Cheshire County Vacations & Trips from $239
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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
$239
per person
Nov 15 - Nov 18
found 1 day ago
Roundtrip flight included
Washington (WAS) to Manchester (MHT)
8.6/10 Excellent! (65 reviews)
The location is the best and everything was easy to get to. It was quiet, clean and refreshing. Only minutes from anything you need.
The only thing was the bed was very uncomfortable you could feel the springs in the mattress. Other than that it was perfect
Reviewed on Sep 2, 2026
Cranmore Mountain Lodge Bed & Breakfast
Kearsarge
$1,213
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Manchester (MHT)
8.8/10 Excellent! (259 reviews)
This place was excellent, can't say enough about the staff members,treated you like family, breakfast was awesome !!!
Reviewed on Sep 3, 2026
Hideaway Inn Mt.Sunapee
$651
per person
Oct 19 - Oct 24
found 22 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Manchester (MHT)
8.4/10 Very Good! (257 reviews)
This is a good basic place to stay- there isn't many frills. It provides a nice bed and bathroom. Good for a stay when you just need the essentials.
Location for Mt Sunapee is excellent.
Reviewed on Sep 1, 2026
Attitash Mountain Village
$1,174
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Manchester (MHT)
8.6/10 Excellent! (570 reviews)
Everything was 10/10 for us, the whirlpool tub in the bathroom was worth it on its own but the amount of amenities you get is sooo good. Washer & dryer in the room.. a little balcony. The restaurant service was great, good drinks. The pool area was super nice they had a toddler pool just for my 1 year old lol not literally but he was the only one using it & it was actually perfect for him. I would stay here every-time we’re in the area it was that good!
Reviewed on Aug 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
$141 nightly
$153 total
Sep 21 - Sep 22
Total with taxes and fees
8.6/10 Excellent! (1,003 reviews)
"The property was very nice. Clean rooms. Plenty of towels. Comfortable bed and pillows."
Reviewed on Sep 4, 2026
Days Inn by Wyndham Keene NH
3 Ash Brook Road Keene NH
Fully refundableReserve now, pay when you stay
$93 nightly
$101 total
Sep 9 - Sep 10
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 7 - Sep 8
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.
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.
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.
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.
Granite Lake
Commune with nature and explore the great outdoors at Granite Lake during your travels in Nelson.
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.
