Cheshire County Holidays

Book a Hotel + Flight or Car together to unlock savings

Top destinations in Cheshire County

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Rindge

Rindge
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Jaffrey

Jaffrey

Top hotels in Cheshire County

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 refundableReserve now, pay when you stay
The price is 2.824.870 ₫ per night from 2 Nov to 3 Nov
2.824.870 ₫
3.064.984 ₫ total
2 Nov - 3 Nov
includes taxes & fees
8.4/10 Very Good! (908 reviews)
"Very clean, up to date, affordable"

Reviewed on 29 Sept 2025

Keene Elm City Hotel, an Ascend Collection Hotel
Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

2.5 out of 5
20 Riverside Drive, West Chesterfield, NH
Fully refundableReserve now, pay when you stay
The price is 4.013.108 ₫ per night from 27 Oct to 28 Oct
4.013.108 ₫
4.354.150 ₫ total
27 Oct - 28 Oct
includes taxes & fees
9.4/10 Exceptional! (603 reviews)
"What a lovely delight near the New Hampshire/Vermont border! The staff is very welcoming, the room is beautiful and clean, and the sunrise/sunset on the river are remarkable! When I accidently left behind something precious, they were quick to send it to me. This is an overall gem of a hotel."

Reviewed on 29 Sept 2025

Riverside Hotel, an Ascend Collection Hotel
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St, Keene, NH
Fully refundableReserve now, pay when you stay
The price is 3.692.376 ₫ per night from 3 Nov to 4 Nov
3.692.376 ₫
4.006.228 ₫ total
3 Nov - 4 Nov
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"Would definitely stay again. Very convenient location"

Reviewed on 1 Oct 2025

Best Western Plus Keene Hotel
See all 2,008 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.

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 1null000null000 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.