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.
Quality Inn Merrimack - Nashua

Quality Inn Merrimack - Nashua

2.5 out of 5
Price was CA $822, price is now CA $771 per person
CA $771
per person
Oct 29 - Nov 1
found 4 hours ago
Roundtrip flight included
Ottawa (YOW) to Manchester (MHT)
Book a stay at this business-friendly hotel in Merrimack. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Merrimack Premium Outlets and Greeley Park are located nearby.
Fairfield Inn & Suites by Marriott Portsmouth Exeter

Fairfield Inn & Suites by Marriott Portsmouth Exeter

3 out of 5
Price was CA $942, price is now CA $850 per person
CA $850
per person
Oct 29 - Nov 1
found 4 hours ago
Roundtrip flight included
Ottawa (YOW) 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.
Exeter Inn

Exeter Inn

3.5 out of 5
Price was CA $868, price is now CA $794 per person
CA $794
per person
Oct 18 - Oct 21
found 8 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Manchester (MHT)
Book a stay at this business-friendly hotel in Exeter. Enjoy free breakfast, free WiFi, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Exeter Historical Society and American Independence Museum are located nearby.
Nootka Lodge

Nootka Lodge

2 out of 5
Price was CA $1,448, price is now CA $1,391 per person
CA $1,391
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Manchester (MHT)
Book a stay at this business-friendly hotel in Woodsville. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Woodsville Free Public Library and Haverhill-Bath Covered Bridge are located nearby.
Hampton Inn & Suites Manchester-Bedford

Hampton Inn & Suites Manchester-Bedford

2.5 out of 5
Price was CA $797, price is now CA $777 per person
CA $777
per person
Oct 29 - Nov 1
found 4 hours ago
Roundtrip flight included
Ottawa (YOW) to Manchester (MHT)
Book a stay at this business-friendly hotel in Bedford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Filotimo Casino and Mall of New Hampshire 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 $165 per night
CA $165
CA $179 total
Sep 1 - Sep 2
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 $133 per night
CA $133
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 $205 per night
CA $205
CA $222 total
Aug 25 - Aug 26
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.
Pool
Breakfast included
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 $209 per night
CA $209
CA $227 total
Sep 20 - Sep 21
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.
Parking included
Free WiFi
Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown

3 out of 5
30 Main Street Keene NH
Free cancellation
Reserve now, pay when you stay
The price is CA $280 per night
CA $280
CA $304 total
Sep 13 - Sep 14
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.
Breakfast included
Parking included
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 $252 per night
CA $252
CA $281 total
Aug 25 - Aug 26
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.
Pool
Restaurant
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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 $771 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.