Cheshire County Vacations & Trips from $394
Book a Hotel + Flight or Car together to unlock savings
Photo by mike dobias
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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
Walpole
The Latest Cheshire County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Stonybrook Motel & Lodge
Price was $532, price is now $394 per person
$394
per person
Jun 5 - Jun 7
found 1 day ago
Roundtrip flight included
Miami (MIA) to Manchester (MHT)
7.6/10 Good! (1,000 reviews)
This motel is great for a one-night last-min ski trip. You get what you pay for. No frills and the rooms are outdated but the location was great for skiing and a fraction of the cost of everything else around. I will definitely be back.
Reviewed on Mar 23, 2026
The Centennial
Price was $1,124, price is now $777 per person
$777
per person
Jun 5 - Jun 12
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Manchester (MHT)
8.8/10 Excellent! (1,003 reviews)
Room and bathroom were great; bed / pillows so comfortable; love the robes. Breakfast had just the right amount of variety / selections.
Elevator was not working but we were ok with stairs. It had been not working in our December visit either.
Reviewed on Mar 22, 2026
Hideaway Inn Mt.Sunapee
Price was $612, price is now $475 per person
$475
per person
Jun 5 - Jun 7
found 1 day ago
Roundtrip flight included
Miami (MIA) to Manchester (MHT)
8.8/10 Excellent! (150 reviews)
The rooms were clean but were starting to show signs of age. The bed would squeak and the mattress would sink in the middle. There was a fly in the room, which took forever to get it out. I thought the decor was nice. The concept is of Airbnb rooms but within a hotel. There’s no onsite front desk but there’s daily maintenance it seems. The living room lodge is cozy, the free cocoa/coffee was great, and the game room/pool was nice. Overall, it was a great value and would gladly return.
Reviewed on Mar 26, 2026
The Grand at Bedford Village Inn
Price was $1,793, price is now $1,421 per person
$1,421
per person
Jun 5 - Jun 12
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Manchester (MHT)
9.6/10 Exceptional! (362 reviews)
Everything was above and beyond. Our room was lovely. Every staff member was great! I would highly recommend the BVI.
Reviewed on Jan 29, 2026
Cold Spring Plymouth Resort
Price was $1,121, price is now $901 per person
$901
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Manchester (MHT)
9.2/10 Wonderful! (203 reviews)
Very clean property, great price! Unit was great, plenty of space, well equipped. Great location, easy drive to multiple ski resorts.
Reviewed on Mar 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
Best Western Plus Keene Hotel
401 Winchester St Keene NH
Fully refundableReserve now, pay when you stay
$154 nightly
The price is $167 total per night from Apr 5 to Apr 6
$167 total
Apr 5 - Apr 6
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
One of the better franchise hotels I've stayed at for this price point.
Reviewed on Mar 31, 2026
Keene Elm City Hotel, an Ascend Collection Hotel
175 Key Rd Keene NH
Fully refundable
$126 nightly
The price is $137 total per night from Apr 23 to Apr 24
$137 total
Apr 23 - Apr 24
Total with taxes and fees
8.6/10 Excellent! (999 reviews)
Nice
Reviewed on Mar 24, 2026
Days Inn by Wyndham Keene NH
3 Ash Brook Road Keene NH
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $113 total per night from Apr 14 to Apr 15
$113 total
Apr 14 - Apr 15
Total with taxes and fees
7/10 Good! (1,001 reviews)
Room was clean looking, some broken fixtures.
Reviewed on Mar 28, 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.
Explore a world of travel with Expedia
Other vacations you might like
- Top cities in Cheshire County
- Vacations and getaways similar to Cheshire County
- Best vacation destinations by month
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
