Book Exclusive Cheshire County Vacation Packages

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Cheshire County flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Colonial Motel

Colonial Motel

3 out of 5
Price was CA $850, price is now CA $815 per person
CA $815
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
Book a stay at this business-friendly motel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Brattleboro Bowl and New England Center for Circus Arts are located nearby.
Fairfield Inn & Suites by Marriott Portsmouth Exeter

Fairfield Inn & Suites by Marriott Portsmouth Exeter

3 out of 5
Price was CA $961, price is now CA $868 per person
CA $868
per person
Oct 19 - Oct 23
found 16 hours ago
Roundtrip flight included
Toronto (YYZ) to Manchester (MHT)
Book a stay at this business-friendly hotel in Exeter. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions American Independence Museum and Exeter Historical Society are located nearby.
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
Price was CA $1,158, price is now CA $1,058 per person
CA $1,058
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
Stay at this B&B in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Bonnie's Bundles Dolls and DaVallia Art & Accents are located nearby.
The Carriage Barn Inn

The Carriage Barn Inn

3 out of 5
Price was CA $1,146, price is now CA $1,070 per person
CA $1,070
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Manchester (MHT)
Stay at this B&B in Keene. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thorne-Sagendorph Art Gallery and Redfern Arts Center are located nearby.
Holiday Inn Express Durham by IHG

Holiday Inn Express Durham by IHG

2.5 out of 5
Price was CA $929, price is now CA $875 per person
CA $875
per person
Oct 19 - Oct 23
found 16 hours ago
Roundtrip flight included
Toronto (YYZ) to Manchester (MHT)
Book a stay at this business-friendly hotel in Durham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Smith Chapel and Betty and Barney Hill Archive are located nearby.

Top Cheshire County hotels 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
Free cancellation
Reserve now, pay when you stay
The price is CA $195 per night
CA $195
CA $212 total
Aug 27 - Aug 28
includes taxes & fees
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Ashuelot River and Cheshire Children's Museum are located nearby.
Pool
Breakfast included
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2 out of 5
3 Ash Brook Road Keene NH
Free cancellation
Reserve now, pay when you stay
The price is CA $134 per night
CA $134
CA $145 total
Sep 16 - Sep 17
includes taxes & fees
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Ashuelot River and Cheshire Children's Museum are located nearby.
Breakfast included
Pet-friendly
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
Free cancellation
Reserve now, pay when you stay
The price is CA $206 per night
CA $206
CA $224 total
Aug 27 - Aug 28
includes taxes & fees
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Ashuelot River and Redfern Arts Center are located nearby.
Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

2.5 out of 5
20 Riverside Drive West Chesterfield NH
Free cancellation
The price is CA $223 per night
CA $223
CA $242 total
Sep 21 - Sep 22
includes taxes & fees
Book a stay at this business-friendly hotel in West Chesterfield. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown

3 out of 5
30 Main Street Keene NH
The price is CA $249 per night
CA $249
CA $270 total
Sep 2 - Sep 3
includes taxes & fees
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Central Square and CC&H Framing / Pepper Pete's Hot Shop are located nearby.
Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

3.5 out of 5
150 Great Wolf Dr Fitchburg MA
The price is CA $253 per night
CA $253
CA $283 total
Aug 27 - Aug 28
includes taxes & fees
Book a stay at this family-friendly resort in Fitchburg. Enjoy 4 indoor pools, free water park access, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Great Wolf Lodge Waterpark and Wachusett Brewing Company are located nearby.
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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.

Stay near popular Cheshire County attractions

A rocky field with autumn-colored trees and a mountain in the background.

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.
See properties

Photos of local treasures

Browse Cheshire County vacation photos for more inspiration

A large rock with carved faces and a river in the background.
A vintage train with 'GREEN MOUNTAIN' written on it, passing through a rural area with greenery and power lines.
A railroad crossing with a brick building in the background.
A calm river with a bridge, a forested hill, and industrial buildings in the background.
A field with grazing cattle and a sunset in the background.

Frequently asked questions

How much are vacation packages to Cheshire County?
CA $815 is all you'll need for a fantastic escape in Cheshire County. Bundle your hotel and flights into a vacation package with Travelocity and see your savings grow. With these kinds of prices, there's never been a better time to travel.
Where can I get the best vacation package deals for Cheshire County?
You'll come across a fantastic range of Cheshire County package deals on Travelocity. With as many as 400 air carriers and 1,000,000 properties worldwide, arranging your dream getaway will be a breeze.
Why should I book my Cheshire County vacation bundle with Travelocity?
You'll not only enjoy big savings, but you'll also have access to our round-the-clock support, excellent service and a Price Match Guarantee. Roam across the globe, uncover hidden gems and forge unforgettable memories — we'll take care of the little details.
Can I save on my Cheshire County car rental if I bundle it with a hotel or flight?
Bundling your bookings into a Cheshire County vacation package will certainly save you money. You can combine a flight and car; a flight, car and hotel; or a car and hotel. You won't find a better way to explore the greater Cheshire County area than from the comfort of your own rental car. You can also add tours and experiences to your Travelocity package.
Which airport is best for Cheshire County?
For passengers contemplating flying in and out of Cheshire County, the most commonly used airports are Manchester-Boston Regional Airport (MHT), Lebanon Municipal Airport (LEB) and Rutland Southern Vermont Regional Airport (RUT).
What is there to do in Cheshire County?
Cheshire County has hidden surprises around every turn, but make sure you plan a trip to Friendly Farm and Walpole Mountain View Winery during your stay. These landmarks should be on your to-do list.