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Hotels in Winchester

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The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road Gardner MA
  • 44 min drive from Winchester Speedpark
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! (1,001 reviews)
A hidden gem! The check-in was quick, the room was clean & spacious, comfortable bed, the restaurant and bar were also perfect; located right on property and had delicious drinks, a large bar, friendly bartender and waitstaff, a breakfast buffet... just 20 minutes to Fitchburg State, less than 10 ...

Reviewed on Apr 25, 2026

The Colonial Hotel
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd Brattleboro VT
  • 18 min drive from Winchester Speedpark
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 (1,001 reviews)
Awesome and clean and quiet love the staff

Reviewed on Apr 14, 2026

Colonial Motel And Spa
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
  • 19 min drive from Winchester Speedpark
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! (967 reviews)
We were well taken care of the whole time. Just a great all around experience

Reviewed on Apr 28, 2026

Hampton Inn Brattleboro
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
360 Viking Village Drive Guilford VT
  • 17 min drive from Winchester Speedpark
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! (184 reviews)
Place was amazing. Can’t wait to come back.

Reviewed on Apr 26, 2026

Vikings Villages Resort
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
  • 20 min drive from Winchester Speedpark
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 ...
8.6/10 Excellent! (1,000 reviews)
Clean room. Quiet. Black out shade

Reviewed on Apr 26, 2026

Keene Elm City Hotel, an Ascend Collection Hotel
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
  • 20 min drive from Winchester Speedpark
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! (1,000 reviews)
Staff were very helpful

Reviewed on Apr 24, 2026

Best Western Plus Keene Hotel
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
  • 15 min drive from Winchester Speedpark
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. ...
8.6/10 Excellent! (871 reviews)
I enjoyed my stay at the Latchis very much. It was my first time there since 2018 and hope to make a return trip again very soon!

Reviewed on Apr 27, 2026

Latchis Hotel
The Putney Inn

The Putney Inn

2.5 out of 5
57 Putney Landing Rd Putney VT
  • 28 min drive from Winchester Speedpark
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! (1,000 reviews)
Very friendly staff (owner). Older roadside motel type property but very convenient for Landmark College and very clean. Definitely would stay again when visiting our kiddo at school.

Reviewed on Apr 26, 2026

The Putney Inn
Econo Lodge Brattleboro South

Econo Lodge Brattleboro South

2 out of 5
515 Canal St Brattleboro VT
  • 14 min drive from Winchester Speedpark
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 (632 reviews)
Room had holes in the wall, no cover on the lamp shade. Only one employee doing everything. Pizza place across the street had great food

Reviewed on Apr 17, 2026

Econo Lodge Brattleboro South
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

2.5 out of 5
184 Shelburne Rd Greenfield MA
  • 39 min drive from Winchester Speedpark
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! (908 reviews)
The staff is excellent. Rooms are roomy and clean. Breakfast is very good! The grounds around the hotel and the parking area could be cleaner (littered) and groomed better.

Reviewed on Apr 26, 2026

Hampton Inn & Suites Greenfield
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road Brattleboro VT
  • 18 min drive from Winchester Speedpark
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! (1,000 reviews)
When we arrived at the hotel, the area was indeed full of homeless people. We decided not to stay, canceled our reservation, and left. We contacted Expedia, and they reached out to the hotel and processed a refund for us.

Reviewed on Apr 20, 2026

The Covered Bridge Inn
Four Columns Inn

Four Columns Inn

4 out of 5
21 West Street Newfane VT
  • 37 min drive from Winchester Speedpark
Stay at this B&B in Newfane. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Moore Free Library and Rock River Preserve are located ...
9.8/10 Exceptional! (34 reviews)
Clean and the feel of our room was like a cabin and very welcoming but one star off for people and detritus splayed out in the reception

Reviewed on Apr 26, 2026

Four Columns Inn
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.

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