Deals on vacations and trips to Cheshire County

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A street with historic buildings, a church steeple, and autumn foliage.

Keene

Vacations
Keene

Cheshire County flight + hotel vacation packages

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

Attitash Mountain Village

3 out of 5
Save 100% on your flight
Price was $1,284, price is now $749 per person
$749
per person
Sep 26 - Oct 2
found 9 hours ago
Roundtrip flight included
Pittsburgh (PIT) 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 Village of Loon Mountain Fixed Rooms

The Village of Loon Mountain Fixed Rooms

2 out of 5
Save 100% on your flight
Price was $1,416, price is now $929 per person
$929
per person
Sep 26 - Oct 2
found 9 hours ago
Roundtrip flight included
Pittsburgh (PIT) to Manchester (MHT)
A seasonal outdoor pool, free self parking, and barbecue grills are featured at this aparthotel. A terrace and a picnic area are also provided.
The Village of Loon Mountain

The Village of Loon Mountain

3 out of 5
Save 100% on your flight
Price was $1,246, price is now $908 per person
$908
per person
Sep 26 - Oct 2
found 9 hours ago
Roundtrip flight included
Pittsburgh (PIT) to Manchester (MHT)
2 indoor pools, 12 outdoor tennis courts, and a hot tub are all featured at this smoke-free aparthotel. Enjoy the free ski shuttle and onsite ski storage. Enjoy the gym and perks like free self parking and free WiFi.
Eagle Mountain House & Golf Club

Eagle Mountain House & Golf Club

3.5 out of 5
Save 100% on your flight
Price was $1,161, price is now $868 per person
$868
per person
Sep 26 - Oct 2
found 9 hours ago
Roundtrip flight included
Pittsburgh (PIT) 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.
Hideaway Inn Franconia Notch

Hideaway Inn Franconia Notch

2 out of 5
Save 100% on your flight
Price was $1,072, price is now $814 per person
$814
per person
Sep 26 - Oct 2
found 9 hours ago
Roundtrip flight included
Pittsburgh (PIT) to Manchester (MHT)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, a communal living room, and a picnic area are also on offer.

Top Cheshire County hotels deals

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
$120 nightly
The price is $130 total per night
$130 total
Sep 1 - Sep 2
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
$97 nightly
The price is $105 total per night
$105 total
Sep 16 - Sep 17
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
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
Aug 26 - Aug 27
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
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
$152 nightly
The price is $165 total per night
$165 total
Sep 20 - Sep 21
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
Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown

3 out of 5
30 Main Street Keene NH
Free Cancellation
Reserve now, pay when you stay
$180 nightly
The price is $195 total per night
$195 total
Aug 31 - Sep 1
Total with taxes and fees
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Breakfast included
Parking included
Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

3.5 out of 5
150 Great Wolf Dr Fitchburg MA
$183 nightly
The price is $204 total per night
$204 total
Aug 26 - Aug 27
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.

Stay near popular Cheshire County attractions

A rocky field with autumn-colored trees and a mountain in the background.

Monadnock State Park

9.6/10 (45 reviews)
You can take time to visit Monadnock State Park during your travels to Jaffrey. Discover the coffeehouses and its festivals while you're in the area.
See properties

Photos of local treasures

Browse Cheshire County vacation photos for more inspiration

A large rock with carved faces and a river in the background.
A vintage train with 'GREEN MOUNTAIN' written on it, passing through a rural area with greenery and power lines.
A railroad crossing with a brick building in the background.
A calm river with a bridge, a forested hill, and industrial buildings in the background.
A field with grazing cattle and a sunset in the background.

Frequently asked questions

How much are vacation packages to Cheshire County?
$749 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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