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.
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was CA $1,506, price is now CA $1,281 per person
CA $1,281
per person
Jun 3 - Jun 9
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to Springfield (VSF)
8.6/10 Excellent! (851 reviews)
No inflatable mattress offered anymore.

Reviewed on Mar 18, 2026

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was CA $1,698, price is now CA $1,420 per person
CA $1,420
per person
Jun 3 - Jun 9
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to Springfield (VSF)
8.8/10 Excellent! (918 reviews)
The Shire is in a wonderful location and I would recommend for a short stay. They are in the midst of a renovation and the rooms and exterior are nice and well kept. My only issue was that the coffee bars were not well stocked all the time with the same variety and the ice machine was not well stocked as it ran out of water to produce ice during our 2 night stay. Otherwise, the place and location is wonderful.

Reviewed on Apr 19, 2026

Holiday Inn Express Hotel & Suites White River Junction by IHG

Holiday Inn Express Hotel & Suites White River Junction by IHG

2.5 out of 5
Price was CA $1,874, price is now CA $1,595 per person
CA $1,595
per person
Jun 3 - Jun 9
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to Manchester (MHT)
8.6/10 Excellent! (1,001 reviews)
Room was a great size

Reviewed on Apr 21, 2026

White River Inn and Suites

White River Inn and Suites

2.5 out of 5
Price was CA $1,595, price is now CA $1,367 per person
CA $1,367
per person
Jun 3 - Jun 9
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to Manchester (MHT)
7/10 Good! (1,002 reviews)
Great value for the price

Reviewed on Apr 21, 2026

Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
Clock Tower Base Area
Price was CA $1,646, price is now CA $1,431 per person
CA $1,431
per person
Jun 3 - Jun 9
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to Springfield (VSF)
8.8/10 Excellent! (26 reviews)
The place was not cleaned well. The water was off we had to call the front desk. The Diswasher was fully of dishes. There was only one roll of toilet paper in the bathroom. No paper towel in the kitchen, not even one to start. The wall in the kitchen was dirty

Reviewed on Dec 1, 2025

Cheshire County Hotel Deals

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 $184 per night from Apr 23 to Apr 24
CA $184
CA $200 total
Apr 23 - Apr 24
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
I would definitely recommend this hotel. It was reasonably priced, the staff were all very friendly and helpful, the hot breakfast was very good, the room was very clean and it is pet friendly if you have a puppy!

Reviewed on Apr 20, 2026

Keene Elm City Hotel, an Ascend Collection Hotel
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 $197 per night from Apr 23 to Apr 24
CA $197
CA $213 total
Apr 23 - Apr 24
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
The room was as described and met our needs. We found it very handy to have a sliding glass door that opens directly onto the parking lot, in addition to the regular door opening to the hallway, so that we were able to bring our dog in and out without encountering any other guests. It was also handy ...

Reviewed on Apr 21, 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 $142 per night from Apr 23 to Apr 24
CA $142
CA $154 total
Apr 23 - Apr 24
includes taxes & fees
7/10 Good! (1,001 reviews)
This property was definitely on the older side and could use some renos. All of the towels in my room were stained, and the kleenex boxes left empty. I don't think one single staff member greeted me during the 3 nights I stayed there. They just sat behind the desk or walked about but never said hello ...

Reviewed on Apr 15, 2026

Days Inn by Wyndham Keene NH
See all 2,043 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 $1,281, 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.