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Winchester

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Winchester Flights as Low as $93

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Cheap Flights to Winchester

Fall in love at first flight with your vacation to Winchester by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Winchester on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Winchester, the good times start rolling. So buckle up, you’re in for a fun ride.

Just the right flight

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Winchester with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the EEN airport.

Frequently Asked Questions About flights to Winchester

What is the cheapest month to fly to Winchester?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Winchester are in June, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Winchester?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 13 to choose from for your flight to Winchester.

What airport is best to fly into Winchester?

When you’re planning your trip to Winchester, convenience is the name of the game. Luckily, Winchester Hartness State Airport is nearby so you can deplane and get going on checking off everything on your Winchester must-do list.

How much are flights to Winchester?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Winchester on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $93, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Winchester?

The trick to saving a stack of cash on your flight to Winchester? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $93 right now, why wait?

Can I fly to Winchester right now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to  right now?” When it’s time to book your flight, be sure to check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

Winchester Flight Information
Destination airport
Bradley Intl.
Destination airport IATA code
BDL
Roundtrip price
$92

Last Minute Hotel Deals in Winchester

The Covered Bridge Inn
The Covered Bridge Inn
2.5 out of 5
1043 Putney Road, Brattleboro, VT
The price is $85 per night from May 30 to May 31
$85
per night
May 30 - May 31
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.2/10 Very Good! (1,004 reviews)
"This was a clean comfortable place to stay ."

Reviewed on May 27, 2024

The Covered Bridge Inn
Colonial Motel And Spa
Colonial Motel And Spa
3 out of 5
889 Putney Rd, Brattleboro, VT
The price is $98 per night from May 30 to May 31
$98
per night
May 30 - May 31
Stay at this 3-star spa motel in Brattleboro. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in our ...
6.8/10 (1,001 reviews)
"Nice motel, room was in good condition and clean. I didn’t try the pool."

Reviewed on May 25, 2024

Colonial Motel And Spa
The Colonial Hotel
The Colonial Hotel
3 out of 5
625 Betty Spring Road, Gardner, MA
The price is $160 per night from Jun 2 to Jun 3
$160
per night
Jun 2 - Jun 3
Stay at this 3-star business-friendly hotel in Gardner. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
8.4/10 Very Good! (833 reviews)
"Great property!"

Reviewed on May 25, 2024

The Colonial Hotel
Hampton Inn Brattleboro
Hampton Inn Brattleboro
2.5 out of 5
1378 Putney Road, Brattleboro, VT
The price is $152 per night from Jun 17 to Jun 18
$152
per night
Jun 17 - Jun 18
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the ...
8.2/10 Very Good! (902 reviews)
"Good value, close to town"

Reviewed on May 23, 2024

Hampton Inn Brattleboro
Days Inn by Wyndham Keene NH
Days Inn by Wyndham Keene NH
2 out of 5
3 Ash Brook Road, Keene, NH
The price is $94 per night from Jun 2 to Jun 3
$94
per night
Jun 2 - Jun 3
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular ...
7.2/10 Good! (876 reviews)
"Clean, quiet and lovely breakfast options"

Reviewed on May 19, 2024

Days Inn by Wyndham Keene NH
The Putney Inn
The Putney Inn
2.5 out of 5
57 Putney Landing Rd, Putney, VT
The price is $142 per night from Jun 3 to Jun 4
$142
per night
Jun 3 - Jun 4
Book a stay at this business-friendly motel in Putney. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
8.2/10 Very Good! (908 reviews)
"Easy, quick check in, friendly staff. Some noise from neighbors to be expected. Very clean, good sleep, pleasant stay. Would return."

Reviewed on May 21, 2024

The Putney Inn
Latchis Hotel
Latchis Hotel
2.5 out of 5
50 Main Street, Brattleboro, VT
The price is $140 per night from Jun 9 to Jun 10
$140
per night
Jun 9 - Jun 10
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Latchis Theatre and Brattleboro Museum & Art Center ...
8.2/10 Very Good! (566 reviews)
"It was a great experience. But extremely pricey for the quality of the room."

Reviewed on May 13, 2024

Latchis Hotel
Courtyard by Marriott Keene Downtown
Courtyard by Marriott Keene Downtown
3 out of 5
75 Railroad St, Keene, NH
The price is $146 per night from Jun 27 to Jun 28
$146
per night
Jun 27 - Jun 28
Stay at this 3-star business-friendly hotel in Keene. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (904 reviews)
"NA"

Reviewed on May 23, 2024

Courtyard by Marriott Keene Downtown
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.