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Winchester

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Winchester Flights as Low as $152

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

Frontier Airlines
Tue, Jun 9 - Wed, Jun 10
ATL
Hartsfield-Jackson Atlanta Intl.
BOS
Logan Intl.
$152 Roundtrip, found 3 days ago
$152
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Jun 9 from Hartsfield-Jackson Atlanta Intl. to Logan Intl., returning Wed, Jun 10, priced at $152 found 3 days ago
Frontier Airlines
Tue, Jun 9 - Tue, Jun 23
ATL
Hartsfield-Jackson Atlanta Intl.
BOS
Logan Intl.
$177 Roundtrip, found 2 days ago
$177
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Jun 9 from Hartsfield-Jackson Atlanta Intl. to Logan Intl., returning Tue, Jun 23, priced at $177 found 2 days ago
United
Tue, Aug 4 - Wed, Aug 12
ATL
Hartsfield-Jackson Atlanta Intl.
BOS
Logan Intl.
$212 Roundtrip, found 2 days ago
$212
Roundtrip
found 2 days ago
Select United flight, departing Tue, Aug 4 from Hartsfield-Jackson Atlanta Intl. to Logan Intl., returning Wed, Aug 12, priced at $212 found 2 days ago
American Airlines
Wed, Aug 12 - Wed, Aug 26
ATL
Hartsfield-Jackson Atlanta Intl.
BOS
Logan Intl.
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Aug 12 from Hartsfield-Jackson Atlanta Intl. to Logan Intl., returning Wed, Aug 26, priced at $217 found 1 day ago
JetBlue Airways
Tue, Jun 9 - Wed, Jun 10
ATL
Hartsfield-Jackson Atlanta Intl.
BOS
Logan Intl.
$222 Roundtrip, found 3 days ago
$222
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Jun 9 from Hartsfield-Jackson Atlanta Intl. to Logan Intl., returning Wed, Jun 10, priced at $222 found 3 days ago
Frontier Airlines
Wed, Jul 29 - Wed, Aug 19
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$240 Roundtrip, found 1 day ago
$240
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Jul 29 from Hartsfield-Jackson Atlanta Intl. to Bradley Intl., returning Wed, Aug 19, priced at $240 found 1 day ago
Delta
Wed, Aug 12 - Wed, Aug 26
ATL
Hartsfield-Jackson Atlanta Intl.
BOS
Logan Intl.
$267 Roundtrip, found 1 day ago
$267
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Aug 12 from Hartsfield-Jackson Atlanta Intl. to Logan Intl., returning Wed, Aug 26, priced at $267 found 1 day ago
Bargain Flight
Tue, Aug 25 - Wed, Sep 2
PHX
Sky Harbor Intl.
BOS
Logan Intl.
$288 Roundtrip, found 4 days ago
$288
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Tue, Aug 25 from Sky Harbor Intl. to Logan Intl., returning Wed, Sep 2, priced at $288 found 4 days ago
Bargain Flight
Tue, Jun 2 - Tue, Jun 16
ATL
Hartsfield-Jackson Atlanta Intl.
MHT
Manchester-Boston Regional
$295 Roundtrip, found 4 hours ago
$295
Roundtrip
found 4 hours ago
Select Bargain Flight flight, departing Tue, Jun 2 from Hartsfield-Jackson Atlanta Intl. to Manchester-Boston Regional, returning Tue, Jun 16, priced at $295 found 4 hours ago
JetBlue Airways
Tue, Aug 11 - Tue, Aug 25
ATL
Hartsfield-Jackson Atlanta Intl.
PVD
T.F. Green
$335 Roundtrip, found 3 days ago
$335
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Aug 11 from Hartsfield-Jackson Atlanta Intl. to T.F. Green, returning Tue, Aug 25, priced at $335 found 3 days ago
JetBlue Airways
Tue, Jul 14 - Tue, Jul 28
ATL
Hartsfield-Jackson Atlanta Intl.
ALB
Albany Intl.
$343 Roundtrip, found 6 days ago
$343
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Tue, Jul 14 from Hartsfield-Jackson Atlanta Intl. to Albany Intl., returning Tue, Jul 28, priced at $343 found 6 days ago
Delta
Thu, Jul 16 - Thu, Jul 23
PHX
Sky Harbor Intl.
BDL
Bradley Intl.
$345 Roundtrip, found 3 hours ago
$345
Roundtrip
found 3 hours ago
Select Delta flight, departing Thu, Jul 16 from Sky Harbor Intl. to Bradley Intl., returning Thu, Jul 23, priced at $345 found 3 hours ago
Alaska Airlines
Tue, Oct 20 - Wed, Nov 11
PHX
Sky Harbor Intl.
BOS
Logan Intl.
$351 Roundtrip, just found
$351
Roundtrip
just found
Select Alaska Airlines flight, departing Tue, Oct 20 from Sky Harbor Intl. to Logan Intl., returning Wed, Nov 11, priced at $351 just found
Breeze Airways
Thu, Oct 15 - Mon, Oct 19
PHX
Sky Harbor Intl.
BDL
Bradley Intl.
$432 Roundtrip, found 1 day ago
$432
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Oct 15 from Sky Harbor Intl. to Bradley Intl., returning Mon, Oct 19, priced at $432 found 1 day ago
United
Tue, Jul 7 - Thu, Jul 9
PHX
Sky Harbor Intl.
ALB
Albany Intl.
$439 Roundtrip, found 3 hours ago
$439
Roundtrip
found 3 hours ago
Select United flight, departing Tue, Jul 7 from Sky Harbor Intl. to Albany Intl., returning Thu, Jul 9, priced at $439 found 3 hours ago
Sun Country Airlines
Sun, May 31 - Fri, Jun 5
PHX
Sky Harbor Intl.
BDL
Bradley Intl.
$544 Roundtrip, found 1 day ago
$544
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Sun, May 31 from Sky Harbor Intl. to Bradley Intl., returning Fri, Jun 5, priced at $544 found 1 day 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 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 14 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 $152, 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 $152 right now, why wait?

