Cheshire County Vacations & Trips from $570
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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.
Riverhouse by Weekender (Formerly Jack Daniels Inn)
$1,148
per person
Dec 25 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Manchester (MHT)
9.2/10 Wonderful! (479 reviews)
Nobody is at the reception if you arrive after 6 pm.
You cannot open the window in the room anymore.
Reviewed on Oct 11, 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
3 Ash Brook Road Keene NH
Fully refundableReserve now, pay when you stay
$93 nightly
$101 total
Oct 28 - Oct 29
Total with taxes and fees
Best Western Plus Keene Hotel
401 Winchester St Keene NH
Fully refundableReserve now, pay when you stay
$142 nightly
$154 total
Nov 1 - Nov 2
Total with taxes and fees
8.2/10 Very Good! (1,003 reviews)
"My room was not "made up" the entire day. When I called the front desk the clerk said that she would send someone up "now" to do the job. No one showed up and I received no service that day."
Reviewed on Oct 25, 2026
Keene Elm City Hotel, an Ascend Collection Hotel
175 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
$130 nightly
$141 total
Oct 29 - Oct 30
Total with taxes and fees
8.6/10 Excellent! (1,006 reviews)
"You can hear everything in hallway and above you. Literally people walking above which isn’t bad except for the late and early morning. The hot water was room temperature at best in shower but scolding got in sink. The front desk and housekeeping were super nice and helpful."
Reviewed on Oct 25, 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 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.
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.
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.
Shattuck Golf Course
9.0/10 (4 reviews)
Enjoy a round of golf in Jaffrey at Shattuck Golf Course. Take in the musical theater and mountain views in the area.
Brentwood Golf Course
8.8/10 (13 reviews)
Enjoy a round of golf in Keene at Brentwood Golf Course. Discover the coffeehouses and festivals in this family-friendly area.
Laurel Lake
8.0/10 (1 review)
Commune with nature and explore the great outdoors at Laurel Lake during your travels in Fitzwilliam. Amble around the area's parks or visit its shops.
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.