Cheshire County Vacations & Trips from $530
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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.
The Village of Loon Mountain Fixed Rooms
$530
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Manchester (MHT)
8.6/10 Excellent! (65 reviews)
Staying here was one of our favorite memories from this last summer. Beautiful location/views, large outdoor/indoor pool, and LARGE accomodations. If you have a family, this is where you should stay to get enough space.
Reviewed on Sep 17, 2026
Vikings Villages Resort
$765
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Springfield (VSF)
10/10 Exceptional! (232 reviews)
Wonderful experience. Beautiful and unique. Deco was lovely. Very quiet place to relax and enjoy the stay. We enjoyed the scenery. Nice set up. Had a fireplace and we did not use it since there was no need to. Kitchen had all the amenities. We did not have to clean up after the stay. It will be a perfect place to have an event!
Reviewed on Sep 17, 2026
Eagle Mountain House & Golf Club
$670
per person
Dec 6 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Manchester (MHT)
9/10 Wonderful! (1,003 reviews)
Hotel needs significant upgrades, improvements and repair. The rates on line when booked had included breakfast but at arrival and check-in, we were told no. Beds were comfy however. Unlikely to stay here again in the future.
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 20 - Sep 21
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
"Not a good hotel"
Reviewed on Sep 18, 2026
Best Western Plus Keene Hotel
401 Winchester St Keene NH
Fully refundableReserve now, pay when you stay
$149 nightly
$162 total
Sep 20 - Sep 21
Total with taxes and fees
8.4/10 Very Good! (1,003 reviews)
"Great place to go"
Reviewed on Sep 16, 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 21 - Sep 22
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 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.
