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Winchester

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Winchester Flights as Low as $107

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

Breeze Airways
Fri, Sep 5 - Mon, Sep 8
TPA
Tampa Intl.
PVD
T.F. Green
$107 Roundtrip, found 2 hours ago
$107
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Fri, Sep 5 from Tampa Intl. to T.F. Green, returning Mon, Sep 8, priced at $107 found 2 hours ago
Frontier Airlines
Tue, Aug 5 - Tue, Aug 12
TPA
Tampa Intl.
BOS
Logan Intl.
$130 Roundtrip, found 4 days ago
$130
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Aug 5 from Tampa Intl. to Logan Intl., returning Tue, Aug 12, priced at $130 found 4 days ago
Breeze Airways
Fri, Sep 19 - Mon, Sep 22
TPA
Tampa Intl.
BDL
Bradley Intl.
$137 Roundtrip, found 11 hours ago
$137
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Fri, Sep 19 from Tampa Intl. to Bradley Intl., returning Mon, Sep 22, priced at $137 found 11 hours ago
American Airlines
Mon, Sep 15 - Wed, Sep 17
DCA
Ronald Reagan Washington National
ALB
Albany Intl.
$137 Roundtrip, found 8 hours ago
$137
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Mon, Sep 15 from Ronald Reagan Washington National to Albany Intl., returning Wed, Sep 17, priced at $137 found 8 hours ago
American Airlines
Thu, Sep 18 - Tue, Sep 23
DCA
Ronald Reagan Washington National
PVD
T.F. Green
$137 Roundtrip, just found
$137
Roundtrip
just found
Select American Airlines flight, departing Thu, Sep 18 from Ronald Reagan Washington National to T.F. Green, returning Tue, Sep 23, priced at $137 just found
American Airlines
Tue, Oct 28 - Tue, Nov 4
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$137 Roundtrip, just found
$137
Roundtrip
just found
Select American Airlines flight, departing Tue, Oct 28 from Ronald Reagan Washington National to Logan Intl., returning Tue, Nov 4, priced at $137 just found
Delta
Tue, Oct 28 - Tue, Nov 4
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$137 Roundtrip, just found
$137
Roundtrip
just found
Select Delta flight, departing Tue, Oct 28 from Ronald Reagan Washington National to Logan Intl., returning Tue, Nov 4, priced at $137 just found
JetBlue Airways
Tue, Sep 9 - Tue, Sep 16
TPA
Tampa Intl.
BOS
Logan Intl.
$137 Roundtrip, found 2 hours ago
$137
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Tue, Sep 9 from Tampa Intl. to Logan Intl., returning Tue, Sep 16, priced at $137 found 2 hours ago
United
Tue, Oct 28 - Tue, Nov 4
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$157 Roundtrip, just found
$157
Roundtrip
just found
Select United flight, departing Tue, Oct 28 from Ronald Reagan Washington National to Logan Intl., returning Tue, Nov 4, priced at $157 just found
JetBlue Airways
Fri, Aug 8 - Thu, Aug 14
TPA
Tampa Intl.
MHT
Manchester-Boston Regional
$169 Roundtrip, found 1 hour ago
$169
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Fri, Aug 8 from Tampa Intl. to Manchester-Boston Regional, returning Thu, Aug 14, priced at $169 found 1 hour ago
Spirit Airlines
Thu, Jul 31 - Sat, Aug 9
TPA
Tampa Intl.
BOS
Logan Intl.
$178 Roundtrip, found 2 hours ago
$178
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Thu, Jul 31 from Tampa Intl. to Logan Intl., returning Sat, Aug 9, priced at $178 found 2 hours ago
Delta
Tue, Jul 29 - Tue, Aug 5
DCA
Ronald Reagan Washington National
ORH
Worcester Regional
$180 Roundtrip, just found
$180
Roundtrip
just found
Select Delta flight, departing Tue, Jul 29 from Ronald Reagan Washington National to Worcester Regional, returning Tue, Aug 5, priced at $180 just found
American Airlines
Fri, Aug 1 - Sun, Aug 3
DCA
Ronald Reagan Washington National
MHT
Manchester-Boston Regional
$189 Roundtrip, found 3 days ago
$189
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Aug 1 from Ronald Reagan Washington National to Manchester-Boston Regional, returning Sun, Aug 3, priced at $189 found 3 days ago
Delta
Mon, Aug 18 - Fri, Aug 22
TPA
Tampa Intl.
ALB
Albany Intl.
$213 Roundtrip, found 3 days ago
$213
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Aug 18 from Tampa Intl. to Albany Intl., returning Fri, Aug 22, priced at $213 found 3 days ago
American Airlines
Mon, Sep 8 - Mon, Sep 15
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$361 Roundtrip, just found
$361
Roundtrip
just found
Select American Airlines flight, departing Mon, Sep 8 from Ronald Reagan Washington National to Lebanon Municipal, returning Mon, Sep 15, priced at $361 just found
JetBlue Airways
Wed, Sep 10 - Tue, Sep 16
TPA
Tampa Intl.
LEB
Lebanon Municipal
$365 Roundtrip, found 11 hours ago
$365
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Wed, Sep 10 from Tampa Intl. to Lebanon Municipal, returning Tue, Sep 16, priced at $365 found 11 hours 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 September, 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 $107, 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 $107 right now, why wait?

Winchester Flight Information
Destination airport
Logan Intl.
Destination airport IATA code
BOS
Roundtrip price
$88

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! (1,002 reviews)
"We stay here every time we visit and it is always a good experience. Cherry on top is they allow dogs which is a huge help because there are not many hotels in this are much less ones that allow pets. It's always clean and a good experience. Just a warning though, the pool and hot tub always has ..."

Reviewed on Jul 4, 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 (1,002 reviews)
"We like the room. Nice and spacious. Er"

Reviewed on Jul 2, 2025

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Colonial Motel And Spa
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! (1,000 reviews)
"Nice hotel"

Reviewed on Jun 28, 2025

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Best Western Plus Keene Hotel
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! (841 reviews)
"Great for the price"

Reviewed on Jun 28, 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! (753 reviews)
A Brattleboro Gem
"It was a nice treat to find a room in a renovated Southern Vermont hotel. Brattleboro has not had an easy time, and it has a marvelous past concealed by a slightly downscale present. The hotel, the room, the management-all great!!"

Reviewed on Jul 2, 2025

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Latchis Hotel
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! (649 reviews)
"Buffer not always filled up Not always someone to the front desk 7: 10"

Reviewed on Jun 20, 2025

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Comfort Inn & Suites Brattleboro I-91
The Covered Bridge Inn
The Covered Bridge Inn
2.5 out of 5
1043 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 breakfast and the helpful ...
7.8/10 Good! (1,001 reviews)
"Nice"

Reviewed on Jun 25, 2025

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The Covered Bridge Inn
Hampton Inn & Suites Greenfield
Hampton Inn & Suites Greenfield
2.5 out of 5
184 Shelburne Rd, Greenfield, MA
Book a stay at this business-friendly hotel in Greenfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (812 reviews)
"It is the perfect location for the Green River Festival"

Reviewed on Jun 22, 2025

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Hampton Inn & Suites Greenfield
See all 416 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.