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

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.
Cold Spring Plymouth Resort

Cold Spring Plymouth Resort

3.5 out of 5
Price was $764, price is now $603 per person
$603
per person
Oct 24 - Oct 30
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to Manchester (MHT)
A golf course and an outdoor pool are featured at this aparthotel. Enjoy the indoor pool and perks like free WiFi. There's a gym on site, and laundry facilities and barbecue grills are also offered.
The Chandler Inn Bethlehem - Littleton, an Ascend Collection Hotel

The Chandler Inn Bethlehem - Littleton, an Ascend Collection Hotel

3 out of 5
Price was $890, price is now $652 per person
$652
per person
Oct 24 - Oct 30
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to Manchester (MHT)
This hotel features an indoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the sauna and perks like free self parking.
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Save 100% on your flight
Price was $4,237, price is now $3,205 per person
$3,205
per person
Oct 20 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Springfield (VSF)
This luxury resort features a golf course, a full-service spa, and 4 restaurants. Enjoy the 2 indoor tennis courts and perks like free valet parking and free WiFi. Relax with a drink at one of the 2 bars/lounges and enjoy the 2 hot tubs and indoor pool.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Save 100% on your flight
Price was $3,388, price is now $2,569 per person
$2,569
per person
Oct 20 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) 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.
RiverWalk Resort at Loon Mountain

RiverWalk Resort at Loon Mountain

3.5 out of 5
Save 100% on your flight
Price was $1,361, price is now $1,069 per person
$1,069
per person
Oct 24 - Oct 30
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) 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.

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
$141 nightly
The price is $153 total per night
$153 total
Sep 6 - Sep 7
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
$95 nightly
The price is $103 total per night
$103 total
Sep 8 - Sep 9
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
Sep 7 - Sep 8
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
$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.
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
$194 nightly
The price is $210 total per night
$210 total
Sep 9 - Sep 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
The Burrell House

The Burrell House

2.5 out of 5
112 Washington St Keene NH
$130 nightly
The price is $141 total per night
$141 total
Sep 8 - Sep 9
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
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.

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?
$603 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