Cheshire County Vacations & Trips from $492
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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
Price found within the past 48 hours. Click for updated prices.
The Village of Loon Mountain Fixed Rooms
Save 100% on your flight
Price was $896, price is now $578 per person
$578
per person
Sep 3 - Sep 7
found 20 hours ago
Roundtrip flight included
Baltimore (BWI) to Manchester (MHT)
8.8/10 Excellent! (56 reviews)
There was not adequate parking. The indoor and outdoor pools were freezing with the exception of one, but that one was loaded with children.
The paint was peeling everywhere. There were much needed repairs visible in the room, as well as in the pool area. The hotel only allowed one pool towel. The room had a fireplace that did not work and a toaster that also did not work.
We would never recommend this place.
Reviewed on Jul 22, 2026
Cold Spring Plymouth Resort
Save 100% on your flight
Price was $670, price is now $499 per person
$499
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Manchester (MHT)
9.2/10 Wonderful! (234 reviews)
Staff extremely friendly. Had issues with cable 2 nd night but they got back going quickly!!
Reviewed on Jul 26, 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
Keene Elm City Hotel, an Ascend Collection Hotel
175 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $140 total per night from Jul 30 to Jul 31
$140 total
Jul 30 - Jul 31
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
"Great place"
Reviewed on Jul 29, 2026
Best Western Plus Keene Hotel
401 Winchester St Keene NH
$139 nightly
The price is $151 total per night from Jul 30 to Jul 31
$151 total
Jul 30 - Jul 31
Total with taxes and fees
8.4/10 Very Good! (1,000 reviews)
"The staff were all courteous and professional. The room was clean, housekeeping staff were friendly. The breakfast was amazing with so many choices of food. Lori was a prize of an employee running the breakfast room! Can’t think of any negatives at all."
Reviewed on Jul 27, 2026
Days Inn by Wyndham Keene NH
3 Ash Brook Road Keene NH
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $101 total per night from Aug 3 to Aug 4
$101 total
Aug 3 - Aug 4
Total with taxes and fees
7/10 Good! (1,008 reviews)
"The breakfast was bad. The coffee was undrinkable. There is a Panera across the street so that was a savior. This property is pretty run down, but the small gym was convenient and clean. The room is very outdated but it was sufficiently clean."
Reviewed on Jul 29, 2026
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.
Stay near popular Cheshire County attractions
What to do in Cheshire County
Mindful Forest Escape: Rebalance, reflect and connect
$95
per adult
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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.
