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
Sat, Aug 30 - Mon, Sep 1
MCO
Orlando Intl.
BDL
Bradley Intl.
$89 Roundtrip, found 1 day ago
$89
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Aug 30 from Orlando Intl. to Bradley Intl., returning Mon, Sep 1, priced at $89 found 1 day ago
Breeze Airways
Sat, Aug 30 - Sun, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$93 Roundtrip, just found
$93
Roundtrip
just found
Select Breeze Airways flight, departing Sat, Aug 30 from Orlando Intl. to Bradley Intl., returning Sun, Aug 31, priced at $93 just found
Frontier Airlines
Wed, Aug 13 - Sat, Aug 16
TPA
Tampa Intl.
BOS
Logan Intl.
$97 Roundtrip, found 1 day ago
$97
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Aug 13 from Tampa Intl. to Logan Intl., returning Sat, Aug 16, priced at $97 found 1 day ago
Spirit Airlines
Sat, Aug 30 - Sun, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$100 Roundtrip, just found
$100
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Aug 30 from Orlando Intl. to Bradley Intl., returning Sun, Aug 31, priced at $100 just found
Breeze Airways
Wed, Oct 22 - Wed, Oct 22
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$102 Roundtrip, found 13 hours ago
$102
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Wed, Oct 22 from Orlando Intl. to Portsmouth Intl., returning Wed, Oct 22, priced at $102 found 13 hours ago
Spirit Airlines
Mon, Aug 25 - Mon, Aug 25
MCO
Orlando Intl.
BOS
Logan Intl.
$115 Roundtrip, found 13 hours ago
$115
Roundtrip
found 13 hours ago
Select Spirit Airlines flight, departing Mon, Aug 25 from Orlando Intl. to Logan Intl., returning Mon, Aug 25, priced at $115 found 13 hours ago
Breeze Airways
Fri, Sep 5 - Mon, Sep 8
TPA
Tampa Intl.
PVD
T.F. Green
$117 Roundtrip, found 4 hours ago
$117
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Fri, Sep 5 from Tampa Intl. to T.F. Green, returning Mon, Sep 8, priced at $117 found 4 hours ago
Breeze Airways
Wed, Aug 6 - Wed, Aug 13
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$130 Roundtrip, found 1 day ago
$130
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Aug 6 from Orlando Intl. to Manchester-Boston Regional, returning Wed, Aug 13, priced at $130 found 1 day ago
Breeze Airways
Tue, Aug 26 - Sat, Aug 30
MCO
Orlando Intl.
PVD
T.F. Green
$132 Roundtrip, found 2 hours ago
$132
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Tue, Aug 26 from Orlando Intl. to T.F. Green, returning Sat, Aug 30, priced at $132 found 2 hours ago
Breeze Airways
Fri, Oct 24 - Mon, Oct 27
TPA
Tampa Intl.
BDL
Bradley Intl.
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Oct 24 from Tampa Intl. to Bradley Intl., returning Mon, Oct 27, priced at $137 found 1 day ago
JetBlue Airways
Sat, Aug 30 - Sun, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$137 Roundtrip, just found
$137
Roundtrip
just found
Select JetBlue Airways flight, departing Sat, Aug 30 from Orlando Intl. to Bradley Intl., returning Sun, Aug 31, priced at $137 just found
Delta
Wed, Sep 10 - Tue, Sep 16
TPA
Tampa Intl.
BOS
Logan Intl.
$140 Roundtrip, found 17 hours ago
$140
Roundtrip
found 17 hours ago
Select Delta flight, departing Wed, Sep 10 from Tampa Intl. to Logan Intl., returning Tue, Sep 16, priced at $140 found 17 hours ago
American Airlines
Wed, Sep 3 - Thu, Sep 4
MCO
Orlando Intl.
ALB
Albany Intl.
$143 Roundtrip, found 17 hours ago
$143
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Wed, Sep 3 from Orlando Intl. to Albany Intl., returning Thu, Sep 4, priced at $143 found 17 hours ago
American Airlines
Tue, Aug 19 - Wed, Aug 20
MCO
Orlando Intl.
ORH
Worcester Regional
$181 Roundtrip, found 4 days ago
$181
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Aug 19 from Orlando Intl. to Worcester Regional, returning Wed, Aug 20, priced at $181 found 4 days ago
Delta
Mon, Aug 18 - Fri, Aug 22
TPA
Tampa Intl.
ALB
Albany Intl.
$218 Roundtrip, found 9 hours ago
$218
Roundtrip
found 9 hours ago
Select Delta flight, departing Mon, Aug 18 from Tampa Intl. to Albany Intl., returning Fri, Aug 22, priced at $218 found 9 hours ago
American Airlines
Tue, Aug 12 - Sun, Aug 17
TPA
Tampa Intl.
MHT
Manchester-Boston Regional
$248 Roundtrip, found 5 days ago
$248
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Aug 12 from Tampa Intl. to Manchester-Boston Regional, returning Sun, Aug 17, priced at $248 found 5 days ago

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

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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

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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

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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

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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

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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

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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

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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

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Best Western Plus Keene Hotel
See all 415 properties in Winchester
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.