Name: Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.
Rating: 10

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 featuring a city and a church or cathedral

The Latest Cheshire County Vacation Packages

Price found within the past 48 hours. Click for updated prices.

Hideaway Inn Mt.Sunapee

$508

per person

Mar 20 - Mar 22

found 16 hours ago

Roundtrip non-stop flight included

Charlotte (CLT) to Manchester (MHT)

9.4/10 Exceptional! (38 reviews)

Staff were super friendly. Rooms were cozy. Our dog was welcome. A great experience!

Reviewed on Feb 6, 2026

The Centennial

$621

per person

May 12 - May 16

found 23 hours ago

Roundtrip flight included

Charlotte (CLT) to Manchester (MHT)

8.8/10 Excellent! (1,000 reviews)

The bed is very comfortable. But the elevator stop working for 5 -10 min when I was inside. I told the staff, and they were just like, ok. This place is fine but over-rated.

Reviewed on Jan 6, 2026

Winnisquam Lake Inn

$540

per person

Apr 30 - May 8

found 12 hours ago

Roundtrip non-stop flight included

Savannah (SAV) to Manchester (MHT)

6.8/10 (803 reviews)

room was warm (it was 9 degrees outside), spotless, bathroom too. people at desk helpful and friendly.

Reviewed on Feb 9, 2026

Extended Stay America Suites - Nashua - Merrimack

$536

per person

May 12 - May 16

found 23 hours ago

Roundtrip flight included

Charlotte (CLT) to Manchester (MHT)

7.2/10 Good! (842 reviews)

Staff was friendly. Room was a little dirty

Reviewed on Jan 15, 2026

Holiday Inn Express Hotel & Suites Tilton - Lakes Region by IHG

$740

per person

Apr 30 - May 8

found 12 hours ago

Roundtrip non-stop flight included

Savannah (SAV) to Manchester (MHT)

9.4/10 Exceptional! (1,000 reviews)

Friendly staff. Good breakfast.

Reviewed on Feb 1, 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

$139 nightly

$151 total

Feb 16 - Feb 17

Total with taxes and fees

8.2/10 Very Good! (1,003 reviews)

Spots on wall by garbage.

Reviewed on Jan 19, 2026

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

Fully refundableReserve now, pay when you stay

$119 nightly

$129 total

Feb 17 - Feb 18

Total with taxes and fees

8.4/10 Very Good! (982 reviews)

Clean room, comfortable bed, friendly staff

Reviewed on Feb 8, 2026

Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.

Fitzwilliam NH

10/10 Exceptional! (10 reviews)

It was a lovely stay! Lake is beautiful and the house is cozy.

Reviewed on Oct 16, 2025

Get rates

See all 2,062 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.