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.
Colby Hill Inn

Colby Hill Inn

3.5 out of 5
Price was $783, price is now $627 per person
$627
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Manchester (MHT)
Ski-in/ski-out access and an outdoor pool are featured at this smoke-free inn. Enjoy the seasonal outdoor pool and free perks like full breakfast and free self parking. You'll find a restaurant and a bar/lounge onsite for dining and drinks, along with a terrace.
Hideaway Inn Mt.Sunapee

Hideaway Inn Mt.Sunapee

2 out of 5
Price was $1,028, price is now $838 per person
$838
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Manchester (MHT)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Bring the family and enjoy the arcade/game room, along with hiking/biking trails. There's an indoor pool on site, and a fireplace in the lobby and a communal living room are also provided.
Holiday Inn Express Hotel & Suites White River Junction by IHG

Holiday Inn Express Hotel & Suites White River Junction by IHG

2.5 out of 5
Price was $1,009, price is now $831 per person
$831
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Manchester (MHT)
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.
The Hotel Concord

The Hotel Concord

3.5 out of 5
Downtown Concord
Price was $1,221, price is now $1,015 per person
$1,015
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Manchester (MHT)
A restaurant and a 24-hour gym are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A 24-hour business center, a lobby fireplace, and express check-out are also on offer.
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was $798, price is now $682 per person
$682
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Springfield (VSF)
Ski-in/ski-out access, 2 restaurants, and 3 hot tubs are all featured at this smoke-free hotel. There's a free ski shuttle, and ski lessons, ski passes and ski storage are available on site. Bring the family and enjoy the mini golf, playground, and arcade/game room.

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
$119 nightly
The price is $129 total per night
$129 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
$78 nightly
The price is $85 total per night
$85 total
Sep 1 - Sep 2
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 3 - Aug 4
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
$146 nightly
The price is $159 total per night
$159 total
Sep 1 - Sep 2
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
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

3 out of 5
75 Railroad St Keene NH
Free Cancellation
Reserve now, pay when you stay
$180 nightly
The price is $195 total per night
$195 total
Aug 9 - Aug 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 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
Pool
Pet friendly
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
$161 nightly
The price is $174 total per night
$174 total
Aug 9 - Aug 10
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
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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?
$627 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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