Cheshire County Vacations & Trips from $621
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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.
Attitash Mountain Village
$621
per person
Sep 29 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Manchester (MHT)
8.6/10 Excellent! (568 reviews)
Very nice condo. Must be very popular in the winter. Spacious room with a Murphy bed. Slept very good. Restaurant on side was not open but very friendly staff directed us to thing to see in the neighborhood and places to eat
Reviewed on Aug 20, 2026
Wildcat Inn & Tavern
$1,076
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Manchester (MHT)
9/10 Wonderful! (331 reviews)
We had a great experience at this historic Inn. Our room was meticulously clean, and comfortable with good amenities. Check in was seemless and staff were friendly and helpful.
Reviewed on Aug 21, 2026
Extended Stay America Suites - Nashua - Merrimack
$901
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Manchester (MHT)
7.2/10 Good! (955 reviews)
As far as we are concerned this hotel should not even be on the Expedia website! when we checked in we were told that breakfast was a grab n go bag, also had to bring our trash out. Carpet on the floor we were on was dirty. Upon entering our room the fake leather couch was peeling, couldn't tell if the floor was clean. Went right back downstairs and checked out! Girl at the desk said we would not be charged and we would receive an email. Still waiting on an email and room was charged. If you look at the pictures on Expedia and what we actually walked into it's like night and day.
I wouldn't recommend this hotel to my worst enemy.
Reviewed on Aug 24, 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
8.6/10 Excellent! (1,013 reviews)
"The room was clean and stocked with the amenities expected, including a fridge and a microwave. Staff was very helpful and kind on check in. Breakfast was a standard continental. Not the best food but there was an array of options."
Reviewed on Aug 24, 2026
Days Inn by Wyndham Keene NH
3 Ash Brook Road Keene NH
Fully refundableReserve now, pay when you stay
$97 nightly
$105 total
Sep 16 - Sep 17
Total with taxes and fees
7/10 Good! (1,004 reviews)
"The room smelled of mold and urine and the floor carpet felt wet. Would not recommend this property."
Reviewed on Aug 22, 2026
Best Western Plus Keene Hotel
401 Winchester St Keene NH
Fully refundableReserve now, pay when you stay
$149 nightly
$162 total
Aug 25 - Aug 26
Total with taxes and fees
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.
Rindge Town Hall
Rindge Town Hall is just one of the places to see in Rindge, so why not enjoy the other things to explore during your travels? While you're in the area, stroll along the lakeside.
What to do in Cheshire County
Mindful Forest Escape: Rebalance, reflect and connect
$95
per adult
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