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 Cheshire County Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Mountaineer Inn

Mountaineer Inn

2 out of 5
Price was £1,134, price is now £954 per person
£954
per person
13 Oct - 20 Oct
found 1 day ago
Return flight included
Manchester (MAN) to Springfield (VSF)
8.8/10 Excellent! (499 reviews)
Easy in and out. All transactions with this property are handled online; there was no person-to-person interaction while on the site. The rooms and bathrooms were clean, and the beds were comfortable. We'd consider this again in the future.

Reviewed on 23 Aug 2025

Deerfield Valley Inn

Deerfield Valley Inn

3 out of 5
Save 100% on your flight
Price was £2,618, price is now £1,945 per person
£1,945
per person
13 Oct - 20 Oct
found 1 day ago
Return flight included
Manchester (MAN) to Springfield (VSF)
9.6/10 Exceptional! (57 reviews)
Very authentic and comfortable.

Reviewed on 22 Aug 2025

Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
Price was £1,259, price is now £1,082 per person
£1,082
per person
13 Oct - 20 Oct
found 1 day ago
Return flight included
Manchester (MAN) to Springfield (VSF)
8.6/10 Excellent! (214 reviews)
The hotel has a 4:00 check-in which is later than most. We called a week in advance to request an early check-in as we were attending a local wedding that was called for 4:15 and we wanted to be able to get in our room to get ready as we were coming from out of state. They said they couldn’t guarantee anything, but to call back the day before. We did as they suggested and not only would they still not guarantee our request, the man at the front desk could not be less accommodating. As it turns out, we did get into our room at 3:00, but at that point we had already prepared for being unable to get into a room. The room itself was uncomfortable, and uninviting. The sheets weren’t soft or tucked fully under the mattress. Lamps and the alarm clock were left unplugged requiring us to move furniture to plug them in and a bottle of disinfectant was left in our bathroom. Needless to say we won’t be back.

Reviewed on 18 Aug 2025

Inn At Mount Snow

Inn At Mount Snow

2 out of 5
Price was £1,548, price is now £1,371 per person
£1,371
per person
13 Oct - 20 Oct
found 1 day ago
Return flight included
Manchester (MAN) to Springfield (VSF)
10/10 Exceptional! (21 reviews)
Staff was so knowledgeable and welcoming. A great stay!

Reviewed on 18 Aug 2025

Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
Price was £1,073, price is now £957 per person
£957
per person
13 Oct - 20 Oct
found 1 day ago
Return flight included
Manchester (MAN) to Springfield (VSF)
6.8/10 (1,008 reviews)
Appears to house a lot of homeless.

Reviewed on 22 Aug 2025

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

Top hotels in Cheshire County

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 £100 per night from 31 Aug to 1 Sept
£100
31 Aug - 1 Sept
includes taxes & fees
8.4/10 Very Good! (882 reviews)
"Great experience but our only issue was that the sink was outside of the bathroom in the sleeping area other than that I would definitely recommend this hotel and stay again. The hotel was spotless and the breakfast was very good for what we paid for the room, 9 out of 10 just because of the wash ..."

Reviewed on 23 Aug 2025

Keene Elm City Hotel, Ascend Hotel Collection
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 £89 per night from 1 Sept to 2 Sept
£89
1 Sept - 2 Sept
includes taxes & fees
7/10 Good! (1,000 reviews)
"Would stay again"

Reviewed on 16 Aug 2025

Days Inn by Wyndham Keene NH
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 £124 per night from 26 Aug to 27 Aug
£124
26 Aug - 27 Aug
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"Clean, comfortable room, great breakfast & friendly staff."

Reviewed on 17 Aug 2025

Best Western Plus Keene Hotel
See all 1,965 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 Holidays
All Inclusive Holidays
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Beach Holidays
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Family Friendly Holidays

Frequently asked questions

How much does a Cheshire County travel package cost?
Our Cheshire County packages, which start from just £954, are the best way to save loads of cash. Pick your preferred hotels, flights and more to create your ideal trip.
If I'm not able to travel, can I cancel my Cheshire County travel package?
If your travel plans in Cheshire County have changed, it's comforting to know that you can cancel or amend your booking. If you booked within the last 24 hours, you may be able to get a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may charge a fee. To find out more, check our Customer Service Portal.
How do I get a cheap travel package to Cheshire County?
Crafting your own Cheshire County holiday package with Expedia is one of the best ways to save. We have over 550 air carriers and 1,000,000 hotels spread across the globe. With such an awesome range to pick from, you'll have no difficulty putting together your next dream holiday.
Does Expedia offer Book Now, Pay Later Cheshire County holidays?
Your bank balance shouldn't stop you from escaping on holiday, so Expedia has worked out a solution to help. Thanks to our partnership with online lender Klarna, it's easier than ever to book a terrific getaway without exhausting your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your escape. Consider one of these flexible payment options:

  • Pay monthly holidays: Klarna has manageable monthly payment plans that work for all budget sizes, so you can have that well-deserved holiday now.
  • Pay in instalments holidays: Like the idea of paying for your holiday in multiple transactions? Then check out this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: Clicking on the "book now" button is easier with this payment option. Simply put down a small deposit on your booking and then get on your way.

What are the top hotels in Cheshire County?
Best Western Plus Keene Hotel and Courtyard by Marriott Keene Downtown know how to make their guests feel at home in Harrisville. If you also plan to explore Rindge, check out Best Western Plus Keene Hotel and Courtyard by Marriott Keene Downtown. Both are very popular with travellers.
How far in advance should I book my Cheshire County holiday?
It's hard to pick the perfect time for airfares, but we generally say the earlier, the better. Most international flights on Expedia become available up to a year in advance. If you're booking late, don't worry. Low prices occasionally appear within a few weeks of departure dates.
What does an Expedia Cheshire County travel package include?
From hotels and flights to rental cars, Expedia can help you shape a Cheshire County package that's ideal for you. Holidaying for a while? Consider a flight, rental car and hotel bundle. If you're taking a short break, a hotel and airfare deal could be what you're after. Experiences can also be added once you've made your booking. Our travel packages make it a breeze to plan and save.
What should I know before booking a Cheshire County travel package?
A travel package can be tailored to your budget and is an easy way to make your budget go further. How little or much you include is totally up to you. Hotels, rental cars and flights — decide on a combination that suits your style.
Can I choose my airline with a Cheshire County Expedia travel package?
Expedia offers access to more than 550 partner airlines worldwide, so you definitely can. Just choose your preferred air carrier and craft your ideal Cheshire County getaway.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.