Cheshire County Vacations & Trips from $419
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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
Walpole
The Latest Cheshire County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Centennial
Save 100% on your flight
Price was $680, price is now $465 per person
$465
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Manchester (MHT)
8.8/10 Excellent! (1,000 reviews)
Lovely and very helpful staff - Late night and early morning! Bed was very comfortable and breakfast was out early and very nice.
Reviewed on Apr 6, 2026
Hampton Inn & Suites Exeter
Save 100% on your flight
Price was $793, price is now $616 per person
$616
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Manchester (MHT)
9.2/10 Wonderful! (1,006 reviews)
Breakfast menu was good and parking was safe and easy. All the facilities and room was clean.
Reviewed on Apr 15, 2026
The Grand at Bedford Village Inn
Save 100% on your flight
Price was $1,066, price is now $852 per person
$852
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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
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
$144 nightly
The price is $156 total per night from Apr 19 to Apr 20
$156 total
Apr 19 - Apr 20
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
The breakfast nook was excellent ! Many choices laid out neat and easy.
Reviewed on Apr 16, 2026
Keene Elm City Hotel, an Ascend Collection Hotel
175 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $146 total per night from Apr 19 to Apr 20
$146 total
Apr 19 - Apr 20
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
The room was very clean and the staff was very nice and there was plenty of parking. It was also within walkable distance of a movie theater and several fast food restaurants. Perf
Reviewed on Apr 12, 2026
Days Inn by Wyndham Keene NH
3 Ash Brook Road Keene NH
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $106 total per night from Apr 28 to Apr 29
$106 total
Apr 28 - Apr 29
Total with taxes and fees
7/10 Good! (1,000 reviews)
This property was definitely on the older side and could use some renos. All of the towels in my room were stained, and the kleenex boxes left empty. I don't think one single staff member greeted me during the 3 nights I stayed there. They just sat behind the desk or walked about but never said hello ...
Reviewed on Apr 15, 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.
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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.
