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 €101 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
€277

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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.
8.8/10 Excellent! (1,006 reviews)
"It’s great hotel"

Reviewed on 22 Aug 2025

The Colonial Hotel
Keene Elm City Hotel, Ascend Hotel Collection

Keene Elm City Hotel, Ascend Hotel Collection

2.5 out of 5
175 Key Rd, Keene, NH
The price is €116 per night from 1 Sept to 2 Sept
€116
1 Sept - 2 Sept
includes taxes & fees
Our customers tell us that they can't get enough of the free breakfast at Keene Elm City Hotel, Ascend Hotel Collection. During your stay, you'll be within walking distance of Ashuelot River. Free WiFi in public areas, free self-parking and an indoor pool are available.
8.4/10 Very Good! (882 reviews)
"Great experience but our only issue was that the sink was outside of the bathroom in the sleeping area other than that I would definitely recommend this hotel and stay again. The hotel was spotless and the breakfast was very good for what we paid for the room, 9 out of 10 just because of the wash ..."

Reviewed on 23 Aug 2025

Keene Elm City Hotel, Ascend Hotel Collection
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! (1,003 reviews)
"My stay here was perfect for what I was looking for, just a one night stay in the area. The property is dated but the accommodations are clean and the surrounding area is extremely quiet and secluded, but the parking lot is well lit and safe. I would stay here again if I needed a short term ..."

Reviewed on 22 Aug 2025

The Putney Inn
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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 €143 per night from 26 Aug to 27 Aug
€143
26 Aug - 27 Aug
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)
"Clean, comfortable room, great breakfast & friendly staff."

Reviewed on 17 Aug 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 €112 per night from 2 Sept to 3 Sept
€112
2 Sept - 3 Sept
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! (870 reviews)
"very friendly , clean and quiet, i would for sure stay if i come this way again. room is nice, beds comfy ,bathroom nice."

Reviewed on 20 Aug 2025

Hampton Inn Brattleboro
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
The price is €131 per night from 26 Aug to 27 Aug
€131
26 Aug - 27 Aug
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 (1,003 reviews)
"Appears to house a lot of homeless."

Reviewed on 22 Aug 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.