Cheshire County Vacation Packages
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Your Cheshire County Vacation
Book a vacation 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 vacation. From flights and hotels, to activities and more, we know how to curate a travel experience like no other.
Top vacation destinations in Cheshire County
Jaffrey
Top Cheshire County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hideaway Inn Mt.Sunapee
CA $1,084
per person
Nov 27 - Nov 30
just found
Roundtrip flight included
Toronto (YYZ) to Manchester (MHT)
8.4/10 Very good! (280 reviews)
The check in process was great.There was 24 hour coffee.Our room was spacious and it had a record player with 3 classic albums...one by Little Feat that we played.There were many other albums available in the living room near the entrance.We were happy to have been able to go on a boat cruise that included dinner and a lovely sunset.There were other nice places to eat.We really enjoyed our one day stay and will come again!
Reviewed on Oct 23, 2026
Okemo Mountain Lodging by Vail Resorts
Clock Tower Base Area
CA $1,477
per person
Nov 27 - Nov 30
just found
Roundtrip flight included
Toronto (YYZ) to Springfield (VSF)
7.8/10 Good! (28 reviews)
Don’t ever rent at this place for the condo rentals they sent us to the wrong address, I could not get in contact with the so-called property manager for over an hour or more. We had no toilet paper, we had no hairdryer, no paper towels, we didn’t even know where the keys were or shampoo or soap. Basically this was an utter disaster. I tried to work it out with resort management and they offered certain things and I countered and I got at that point what I wanted, but it just continued to spiral downhill and then when I communicate further issues, I had to be on the phone with them, trying to explain to them what the problem was up until 11 PM at night, that night was in the 30s and they left the air conditioner on in the house didn’t warm up until after 1 AM. This was by far the worst experience I’ve ever had with a supposedly high-end resort. I’m telling you do not rent from their condo selection. It’s terrible. It’s expensive and it is just a waste of time.
Reviewed on Oct 15, 2026
Cheshire County Hotel Deals
Best Western Plus Keene Hotel
401 Winchester St Keene NH
Fully refundableReserve now, pay when you stay
CA $198
per night
Nov 5 - Nov 6
8.2/10 Very good! (1,000 reviews)
"Excellent place to stay"
Reviewed on Oct 19, 2026
Days Inn by Wyndham Keene NH
3 Ash Brook Road Keene NH
Fully refundableReserve now, pay when you stay
CA $130
per night
Oct 26 - Oct 27
7/10 Good! (1,000 reviews)
"Clean comfortable room with a comfortable bed. I didn’t like the smell of whatever cleaning product they used, it was a bit bit strong let the kind you used to cover up something. Was this recently a smoking hotel? Also I missed an cycle in the fitness center, although the machines that were there ..."
Reviewed on Oct 20, 2026
Keene Elm City Hotel, an Ascend Collection Hotel
175 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
CA $178
per night
Oct 26 - Oct 27
8.6/10 Excellent! (1,002 reviews)
"Good location. Well appointed room. Clean, updated. Comp breakfast was okay. TV was outdated but WiFi was strong."
Reviewed on Oct 22, 2026
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 vacation package cost?
Starting from just CA $1,084, a vacation 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 vacation 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 fulfill those vacation dreams.
What are the top hotels in Cheshire County?
For hotels in Harrisville with cozy 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 vacation?
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 traveling 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 vacation 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 vacation package?
We get that the universe can throw the odd curveball. If you've booked a Cheshire County vacation 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 coffeehouses and its festivals while you're in the area.
Historic Main Street
9.2/10 (107 reviews)
Find out about the history of Keene when you spend time at Historic Main Street. Visit the area's shops, or simply enjoy its restaurants.
Photo by Ed Gaffny
Cathedral of the Pines
10.0/10 (2 reviews)
You can spend an afternoon browsing the exhibits at Cathedral of the Pines during your travels in Rindge. Take in the musical theater and mountain views in the area.
Colonial Theatre
8.4/10 (36 reviews)
You can make plans for a show at Colonial Theatre during your trip to Keene. Experience the festivals or attend a sporting event in this family-friendly area.
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.
Shattuck Golf Course
9.0/10 (4 reviews)
Enjoy a round of golf in Jaffrey at Shattuck Golf Course. Take in the musical theater and mountain views in the area.
Brentwood Golf Course
8.8/10 (13 reviews)
Enjoy a round of golf in Keene at Brentwood Golf Course. Discover the coffeehouses and festivals in this family-friendly area.
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.
What to do in Cheshire County
Mindful Forest Escape: Rebalance, reflect and connect
CA $133
per adult
Colonial Flintlock Musket Experience
CA $180
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.
