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.
Stonybrook Motel & Lodge

Stonybrook Motel & Lodge

2 out of 5
Price was $636, price is now $434 per person
$434
per person
Nov 27 - Nov 30
found 19 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Manchester (MHT)
This motel features free WiFi in public areas, barbecue grills, and free self parking. Enjoy the free on-the-go breakfast each morning. A garden, a lobby fireplace, and a picnic area are also on offer.
The Village of Loon Mountain Fixed Rooms

The Village of Loon Mountain Fixed Rooms

2 out of 5
Price was $1,067, price is now $770 per person
$770
per person
Oct 22 - Oct 25
found 12 hours ago
Roundtrip flight included
Orlando (MCO) 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.
RiverWalk Resort at Loon Mountain

RiverWalk Resort at Loon Mountain

3.5 out of 5
Price was $769, price is now $569 per person
$569
per person
Nov 27 - Nov 30
found 19 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Manchester (MHT)
This smoke-free hotel features an attached winery, a full-service spa, and a restaurant. Families will appreciate the arcade/game room and barbecue grills. Enjoy the outdoor pool and perks like free self parking and free WiFi.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,452, price is now $1,141 per person
$1,141
per person
Dec 2 - Dec 8
found 23 hours ago
Roundtrip non-stop flight included
San Juan (SJU) 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.
White River Inn and Suites

White River Inn and Suites

2.5 out of 5
Price was $710, price is now $563 per person
$563
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) 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.

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
$152 nightly
The price is $166 total per night
$166 total
Sep 29 - Sep 30
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.
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
$149 nightly
The price is $162 total per night
$162 total
Sep 17 - Sep 18
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
$106 nightly
The price is $115 total per night
$115 total
Sep 20 - Sep 21
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 $174 total per night
$174 total
Sep 29 - Sep 30
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.
Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown

3 out of 5
30 Main Street Keene NH
$214 nightly
The price is $232 total per night
$232 total
Sep 17 - Sep 18
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.
The Burrell House

The Burrell House

2.5 out of 5
112 Washington St Keene NH
$141 nightly
The price is $153 total per night
$153 total
Sep 17 - Sep 18
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.
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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.
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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?
$434 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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