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Winchester

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Winchester Flights as Low as $257

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

JetBlue Airways
Mon, Aug 10 - Fri, Aug 21
SAN
San Diego Intl.
BOS
Logan Intl.
$257 Roundtrip, found 5 days ago
$257
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Mon, Aug 10 from San Diego Intl. to Logan Intl., returning Fri, Aug 21, priced at $257 found 5 days ago
Delta
Mon, Aug 10 - Tue, Aug 18
SAN
San Diego Intl.
BOS
Logan Intl.
$257 Roundtrip, found 5 days ago
$257
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Aug 10 from San Diego Intl. to Logan Intl., returning Tue, Aug 18, priced at $257 found 5 days ago
United
Sat, Sep 5 - Tue, Sep 22
SAN
San Diego Intl.
ALB
Albany Intl.
$263 Roundtrip, found 1 day ago
$263
Roundtrip
found 1 day ago
Select United flight, departing Sat, Sep 5 from San Diego Intl. to Albany Intl., returning Tue, Sep 22, priced at $263 found 1 day ago
United
Wed, Aug 12 - Thu, Aug 20
SAN
San Diego Intl.
BOS
Logan Intl.
$263 Roundtrip, found 5 days ago
$263
Roundtrip
found 5 days ago
Select United flight, departing Wed, Aug 12 from San Diego Intl. to Logan Intl., returning Thu, Aug 20, priced at $263 found 5 days ago
American Airlines
Wed, Aug 12 - Thu, Aug 20
SAN
San Diego Intl.
BOS
Logan Intl.
$263 Roundtrip, found 5 days ago
$263
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Aug 12 from San Diego Intl. to Logan Intl., returning Thu, Aug 20, priced at $263 found 5 days ago
JetBlue Airways
Wed, Aug 12 - Fri, Aug 21
SAN
San Diego Intl.
BOS
Logan Intl.
$263 Roundtrip, found 5 days ago
$263
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Wed, Aug 12 from San Diego Intl. to Logan Intl., returning Fri, Aug 21, priced at $263 found 5 days ago
Alaska Airlines
Wed, Aug 12 - Thu, Aug 20
SAN
San Diego Intl.
BOS
Logan Intl.
$263 Roundtrip, found 5 days ago
$263
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Wed, Aug 12 from San Diego Intl. to Logan Intl., returning Thu, Aug 20, priced at $263 found 5 days ago
American Airlines
Sat, Sep 5 - Tue, Sep 22
SAN
San Diego Intl.
ALB
Albany Intl.
$268 Roundtrip, found 1 day ago
$268
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Sep 5 from San Diego Intl. to Albany Intl., returning Tue, Sep 22, priced at $268 found 1 day ago
Delta
Thu, Aug 20 - Mon, Aug 24
SAN
San Diego Intl.
BDL
Bradley Intl.
$288 Roundtrip, found 1 hour ago
$288
Roundtrip
found 1 hour ago
Select Delta flight, departing Thu, Aug 20 from San Diego Intl. to Bradley Intl., returning Mon, Aug 24, priced at $288 found 1 hour ago
Breeze Airways
Thu, Aug 20 - Mon, Aug 24
SAN
San Diego Intl.
BDL
Bradley Intl.
$317 Roundtrip, found 1 hour ago
$317
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Thu, Aug 20 from San Diego Intl. to Bradley Intl., returning Mon, Aug 24, priced at $317 found 1 hour ago
American Airlines
Wed, Feb 17 - Wed, Feb 24
SAN
San Diego Intl.
PVD
T.F. Green
$337 Roundtrip, found 1 day ago
$337
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Feb 17 from San Diego Intl. to T.F. Green, returning Wed, Feb 24, priced at $337 found 1 day ago
United
Sat, Sep 5 - Fri, Sep 18
CLD
McClellan-Palomar
ALB
Albany Intl.
$377 Roundtrip, found 1 day ago
$377
Roundtrip
found 1 day ago
Select United flight, departing Sat, Sep 5 from McClellan-Palomar to Albany Intl., returning Fri, Sep 18, priced at $377 found 1 day ago
American Airlines
Wed, Aug 12 - Thu, Aug 20
CLD
McClellan-Palomar
BOS
Logan Intl.
$381 Roundtrip, found 5 days ago
$381
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Aug 12 from McClellan-Palomar to Logan Intl., returning Thu, Aug 20, priced at $381 found 5 days ago
American Airlines
Mon, Sep 14 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$482 Roundtrip, found 1 day ago
$482
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $482 found 1 day ago
Sun Country Airlines
Sat, Jul 11 - Thu, Jul 16
SAN
San Diego Intl.
BOS
Logan Intl.
$636 Roundtrip, found 5 days ago
$636
Roundtrip
found 5 days ago
Select Sun Country Airlines flight, departing Sat, Jul 11 from San Diego Intl. to Logan Intl., returning Thu, Jul 16, priced at $636 found 5 days ago
American Airlines
Sat, Sep 12 - Sat, Sep 26
CLD
McClellan-Palomar
RUT
Rutland Southern Vermont Regional
$680 Roundtrip, found 2 days ago
$680
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Sep 12 from McClellan-Palomar to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $680 found 2 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 $257, 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 $257 right now, why wait?

