Search Cheap Flights to
Winchester

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Winchester Flights as Low as $89

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

Frontier Airlines
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American Airlines

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.

Frequently Asked Questions About flights to Winchester

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.

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 August, 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 16 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 $89, 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 $89 right now, why wait?

Winchester Flight Information
Destination airport
Bradley Intl.
Destination airport IATA code
BDL
Roundtrip price
$98

Last Minute Hotel Deals in Winchester

The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road, Gardner, MA
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 ...
8.6/10 Excellent! (1,013 reviews)
"I reached out to this property a couple days in advance. Because I was going to be arriving quite late, and wanted to make sure that check in at that time of night was alright. I also inquired about a late check out. The property management responded to me within 24 hours and were able to to accommodate ..."

Reviewed on Jul 25, 2025

The Colonial Hotel
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
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 ...
6.6/10 (1,006 reviews)
"Lovely property. Staff is amazing. Room clean, spacious"

Reviewed on Jul 23, 2025

Colonial Motel And Spa
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
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 ...
8/10 Very Good! (852 reviews)
"The peoplw were nice The room was clean For the price upgrades are needed"

Reviewed on Jul 20, 2025

Hampton Inn Brattleboro
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street, Brattleboro, VT
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. ...
8.4/10 Very Good! (761 reviews)
Comfortable and central Location
"The room was ok. The a/c was too cold and was unable to control because the vent was too high up on the wall to reach. Cleaning the room had to be arranged at a certain period of time. Its location was central to Brattleboro right near the Brattleboro art museum and some restaurants. However a lot ..."

Reviewed on Jul 22, 2025

Latchis Hotel
Keene Elm City Hotel, Ascend Hotel Collection

Keene Elm City Hotel, Ascend Hotel Collection

2.5 out of 5
175 Key Rd, Keene, NH
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 ...
8.2/10 Very Good! (863 reviews)
"Dillon, your front desk associate was amazing. Easy to work with and extremely accommodating. A real asset to the hotel."

Reviewed on Jul 26, 2025

Keene Elm City Hotel, Ascend Hotel Collection
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road, Brattleboro, VT
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (660 reviews)
"Not a luxury hotel, but fair prices. Mainly we liked the staff--friendly and REALLY helpful"

Reviewed on Jul 20, 2025

Comfort Inn & Suites Brattleboro I-91
The Putney Inn

The Putney Inn

2.5 out of 5
57 Putney Landing Rd, Putney, VT
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 ...
8.4/10 Very Good! (1,010 reviews)
"Nice, quiet spot for a night heading up to camp. Older building but kept clean and comfortable."

Reviewed on Jul 21, 2025

The Putney Inn
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St, Keene, NH
Stay at this 3-star business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.2/10 Very Good! (1,005 reviews)
Great location
"We love staying at this place. It was very muggy outside and the air conditioner was running constantly the rooms/sheets on the beds felt damp"

Reviewed on Jul 22, 2025

Best Western Plus Keene Hotel
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.