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.
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 out of 5
Price was CA $1,375, price is now CA $1,291 per person
CA $1,291
per person
Nov 19 - Nov 24
found 1 day ago
Roundtrip flight included
Edmonton (YEA) to Springfield (VSF)
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Brattleboro Bowl and New England Center for Circus Arts are located nearby.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was CA $1,462, price is now CA $1,330 per person
CA $1,330
per person
Dec 19 - Dec 22
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
Stay at this B&B in Jericho. Enjoy free breakfast, free WiFi, and in-room massages. Our guests praise the breakfast in our reviews. Popular attractions Veterans' Park and Mills Riverside Park are located nearby.
Cranmore Condominium Lodging

Cranmore Condominium Lodging

3.5 out of 5
Brookside
Price was CA $1,692, price is now CA $1,549 per person
CA $1,549
per person
Nov 10 - Nov 17
found 19 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Manchester (MHT)
Book a stay at this ski condo in North Conway. Enjoy free WiFi, free parking, and mountain biking on site. Popular attractions Cranmore Mountain Resort and Conway Scenic Railway are located nearby.
Farm Road Estate

Farm Road Estate

3 out of 5
Price was CA $1,847, price is now CA $1,701 per person
CA $1,701
per person
Nov 19 - Nov 24
found 1 day ago
Roundtrip flight included
Edmonton (YEA) to Springfield (VSF)
Book a stay at this golf hotel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.
RIVENDELL HAVEN

RIVENDELL HAVEN

3 out of 5
Price was CA $2,511, price is now CA $2,331 per person
CA $2,331
per person
Nov 10 - Nov 17
found 19 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Manchester (MHT)
Stay at this lodge in Glen. Enjoy free WiFi, free parking, and a private beach. Popular attractions Story Land and Conway Scenic Railway are located nearby.

Top Cheshire County hotels deals

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 $201 per night
CA $201
CA $218 total
Nov 1 - Nov 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 Redfern Arts Center 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 $132 per night
CA $132
CA $143 total
Oct 25 - Oct 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 helpful staff in our reviews. Popular attractions Ashuelot River and Cheshire Children's Museum are located nearby.
Breakfast included
Pet-friendly
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 $169 per night
CA $169
CA $184 total
Nov 2 - Nov 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 breakfast and the helpful staff in our reviews. Popular attractions Ashuelot River and Cheshire Children's Museum 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 $216 per night
CA $216
CA $235 total
Nov 8 - Nov 9
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 $247 per night
CA $247
CA $268 total
Nov 1 - Nov 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 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 $266 per night
CA $266
CA $297 total
Oct 12 - Oct 13
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 $1,291 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.