Search Cheap Flights to
Winchester

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Winchester Flights as Low as $247

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

Alaska Airlines
Tue, May 6 - Wed, May 7
SEA
Seattle - Tacoma Intl.
BOS
Logan Intl.
$247 Roundtrip, found 6 days ago
$247
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Tue, May 6 from Seattle - Tacoma Intl. to Logan Intl., returning Wed, May 7, priced at $247 found 6 days ago
Delta
Sun, May 25 - Wed, May 28
SEA
Seattle - Tacoma Intl.
BOS
Logan Intl.
$247 Roundtrip, found 5 days ago
$247
Roundtrip
found 5 days ago
Select Delta flight, departing Sun, May 25 from Seattle - Tacoma Intl. to Logan Intl., returning Wed, May 28, priced at $247 found 5 days ago
Alaska Airlines
Fri, May 9 - Wed, May 14
SEA
Seattle - Tacoma Intl.
BOS
Logan Intl.
$251 Roundtrip, found 6 days ago
$251
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Fri, May 9 from Seattle - Tacoma Intl. to Logan Intl., returning Wed, May 14, priced at $251 found 6 days ago
American Airlines
Tue, May 13 - Mon, May 19
MEM
Memphis Intl.
BOS
Logan Intl.
$257 Roundtrip, found 6 days ago
$257
Roundtrip
found 6 days ago
Select American Airlines flight, departing Tue, May 13 from Memphis Intl. to Logan Intl., returning Mon, May 19, priced at $257 found 6 days ago
Alaska Airlines
Tue, May 27 - Wed, May 28
SEA
Seattle - Tacoma Intl.
BOS
Logan Intl.
$261 Roundtrip, found 5 days ago
$261
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Tue, May 27 from Seattle - Tacoma Intl. to Logan Intl., returning Wed, May 28, priced at $261 found 5 days ago
JetBlue Airways
Wed, May 28 - Sat, May 31
SEA
Seattle - Tacoma Intl.
BOS
Logan Intl.
$261 Roundtrip, found 5 days ago
$261
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Wed, May 28 from Seattle - Tacoma Intl. to Logan Intl., returning Sat, May 31, priced at $261 found 5 days ago
United
Tue, May 13 - Mon, May 19
MEM
Memphis Intl.
BOS
Logan Intl.
$262 Roundtrip, found 6 days ago
$262
Roundtrip
found 6 days ago
Select United flight, departing Tue, May 13 from Memphis Intl. to Logan Intl., returning Mon, May 19, priced at $262 found 6 days ago
JetBlue Airways
Sat, May 31 - Tue, Jun 3
SEA
Seattle - Tacoma Intl.
BOS
Logan Intl.
$267 Roundtrip, found 4 days ago
$267
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Sat, May 31 from Seattle - Tacoma Intl. to Logan Intl., returning Tue, Jun 3, priced at $267 found 4 days ago
Delta
Wed, May 7 - Sat, May 10
MEM
Memphis Intl.
PVD
T.F. Green
$283 Roundtrip, found 5 days ago
$283
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, May 7 from Memphis Intl. to T.F. Green, returning Sat, May 10, priced at $283 found 5 days ago
American Airlines
Sat, May 31 - Tue, Jun 3
SEA
Seattle - Tacoma Intl.
BOS
Logan Intl.
$286 Roundtrip, found 4 days ago
$286
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, May 31 from Seattle - Tacoma Intl. to Logan Intl., returning Tue, Jun 3, priced at $286 found 4 days ago
Bargain Flight
Tue, May 20 - Wed, May 28
SEA
Seattle - Tacoma Intl.
MHT
Manchester-Boston Regional
$289 Roundtrip, found 1 day ago
$289
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, May 20 from Seattle - Tacoma Intl. to Manchester-Boston Regional, returning Wed, May 28, priced at $289 found 1 day ago
Spirit Airlines
Tue, Jul 29 - Wed, Jul 30
MEM
Memphis Intl.
BOS
Logan Intl.
$293 Roundtrip, found 1 day ago
$293
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Jul 29 from Memphis Intl. to Logan Intl., returning Wed, Jul 30, priced at $293 found 1 day ago
Delta
Tue, May 20 - Wed, May 28
SEA
Seattle - Tacoma Intl.
PVD
T.F. Green
$312 Roundtrip, found 1 day ago
$312
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, May 20 from Seattle - Tacoma Intl. to T.F. Green, returning Wed, May 28, priced at $312 found 1 day ago
American Airlines
Thu, Jul 31 - Sat, Aug 2
MEM
Memphis Intl.
MHT
Manchester-Boston Regional
$352 Roundtrip, found 1 day ago
$352
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Jul 31 from Memphis Intl. to Manchester-Boston Regional, returning Sat, Aug 2, priced at $352 found 1 day ago
Delta
Fri, Jun 20 - Tue, Jun 24
SEA
Seattle - Tacoma Intl.
ALB
Albany Intl.
$421 Roundtrip, found 3 days ago
$421
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Jun 20 from Seattle - Tacoma Intl. to Albany Intl., returning Tue, Jun 24, priced at $421 found 3 days ago
Alaska Airlines
Wed, May 28 - Sat, May 31
PAE
Seattle Paine Field Intl. Airport
BOS
Logan Intl.
$577 Roundtrip, found 5 days ago
$577
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Wed, May 28 from Seattle Paine Field Intl. Airport to Logan Intl., returning Sat, May 31, priced at $577 found 5 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 May, 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 15 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 $247, 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 $247 right now, why wait?

