Cheap Vacations in Cheshire County

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Cheshire County vacations

Price found within the past 48 hours. Click for updated prices.
Deerfield Valley Inn

Deerfield Valley Inn

2 out of 5
Price was $737, price is now $642 per person
$642
per person
Oct 1 - Oct 4
found 3 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was $939, price is now $765 per person
$765
per person
Oct 10 - Oct 15
found 19 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
Clock Tower Base Area
Price was $1,130, price is now $934 per person
$934
per person
Oct 10 - Oct 15
found 19 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Mount Snow Lodging by Vail Resorts

Mount Snow Lodging by Vail Resorts

3 out of 5
Price was $1,041, price is now $867 per person
$867
per person
Oct 10 - Oct 15
found 19 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
Price was $869, price is now $734 per person
$734
per person
Oct 10 - Oct 15
found 19 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Mountain Lodge at Okemo, A Vail Resorts Property

Mountain Lodge at Okemo, A Vail Resorts Property

3 out of 5
Clock Tower Base Area
Price was $885, price is now $748 per person
$748
per person
Oct 10 - Oct 15
found 19 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
1846 Inn and Tavern

1846 Inn and Tavern

3 out of 5
Price was $1,154, price is now $980 per person
$980
per person
Oct 10 - Oct 15
found 19 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $970, price is now $830 per person
$830
per person
Oct 8 - Oct 12
found 1 hour ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
White River Inn and Suites

White River Inn and Suites

2.5 out of 5
Price was $1,058, price is now $919 per person
$919
per person
Oct 10 - Oct 15
found 19 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Manchester (MHT)
Chalet 239

Chalet 239

2 out of 5
Price was $863, price is now $760 per person
$760
per person
Oct 10 - Oct 15
found 19 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)

3-night Cheshire County vacations

Price found within the past 48 hours. Click for updated prices.
Exeter Inn

Exeter Inn

3.5 out of 5
Price was $531, price is now $408 per person
$408
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Miami (MIA) to Manchester (MHT)
Deerfield Valley Inn

Deerfield Valley Inn

2 out of 5
Price was $737, price is now $642 per person
$642
per person
Oct 1 - Oct 4
found 3 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
1846 Inn and Tavern

1846 Inn and Tavern

3 out of 5
Price was $864, price is now $768 per person
$768
per person
Oct 1 - Oct 4
found 3 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Hampton Inn & Suites Exeter

Hampton Inn & Suites Exeter

2.5 out of 5
Price was $590, price is now $530 per person
$530
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Miami (MIA) to Manchester (MHT)
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Price was $797, price is now $717 per person
$717
per person
Oct 1 - Oct 4
found 3 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Mount Snow Lodging by Vail Resorts

Mount Snow Lodging by Vail Resorts

3 out of 5
Price was $828, price is now $757 per person
$757
per person
Oct 1 - Oct 4
found 3 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Black Mountain Inn

Black Mountain Inn

2 out of 5
Price was $742, price is now $683 per person
$683
per person
Oct 1 - Oct 4
found 3 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Mountain Lodge at Okemo, A Vail Resorts Property

Mountain Lodge at Okemo, A Vail Resorts Property

3 out of 5
Price was $761, price is now $703 per person
$703
per person
Oct 1 - Oct 4
found 3 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Colonial Motel

Colonial Motel

3 out of 5
Price was $613, price is now $574 per person
$574
per person
Oct 1 - Oct 4
found 3 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Doveberry Inn

Doveberry Inn

2 out of 5
Price was $704, price is now $682 per person
$682
per person
Oct 1 - Oct 4
found 3 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
Price was $868, price is now $849 per person
$849
per person
Oct 1 - Oct 4
found 3 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 out of 5
Price was $998, price is now $983 per person
$983
per person
Oct 1 - Oct 4
found 3 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)

4-night Cheshire County vacations

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

Colonial Motel

3 out of 5
Price was $673, price is now $632 per person
$632
per person
Oct 1 - Oct 5
found 1 hour ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
White River Inn and Suites

White River Inn and Suites

2.5 out of 5
Price was $1,212, price is now $1,011 per person
$1,011
per person
Oct 1 - Oct 5
found 1 hour ago
Roundtrip non-stop flight included
Miami (MIA) to Manchester (MHT)
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $970, price is now $830 per person
$830
per person
Oct 8 - Oct 12
found 1 hour ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
1846 Inn and Tavern

1846 Inn and Tavern

3 out of 5
Price was $1,012, price is now $901 per person
$901
per person
Oct 1 - Oct 5
found 1 hour ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Okemo Mountain Lodging by Vail Resorts

Okemo Mountain Lodging by Vail Resorts

3.5 out of 5
Price was $1,314, price is now $1,174 per person
$1,174
per person
Oct 8 - Oct 12
found 1 hour ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Price was $906, price is now $815 per person
$815
per person
Oct 1 - Oct 5
found 1 hour ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
Price was $885, price is now $818 per person
$818
per person
Oct 1 - Oct 5
found 1 hour ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Mountain Lodge at Okemo, A Vail Resorts Property

