
Cheap flights from Cheshire County
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Cheap round-trip flights from Cheshire County
The lowest prices found within the past 7 days from Cheshire County to were CHF 74 for one-way flights and CHF 96 for return flights, for the period specified. Prices and availability are subject to change. Additional terms apply.
ORH
Worcester Regional
MCO
Orlando Intl.
CHF 96 Return, found 4 days ago
CHF 96
Return
found 4 days ago
ORH
Worcester Regional
MCO
Orlando Intl.
CHF 98 Return, found 6 days ago
CHF 98
Return
found 6 days ago
ORH
Worcester Regional
MCO
Orlando Intl.
CHF 99 Return, found 5 days ago
CHF 99
Return
found 5 days ago
ORH
Worcester Regional
MCO
Orlando Intl.
CHF 99 Return, found 4 days ago
CHF 99
Return
found 4 days ago
ORH
Worcester Regional
MCO
Orlando Intl.
CHF 107 Return, found 6 days ago
CHF 107
Return
found 6 days ago
ORH
Worcester Regional
MCO
Orlando Intl.
CHF 111 Return, found 4 days ago
CHF 111
Return
found 4 days ago
Origin airport IATA code | VSF |
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Featured Hotels near Cheshire County

Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.
Fitzwilliam NH
During your stay at Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond., you're just a quick walk from Sportsman Pond. Features include laundry facilities.
10/10 Exceptional! (10 reviews)
It was a lovely stay! Lake is beautiful and the house is cozy.
Reviewed on 16 Oct 2025

The Colonial Hotel
625 Betty Spring Road Gardner MA
Our customers tell us they can't get enough of The Colonial Hotel's great location. During your stay, you'll be within walking distance of Dunn State Park. You'll find features such as free WiFi in public areas and free self-parking, plus an indoor pool.
8.8/10 Excellent! (1,001 reviews)
Friendly staff, clean room, gym and poll area.
Reviewed on 4 Feb 2026

Pointe at Castle Hill Resort
2940 State Route 103 Cavendish VT
The price is CHF 150 per night from 1 Mar to 2 Mar
CHF 150
1 Mar - 2 Mar
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at Pointe at Castle Hill Resort. During your stay, you'll be close to Okemo Mountain Resort. You'll find features such as free WiFi in public areas and free self-parking, plus a full-service spa.
8.8/10 Excellent! (972 reviews)
Clean. Convenient. Nice.
Reviewed on 4 Feb 2026
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Hideaway Inn Mt.Sunapee
1403 New Hampshire Rte 103 Newbury NH
The price is CHF 115 per night from 10 Feb to 11 Feb
CHF 115
10 Feb - 11 Feb
includes taxes & fees
During your stay at Hideaway Inn Mt.Sunapee, you're just a quick walk from Mount Sunapee State Park. Features include free WiFi in public areas and free self-parking, plus an indoor pool.
8.6/10 Excellent! (104 reviews)
Staff were super friendly. Rooms were cozy. Our dog was welcome. A great experience!
Reviewed on 6 Feb 2026

Great Wolf Lodge Boston / Fitchburg, MA
150 Great Wolf Dr Fitchburg MA
The price is CHF 124 per night from 3 Mar to 4 Mar
CHF 124
3 Mar - 4 Mar
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at Great Wolf Lodge Boston / Fitchburg, MA. During your stay, you're just a quick walk from Great Wolf Lodge Waterpark. You'll find features such as 4 indoor pools, a restaurant and a poolside bar.
8.4/10 Very Good! (1,000 reviews)
.
Reviewed on 27 Jan 2026

Best Western Plus Keene Hotel
401 Winchester St Keene NH
The price is CHF 117 per night from 10 Feb to 11 Feb
CHF 117
10 Feb - 11 Feb
includes taxes & fees
Our customers tell us that they can't get enough of the free breakfast at Best Western Plus Keene Hotel. During your stay, you'll be within walking distance of Keene State College. Enjoy features like free WiFi in public areas and free self-parking, plus an indoor pool. This property offers pet-friendly amenities, such as an off-lead area.
8.2/10 Very Good! (1,003 reviews)
Spots on wall by garbage.
Reviewed on 19 Jan 2026
Don't see what you're looking for?
See all available properties in Cheshire County
View all propertiesLowest 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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