Cheshire County Vacations & Trips from $561
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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.
Sinclair Inn Bed and Breakfast
$1,166
per person
Oct 26 - Oct 29
found 12 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Springfield (VSF)
10/10 Exceptional! (123 reviews)
Such a charming place with warm and friendly hosts. Room was comfortable and had everything we needed. Breakfast was delightful and delicious, serving locally sourced ingredients. Will definitely stay again. 10/10 recommend.
Reviewed on Sep 18, 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
$134 nightly
$145 total
Sep 21 - Sep 22
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
Sep 21 - Sep 22
Total with taxes and fees
8.4/10 Very Good! (1,004 reviews)
"Everything was excellent and will definitely come back"
Reviewed on Sep 20, 2026
Days Inn by Wyndham Keene NH
3 Ash Brook Road Keene NH
Fully refundableReserve now, pay when you stay
$94 nightly
$102 total
Sep 22 - Sep 23
Total with taxes and fees
7/10 Good! (1,001 reviews)
"Location is good. Everything you could need is close by. Parking is great. Breakfast could use a little attention. Two types of sausage, only boiled eggs which were gone. Room was comfortable. The only real problem is the room had no hot water no matter how long it was running. Definitely needs to ..."
Reviewed on Sep 19, 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 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.
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.
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.
Friendly Farm
Enjoy a stop at Friendly Farm, an entertaining place to visit in Dublin. Discover the coffeehouses and its festivals while you're in the area.
What to do in Cheshire County
Mindful Forest Escape: Rebalance, reflect and connect
$95
per adult
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
