Cheap flights from Winchester

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Cheap round-trip flights from Winchester

The lowest prices found within the past 7 days from Winchester to were for one-way flights and CHF 138 for return flights, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, 9 Feb - Wed, 18 Feb
BOS
Logan Intl.
TPA
Tampa Intl.
CHF 138 Return, found 5 days ago
CHF 138
Return
found 5 days ago
Select Delta flight, departing Mon, 9 Feb from Logan Intl. to Tampa Intl., returning Wed, 18 Feb, priced at CHF 138 found 5 days ago
Mon, 9 Feb - Wed, 18 Feb
BOS
Logan Intl.
TPA
Tampa Intl.
CHF 139 Return, found 5 days ago
CHF 139
Return
found 5 days ago
Select JetBlue Airways flight, departing Mon, 9 Feb from Logan Intl. to Tampa Intl., returning Wed, 18 Feb, priced at CHF 139 found 5 days ago
Thu, 22 Jan - Thu, 29 Jan
PSM
Portsmouth Intl.
MCO
Orlando Intl.
CHF 141 Return, found 3 days ago
CHF 141
Return
found 3 days ago
Select Breeze Airways flight, departing Thu, 22 Jan from Portsmouth Intl. to Orlando Intl., returning Thu, 29 Jan, priced at CHF 141 found 3 days ago
Mon, 9 Feb - Wed, 18 Feb
BOS
Logan Intl.
TPA
Tampa Intl.
CHF 146 Return, found 5 days ago
CHF 146
Return
found 5 days ago
Select Delta flight, departing Mon, 9 Feb from Logan Intl. to Tampa Intl., returning Wed, 18 Feb, priced at CHF 146 found 5 days ago
Thu, 22 Jan - Thu, 29 Jan
PSM
Portsmouth Intl.
MCO
Orlando Intl.
CHF 148 Return, found 3 days ago
CHF 148
Return
found 3 days ago
Select Breeze Airways flight, departing Thu, 22 Jan from Portsmouth Intl. to Orlando Intl., returning Thu, 29 Jan, priced at CHF 148 found 3 days ago
Thu, 22 Jan - Thu, 29 Jan
PSM
Portsmouth Intl.
MCO
Orlando Intl.
CHF 149 Return, found 3 days ago
CHF 149
Return
found 3 days ago
Select Breeze Airways flight, departing Thu, 22 Jan from Portsmouth Intl. to Orlando Intl., returning Thu, 29 Jan, priced at CHF 149 found 3 days ago
Fri, 30 Jan - Tue, 3 Feb
BOS
Logan Intl.
MIA
Miami Intl.
CHF 150 Return, found 4 days ago
CHF 150
Return
found 4 days ago
Select Delta flight, departing Fri, 30 Jan from Logan Intl. to Miami Intl., returning Tue, 3 Feb, priced at CHF 150 found 4 days ago
Mon, 9 Feb - Wed, 18 Feb
BOS
Logan Intl.
TPA
Tampa Intl.
CHF 155 Return, found 5 days ago
CHF 155
Return
found 5 days ago
Select JetBlue Airways flight, departing Mon, 9 Feb from Logan Intl. to Tampa Intl., returning Wed, 18 Feb, priced at CHF 155 found 5 days ago
Thu, 22 Jan - Thu, 29 Jan
BOS
Logan Intl.
MCO
Orlando Intl.
CHF 206 Return, found 5 days ago
CHF 206
Return
found 5 days ago
Select Delta flight, departing Thu, 22 Jan from Logan Intl. to Orlando Intl., returning Thu, 29 Jan, priced at CHF 206 found 5 days ago
Mon, 9 Feb - Wed, 18 Feb
BOS
Logan Intl.
TPA
Tampa Intl.
CHF 212 Return, found 5 days ago
CHF 212
Return
found 5 days ago
Select American Airlines flight, departing Mon, 9 Feb from Logan Intl. to Tampa Intl., returning Wed, 18 Feb, priced at CHF 212 found 5 days ago
Mon, 9 Feb - Wed, 18 Feb
BOS
Logan Intl.
TPA
Tampa Intl.
CHF 225 Return, found 5 days ago
CHF 225
Return
found 5 days ago
Select United flight, departing Mon, 9 Feb from Logan Intl. to Tampa Intl., returning Wed, 18 Feb, priced at CHF 225 found 5 days ago
Wed, 18 Mar - Sat, 21 Mar
BOS
Logan Intl.
LAS
Harry Reid Intl.
CHF 270 Return, found 5 days ago
CHF 270
Return
found 5 days ago
Select JetBlue Airways flight, departing Wed, 18 Mar from Logan Intl. to Harry Reid Intl., returning Sat, 21 Mar, priced at CHF 270 found 5 days ago
Winchester Flight Information
Origin airport IATA code
BOS
Return price
CHF 149

Are you looking for a cheap flight from Winchester? Take a look on our website Ebookers as we are offering many low priced flights from Winchester

Flights from Winchester- Ebookers: low priced flights from Winchester

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Low priced flights from Winchester on Ebookers

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Featured Hotels near Winchester

Vikings Villages Resort

Vikings Villages Resort

2 out of 5
360 Viking Village Drive Guilford VT
The price is CHF 194 per night from 15 Feb to 16 Feb
CHF 194
15 Feb - 16 Feb
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at Vikings Villages Resort. During your stay, you'll be close to Sweet Pond State Park. You'll find features such as free WiFi in public areas and free self-parking, plus a rooftop terrace.
10/10 Exceptional! (158 reviews)
Perfect accommodation. Rare combo of rustic feel and both clean and dry. Beds just how we like it. Kitchen very well equipped. Perfect for 4 people. Nice bathroom. Hot shower. Grounds perfectly described as Viking village. Staff very welcoming. Nice fire at the fire pit and the sheep are sure to ...

Reviewed on 18 Jan 2026

Opens in a new windowVikings Villages Resort
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! (1,001 reviews)
Friendly staff, nice hotel, Great hot water & water pressure.

Reviewed on 15 Jan 2026

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Opens in a new windowThe Colonial Hotel
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 CHF 117 per night from 29 Jan to 30 Jan
CHF 117
29 Jan - 30 Jan
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! (758 reviews)
Great staff

Reviewed on 5 Jan 2026

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

The Putney Inn

2.5 out of 5
57 Putney Landing Rd Putney VT
Our customers tell us that they can't get enough of the helpful staff at The Putney Inn. 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! (1,005 reviews)
Not fancy but a great place to stay. Owners are very nice and accommodating. I’ve been a customer for 25 years

Reviewed on 20 Jan 2026

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Opens in a new windowThe Putney Inn
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
The price is CHF 115 per night from 21 Jan to 22 Jan
CHF 115
21 Jan - 22 Jan
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at Latchis Hotel. During your stay, you're just a quick walk from Latchis Theatre. Free WiFi in public areas, free self-parking and a restaurant are available.
8.4/10 Very Good! (843 reviews)
Comfy room!

Reviewed on 4 Jan 2026

Opens in a new windowLatchis Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
The price is CHF 129 per night from 27 Jan to 28 Jan
CHF 129
27 Jan - 28 Jan
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! (936 reviews)
As always, Hampton Inn are great. I think I’m reliable, super comfortable, good breakfast. What makes this location stand out was the really outstanding customer service. Everyone was so helpful and engaging and funny! Which always helps. So, we’ll definitely be back.

Reviewed on 17 Jan 2026

Opens in a new windowHampton Inn Brattleboro
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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.

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