Cheshire County Vacations & Trips from $619
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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
Jaffrey
West Chesterfield
Walpole
Chesterfield
Stoddard
The Latest Cheshire County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Stonybrook Motel & Lodge
$619
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Manchester (MHT)
7.6/10 Good! (1,001 reviews)
We were not happy with the rooms as they were so dated. Paneling on the wall with holes of past thing’s been hung over the years . The vanity must have been broke at some point because of the huge crack and was glued back together. Also the indoor pool wasn’t working and needed to be fixed, We will never go there again , it’s too bad it could be a really nice place ,
Reviewed on Aug 15, 2026
The Village of Loon Mountain Fixed Rooms
$1,143
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Manchester (MHT)
8.6/10 Excellent! (59 reviews)
Nice front desk assistance. Property was good not great. A little overpriced but a fine stay.
Reviewed on Aug 15, 2026
The Shire Woodstock
$1,830
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
8.8/10 Excellent! (969 reviews)
The staff was helpful. The room was clean. There was some 1st floor construction that it would have been nice to know about prior to check in. It didn’t impact our stay but made things a bit dusty. Very conveniently located to downtown area.
Reviewed on Aug 13, 2026
The Inn at Thorn Hill & Spa
$1,754
per person
Oct 1 - Oct 4
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Manchester (MHT)
9.8/10 Exceptional! (1,001 reviews)
We have been going here for 6 years. This last we were 10 minutes early to check in they said our room wasn’t ready and that they would come get us when it was ready. Were getting checked in my husband and I went to the desk and the lady said oh there you are when the previous lady said she would come get us. Normally we are greeted with Prosecco and this time we weren’t offered it kind of a disappointment other than that it was good.
Reviewed on Aug 15, 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
$114 nightly
$124 total
Sep 1 - Sep 2
Total with taxes and fees
Days Inn by Wyndham Keene NH
3 Ash Brook Road Keene NH
Fully refundableReserve now, pay when you stay
$93 nightly
$101 total
Aug 23 - Aug 24
Total with taxes and fees
7/10 Good! (1,002 reviews)
"Dirty & gross. Not recommended."
Reviewed on Aug 14, 2026
Best Western Plus Keene Hotel
401 Winchester St Keene NH
Fully refundableReserve now, pay when you stay
$149 nightly
$162 total
Aug 17 - Aug 18
Total with taxes and fees
8.4/10 Very Good! (1,003 reviews)
"The room was clean and quiet and the air conditioning worked well. There is a full breakfast and a nice work out room. This is the second time I have stayed at this Best Western, and I will stay there again the next time I am in Keane NH."
Reviewed on Aug 13, 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
Monadnock State Park
9.6/10 (45 reviews)
You can take time to visit Monadnock State Park during your travels to Jaffrey. Discover the coffeehouses and its festivals while you're in the area.
Historic Main Street
9.2/10 (107 reviews)
Find out about the history of Keene when you spend time at Historic Main Street. Visit the area's shops, or simply enjoy its restaurants.
Photo by Heather Beaudry
Madame Sherri Forest
8.0/10 (4 reviews)
Explore the great outdoors at Madame Sherri Forest, a lovely green space in West Chesterfield. Wander around the forests or experience the area's entertainment venues.
Photo by Ed Gaffny
Cathedral of the Pines
10.0/10 (2 reviews)
You can spend an afternoon browsing the exhibits at Cathedral of the Pines during your travels in Rindge. Take in the musical theater and mountain views in the area.
Spofford Lake
8.8/10 (38 reviews)
Commune with nature and explore the great outdoors at Spofford Lake during your travels in Spofford. Discover the area's entertainment venues, or seek out its ski slopes.
Colonial Theatre
8.4/10 (36 reviews)
You can make plans for a show at Colonial Theatre during your trip to Keene. Experience the festivals or attend a sporting event in this family-friendly area.
Stonewall Farm
7.8/10 (20 reviews)
Explore the campus of Stonewall Farm, during your travels in Keene. Stroll along the riverfront or experience the area's festivals.
Sunset Beach
Why not spend a lazy afternoon at Sunset Beach during your trip to Harrisville?
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.
