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Hotels in Winchester

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Choose from 455 Winchester Hotel Deals

The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road Gardner MA
  • 50 min drive from Pisgah State Park
Book a stay at this 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! (1,000 reviews)
Friendly stadd

Reviewed on Dec 25, 2025

The Colonial Hotel
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road Brattleboro VT
  • 11 min drive from Pisgah State Park
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.6/10 Good! (1,003 reviews)
Front Desk boy was super cute, but no breakfast served. Very quiet for being such a busy street.

Reviewed on Dec 21, 2025

The Covered Bridge Inn
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road Brattleboro VT
  • 12 min drive from Pisgah State Park
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.4/10 Very Good! (753 reviews)
The room was clean and the staff was wonderful

Reviewed on Jan 2, 2026

Comfort Inn & Suites Brattleboro I-91
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
  • 12 min drive from Pisgah State Park
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the ...
8.2/10 Very Good! (931 reviews)
Good breakfast, great staff and very good location

Reviewed on Dec 29, 2025

Hampton Inn Brattleboro
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
  • 9 min drive from Pisgah State Park
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.4/10 Very Good! (843 reviews)
Comfy room!

Reviewed on Jan 4, 2026

Latchis Hotel
Econo Lodge Brattleboro

Econo Lodge Brattleboro

2 out of 5
515 Canal St Brattleboro VT
  • 9 min drive from Pisgah State Park
Stay at this motel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Vermont Marketplace and Estey Organ Museum are located ...
5.2/10 (605 reviews)
Shops nearby. Heater worked good. 0lder motel but kept up quite well.

Reviewed on Dec 15, 2025

Econo Lodge Brattleboro
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

2.5 out of 5
184 Shelburne Rd Greenfield MA
  • 43 min drive from Pisgah State Park
Book a stay at this business-friendly hotel in Greenfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (884 reviews)
very quiet

Reviewed on Dec 30, 2025

Hampton Inn & Suites Greenfield
The Putney Inn

The Putney Inn

2.5 out of 5
57 Putney Landing Rd Putney VT
  • 22 min drive from Pisgah State Park
Book a stay at this business-friendly motel in Putney. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (1,001 reviews)
Staff was courteous

Reviewed on Dec 23, 2025

The Putney Inn
Gardner Inn

Gardner Inn

2 out of 5
22 Pearson Blvd Gardner MA
  • 50 min drive from Pisgah State Park
Stay at this hotel in Gardner. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Dunn State Park and 1761 Old Mill Gift Shop are located ...
5.4/10 (18 reviews)
Clean room, comfy bed, quiet guests around my room. Staff was cordial when I checked in.

Reviewed on Oct 22, 2025

Gardner Inn
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
360 Viking Village Drive Guilford VT
  • 17 min drive from Pisgah State Park
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions ...
10/10 Exceptional! (156 reviews)
Clean room, friendly staff, great location, really unique. Exceeded our expectations

Reviewed on Jan 5, 2026

Vikings Villages Resort
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd Brattleboro VT
  • 11 min drive from Pisgah State Park
Book a stay at this spa motel in Brattleboro. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in our ...
6.8/10 (1,000 reviews)
Great location and service

Reviewed on Dec 29, 2025

Colonial Motel And Spa
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
  • 18 min drive from Pisgah State Park
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! (976 reviews)
Nice clean room, very good shower, friendly staff

Reviewed on Jan 3, 2026

Keene Elm City Hotel, an Ascend Collection Hotel
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.

Find cheap hotels in Winchester

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Frequently Asked Questions About Winchester hotels

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