Mountain Lodge at Okemo, A Vail Resorts Property

3 out of 5
Price was $866, price is now $802 per person
$802
per person
Oct 1 - Oct 5
found 1 hour ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
The Hartness House

The Hartness House

3 out of 5
Price was $1,277, price is now $1,184 per person
$1,184
per person
Oct 8 - Oct 12
found 1 hour ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Black Mountain Inn

Black Mountain Inn

2 out of 5
Price was $832, price is now $772 per person
$772
per person
Oct 1 - Oct 5
found 1 hour ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Doveberry Inn

Doveberry Inn

2 out of 5
Price was $800, price is now $773 per person
$773
per person
Oct 1 - Oct 5
found 1 hour ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

3 out of 5
Price was $780, price is now $755 per person
$755
per person
Oct 1 - Oct 5
found 1 hour ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)

5-night Cheshire County vacations

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

Colonial Motel

3 out of 5
Price was $664, price is now $599 per person
$599
per person
Oct 10 - Oct 15
found 19 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Price was $939, price is now $765 per person
$765
per person
Oct 10 - Oct 15
found 19 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
Price was $1,130, price is now $934 per person
$934
per person
Oct 10 - Oct 15
found 19 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Mount Snow Lodging by Vail Resorts

Mount Snow Lodging by Vail Resorts

3 out of 5
Price was $1,041, price is now $867 per person
$867
per person
Oct 10 - Oct 15
found 19 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
Price was $869, price is now $734 per person
$734
per person
Oct 10 - Oct 15
found 19 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Mountain Lodge at Okemo, A Vail Resorts Property

Mountain Lodge at Okemo, A Vail Resorts Property

3 out of 5
Price was $885, price is now $748 per person
$748
per person
Oct 10 - Oct 15
found 19 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
1846 Inn and Tavern

1846 Inn and Tavern

3 out of 5
Price was $1,154, price is now $980 per person
$980
per person
Oct 10 - Oct 15
found 19 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
White River Inn and Suites

White River Inn and Suites

2.5 out of 5
Price was $1,058, price is now $919 per person
$919
per person
Oct 10 - Oct 15
found 19 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Manchester (MHT)
Chalet 239

Chalet 239

2 out of 5
Price was $863, price is now $760 per person
$760
per person
Oct 10 - Oct 15
found 19 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 out of 5
Price was $1,259, price is now $1,161 per person
$1,161
per person
Oct 10 - Oct 15
found 19 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Black Mountain Inn

Black Mountain Inn

2 out of 5
Price was $837, price is now $784 per person
$784
per person
Oct 10 - Oct 15
found 19 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
Price was $932, price is now $873 per person
$873
per person
Oct 10 - Oct 15
found 19 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)

Top places to visit in Cheshire County

A street with historic buildings, a church steeple, and autumn foliage.
FlightsFlightsHotelsHotels

Keene

Keene

Flight deals to Cheshire County

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sat, Sep 26 - Sat, Oct 3
MCO
Orlando
MHT
Manchester
$200 Roundtrip, found 1 day ago
$200
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Sep 26 from Orlando to Manchester, returning Sat, Oct 3, priced at $200 found 1 day ago
Mon, Oct 19 - Wed, Oct 21
ATL
Atlanta
ORH
Worcester
$306 Roundtrip, found 13 hours ago
$306
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Mon, Oct 19 from Atlanta to Worcester, returning Wed, Oct 21, priced at $306 found 13 hours ago
Sat, Sep 12 - Mon, Sep 14
DCA
Washington
ORH
Worcester
$332 Roundtrip, found 6 days ago
$332
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Sep 12 from Washington to Worcester, returning Mon, Sep 14, priced at $332 found 6 days ago

Top rated hotels for your Cheshire County vacation

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
1.08 mi from city center
$141 nightly
The price is $153 total per night
$153 total
Sep 2 - Sep 3
Total with taxes and fees
With a stay at Keene Elm City Hotel, an Ascend Collection Hotel in Keene, you'll be within a 5-minute drive of Cheshire Children's Museum and Historic Main Street.
Pool
Breakfast included
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
1.15 mi from city center
$149 nightly
The price is $162 total per night
$162 total
Sep 2 - Sep 3
Total with taxes and fees
Located in Keene, Best Western Plus Keene Hotel is in the suburbs, within a 5-minute drive of Cheshire Children's Museum and Keene State College.
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
1.55 mi from city center
$88 nightly
The price is $96 total per night
$96 total
Sep 3 - Sep 4
Total with taxes and fees
Located in Keene, Days Inn by Wyndham Keene NH is in a shopping district, within a 5-minute drive of Cheshire Children's Museum and Historical Society of Cheshire County.
Breakfast included
Pet friendly
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See all available properties in Cheshire County
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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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.