Cheshire County Vacations & Trips from $613
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.
The Villager Motel
$613
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Manchester (MHT)
8.2/10 Very Good! (447 reviews)
The room was very good size and had plenty of room, much larger than most I've been to. Its a bit run down but has its own charm kind of a throw back feeling, It was very close to almost everything in the white mountains area.
Reviewed on Aug 10, 2026
The Village of Loon Mountain Fixed Rooms
$1,082
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)
Property is dated but has everything you need and nice walkable trails.
Reviewed on Aug 11, 2026
Cranmore Mountain Lodge Bed & Breakfast
Kearsarge
$1,225
per person
Oct 4 - Oct 9
found 7 hours ago
Roundtrip non-stop flight included
Fort Myers (RSW) to Manchester (MHT)
8.8/10 Excellent! (259 reviews)
Krista was an excellent host! The breakfast was delicious. We loved dipping into the creek in back and enjoying the jacuzzi after a long couple days hiking. Close to downtown but felt removed from the chaos. Will definitely stay again!
Reviewed on Aug 2, 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
$92 nightly
$100 total
Aug 23 - Aug 24
Total with taxes and fees
Best Western Plus Keene Hotel
401 Winchester St Keene NH
Fully refundableReserve now, pay when you stay
$149 nightly
$162 total
Aug 13 - Aug 14
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.
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
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.
