Cheshire County Vacations & Trips from $428
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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
Keene
The Latest Cheshire County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Stonybrook Motel & Lodge
Save 100% on your flight
Price was $1,272, price is now $744 per person
$744
per person
Dec 24 - Jan 2
found 18 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Manchester (MHT)
7.6/10 Good! (1,001 reviews)
No pool! And a run down property.
I did not get the deluxe double room that I booked on Hotels.com (Expedia on their end). He said this is the 3rd time it has happened. I told him to call and fix it. He knows. He at first gave me a queen room when my booking was 2 beds. Then switched to a 2 bed room but so bad! The toilet overflowed from the tank and he came and did not fix it. Did again the next day. He should have given me the nice room that i n
Reviewed on Nov 11, 2026
Christmas Farm Inn and Spa
Save 100% on your flight
Price was $2,373, price is now $1,543 per person
$1,543
per person
Dec 24 - Jan 2
found 18 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Manchester (MHT)
8.8/10 Excellent! (1,010 reviews)
Charming place. Highly recommend it.
Reviewed on Nov 14, 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
Days Inn by Wyndham Keene NH
3 Ash Brook Road Keene NH
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $109 total per night from Nov 17 to Nov 18
$109 total
Nov 17 - Nov 18
Total with taxes and fees
Best Western Plus Keene Hotel
401 Winchester St Keene NH
Fully refundableReserve now, pay when you stay
$142 nightly
The price is $154 total per night from Nov 17 to Nov 18
$154 total
Nov 17 - Nov 18
Total with taxes and fees
Keene Elm City Hotel, an Ascend Collection Hotel
175 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $143 total per night from Nov 16 to Nov 17
$143 total
Nov 16 - Nov 17
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
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.