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.
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
Price was CA $1,196, price is now CA $1,004 per person
CA $1,004
per person
Aug 2 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Springfield (VSF)
Book a stay at this spa resort in West Dover. Enjoy free WiFi, a full-service spa, and 2 hot tubs. Popular attractions Mount Snow and Tumbleweed Ski Lift are located nearby.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was CA $1,319, price is now CA $1,009 per person
CA $1,009
per person
Aug 2 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Springfield (VSF)
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Latchis Theatre and Brattleboro Museum & Art Center are located nearby.
Chalet 239

Chalet 239

2 out of 5
Price was CA $1,351, price is now CA $1,144 per person
CA $1,144
per person
Jun 30 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
Stay at this motel in West Dover. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.
Mount Snow Lodging by Vail Resorts

Mount Snow Lodging by Vail Resorts

3 out of 5
Price was CA $1,495, price is now CA $1,304 per person
CA $1,304
per person
Jun 30 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
Book a stay at this ski hotel in West Dover. Enjoy free WiFi, free parking, and ski-in/ski-out access. Popular attractions Mount Snow and Ego Alley Ski Lift are located nearby.
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

3 out of 5
Price was CA $1,254, price is now CA $1,117 per person
CA $1,117
per person
Jun 30 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
Book a stay at this ski hotel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mount Snow and Heavy Metal Ski Lift 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 $212 per night
CA $212
CA $230 total
May 24 - May 25
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 $134 per night
CA $134
CA $145 total
May 25 - May 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 $193 per night
CA $193
CA $209 total
May 26 - May 27
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
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

2.5 out of 5
126 Key Rd Keene NH
Free cancellation
Reserve now, pay when you stay
The price is CA $217 per night
CA $217
CA $235 total
Jun 7 - Jun 8
includes taxes & fees
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free parking, and room service. 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 $209 per night
CA $209
CA $227 total
Jun 7 - Jun 8
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
Jun 7 - Jun 8
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
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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.

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Frequently asked questions

How much are vacation packages to Cheshire County?
CA $1,004 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.