Cheshire County Vacation Packages 2026 from $479

Search vacation packages deals in Cheshire County's top destinations

Keene

Vacations

Cheshire County flight + hotel vacation packages

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

Cranmore Mountain Lodge Bed & Breakfast

Kearsarge

$479

per person

Feb 27 - Mar 1

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) to Manchester (MHT)

A restaurant and a seasonal outdoor pool are featured at this bed & breakfast. Enjoy the hot tub and free perks like continental breakfast and free self parking. Free WiFi in public areas, a terrace, and a garden are also on offer.

Eagle Mountain House & Golf Club

$532

per person

Feb 27 - Mar 1

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) to Manchester (MHT)

A golf course, a 24-hour gym, and a restaurant are all featured at this historic hotel. Take advantage of ski passes on site, and enjoy cross-country skiing and snowshoeing. Enjoy the seasonal outdoor pool and unwind at the bar/lounge and poolside bar.

Attitash Mountain Village

$542

per person

Feb 27 - Mar 1

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) to Manchester (MHT)

2 outdoor pools, 4 outdoor tennis courts, and an indoor pool are all featured at this smoke-free aparthotel. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site. Enjoy the sauna and perks like free self parking and free WiFi.

The Glen House Hotel

$564

per person

Feb 27 - Mar 1

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) to Manchester (MHT)

Ski-in/ski-out access and an indoor pool are featured at this traditional hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Eastern Slope Inn Resort

North Conway Village

$534

per person

Feb 27 - Mar 1

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) to Manchester (MHT)

This smoke-free hotel features 2 outdoor tennis courts, an indoor pool, and a restaurant. Enjoy the gym and perks like free self parking and free WiFi. There's a bar/lounge on site, and laundry facilities and concierge services are also provided.

Top Cheshire County hotels deals

The Burrell House

112 Washington St Keene NH

$185 nightly

$201 total

Jan 26 - Jan 27

Total with taxes and fees

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A picnic area is also provided.

Parking included

Free WiFi

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

Fitzwilliam NH

Get rates

Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Sportsman Pond and Laurel Lake are located nearby.

Owl's Nest Treehouse

Alstead NH

$315 nightly

$342 total

Jan 20 - Jan 21

Total with taxes and fees

A hot tub is available at this cabin.

Hot Tub

Kitchen

Great Wolf Lodge Boston / Fitchburg, MA

150 Great Wolf Dr Fitchburg MA

Free Cancellation

$179 nightly

$200 total

Jan 20 - Jan 21

Total with taxes and fees

This smoke-free resort features free water park access, 4 indoor pools, and a restaurant. Bring the family and enjoy the lazy river, bowling alley, and mini golf. Enjoy the seasonal outdoor pool and unwind at the bar/lounge and poolside bar.

Pointe at Castle Hill Resort

2940 State Route 103 Cavendish VT

$163 nightly

$177 total

Jan 26 - Jan 27

Total with taxes and fees

A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Pool

Hot Tub

The Colonial Hotel

625 Betty Spring Road Gardner MA

Free Cancellation

Reserve now, pay when you stay

$160 nightly

$179 total

Jan 19 - Jan 20

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Don't see what you're looking for?

See all available properties in Cheshire County

View all properties

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.

Photos of local treasures

Browse Cheshire County vacation photos for more inspiration

Keene featuring fall colors and street scenes

Keene which includes fall colors and a city

Keene featuring a river or creek and autumn leaves

Frequently asked questions

How much are vacation packages to Cheshire County?

$479 is all you'll need for a fantastic escape in Cheshire County. Bundle your hotel and flights into a vacation package with Travelocity and see your savings grow. With these kinds of prices, there's never been a better time to travel.

Where can I get the best vacation package deals for Cheshire County?

You'll come across a fantastic range of Cheshire County package deals on Travelocity. With as many as 400 air carriers and 1,000,000 properties worldwide, arranging your dream getaway will be a breeze.

Why should I book my Cheshire County vacation bundle with Travelocity?

You'll not only enjoy big savings, but you'll also have access to our round-the-clock support, excellent service and a Price Match Guarantee. Roam across the globe, uncover hidden gems and forge unforgettable memories — we'll take care of the little details.

Can I save on my Cheshire County car rental if I bundle it with a hotel or flight?

Bundling your bookings into a Cheshire County vacation package will certainly save you money. You can combine a flight and car; a flight, car and hotel; or a car and hotel. You won't find a better way to explore the greater Cheshire County area than from the comfort of your own rental car. You can also add tours and experiences to your Travelocity package.

Which airport is best for Cheshire County?

For passengers contemplating flying in and out of Cheshire County, the most commonly used airports are Manchester-Boston Regional Airport (MHT), Lebanon Municipal Airport (LEB) and Rutland Southern Vermont Regional Airport (RUT).

What is there to do in Cheshire County?

Cheshire County has hidden surprises around every turn, but make sure you plan a trip to Friendly Farm and Walpole Mountain View Winery during your stay. These landmarks should be on your to-do list.