Deals on vacations and trips to Cheshire County

Save when you book Cheshire County, NH package deals

Choose two or more items and save on your trip:

Search vacation packages deals in Cheshire County's top destinations

Keene featuring a city and a church or cathedral

Keene

Vacations
Keene

Cheshire County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

2 out of 5
Price was $642, price is now $590 per person
$590
per person
Jun 5 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Springfield (VSF)
This hotel features a seasonal outdoor pool and a sauna. Enjoy the free ski shuttle and onsite ski storage. Guests will appreciate free perks like free self parking and WiFi in public areas.
The Centennial

The Centennial

4 out of 5
Price was $897, price is now $804 per person
$804
per person
May 15 - May 17
found 6 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Manchester (MHT)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 4 conference rooms, free WiFi in public areas, and express check-out. Guests will appreciate freebies like continental breakfast and free self parking.
Chalet 239

Chalet 239

2 out of 5
Price was $669, price is now $610 per person
$610
per person
Jun 5 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Springfield (VSF)
The motel doesn't skimp on freebies - guests receive free on-the-go breakfast and free self parking. A picnic area and a virtual front desk are also provided.
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
Price was $689, price is now $636 per person
$636
per person
Jun 5 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Springfield (VSF)
Ski-in/ski-out access, a full-service spa, and 2 hot tubs are all featured at this smoke-free resort. Enjoy a meal from the restaurant and freebies like WiFi in public areas and an area shuttle. You'll appreciate the outdoor pool, bar/lounge, and laundry facilities.
The Grand at Bedford Village Inn

The Grand at Bedford Village Inn

5 out of 5
Price was $940, price is now $879 per person
$879
per person
May 15 - May 17
found 6 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Manchester (MHT)
A full-service spa, 3 restaurants, and an outdoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Relax with a drink at one of the 3 bars/lounges and enjoy perks like free valet parking.

Top Cheshire County hotels deals

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
Free Cancellation
Reserve now, pay when you stay
$149 nightly
The price is $162 total per night
$162 total
Mar 19 - Mar 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 24-hour gym and free perks like buffet breakfast and free self parking.
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2 out of 5
3 Ash Brook Road Keene NH
Free Cancellation
Reserve now, pay when you stay
$81 nightly
The price is $88 total per night
$88 total
Mar 22 - Mar 23
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. There's a gym on site, and a snack bar/deli and a picnic area are also provided.
Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

2.5 out of 5
20 Riverside Drive West Chesterfield NH
Free Cancellation
$161 nightly
The price is $175 total per night
$175 total
Mar 24 - Mar 25
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the express check-out, conference center, and conference space. There's a 24-hour gym on site, and concierge services and wedding services are also offered.
The Burrell House

The Burrell House

2.5 out of 5
112 Washington St Keene NH
$156 nightly
The price is $169 total per night
$169 total
Mar 21 - Mar 22
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
Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

3.5 out of 5
150 Great Wolf Dr Fitchburg MA
$179 nightly
The price is $200 total per night
$200 total
Mar 23 - Mar 24
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.
The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road Gardner MA
Free Cancellation
Reserve now, pay when you stay
$160 nightly
The price is $179 total per night
$179 total
Mar 22 - Mar 23
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

Petroglyphs carved into the rocks along the connecticut river in vt.
Right before the bridge there are these cool old railway cars
Old rail station
Neat little town in the Green Mountains
Perfect Sunrise stop

Frequently asked questions

How much are vacation packages to Cheshire County?
$590 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.

Explore More Ways to Travel with Travelocity