Cheshire County Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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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

FlightsFlightsHotelsHotels

Jaffrey

Jaffrey
FlightsFlightsHotelsHotels

Dublin

Dublin

Top Cheshire County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Exeter

Hampton Inn & Suites Exeter

2.5 out of 5
Price was CA $1,485, price is now CA $1,477 per person
CA $1,477
per person
Jul 24 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Saskatoon (YXE) to Manchester (MHT)
9.4/10 Exceptional! (1,006 reviews)
Check in was a breeze. Our suite had more than enough space for a family of four and a baby. Rooms were clean, staff was very responsive, and we enjoyed the amentities.

Reviewed on May 30, 2026

Exeter Inn

Exeter Inn

3.5 out of 5
Price was CA $1,693, price is now CA $1,575 per person
CA $1,575
per person
Jul 24 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Saskatoon (YXE) to Manchester (MHT)
9/10 Wonderful! (1,001 reviews)
So quiet. Great sleeping. Yay. Continental breakfast was good, but nobody refilled anything. Plates were all out. Disappointing that the restaurant is closed

Reviewed on May 26, 2026

Cheshire County Hotel Deals

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 CA $166 per night from Jun 10 to Jun 11
CA $166
CA $180 total
Jun 10 - Jun 11
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
"Was decent"

Reviewed on Jun 6, 2026

Best Western Plus Keene Hotel
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2 out of 5
3 Ash Brook Road Keene NH
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Jun 24 to Jun 25
CA $135
CA $147 total
Jun 24 - Jun 25
includes taxes & fees
7/10 Good! (1,002 reviews)
"Average at best- very dated and so noisy throughout the night. Couple lights didn’t work, definitely no frills, but if you can suck it up for one night, it’ll do."

Reviewed on May 31, 2026

Days Inn by Wyndham Keene NH
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 CA $146 per night from Jun 8 to Jun 9
CA $146
CA $159 total
Jun 8 - Jun 9
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"Very clean spacious room. Quiet. Staff friendly and helpful. Breakfast buffet was ample and good choices."

Reviewed on May 31, 2026

Keene Elm City Hotel, an Ascend Collection Hotel
See all 2,035 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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Cheshire County vacation package cost?
Starting from just CA $1,477, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.