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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! (1,004 reviews)
Bathroom should have a safety grab bar in the shower as well as hooks for towels.

Reviewed on Apr 5, 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 (1,002 reviews)
Older motel style not fancy. Good hot tub in pool area. Ok for overnight on a budget.

Reviewed on Apr 6, 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! (956 reviews)
Nice

Reviewed on Mar 29, 2026

Hampton Inn Brattleboro
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road Brattleboro VT
  • 19 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 helpful staff in our reviews. ...
8.6/10 Excellent! (791 reviews)
Good value.

Reviewed on Mar 21, 2026

Comfort Inn & Suites Brattleboro I-91
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! (181 reviews)
Peaceful location. Great home base for day trips.

Reviewed on Apr 7, 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! (1,002 reviews)
Nice place

Reviewed on Apr 5, 2026

Best Western Plus Keene Hotel
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)
Nice

Reviewed on Mar 24, 2026

Keene Elm City Hotel, an Ascend Collection Hotel
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road Brattleboro VT
  • 18 min drive from Winchester Speedpark
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the breakfast and the helpful staff in our reviews. ...
7.6/10 Good! (1,002 reviews)
The rrooms were clean, shower was great. Hallways dark, parking lot not to much lighting. There is no breakfast just coffee.

Reviewed on Mar 29, 2026

The Covered Bridge 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 ...
8.4/10 Very Good! (1,001 reviews)
Very disappointing. This hotel was rated very good an 8.4 but it was far from it. It is very dated and it was dirty and smelled musty. The lamp shades were stained and the lamps were rusty and old. There was mould and dirt all around the window and baseboards. I do NOT recommend this hotel.

Reviewed on Apr 7, 2026

The Putney Inn
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 out of 5
100 Chickering Drive 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 ...
8.8/10 Excellent! (1,000 reviews)
Very pleasant stay! Room was clean staff friendly and breakfast hearty.

Reviewed on Apr 3, 2026

Holiday Inn Express Hotel & Suites Brattleboro by IHG
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! (861 reviews)
If you love retro/vintage/history/ quiet and pet friendly this place is wonderful for a short stay and lowkey weekend. So many cool local businesses and delicious food. We went for a show at the stone church- walking distance from hotel! And everything we could have needed was easily accessible. ...

Reviewed on Mar 30, 2026

Latchis Hotel
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! (902 reviews)
A lot of ski racers go there. It will be nice to have a ski tuning room instead of having people sharpen and wax their skis in the rooms or parking lot.

Reviewed on Mar 28, 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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