Name: Keene Elm City Hotel, an Ascend Collection Hotel
Price range: $144 total

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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

A street with a clock, red brick buildings, and autumn leaves.

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

$744

per person

Dec 24 - Jan 2

found 1 day ago

Roundtrip non-stop flight included

Miami (MIA) to Manchester (MHT)

7.6/10 Good! (1,001 reviews)

Thanks!

Reviewed on Nov 14, 2026

Presidential Mountain Resort

Save 100% on your flight

$1,423

per person

Dec 24 - Jan 2

found 1 day ago

Roundtrip non-stop flight included

Miami (MIA) to Manchester (MHT)

9.6/10 Exceptional! (328 reviews)

Christmas Farm Inn and Spa

Save 100% on your flight

$1,543

per person

Dec 24 - Jan 2

found 1 day 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

The Inn at Thorn Hill & Spa

Save 100% on your flight

$2,698

per person

Dec 24 - Jan 2

found 1 day ago

Roundtrip non-stop flight included

Miami (MIA) to Manchester (MHT)

9.8/10 Exceptional! (1,002 reviews)

The Village of Loon Mountain

Save 100% on your flight

$1,796

per person

Dec 24 - Jan 2

found 22 hours ago

Roundtrip non-stop flight included

Miami (MIA) to Manchester (MHT)

8.6/10 Excellent! (623 reviews)

very spacious and it was very clean

Reviewed on Nov 11, 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

$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

$154 total

Nov 17 - Nov 18

Total with taxes and fees

8.2/10 Very Good! (1,002 reviews)

"Room Was dirty. Pool was dirty. Ceiling titles missing in hallway. Their was a group of 30 plus tree workers by my room and loud. Parking lot party. Highly recommend staying clear! Rooms where broken down. Phone in room didnt work to call fromt desk about issues."

Reviewed on Nov 15, 2026

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

Fully refundableReserve now, pay when you stay

$133 nightly

$144 total

Nov 16 - Nov 17

Total with taxes and fees

See all 2,057 properties in Cheshire County

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.