Cheshire County Vacations & Trips from $531
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.
Vikings Villages Resort
$740
per person
Nov 21 - Nov 24
found 20 hours ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Springfield (VSF)
10/10 Exceptional! (228 reviews)
Absolutely beautiful, highly recommend you staying here. Gave great local options of visiting such as the green covered bridge, local food venues. I would say stop at a grocery store and you can make dinner there. We did go to the local co op in Brattleboro. Hands down the ax throwing was a fan favorite.
Reviewed on Aug 29, 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
$128 nightly
$139 total
Aug 31 - Sep 1
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
"Has everything necessary for a two night stay."
Reviewed on Aug 28, 2026
Best Western Plus Keene Hotel
401 Winchester St Keene NH
Fully refundableReserve now, pay when you stay
$149 nightly
$162 total
Aug 31 - Sep 1
Total with taxes and fees
8.4/10 Very Good! (1,002 reviews)
"Mattress was hard and some door locks for key cards didn't work."
Reviewed on Aug 26, 2026
Days Inn by Wyndham Keene NH
3 Ash Brook Road Keene NH
Fully refundableReserve now, pay when you stay
$98 nightly
$106 total
Sep 14 - Sep 15
Total with taxes and fees
7/10 Good! (1,002 reviews)
"The staff was helpful. Parking was easy. It was an ok stay. I would stay there again for the price."
Reviewed on Aug 28, 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.
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
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.
