Winchester

Travel Guide

Photo by Donny Campos
Photo by Donny Campos
The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road, Gardner, MA
Stay at this 3-star business-friendly hotel in Gardner. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
8.8/10 Excellent! (1,018 reviews)
"Fantastic 9 day stay. Room (especially the bed) was very comfortable."

Reviewed on 29 Sept 2025

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The Colonial Hotel
Econo Lodge Brattleboro

Econo Lodge Brattleboro

2 out of 5
515 Canal St, Brattleboro, VT
The price is RM286 per night from 2 Nov to 3 Nov
RM286
RM315 total
2 Nov - 3 Nov
includes taxes & fees
Stay at this motel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Vermont Marketplace and Estey Organ Museum are located ...
5.4/10 (568 reviews)
Fine room, right next to I-91 exit.
"Nothing bad about inside the room (108) -- but it was next to the hallway to the stairs to the second floor, so heard occasional foot-stomps during the evening. No other noises, though. Spatious double sinks, very unusual. Huge, firm bed. The manager has quite the beautiful flowers and vegetables ..."

Reviewed on 2 Sept 2025

Econo Lodge Brattleboro
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd, Keene, NH
The price is RM451 per night from 2 Nov to 3 Nov
RM451
RM489 total
2 Nov - 3 Nov
includes taxes & fees
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.4/10 Very Good! (907 reviews)
"The hotel was bright and welcoming. The staff was speedy and knowledgeable checking us in. You can smell how clean the sheets are. Option of firmness of pillows and 2 different toilet paper choices. The eggs at breakfast were just blah. Luckily, there were lots of other breakfast options. We would ..."

Reviewed on 29 Sept 2025

Keene Elm City Hotel, an Ascend Collection Hotel
See all 430 properties in Winchester
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.
Historic Home w/ Modern Updates on < 4 Acres

Historic Home w/ Modern Updates on < 4 Acres

3 out of 5
Royalston
Stay at this 3-star cottage in Royalston. Enjoy free parking, patios, and in-room fireplaces. Popular attractions Doane's Falls and Royalston Common Historic ...
Historic Home w/ Modern Updates on < 4 Acres
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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.

Popular places to visit

New England Sweetwater Farm & Distillery

You can take time to visit New England Sweetwater Farm & Distillery during your travels to Winchester. While you're in the area, stroll along the lakeside.

New England Sweetwater Farm & Distillery

Richmond Wildlife Manangement Area

Explore the great outdoors at Richmond Wildlife Manangement Area, a lovely green space in Richmond.

Richmond Wildlife Manangement Area

Winchester Speedpark

You can take time to visit Winchester Speedpark during your travels to Winchester. While you're in the area, stroll along the lakeside.

Winchester Speedpark

Richmond Town Hall

After visiting Richmond Town Hall, make a plan to see the other sights and activities in Richmond.

Richmond Town Hall

Loring Field

Explore the great outdoors at Loring Field, a lovely green space in Winchester. While you're in the area, stroll along the lakeside.

Loring Field

Bennett Gorge

You can take time to visit Bennett Gorge during your travels to Richmond.

Bennett Gorge