Winchester Flight Information
Destination airport
Bradley Intl.
Destination airport IATA code
BDL
Roundtrip price
$132

Last Minute Hotel Deals in Winchester

The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road Gardner MA
Book a stay at this business-friendly hotel in Gardner. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
8.8/10 Excellent! (1,011 reviews)
"Nice place, bar & restaurant nice. Shower accessory dispensers for the shampoo & conditioner did not pump despite being almost full."

Reviewed on Jul 8, 2026

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The Colonial Hotel
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

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 ...
8.6/10 Excellent! (1,012 reviews)
"Great place to stay while visiting Keene. This hotel is close to all the amenities Keene has to offer. Our room was spacious and clean. The hotel looks as though it’s been recently updated. The breakfast was very good with lots of variety. The staff was kind. Dillion was eager to help with anything ..."

Reviewed on Jul 9, 2026

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Keene Elm City Hotel, an Ascend Collection Hotel
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St 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 ...
8.4/10 Very Good! (1,008 reviews)
"Our room was very clean and smelled wonderful we found a scent disc by the ac and made our room smell refreshed. AC was perfect and we took a to go breakfast with us to continue our vacation to Pittsburg NH . Great place to stay!! restaurant was great and we visited a few breweries while we were ..."

Reviewed on Jul 8, 2026

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Best Western Plus Keene Hotel
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. ...
8.6/10 Excellent! (925 reviews)
"This hotel was the perfect landing place from a lot of traveling. It was clean, had unique historic ambience, and walkable to the whole town. Highly recommend!"

Reviewed on Jul 9, 2026

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Latchis Hotel
Colonial Motel

Colonial Motel

3 out of 5
889 Putney Rd Brattleboro VT
Book a stay at this business-friendly motel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
5.4/10 (13 reviews)
"The bed was hard to sleep on, the outdoor pool was filled with dirt, the indoor pool/spa/massage area is dilapidated, and the continental breakfast offered the bare minimum. When using the shower, switching from tub to shower was a task in itself while the water pressure was weak"

Reviewed on Jul 6, 2026

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Colonial Motel
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 ...
8.2/10 Very Good! (1,005 reviews)
"Clean"

Reviewed on Jul 9, 2026

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Hampton Inn Brattleboro
Gardner Inn

Gardner Inn

2 out of 5
22 Pearson Blvd Gardner MA
Stay at this hotel in Gardner. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Dunn State Park and 1761 Old Mill Gift Shop are located ...
7.6/10 Good! (34 reviews)
"Hotel was nice, good location. Biggest problem is that they don't tell u they charge u 2x plus. There is a charge for being at the property and over $100 in taxes. Then for the room with another $80 in taxes. Parking is $69/ night. (Of course taxed). They have a nice handicap parking area. Very few ..."

Reviewed on Jul 7, 2026

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Gardner Inn
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
360 Viking Village Drive Guilford VT
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions ...
10/10 Exceptional! (207 reviews)
"We had an amazing stay at Viking Village resort! It is an absolute hidden gem and truly felt like a fairytale escape. The cozy wooden houses are free-standing, which gives you excellent privacy, making them perfect for either a family trip or a solo getaway. I was so pleasantly surprised to find ..."

Reviewed on Jul 6, 2026

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Vikings Villages Resort
See all 467 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.