Cheshire County Vacations & Trips from $230
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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.
Hideaway Inn Mt.Sunapee
Price was $293, price is now $230 per person
$230
per person
Jan 13 - Jan 15
found 1 day ago
Roundtrip flight included
New York (JFK) to Manchester (MHT)
9.4/10 Exceptional! (38 reviews)
The room was spotless. The Innkeeper, Josh, was extremely helpful and was very apologetic about the noise from the adjoining room.
A screaming 2 yr old and a barking dog were in the adjoining room. Sound transmitted through the adjoining room door. I would not accept Room 206 again for this reason.
Reviewed on Nov 29, 2025
Latchis Hotel
Price was $426, price is now $326 per person
$326
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Springfield (VSF)
8.4/10 Very Good! (822 reviews)
Great place. Historic—not for people who want fancy but clean with comfortable beds, very walkable to everything. Loved it!
Reviewed on Nov 26, 2025
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 refundable
$109 nightly
The price is $118 total per night from Dec 28 to Dec 29
$118 total
Dec 28 - Dec 29
Total with taxes and fees
8.4/10 Very Good! (957 reviews)
Over all a good stay. The pool window as left open over night so it as very cool in the pool area the next morning. Suggest staff check for that after the pool closes at 10 each night. Thanks
Reviewed on Dec 2, 2025
Hampton Inn & Suites Keene
126 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $160 total per night from Dec 23 to Dec 24
$160 total
Dec 23 - Dec 24
Total with taxes and fees
8.8/10 Excellent! (351 reviews)
Yes the room was spotless. The towels could have been newer and larger and softer. We were not impressed with the breakfast even though there was a variety of options. And we understand the issue with cooking for many and not knowing the favorite choice, but the eggs, and quiche, and sausages were ...
Reviewed on Nov 29, 2025
Best Western Plus Keene Hotel
401 Winchester St Keene NH
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $151 total per night from Dec 7 to Dec 8
$151 total
Dec 7 - Dec 8
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
Staff was accommodating. Got a Free upgrade to my room
Reviewed on Nov 25, 2025
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.