Winchester Travel Guide

Tourist 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 business-friendly hotel in Gardner. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the restaurant and the helpful staff ...
8.8/10 Excellent! (1,002 reviews)
Very nice hotel.

Reviewed on 13 Nov 2025

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The Colonial Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
The price is ₹8,084 per night from 7 Dec to 8 Dec
₹8,084
₹8,892 total
7 Dec - 8 Dec
includes taxes & fees
Stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking and a fitness centre. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (920 reviews)
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Reviewed on 16 Nov 2025

Hampton Inn Brattleboro
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

2.5 out of 5
184 Shelburne Rd Greenfield MA
The price is ₹16,233 per night from 26 Nov to 27 Nov
₹16,233
₹18,133 total
26 Nov - 27 Nov
includes taxes & fees
Stay at this business-friendly hotel in Greenfield. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. ...
8.6/10 Excellent! (873 reviews)
Check in was great!

Reviewed on 13 Nov 2025

Hampton Inn & Suites Greenfield
See all 435 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 MA
Stay at this cottage in Royalston. Enjoy free parking, patios and air conditioning. Popular attractions Doane's Falls and Royalston Common Historic District ...
10/10 Exceptional! (2 reviews)
Great place. Enjoyed our stay. Wish it wasn’t raining so we could’ve enjoyed more of the outdoors.

Reviewed on 25 Oct 2025

Historic Home w/ Modern Updates on < 4 Acres
See all 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.

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

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

Bennett Gorge

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

Bennett Gorge

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

Richmond Wildlife Manangement Area

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

Richmond Wildlife Manangement Area

Conant Public Library

After visiting Conant Public Library, make a plan to see the other sights and activities in Winchester. While you're in the area, stroll along the lakeside.

Conant Public Library