Cheap flights from Winchester

Many airlines offer flexible change policies

Earn BONUS+ rewards on top of your airline points

Enjoy exclusive promotions on the ebookers app!

Cheap round-trip flights from Winchester

The lowest prices found within the past 7 days from Winchester to were for one-way flights and €178 for return flights, for the period specified. Prices and availability are subject to change. Additional terms apply.

Winchester Flight Information
Origin airport IATA code
BOS
Return price
€747

Your cheap flight from Winchester is available right now.

Visit us now at Ebookers to choose from lots of cheap flights leaving Winchester or our last minute air tickets from Winchester at unbeatable prices, specially chosen for those who want the best deal possible. Ebookers continuously compares and updates the choice of air tickets available from Winchester, offered by more than 400 airlines worldwide. Ebookers works 24/7 to find the best deals so that our clients don’t have to waste their valuable time. Wherever you are going, you will find your perfect combination for a fantastic holiday at a budget price right here with our extensive flights database and helpful information; star ratings, reviews, maps and more… Many discount flights with a departure from Winchester and last minute flights from Winchester are available at Ebookers to help you organise your flights the way you want them at a price you can afford. Come and prepare your perfect holiday now at Ebookers.

Fancy a break from Winchester? Book your flight in advance from Winchester!

Thinking about getting away for a while and leaving from Winchester? Visit Ebookers and discover our selection of inexpensive Winchester flights and air tickets from Winchester at unbelievable prices with a great choice of airlines - over 400 in fact. We give excellent service at an affordable price. For a great weekend away from Winchester, visit to Ebookers where we have many available flights departing Winchester on special offer. Check out our deals and find a flight leaving Winchester at a price you never imagined. These special Ebookers offers aren’t just about cheap flights. We have over 95,000 hotels worldwide in our database, so why not stay in a Winchester hotel and start or end your break in style? Combine your choice of flight, hotel and car rental from our vast, reliable database to create your perfect holiday or dream weekend at a discounted price with Ebookers. Don’t wait or you may be too late!

Featured Hotels near Winchester

The Inn At Crumpin Fox

The Inn At Crumpin Fox

2.5 out of 5
71 Northfield Rd Bernardston MA
The price is €126 per night from 30 Nov to 1 Dec
€126
30 Nov - 1 Dec
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at The Inn At Crumpin Fox. During your stay, you'll be within walking distance of Bernardston Town Hall. Features include free WiFi in public areas and free self-parking, plus a conference centre.
9.2/10 Wonderful! (342 reviews)
Room was great, we will be back again, favorite place in the valley thus far to stay.

Reviewed on 10 Nov 2025

Opens in a new windowThe Inn At Crumpin Fox
The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road Gardner MA
Our customers tell us they can't get enough of The Colonial Hotel's great location. During your stay, you'll be within walking distance of Dunn State Park. You'll find features such as free WiFi in public areas and free self-parking, plus an indoor pool.
8.8/10 Excellent! (1,007 reviews)
Room was clean and comfortable

Reviewed on 21 Nov 2025

Opens in a new windowThe Colonial Hotel
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

2.5 out of 5
126 Key Rd Keene NH
The price is €138 per night from 23 Dec to 24 Dec
€138
23 Dec - 24 Dec
includes taxes & fees
Our customers tell us that they can't get enough of the free breakfast at Hampton Inn & Suites Keene. During your stay, you'll be within walking distance of Ashuelot River. You'll find features such as free WiFi in public areas and free self-parking, plus an indoor pool.
8.8/10 Excellent! (348 reviews)
Beautiful room. Breakdadt was good, staff very friendly

Reviewed on 19 Nov 2025

Opens in a new windowHampton Inn & Suites Keene
Save an average of 15% on thousands of hotels when you're signed in
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

2.5 out of 5
184 Shelburne Rd Greenfield MA
The price is €176 per night from 7 Dec to 8 Dec
€176
7 Dec - 8 Dec
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at Hampton Inn & Suites Greenfield. During your stay, you'll be within walking distance of Greenfield Community College. Free breakfast, free WiFi in public areas and free self-parking are available. This property offers pet-friendly amenities, such as food and water bowls.
8.6/10 Excellent! (875 reviews)
Staff was friendly, room was very nice and really appreciate the breakfast.

Reviewed on 25 Nov 2025

Opens in a new windowHampton Inn & Suites Greenfield
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 €115 per night from 7 Dec to 8 Dec
€115
7 Dec - 8 Dec
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at Comfort Inn & Suites Brattleboro I-91. During your stay, you're just a quick walk from Connecticut River. You'll find features such as free breakfast, free WiFi in public areas and free self-parking.
8.4/10 Very Good! (730 reviews)
Great convenient spot just off the highway. The room was clean and the amenities were just right.

Reviewed on 8 Nov 2025

Opens in a new windowComfort Inn & Suites Brattleboro I-91
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
The price is €136 per night from 21 Dec to 22 Dec
€136
21 Dec - 22 Dec
includes taxes & fees
Our customers tell us that they enjoy the free breakfast at Hampton Inn Brattleboro. During your stay, you'll be within walking distance of Brattleboro Bowl. Features include free WiFi in public areas and free self-parking, plus an indoor pool.
8.2/10 Very Good! (923 reviews)
Everything was very nice. I was checked in at the desk by "Jolene" who was cordial, friendly, and welcoming. The room was very clean and it was very quiet. The breakfast in the morning was excellent as was the coffee station. I do miss the little snack bag at the front desk where we could grab 'n ...

Reviewed on 20 Nov 2025

Opens in a new windowHampton Inn Brattleboro
Don't see what you're looking for?
See all available properties in Winchester
View all properties
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.