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Hotels in Winchendon

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Choose from 214 Winchendon Hotel Deals

Modern Waterfront Gem w/ Dock on Lake Monomonac

Modern Waterfront Gem w/ Dock on Lake Monomonac

3 out of 5
Winchendon MA
  • 6 min drive from The Winchendon School
Stay at this cottage in Winchendon. Enjoy free parking and air conditioning. Popular attractions Paradise Island and Blueberry Island are located nearby.
Modern Waterfront Gem w/ Dock on Lake Monomonac
The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road Gardner MA
  • 19 min drive from The Winchendon School
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! (1,013 reviews)
Clean room pool was cold.

Reviewed on Nov 29, 2025

The Colonial Hotel
Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

3.5 out of 5
150 Great Wolf Dr Fitchburg MA
  • 22 min drive from The Winchendon School
Book a stay at this family-friendly resort in Fitchburg. Enjoy 4 indoor pools, free water park access, and room service. Our guests praise the helpful staff ...
8.4/10 Very Good! (1,004 reviews)
We had a great time.. lots to do.

Reviewed on Nov 29, 2025

Great Wolf Lodge Boston / Fitchburg, MA
Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster

4 out of 5
99 Erdman Way Leominster MA
  • 23 min drive from The Winchendon School
Book a stay at this business-friendly hotel in Leominster. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (1,005 reviews)
Always a great place to stay! Friendly, clean and comfortable.

Reviewed on Nov 16, 2025

Doubletree by Hilton Hotel Leominster
Motel 6 Leominster, MA

Motel 6 Leominster, MA

2 out of 5
48 Commercial Rd Leominster MA
  • 25 min drive from The Winchendon School
Stay at this motel in Leominster. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
8/10 Very Good! (1,011 reviews)
Yes

Reviewed on Nov 23, 2025

Motel 6 Leominster, MA
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
  • 45 min drive from The Winchendon School
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! (957 reviews)
Over all a good stay. The pool window as left open over night so it as very cool in the pool area the next morning. Suggest staff check for that after the pool closes at 10 each night. Thanks

Reviewed on Dec 2, 2025

Keene Elm City Hotel, an Ascend Collection Hotel
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

2.5 out of 5
126 Key Rd Keene NH
  • 44 min drive from The Winchendon School
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free parking, and room service. Our guests praise the breakfast and the helpful staff ...
8.8/10 Excellent! (351 reviews)
Yes the room was spotless. The towels could have been newer and larger and softer. We were not impressed with the breakfast even though there was a variety of options. And we understand the issue with cooking for many and not knowing the favorite choice, but the eggs, and quiche, and sausages were ...

Reviewed on Nov 29, 2025

Hampton Inn & Suites Keene
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
  • 44 min drive from The Winchendon School
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 ...
8.2/10 Very Good! (1,000 reviews)
Staff was accommodating. Got a Free upgrade to my room

Reviewed on Nov 25, 2025

Best Western Plus Keene Hotel
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2 out of 5
3 Ash Brook Road Keene NH
  • 45 min drive from The Winchendon School
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! (1,005 reviews)
Very professional people good service good staff

Reviewed on Nov 4, 2025

Days Inn by Wyndham Keene NH
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

3 out of 5
75 Railroad St Keene NH
  • 45 min drive from The Winchendon School
Book a stay at this business-friendly hotel in Keene. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (1,000 reviews)
The staff was courteous and helpful. I didn’t use the pool or exercise room, but they looked very clean.

Reviewed on Dec 1, 2025

Courtyard by Marriott Keene Downtown
Chocksett Inn and Restaurant

Chocksett Inn and Restaurant

3.5 out of 5
59 Laurelwood Road Sterling MA
  • 38 min drive from The Winchendon School
Stay at this hotel in Sterling. Enjoy free WiFi, free parking, and room service. Popular attractions Mary Had a Little Lamb Statue and Davis' Farmland & Mega ...
8.6/10 Excellent! (144 reviews)
Beautiful inn, nice room, friendly staff.

Reviewed on Nov 24, 2025

Chocksett Inn and Restaurant
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 out of 5
80 Concord Street Peterborough NH
  • 35 min drive from The Winchendon School
Stay at this hotel in Peterborough. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Mariposa ...
9.2/10 Wonderful! (431 reviews)
The room was very clean and the place was quiet

Reviewed on Nov 17, 2025

Riverhouse by Weekender (Formerly Jack Daniels 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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