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

The Latest Cheshire County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Exeter Inn
The Lake Estate on Winnisquam
The Centennial
Mountain View Grand Resort & Spa
Moultonborough Inn

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

Days Inn by Wyndham Keene NH

2 out of 5
3 Ash Brook Road Keene NH
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $94 total per night from Jun 29 to Jun 30
$94 total
Jun 29 - Jun 30
Total with taxes and fees
7/10 Good! (1,000 reviews)
"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

Days Inn by Wyndham Keene NH
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
$119 nightly
The price is $129 total per night from Jun 21 to Jun 22
$129 total
Jun 21 - Jun 22
Total with taxes and fees
8.4/10 Very Good! (1,004 reviews)
"Room was clean and very quiet for me. Will be staying again next time I am here on business."

Reviewed on Jun 19, 2026

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 refundableReserve now, pay when you stay
$109 nightly
The price is $118 total per night from Jun 21 to Jun 22
$118 total
Jun 21 - Jun 22
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
"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

Keene Elm City 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.