviewed on Jun 16, 2026

The Lake Estate on Winnisquam
Reviewed on Jun 18, 2026

The Centennial
Reviewed on Jun 16, 2026

Mountain View Grand Resort & Spa
Reviewed on Jun 1, 2026

Moultonborough Inn
Reviewed on Jun 18, 2026
Find the Best Cheshire County Vacation Packages
Cheshire County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Manchester-Boston Regional Airport (MHT) |
Top Sights | Monadnock State Park, Pitcher Mountain and Friendly Farm |
Cheshire County Hotel Deals

Days Inn by Wyndham Keene NH
"Our room smelled like mold, likely because there was a lot of rotting and what looked like mold in the bathroom. The carpets themselves needed to be replaced as they had a musty smell likely from too much moisture or spills. This hotel really needs a lot of work to make it feel inviting. Any fixes ..."
Reviewed on Jun 16, 2026

Best Western Plus Keene Hotel
"Room was clean and very quiet for me. Will be staying again next time I am here on business."
Reviewed on Jun 19, 2026

Keene Elm City Hotel, an Ascend Collection Hotel
"The safety latch on my room door was broken. The staff was very helpful and found a different room for me and got a cart and offered to help. The new room had a dried coffee spill near the fridge and the body wash in the shower was empty or broken- minor inconvenience. Overall a nice stay at a great ..."
Reviewed on Jun 17, 2026
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