Cheshire County Holidays

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Your Cheshire County Holiday

Book a holiday package to Cheshire County and make travel planning easy. With all the logistics arranged before you leave, you can focus on enjoying every minute in this destination. With so much to see on a trip to Cheshire County, it can be tricky to know where to begin. Kick off your journey in Jaffrey at Laurel Lake and Friendly Farm — two popular attractions here. Another top city worth adding to your itinerary is Walpole. Be sure not to miss Vermont Country Store and Bellows Falls Opera House. Expedia is your one-stop shop when it comes to planning your Cheshire County holiday. From flights and hotels, to activities and more, we know how to curate a travel experience like no other.

Cheshire County Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Manchester-Boston Regional Airport (MHT)
Top Sights
Monadnock State Park, Friendly Farm and Pitcher Mountain

Our pick of the best Cheshire County Hotel 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
Fully refundable
The price is AU$192 per night from 18 Dec to 19 Dec
AU$192
per night
18 Dec - 19 Dec
8.4/10 Very Good! (963 reviews)
The room was perfect, and the food was great

Reviewed on 15 Dec 2025

Keene Elm City Hotel, an Ascend Collection Hotel
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

2.5 out of 5
126 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
The price is AU$240 per night from 1 Jan to 2 Jan
AU$240
per night
1 Jan - 2 Jan
8.8/10 Excellent! (353 reviews)
Clean comfy nice staff

Reviewed on 6 Dec 2025

Hampton Inn & Suites Keene
Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

2.5 out of 5
20 Riverside Drive West Chesterfield NH
Fully refundable
The price is AU$249 per night from 14 Jan to 15 Jan
AU$249
per night
14 Jan - 15 Jan
9.6/10 Exceptional! (628 reviews)
All good

Reviewed on 28 Nov 2025

Riverside Hotel, an Ascend Collection Hotel
See all 2,009 properties in Cheshire County
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.
All Inclusive Holidays
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beach holidays
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Beach Holidays

Frequently asked questions

How much does a Cheshire County holiday package cost?
Starting from just , a holiday package is your gateway to cheaper travel. Custom build your Cheshire County getaway by selecting from our huge range of airfares, hotels and rental cars.
How do I get a cheap travel package to Cheshire County?
Simply by bundling. Hotels, flights and rental cars — combine whatever you need into a Cheshire County holiday package to save a ton of cash. Score even more deals when you include extras such as tours or experiences to your booking. But that's not the only good part. You have the freedom to tailor your trip your own way. We offer more than 550 partner airlines and 1 000 000 properties in all corners of the globe, so that everyone has a chance to travel and fulfil those holiday dreams.
What are the top hotels in Cheshire County?
For hotels in Harrisville with cosy beds and friendly service, you can't go past Best Western Plus Keene Hotel and Days Inn by Wyndham Keene NH. If you're stopping by Rindge as well, you can look forward to a great night's sleep at Courtyard by Marriott Keene Downtown or Riverside Hotel, Ascend Hotel Collection.
How far in advance should I book my Cheshire County holiday?
Reserving your seat early with Expedia means one less thing to worry about. Most air carriers advertise prices up to a year in advance. Generally, this is the cheapest time to book. If circumstances have left you booking late, discount prices to Cheshire County sometimes emerge just a few weeks before departure.
What does an Expedia Cheshire County travel package include?
Flights, rental cars and hotels, or any combination of the three — it's your pick! Whether you're exploring Cheshire County on a family road trip or travelling by yourself, there's a bundle to match your budget and style. Once you've made your booking, why not add on a couple of tours as well?
What should I know before booking a Cheshire County travel package?
A travel package can be customized for your budget and is a terrific way to make your money go further. How little or much you include is totally up to you. Hotels, rental cars and flights — choose any combination that works with your plans.
Can I choose my airline with a Cheshire County Expedia holiday package?
Definitely. Expedia has over 550 airline partners to pick from globally. With all that choice at your fingertips, finding the ideal carrier to bring you to Cheshire County shouldn't be hard.
If I'm not able to travel, can I cancel my Cheshire County holiday package?
We get that the universe can throw the odd curveball. If you've booked a Cheshire County holiday package and have to amend or cancel it, we're here to help. We recommend looking up our Customer Service Portal first for information. But generally speaking, if you've booked your package within 24 hours, you may be able to change your itinerary at no cost. If it's been more than 24 hours, your airline, hotel or car rental company may impose a charge.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.