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 €217 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
€333

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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 €218 per night from 5 Apr to 6 Apr
€218
5 Apr - 6 Apr
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! (173 reviews)
Was an amazing stay, the goats were adorable. Staff was phenominal, the cabin was amazing. Will definitely be visiting again!

Reviewed on 2 Mar 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! (1,007 reviews)
This property needs a serious update. The property looks tired. Attempted to use the fitness room and it was dirty and much of the equipment was unusable. The pool and jacuzzi were closed and looked disgusting. The common areas and room felt unclean

Reviewed on 2 Mar 2026

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 €107 per night from 8 Mar to 9 Mar
€107
8 Mar - 9 Mar
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.
8.6/10 Excellent! (777 reviews)
Goo

Reviewed on 5 Mar 2026

Opens in a new windowComfort Inn & Suites Brattleboro I-91
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Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
The price is €111 per night from 8 Mar to 9 Mar
€111
8 Mar - 9 Mar
includes taxes & fees
Our customers tell us that they can't get enough of the free breakfast at Best Western Plus Keene Hotel. During your stay, you'll be within walking distance of Keene State College. Enjoy features like free WiFi in public areas and free self-parking, plus an indoor pool. This property offers pet-friendly amenities, such as an off-lead area.
8.4/10 Very Good! (1,002 reviews)
The room was not clean. There was a big spill of some kind of oil on the nightstand. Really gross!!!

Reviewed on 23 Feb 2026

Opens in a new windowBest Western Plus Keene Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
The price is €100 per night from 16 Mar to 17 Mar
€100
16 Mar - 17 Mar
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! (948 reviews)
Staff and clean room

Reviewed on 22 Feb 2026

Opens in a new windowHampton Inn Brattleboro
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd Brattleboro VT
The price is €90 per night from 8 Mar to 9 Mar
€90
8 Mar - 9 Mar
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at Colonial Motel And Spa. During your stay, you're just a quick walk from Brattleboro Bowl. Features include free WiFi in public areas and free self-parking, plus 2 indoor pools.
6.8/10 (1,005 reviews)
There are two sections to the property. We asked to switch rooms because it smelled moldy on the one side. The other was in much better conditions, no smell, rooms very large, and clean. The pool is run by another company and they are strict about pool hours.

Reviewed on 2 Mar 2026

Opens in a new windowColonial Motel And Spa
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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.