Deals on vacations and trips to Cheshire County

Save when you book Cheshire County, NH package deals

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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.
White River Inn and Suites

White River Inn and Suites

2.5 out of 5
Price was $432, price is now $348 per person
$348
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Manchester (MHT)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. There's an indoor pool on site, and a 24-hour front desk and a terrace are also provided.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $663, price is now $506 per person
$506
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.
Hideaway Inn Mt.Sunapee

Hideaway Inn Mt.Sunapee

2 out of 5
Price was $490, price is now $376 per person
$376
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Manchester (MHT)
An indoor pool, free self parking, and a virtual front desk are featured at this hotel. WiFi in public areas is free. A lobby fireplace, a communal living room, and express check-out are also on offer.
Exeter Inn

Exeter Inn

3.5 out of 5
Price was $726, price is now $567 per person
$567
per person
May 21 - May 26
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Manchester (MHT)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free continental breakfast is served.
The Grand at Bedford Village Inn

The Grand at Bedford Village Inn

5 out of 5
Save 100% on your flight
Price was $1,545, price is now $1,239 per person
$1,239
per person
May 21 - May 26
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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
$119 nightly
The price is $129 total per night
$129 total
Mar 9 - Mar 10
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.
Pool
Breakfast included
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd Keene NH
Free Cancellation
Reserve now, pay when you stay
$109 nightly
The price is $118 total per night
$118 total
Mar 9 - Mar 10
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
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
$104 nightly
The price is $113 total per night
$113 total
Mar 10 - Mar 11
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.
Breakfast included
Pet friendly
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
$156 nightly
The price is $169 total per night
$169 total
Apr 6 - Apr 7
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.
Parking included
Free WiFi
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 9 - Mar 10
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.
Pool
Hot Tub
Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

3.5 out of 5
150 Great Wolf Dr Fitchburg MA
Free Cancellation
Reserve now, pay when you stay
$179 nightly
The price is $200 total per night
$200 total
Mar 9 - Mar 10
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.
Pool
Restaurant
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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.
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

Frequently asked questions

How much are vacation packages to Cheshire County?
$348 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.

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