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Hotels in Winchester

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Choose from 469 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! (1,001 reviews)
"It was ok"

Reviewed on Jun 17, 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! (905 reviews)
"Love the historical aspects of this place."

Reviewed on Jun 17, 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! (995 reviews)
"Room clean if just a bit worn. Sheets had better days. Helpful staff."

Reviewed on Jun 15, 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! (1,000 reviews)
"Our room smelled like mold, likely because there was a lot of rotting and what looked like mold in the bathroom. The carpets themselves needed to be replaced as they had a musty smell likely from too much moisture or spills. This hotel really needs a lot of work to make it feel inviting. Any fixes ..."

Reviewed on Jun 16, 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! (198 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
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 (40 reviews)
"Staff was friendly, anxious to help, and readily available. Lots of shops-eateries, gas stations, grocery, and others nearby. The price was outstanding and fulfilled my needs for 4 days and 3 nights. Very quiet and the parking was not visible from the road. Very easy access back to the highway."

Reviewed on Jun 18, 2026

Gardner Inn
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! (1,002 reviews)
"Checked in and hour after booking, room was perfect my needs, breakfast was delicious."

Reviewed on Jun 16, 2026

Best Western Plus Keene 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 ...
8.6/10 Excellent! (1,001 reviews)
"No complaints would go back"

Reviewed on Jun 19, 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! (1,002 reviews)
"The safety latch on my room door was broken. The staff was very helpful and found a different room for me and got a cart and offered to help. The new room had a dried coffee spill near the fridge and the body wash in the shower was empty or broken- minor inconvenience. Overall a nice stay at a great ..."

Reviewed on Jun 17, 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 (647 reviews)
"Ended up not staying at this place. It looked dirty and not kept. There was an awful smell, blankets were not on one of the beds, only a sheet. Didn’t feel safe."

Reviewed on Jun 15, 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! (1,000 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. ...
8.6/10 Excellent! (917 reviews)
"The room was clean , the staff was amazing and the breakfast was great!!!"

Reviewed on Jun 14, 2026

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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