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Hotels in Winchester

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Choose from 465 Winchester Hotel Deals

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! (1,007 reviews)
"Perfect stay"

Reviewed on Jun 8, 2026

The Colonial 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! (901 reviews)
"This truly a gem! One of two remaining historic hotels in Detroit, everything about this hotel was something special. The room was spacious and creatively decorated with a large selection of LP's in the hallway. This also included a record player. The queen size beds were extremely comfortable. The ..."

Reviewed on Jun 12, 2026

Latchis Hotel
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! (992 reviews)
"Amazing stay! Loved this place!"

Reviewed on Jun 13, 2026

Hampton Inn Brattleboro
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2 out of 5
3 Ash Brook Road 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 helpful staff in our reviews. ...
7/10 Good! (1,008 reviews)
"Great stagf.clean room just a little dated"

Reviewed on Jun 13, 2026

Days Inn by Wyndham Keene NH
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! (197 reviews)
"We loved staying here! We had everything we needed, and then some! What about amazing experience. We will definitely be back. Such wonderful and creative place to relax and feel at home."

Reviewed on Jun 9, 2026

Vikings Villages Resort
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! (1,003 reviews)
"Quiet, nice to have a quick breakfast available, didn't use pool but might next time. By"

Reviewed on Jun 13, 2026

Best Western Plus Keene Hotel
Gardner Inn

Gardner Inn

2 out of 5
22 Pearson Blvd Gardner MA
  • 44 min drive from Winchester Speedpark
Stay at this hotel in Gardner. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Dunn State Park and 1761 Old Mill Gift Shop are located ...
6/10 (37 reviews)
"Worst motel we have ever stayed in, floor was dirty, had to wear socks or shoes all the time. People were coming in and out all not long, talking in the hallway and slamming doors. Had the fire alarm go off at 230 in the morning, drunk lady or high not sure which decided to make popcorn and burned ..."

Reviewed on Jun 7, 2026

Gardner Inn
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 ...
8.6/10 Excellent! (1,002 reviews)
"Excellent basic comfortable hotel room. There is a fridge and microwave, the hotel was quiet, and the staff were courteous. Everything was very clean. Location is convenient. Highly recommended!"

Reviewed on Jun 14, 2026

The Putney Inn
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! (1,003 reviews)
"The room and common areas were clean and well maintained. The front desk staff were very friendly and helpful when we arrived, which made check-in a pleasant experience. The breakfast was good overall; however, breakfast service ended at 9:00 a.m., and by 8:30 a.m. several items had already run out ..."

Reviewed on Jun 11, 2026

Keene Elm City Hotel, an Ascend Collection Hotel
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 ...
5.2/10 (645 reviews)
"Place was absolutely nasty. There is blood on the walls if I wasn't out of state and couldn't get another motel for a decent price.I would have flipped out."

Reviewed on Jun 12, 2026

Econo Lodge Brattleboro South
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! (1,004 reviews)
"Tranquille et personnel gentils. Petit déjeuner copieux et bon."

Reviewed on Jun 10, 2026

The Covered Bridge Inn
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. ...
Hampton Inn & Suites Greenfield
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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