Winchester Flight Information
Destination airport
Logan Intl.
Destination airport IATA code
BOS
Roundtrip price
$187

Last Minute Hotel Deals in Winchester

The Colonial Hotel
The Colonial Hotel
3 out of 5
625 Betty Spring Road, Gardner, MA
The price is $156 per night from Apr 23 to Apr 24
$156
includes taxes & fees
Apr 23 - Apr 24
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! (999 reviews)
"Front desk staff was super welcoming and friendly. Great onsite restaurant that served some good food after we got back from an all day volley ball tournament. Would recommend and stay here again for sure!"

Reviewed on Apr 21, 2025

The Colonial Hotel
Hampton Inn Brattleboro
Hampton Inn Brattleboro
2.5 out of 5
1378 Putney Road, Brattleboro, VT
The price is $117 per night from Apr 29 to Apr 30
$117
includes taxes & fees
Apr 29 - Apr 30
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! (814 reviews)
Will stay there again
"Robert the guest service person was extremely professional and friendly when we checked in. The room was clean. The breakfast was adequate. Had an issue hooking up to the WiFI - also the pool wasn’t available- we did tell the front desk in the morning that the tub was not draining. We hadn’t brought ..."

Reviewed on Apr 8, 2025

Hampton Inn Brattleboro
Colonial Motel And Spa
Colonial Motel And Spa
3 out of 5
889 Putney Rd, Brattleboro, VT
The price is $120 per night from Apr 23 to Apr 24
$120
includes taxes & fees
Apr 23 - Apr 24
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 ...
6.8/10 (1,001 reviews)
"A little steep on nightly accommodation pricing considering the shape things are in which is "in disrepair". Staff was excellent, room okay. I would consider staying again but only if you are negotiable on the nightly rate."

Reviewed on Apr 20, 2025

Colonial Motel And Spa
The Putney Inn
The Putney Inn
2.5 out of 5
57 Putney Landing Rd, Putney, VT
The price is $102 per night from Apr 23 to Apr 24
$102
includes taxes & fees
Apr 23 - Apr 24
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 ...
8.2/10 Very Good! (1,000 reviews)
Good, affordable option close to I-91
"Basic, affordable motel conveniently located off I-91. It’s dated and nothing fancy, but the service is friendly, rooms are spacious, comfortable, and have a fridge and microwave and coffee maker. A basic continental breakfast is included. Everything we needed for our short stay."

Reviewed on Apr 15, 2025

The Putney Inn
Courtyard by Marriott Keene Downtown
Courtyard by Marriott Keene Downtown
3 out of 5
75 Railroad St, Keene, NH
The price is $161 per night from Apr 27 to Apr 28
$161
includes taxes & fees
Apr 27 - Apr 28
Stay at this 3-star business-friendly hotel in Keene. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (1,002 reviews)
"Did the trick: clean, good location near downtown. Easy parking."

Reviewed on Apr 20, 2025

Courtyard by Marriott Keene Downtown
Comfort Inn & Suites Brattleboro I-91
Comfort Inn & Suites Brattleboro I-91
2.5 out of 5
1186 Putney Road, Brattleboro, VT
The price is $119 per night from Apr 28 to Apr 29
$119
includes taxes & fees
Apr 28 - Apr 29
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! (618 reviews)
"All nice"

Reviewed on Apr 5, 2025

Comfort Inn & Suites Brattleboro I-91
Hampton Inn & Suites Greenfield
Hampton Inn & Suites Greenfield
2.5 out of 5
184 Shelburne Rd, Greenfield, MA
The price is $170 per night from Apr 29 to Apr 30
$170
includes taxes & fees
Apr 29 - Apr 30
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! (789 reviews)
"Exactly what we expected"

Reviewed on Apr 11, 2025

Hampton Inn & Suites Greenfield
Latchis Hotel
Latchis Hotel
2.5 out of 5
50 Main Street, Brattleboro, VT
The price is $153 per night from Apr 23 to Apr 24
$153
includes taxes & fees
Apr 23 - Apr 24
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! (726 reviews)
"The ambience of the Latchis makes it a favorite place to stay. I’ve stayed there many times on business trips and have never been disappointed."

Reviewed on Apr 13, 2025

Latchis Hotel
See all 400 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.