Cheshire County Vacations & Trips from $621
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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
$808
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
Cold Spring Plymouth Resort
$680
per person
Oct 22 - Oct 28
found 8 hours ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Manchester (MHT)
9.2/10 Wonderful! (243 reviews)
Pratique et vaste appartement. Vieillot mais confortable. Les employés sont très gentils.
Reviewed on Aug 17, 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! (1,007 reviews)
"Nice stay and good location"
Reviewed on Aug 18, 2026
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! (1,003 reviews)
"It was a very pleasant stay"
Reviewed on Aug 16, 2026
Best Western Plus Keene Hotel
401 Winchester St Keene NH
Fully refundableReserve now, pay when you stay
$149 nightly
$162 total
Aug 19 - Aug 20
Total with taxes and fees
8.4/10 Very Good! (1,005 reviews)
"Rooms were clean and comfortable. Breakfast was good. Wonderful to be able to sit outside in common area and if on first floor right outside your room. The restaurant attached was great."
Reviewed on Aug 17, 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.
What to do in Cheshire County
Mindful Forest Escape: Rebalance, reflect and connect
$95
per adult
Explore a world of travel with Expedia
Other vacations you might like
- Top cities in Cheshire County
- Vacations and getaways similar to Cheshire County
- Best vacation destinations by month
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
