Search Cheap Flights to
Winchester

Photo by Donny Campos

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Winchester Flights as Low as $100

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

Frontier Airlines
Thu, Sep 11 - Sat, Sep 20
TPA
Tampa Intl.
BOS
Logan Intl.
$100 Roundtrip, found 17 hours ago
$100
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Thu, Sep 11 from Tampa Intl. to Logan Intl., returning Sat, Sep 20, priced at $100 found 17 hours ago
Frontier Airlines
Sat, Aug 30 - Thu, Sep 4
TPA
Tampa Intl.
BOS
Logan Intl.
$106 Roundtrip, found 10 hours ago
$106
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Sat, Aug 30 from Tampa Intl. to Logan Intl., returning Thu, Sep 4, priced at $106 found 10 hours ago
Frontier Airlines
Sun, Sep 14 - Sat, Sep 20
TPA
Tampa Intl.
BOS
Logan Intl.
$108 Roundtrip, found 17 hours ago
$108
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Sun, Sep 14 from Tampa Intl. to Logan Intl., returning Sat, Sep 20, priced at $108 found 17 hours ago
Frontier Airlines
Thu, Sep 11 - Thu, Sep 18
TPA
Tampa Intl.
BOS
Logan Intl.
$110 Roundtrip, found 17 hours ago
$110
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Thu, Sep 11 from Tampa Intl. to Logan Intl., returning Thu, Sep 18, priced at $110 found 17 hours ago
Frontier Airlines
Sun, Sep 14 - Thu, Sep 18
TPA
Tampa Intl.
BOS
Logan Intl.
$118 Roundtrip, found 17 hours ago
$118
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Sun, Sep 14 from Tampa Intl. to Logan Intl., returning Thu, Sep 18, priced at $118 found 17 hours ago
Frontier Airlines
Sat, Aug 30 - Sun, Sep 7
TPA
Tampa Intl.
BOS
Logan Intl.
$120 Roundtrip, found 10 hours ago
$120
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Sat, Aug 30 from Tampa Intl. to Logan Intl., returning Sun, Sep 7, priced at $120 found 10 hours ago
Breeze Airways
Mon, Sep 8 - Thu, Sep 11
TPA
Tampa Intl.
PVD
T.F. Green
$123 Roundtrip, found 1 day ago
$123
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Sep 8 from Tampa Intl. to T.F. Green, returning Thu, Sep 11, priced at $123 found 1 day ago
Delta
Tue, Sep 16 - Sat, Sep 20
TPA
Tampa Intl.
BOS
Logan Intl.
$137 Roundtrip, found 17 hours ago
$137
Roundtrip
found 17 hours ago
Select Delta flight, departing Tue, Sep 16 from Tampa Intl. to Logan Intl., returning Sat, Sep 20, priced at $137 found 17 hours ago
JetBlue Airways
Tue, Sep 16 - Tue, Sep 23
TPA
Tampa Intl.
BOS
Logan Intl.
$137 Roundtrip, found 17 hours ago
$137
Roundtrip
found 17 hours ago
Select JetBlue Airways flight, departing Tue, Sep 16 from Tampa Intl. to Logan Intl., returning Tue, Sep 23, priced at $137 found 17 hours ago
Breeze Airways
Fri, Sep 19 - Mon, Sep 22
TPA
Tampa Intl.
BDL
Bradley Intl.
$142 Roundtrip, found 1 day ago
$142
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Sep 19 from Tampa Intl. to Bradley Intl., returning Mon, Sep 22, priced at $142 found 1 day ago
American Airlines
Tue, Oct 28 - Mon, Nov 3
TPA
Tampa Intl.
BOS
Logan Intl.
$159 Roundtrip, found 1 day ago
$159
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Oct 28 from Tampa Intl. to Logan Intl., returning Mon, Nov 3, priced at $159 found 1 day ago
Spirit Airlines
Tue, Sep 9 - Tue, Sep 16
TPA
Tampa Intl.
BOS
Logan Intl.
$162 Roundtrip, found 1 day ago
$162
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Sep 9 from Tampa Intl. to Logan Intl., returning Tue, Sep 16, priced at $162 found 1 day ago
United
Tue, Sep 9 - Tue, Sep 16
TPA
Tampa Intl.
BOS
Logan Intl.
$172 Roundtrip, found 1 day ago
$172
Roundtrip
found 1 day ago
Select United flight, departing Tue, Sep 9 from Tampa Intl. to Logan Intl., returning Tue, Sep 16, priced at $172 found 1 day ago
American Airlines
Sat, Sep 6 - Sat, Sep 13
TPA
Tampa Intl.
MHT
Manchester-Boston Regional
$214 Roundtrip, found 4 days ago
$214
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Sep 6 from Tampa Intl. to Manchester-Boston Regional, returning Sat, Sep 13, priced at $214 found 4 days ago
Delta
Fri, Nov 7 - Mon, Nov 10
TPA
Tampa Intl.
ALB
Albany Intl.
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Nov 7 from Tampa Intl. to Albany Intl., returning Mon, Nov 10, priced at $217 found 1 day ago
JetBlue Airways
Tue, Sep 9 - Tue, Sep 16
TPA
Tampa Intl.
LEB
Lebanon Municipal
$280 Roundtrip, found 2 hours ago
$280
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Tue, Sep 9 from Tampa Intl. to Lebanon Municipal, returning Tue, Sep 16, priced at $280 found 2 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 $100, 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 $100 right now, why wait?

Winchester Flight Information
Destination airport
Logan Intl.
Destination airport IATA code
BOS
Roundtrip price
$89

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 ...
8.8/10 Excellent! (1,000 reviews)
"Stayed here years ago. The rooms haven't changed much. The rooms are pretty standard, but the lobby, staff and food are all better than most hotels. Maybe a little old school, but I love the look of the hotel. The bed was really comfortable. The event banquet food has always been wonderful. They ..."

Reviewed on Aug 12, 2025

Get rates
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 (1,001 reviews)
"The room I was given was quite impressive in size. Plenty accommodating for me and my dog. The a/c worked well, fridge was plenty cold, bed was comfortable and clean, the grounds surrounding the buildings is very nice for traveling with a dog. The front desk help was gracious and accommodating. That ..."

Reviewed on Aug 9, 2025

Get rates
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! (865 reviews)
Nice hotel option in Southern Vermont
"Great hotel to stay when traveling in Vermont. Convenient - right off of I-91, centrally located to a number of restaurants and food options. Pet-friendly hotel, we brought our furry friend and he was comfortable. Amenities were nice and clean including the pool and fitness area. Friendly staff who ..."

Reviewed on Aug 12, 2025

Get rates
Hampton Inn Brattleboro
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 ...
8.4/10 Very Good! (876 reviews)
"Hotel was very clean, and staff was extraordinarily good!"

Reviewed on Aug 10, 2025

Get rates
Keene Elm City Hotel, Ascend Hotel Collection
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! (1,002 reviews)
"The property was clean and comfortable."

Reviewed on Aug 15, 2025

Get rates
The Putney Inn
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! (773 reviews)
"I loved everything about this place. I will be back!"

Reviewed on Aug 14, 2025

Get rates
Latchis Hotel
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! (1,007 reviews)
"It was very clean. Everybody was very polite, and the lady that worked in the breakfast area every morning with the nicest lady she had everything so clean. Very happy with everything."

Reviewed on Aug 15, 2025

Get rates
Best Western Plus Keene Hotel
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! (830 reviews)
"Great place with a walkable eating option"

Reviewed on Aug 14, 2025

Get rates
Hampton Inn & Suites Greenfield
See all 411 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.