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.
Top destinations in Cheshire County
Chesterfield
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
175 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
AU$177
2 Sept - 3 Sept
includes taxes & fees
8.6/10 Excellent! (1,011 reviews)
"Everything was very clean and very well taken care of. The bed was very comfortable the place where I think maybe the stay was lacking was the breakfast, not very exciting. It was adequate and well stocked. I do like that. There was coffee available 24 hours."
Reviewed on 11 Aug 2026
Days Inn by Wyndham Keene NH
3 Ash Brook Road Keene NH
Fully refundableReserve now, pay when you stay
AU$127
1 Sept - 2 Sept
includes taxes & fees
7/10 Good! (1,005 reviews)
"Found front desk noisy in everything after 9m and not available at check out time at 11 am"
Reviewed on 11 Aug 2026
Best Western Plus Keene Hotel
401 Winchester St Keene NH
Fully refundableReserve now, pay when you stay
AU$229
19 Aug - 20 Aug
includes taxes & fees
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 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.
Stay near popular Cheshire County attractions
Monadnock State Park
9.6/10 (45 reviews)
You can take time to visit Monadnock State Park during your travels to Jaffrey. Discover the cafes and its festivals while you're in the area.
Historic Main Street
9.2/10 (107 reviews)
Find out about the history of Keene with a stop at Historic Main Street. Visit the area's shops or simply enjoy its restaurants.
Photo by Heather Beaudry
Madame Sherri Forest
8.0/10 (4 reviews)
Explore the great outdoors at Madame Sherri Forest, a lovely green space in West Chesterfield. Wander around the forests or experience the area's entertainment venues.
Spofford Lake
8.8/10 (38 reviews)
Commune with nature and explore the great outdoors at Spofford Lake during your travels in Spofford. Discover the area's entertainment venues or seek out its ski slopes.
Laurel Lake
8.0/10 (1 review)
Commune with nature and explore the great outdoors at Laurel Lake during your travels in Fitzwilliam. Amble around the area's parks or visit its shops.
Colonial Theatre
8.4/10 (36 reviews)
You can make plans for a show at Colonial Theatre on your trip to Keene. Experience the festivals or attend a sporting event in this family-friendly area.
Stonewall Farm
7.8/10 (20 reviews)
Explore the campus of Stonewall Farm during your travels in Keene. Stroll along the riverfront or experience the area's festivals.
Brentwood Golf Course
8.8/10 (13 reviews)
Enjoy a round of golf in Keene at Brentwood Golf Course. Discover the cafes and festivals in this family-friendly area.
What to do in Cheshire County
Mindful Forest Escape: Rebalance, reflect and connect
AU$136
per adult
Colonial Flintlock Musket Experience
AU$185
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
