Cheshire County Vacations & Trips from $353
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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.
InnSeason Resorts Pollard Brook
$353
per person
Dec 4 - Dec 7
found 11 hours ago
Roundtrip flight included
Baltimore (BWI) to Manchester (MHT)
9.6/10 Exceptional! (947 reviews)
Room was super clean and everything was better than expected. We will definitely be going back in the near future!
Reviewed on Sep 30, 2026
Vikings Villages Resort
$1,069
per person
Dec 8 - Dec 16
found 6 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
10/10 Exceptional! (239 reviews)
Very unique spot. We planned this last minute getaway after another trip was canceled. The cabins are so cute. awe did not partake in the activities but wish we had another day. We did see sheep. Quiet, cute, different.
Reviewed on Sep 30, 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
$120 nightly
$130 total
Nov 1 - Nov 2
Total with taxes and fees
Best Western Plus Keene Hotel
401 Winchester St Keene NH
Fully refundableReserve now, pay when you stay
$139 nightly
$151 total
Oct 25 - Oct 26
Total with taxes and fees
Days Inn by Wyndham Keene NH
3 Ash Brook Road Keene NH
Fully refundableReserve now, pay when you stay
$91 nightly
$99 total
Oct 27 - Oct 28
Total with taxes and fees
7/10 Good! (1,007 reviews)
"I booked at the last minute for an unplanned visit and was pleasantly surprised by the accommodations for the price."
Reviewed on Sep 26, 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.
Cheshire Children's Museum
7.0/10 (15 reviews)
You can take time to visit Cheshire Children's Museum during your travels to Keene. While you're here, you can savor the top-notch restaurants.
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.
