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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
  • 32 min drive from Cass Pond
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! (1,002 reviews)
Great location near Wachusett Mountain, which made it very convenient for a ski trip. The rooms were very nice and the beds were comfortable, which we appreciated after a long day on the mountain. Unfortunately, we were extremely disappointed that the hot tub was not working and the pool was freezing ...

Reviewed on Mar 15, 2026

The Colonial Hotel
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd Brattleboro VT
  • 29 min drive from Cass Pond
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 (1,003 reviews)
It was good to have pool option after a ski day

Reviewed on Mar 10, 2026

Colonial Motel And Spa
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
  • 31 min drive from Cass Pond
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! (952 reviews)
Check in was easy. After first night the internet shut down. Came back on late the second night. This location is under renovations. Strong paint smell and the worker was there until 8pm at night drilling and sawing. Since our plans fell apart, we left two days early. I'm sure when the renovations ...

Reviewed on Mar 13, 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
  • 30 min drive from Cass Pond
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! (783 reviews)
Everything was great. Clean rooms, friendly staff, good stay..

Reviewed on Mar 11, 2026

Comfort Inn & Suites Brattleboro I-91
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
360 Viking Village Drive Guilford VT
  • 20 min drive from Cass Pond
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! (178 reviews)
This was a fun and comfortable place to stay. We were impressed by the size of the cabins as well as their construction. Staff was friendly and the check in/out process easy. A great place to bring kids.

Reviewed on Mar 7, 2026

Vikings Villages Resort
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
  • 30 min drive from Cass Pond
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! (1,005 reviews)
TVs didn’t work. Shower was broken. Heater was very loud and falling out of the wall. Computers were down my entire stay and they disable my door cards by accident. It may be cheap but you def get what you pay for.

Reviewed on Mar 15, 2026

Best Western Plus Keene Hotel
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road Brattleboro VT
  • 30 min drive from Cass Pond
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! (1,001 reviews)
When our TV did t work the front desk came up to help us and fixed the problem. That was very nice.

Reviewed on Mar 9, 2026

The Covered Bridge Inn
The Putney Inn

The Putney Inn

2.5 out of 5
57 Putney Landing Rd Putney VT
  • 41 min drive from Cass Pond
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)
We were doing a ski trip to Mount Snow and this was an excellent low-cost room for a single night. No frills and a good price. Coffee and simple breakfast (yogurt, cereal) was available the next morning on our way out the door.

Reviewed on Mar 15, 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
  • 30 min drive from Cass Pond
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! (995 reviews)
Everything was perfect!

Reviewed on Mar 15, 2026

Keene Elm City Hotel, an Ascend Collection Hotel
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
  • 29 min drive from Cass Pond
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! (1,001 reviews)
Nice, quiet, clean spot handy to I91.

Reviewed on Mar 14, 2026

Holiday Inn Express Hotel & Suites Brattleboro by IHG
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
  • 26 min drive from Cass Pond
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! (853 reviews)
Great location, great staff really cool old building with lots of character

Reviewed on Mar 8, 2026

Latchis Hotel
Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT

2.5 out of 5
1254 Putney Rd Brattleboro VT
  • 30 min drive from Cass Pond
Stay at this motel in Brattleboro. Enjoy free WiFi, free parking, and room service. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl ...
6/10 (762 reviews)
I will not be back. What’s roach motel must be like for roaches. Loud, gross and just no thanks. Glad it’s iver

Reviewed on Mar 8, 2026

Travelodge by Wyndham Brattleboro VT
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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