Winchester Flight Information
Destination airport
Bradley Intl.
Destination airport IATA code
BDL
Roundtrip price
$143

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! (1,004 reviews)
"One suggestion would be to have coffee and tea available in the lobby. Other than that it was a nice stay."

Reviewed on May 25, 2026

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The Colonial 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 ...
8.2/10 Very Good! (980 reviews)
"Easy to get to. Basic amenities. Breakfast ok…"

Reviewed on May 22, 2026

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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. ...
8.6/10 Excellent! (885 reviews)
"The staff was great very helpful!!! Very understanding and had patience with me. Thanks Peace&patience JRC"

Reviewed on May 25, 2026

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Latchis Hotel
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd Brattleboro VT
Book a stay at this 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 ...
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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
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! (1,003 reviews)
"This place is a dump Pretty much a motel Looks and smells dirty The curtains in bathroom are filthy The tub is disgusting and black No pride in the upkeep of this property Dirty walls and carpets Exposed outlets Didn’t even clean our room I only stayed here because Hampton inn was sold out NEVERRR ..."

Reviewed on May 25, 2026

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Best Western Plus Keene Hotel
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2 out of 5
3 Ash Brook Road Keene NH
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
7/10 Good! (1,002 reviews)
"The hotel is visibly aging and requires both upgrades and basic maintenance. During my stay, multiple room fixtures did not function properly, including the sink and the toilet. Additionally, the breakfast bar was sparse; there were no juices or standard breakfast beverages available, leaving water ..."

Reviewed on May 25, 2026

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Days Inn by Wyndham Keene NH
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! (195 reviews)
"Super clean, staff very nice, cabins had kitchens and fireplace that were very nice, but the coffee maker did not work. Nice you could spend just one night but really once there you are going to want to spend at least two. No amenities like pool or gym but they did have the worlds smallest sheep. ..."

Reviewed on May 19, 2026

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Vikings Villages Resort
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! (1,005 reviews)
"Everything was OK, except for the coffee they use (Folgers) It was almosty undrinkable;bitter and harsh."

Reviewed on May 25, 2026

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Keene Elm City Hotel, an Ascend Collection Hotel
See all 468 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.