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

FlightsFlightsHotelsHotels

Jaffrey

Jaffrey

Top Cheshire County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Durham by IHG

Holiday Inn Express Durham by IHG

2.5 out of 5
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Manchester (MHT)
8.6/10 Excellent! (860 reviews)
I didn’t like the price! Almost $400 for a double bed for one night in early June. Highway robbery! I can get a hotel in NYC for less than that!

Reviewed on Jun. 14, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
per person
Oct 17 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8.8/10 Excellent! (772 reviews)
Decent, clean accommodations. Close to downtown. Nice views. Staff were very helpful and worked with our changing plans. Rooms on the lowest level of the River building had a good deal of moisture build-up (like a basement), so things /felt/ a little damp (nice river access, though). One room had virtually no toilet paper left, but that was quickly rectified. Would stay there again, as--on the whole--it was a good experience.

Reviewed on Jul. 28, 2025

Inn At Mount Snow

Inn At Mount Snow

2 out of 5
per person
Oct 17 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
10/10 Exceptional! (7 reviews)
The property was conveniently located near Mt. Sniw.

Reviewed on Jul. 26, 2025

Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
per person
Oct 17 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8.6/10 Excellent! (202 reviews)
I stayed in July when it was 95° and super humid so I appreciated the extra cold air conditioning! I don’t know why they put us in a room so so so far away from the main entrance but other than that long walk, everything was fine that’s super fabulous or anything just fine. The front desk didn’t really know much but we were only there for a night so we figured things out on our own. Definitely go to Trail 87 to eat when you visit here. It’s fantastic!

Reviewed on Jul. 15, 2025

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 $184 per night from Jul 30 to Jul 31
CA $184
CA $200 total
Jul 30 - Jul 31
includes taxes & fees
8.2/10 Very Good! (1,006 reviews)
Clean & Close to Keene State
"Don't judge a book by its cover. We were apprehensive upon arrival, due to exterior look of hotel. Inside it is nice & very clean. Amazing looking restaurant & bar attached, but its only open later in week. We stayed a monday-tuesday. Check in was super slow. Only one person at desk, doing his best ..."

Reviewed on Jul. 27, 2025

Best Western Plus Keene Hotel
Keene Elm City Hotel, Ascend Hotel Collection

Keene Elm City Hotel, Ascend Hotel Collection

2.5 out of 5
175 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Jul 31 to Aug 1
CA $162
CA $176 total
Jul 31 - Aug 1
includes taxes & fees
8.2/10 Very Good! (863 reviews)
"Dillon, your front desk associate was amazing. Easy to work with and extremely accommodating. A real asset to the hotel."

Reviewed on Jul. 26, 2025

Keene Elm City Hotel, Ascend Hotel Collection
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 CA $229 per night from Aug 10 to Aug 11
CA $229
CA $248 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (318 reviews)
Comfortable but not anything special
"Overall the stay was just OK. The room was clean and well equipped. The only thing not working as expected in the room was the sink stopper was broken. The free breakfast was mediocre. The front desk was understaffed but when you finally got attention it was good. The lobby microwave that I used ..."

Reviewed on Jul. 18, 2025

Hampton Inn & Suites Keene
See all 1,956 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.
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Frequently asked questions

How much does a Cheshire County vacation package cost?
Starting from just CA $1,042, 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.