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Winchester

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Winchester Flights as Low as $116

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

Frontier Airlines
Tue, Jun 9 - Tue, Jun 16
ATL
Hartsfield-Jackson Atlanta Intl.
BOS
Logan Intl.
$116 Roundtrip, found 3 hours ago
$116
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Tue, Jun 9 from Hartsfield-Jackson Atlanta Intl. to Logan Intl., returning Tue, Jun 16, priced at $116 found 3 hours ago
Frontier Airlines
Wed, Aug 12 - Tue, Aug 25
ATL
Hartsfield-Jackson Atlanta Intl.
BOS
Logan Intl.
$128 Roundtrip, found 8 hours ago
$128
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Wed, Aug 12 from Hartsfield-Jackson Atlanta Intl. to Logan Intl., returning Tue, Aug 25, priced at $128 found 8 hours ago
Frontier Airlines
Tue, Jul 7 - Wed, Jul 29
ATL
Hartsfield-Jackson Atlanta Intl.
BOS
Logan Intl.
$131 Roundtrip, found 1 day ago
$131
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Jul 7 from Hartsfield-Jackson Atlanta Intl. to Logan Intl., returning Wed, Jul 29, priced at $131 found 1 day ago
Frontier Airlines
Tue, Jul 21 - Wed, Jul 29
ATL
Hartsfield-Jackson Atlanta Intl.
BOS
Logan Intl.
$138 Roundtrip, found 8 hours ago
$138
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Tue, Jul 21 from Hartsfield-Jackson Atlanta Intl. to Logan Intl., returning Wed, Jul 29, priced at $138 found 8 hours ago
Frontier Airlines
Tue, Jun 9 - Fri, Jun 12
ATL
Hartsfield-Jackson Atlanta Intl.
BOS
Logan Intl.
$145 Roundtrip, found 17 hours ago
$145
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Tue, Jun 9 from Hartsfield-Jackson Atlanta Intl. to Logan Intl., returning Fri, Jun 12, priced at $145 found 17 hours ago
Frontier Airlines
Wed, Jun 10 - Fri, Jun 12
ATL
Hartsfield-Jackson Atlanta Intl.
BOS
Logan Intl.
$147 Roundtrip, found 4 hours ago
$147
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Wed, Jun 10 from Hartsfield-Jackson Atlanta Intl. to Logan Intl., returning Fri, Jun 12, priced at $147 found 4 hours ago
Frontier Airlines
Wed, Jun 10 - Thu, Jun 18
ATL
Hartsfield-Jackson Atlanta Intl.
BOS
Logan Intl.
$148 Roundtrip, found 8 hours ago
$148
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Wed, Jun 10 from Hartsfield-Jackson Atlanta Intl. to Logan Intl., returning Thu, Jun 18, priced at $148 found 8 hours ago
Frontier Airlines
Thu, Jun 11 - Tue, Jun 16
ATL
Hartsfield-Jackson Atlanta Intl.
BOS
Logan Intl.
$153 Roundtrip, found 8 hours ago
$153
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Thu, Jun 11 from Hartsfield-Jackson Atlanta Intl. to Logan Intl., returning Tue, Jun 16, priced at $153 found 8 hours ago
Frontier Airlines
Tue, Jun 9 - Tue, Jun 16
ATL
Hartsfield-Jackson Atlanta Intl.
BOS
Logan Intl.
$156 Roundtrip, found 3 hours ago
$156
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Tue, Jun 9 from Hartsfield-Jackson Atlanta Intl. to Logan Intl., returning Tue, Jun 16, priced at $156 found 3 hours ago
American Airlines
Tue, Jun 2 - Tue, Jun 16
MKE
General Mitchell Intl.
BOS
Logan Intl.
$187 Roundtrip, found 2 days ago
$187
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Jun 2 from General Mitchell Intl. to Logan Intl., returning Tue, Jun 16, priced at $187 found 2 days ago
United
Thu, Jul 2 - Tue, Jul 7
MKE
General Mitchell Intl.
BOS
Logan Intl.
$210 Roundtrip, found 2 days ago
$210
Roundtrip
found 2 days ago
Select United flight, departing Thu, Jul 2 from General Mitchell Intl. to Logan Intl., returning Tue, Jul 7, priced at $210 found 2 days ago
JetBlue Airways
Sat, May 30 - Wed, Jun 3
MKE
General Mitchell Intl.
BOS
Logan Intl.
$212 Roundtrip, found 22 hours ago
$212
Roundtrip
found 22 hours ago
Select JetBlue Airways flight, departing Sat, May 30 from General Mitchell Intl. to Logan Intl., returning Wed, Jun 3, priced at $212 found 22 hours ago
Delta
Fri, May 29 - Wed, Jun 10
MKE
General Mitchell Intl.
BOS
Logan Intl.
$212 Roundtrip, found 22 hours ago
$212
Roundtrip
found 22 hours ago
Select Delta flight, departing Fri, May 29 from General Mitchell Intl. to Logan Intl., returning Wed, Jun 10, priced at $212 found 22 hours ago
American Airlines
Tue, Aug 11 - Tue, Aug 25
LAX
Los Angeles Intl.
BOS
Logan Intl.
$237 Roundtrip, found 6 hours ago
$237
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Tue, Aug 11 from Los Angeles Intl. to Logan Intl., returning Tue, Aug 25, priced at $237 found 6 hours ago
Alaska Airlines
Tue, May 19 - Tue, Jun 2
LAX
Los Angeles Intl.
BOS
Logan Intl.
$361 Roundtrip, found 1 day ago
$361
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Tue, May 19 from Los Angeles Intl. to Logan Intl., returning Tue, Jun 2, priced at $361 found 1 day ago
Sun Country Airlines
Mon, Aug 24 - Fri, Aug 28
LAX
Los Angeles Intl.
BOS
Logan Intl.
$548 Roundtrip, found 19 hours ago
$548
Roundtrip
found 19 hours ago
Select Sun Country Airlines flight, departing Mon, Aug 24 from Los Angeles Intl. to Logan Intl., returning Fri, Aug 28, priced at $548 found 19 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 BOS 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 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 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 Laurence G. Hanscom Field 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 $116, 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 $116 right now, why wait?

