Cheshire County Vacations & Trips from $275
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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.
Christmas Farm Inn and Spa
$275
per person
Nov 19 - Nov 22
found 22 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Manchester (MHT)
8.8/10 Excellent! (985 reviews)
We had a fantastic time during our stay.If you love Christmas or any other holiday, you will enjoy your time here! Can’t wait to come back. Thank you!
Reviewed on Oct 16, 2026
Kearsarge Inn
North Conway Village
$1,473
per person
Dec 23 - Jan 2
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Manchester (MHT)
9.8/10 Exceptional! (1,006 reviews)
We stepped into room 16 from a cold and rainy New England October afternoon and instantly felt at home. The room was clean, well appointed and warm. Over the next two nights we really liked this hotel and its setting in the heart of North Conway. Perhaps the bed could have been bigger but it was very comfy. Overall a strong recommendation for this place.
Reviewed on Oct 15, 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
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
8.4/10 Very Good! (1,003 reviews)
"nice pool"
Reviewed on Oct 17, 2026
Days Inn by Wyndham Keene NH
3 Ash Brook Road Keene NH
Fully refundableReserve now, pay when you stay
$93 nightly
$101 total
Oct 25 - Oct 26
Total with taxes and fees
7/10 Good! (1,002 reviews)
"I arrived late and exhausted. Young man at front counter was friendly and efficient. Carpet in hallway slightly warn. Room and bath very clean, no complaints. Bed was large and soft. I slept well. Parking lot safe and quiet. Free breakfast was… nothing special. Other businesses close by. Would definitely ..."
Reviewed on Oct 17, 2026
Keene Elm City Hotel, an Ascend Collection Hotel
175 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
$127 nightly
$138 total
Oct 25 - Oct 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.
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.
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.
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.
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.
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.
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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