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 €119 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
€165

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Featured Hotels near Winchester

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.
8.6/10 Excellent! (1,014 reviews)
"Very good hotel"

Reviewed on 16 Jul 2025

The 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 €127 per night from 27 Jul to 28 Jul
€127
27 Jul - 28 Jul
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! (654 reviews)
"It was clean & comfortable!"

Reviewed on 16 Jul 2025

Comfort Inn & Suites Brattleboro I-91
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street, Brattleboro, VT
The price is €113 per night from 20 Jul to 21 Jul
€113
20 Jul - 21 Jul
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! (757 reviews)
"Amazing building with very knowledgeable and keen staff. Bustling city Centre but delivers comfort & an experience."

Reviewed on 4 Jul 2025

Latchis Hotel
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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 €125 per night from 20 Jul to 21 Jul
€125
20 Jul - 21 Jul
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.
8.2/10 Very Good! (1,000 reviews)
"Great price, clean room, very comfortable King bed. Large TV, A/C worked perfect. Quiet. Nice love seat couch and coffee table made for convenient use plus the desk/chair for laptop use. Plenty of outlets for chargers and plug in devices like a laptop. Close to some very nice restaurants for dinner ..."

Reviewed on 14 Jul 2025

Best Western Plus Keene Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
The price is €120 per night from 17 Aug to 18 Aug
€120
17 Aug - 18 Aug
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.
8/10 Very Good! (847 reviews)
"location right off the interstate and near amenities"

Reviewed on 17 Jul 2025

Hampton Inn Brattleboro
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
The price is €93 per night from 24 Jul to 25 Jul
€93
24 Jul - 25 Jul
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.
6.6/10 (1,002 reviews)
Very good last-minute stay
"I booked this room last-minute but checkin was smooth, room was comfortable. I like that there are two restaurants in walking distance."

Reviewed on 14 Jul 2025

Colonial 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.