Winchester Flight Information
Destination airport
Logan Intl.
Destination airport IATA code
BOS
Roundtrip price
$116

Last Minute Hotel Deals in Winchester

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the restaurant ...
9.6/10 Exceptional! (4,345 reviews)
Everyone was so welcoming, so accommodating, so conveniently located—the highest recommendation.

Reviewed on May 15, 2026

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Seaport Hotel Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Stay at this hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in ...
9/10 Wonderful! (2,606 reviews)
Real Cool Spot, Nice Amenities

Reviewed on May 15, 2026

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The Revolution Hotel
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (4,644 reviews)
This is one of the best decisions I ever made honestly!! They were all so sweet. The hotel was gorgeous and I had written a note for them before coming that it was my birthday and if I could get the highest floor. They had 22 floors and gave me the 20th and not just that but they also had a cup desert ...

Reviewed on May 13, 2026

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Omni Boston Hotel at the Seaport
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
505 Washington Street Boston MA
Book a stay at this boutique hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the restaurant and the ...
9.4/10 Exceptional! (5,057 reviews)
Great area, staff was excellent hotel is extremely clean, I love how every night they had treats like popcorn night, etc

Reviewed on May 14, 2026

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The Godfrey Hotel Boston
Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
161 Devonshire St Boston MA
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
9/10 Wonderful! (3,089 reviews)
Lovely one night stay here before heading to the airport! Loved the coffee machine with free lattes especially. Great staff, comfy bed, awesome restaurant attached to the lobby. No complaints, will stay here again!

Reviewed on May 14, 2026

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Club Quarters Hotel Faneuil Hall, Boston
Omni Parker House

Omni Parker House

4.5 out of 5
60 School St Boston MA
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff ...
9/10 Wonderful! (3,459 reviews)
Tiny room facing a decrepit old building, no sun. Got to the room and all the electrical outlets did not work. Will never stay here again.

Reviewed on May 15, 2026

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Omni Parker House
The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

2 out of 5
220 Huntington Avenue Boston MA
Stay at this hotel in Boston. Enjoy free breakfast, free WiFi, and a fitness center. Popular attractions Copley Square and Fenway Park are located nearby.
8.2/10 Very Good! (335 reviews)
It was really easy to check in and the staff were nice. In a pretty good location with subways entrances nearby. I feel like you get what you paid for. My friends and I would stay again.

Reviewed on May 15, 2026

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The Midtown Hotel MOD Collection by Sonesta
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
Stay at this hotel in Boston. Enjoy free WiFi, a 24-hour front desk, and a business center. Our guests praise the breakfast and the restaurant in our reviews. ...
9.2/10 Wonderful! (6,554 reviews)
We loved our stay here! It was in the perfect location. Clean and comfortable. The staff was so friendly and helpful! Will definitely be staying here again when I’m back in Boston.

Reviewed on May 15, 2026

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Harborside Inn Of Boston
See all 4,196 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.