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Hotels in Winchendon

Choose from 195 Winchendon Hotel Deals

Modern Waterfront Gem w/ Dock on Lake Monomonac

Modern Waterfront Gem w/ Dock on Lake Monomonac

3 out of 5
Winchendon
  • 6 min drive from The Winchendon School
Stay at this 3-star cottage in Winchendon. Enjoy free parking and air conditioning. Popular attractions Paradise Island and Blueberry Island are located ...
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
Stay at this 3-star business-friendly hotel in Gardner. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
8.6/10 Excellent! (1,006 reviews)
"Toilet kept backing up. They issued plunger."

Reviewed on Jul 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
Stay at this 3.5-star 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)
"My kids love it"

Reviewed on Aug 1, 2025

Great Wolf Lodge Boston / Fitchburg, MA
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! (1,001 reviews)
"Quiet, clean, comfortable."

Reviewed on Jul 29, 2025

Motel 6 Leominster, 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
Stay at this 4-star 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! (1,003 reviews)
Nice hotel with poor housekeeping
"Very nice hotel. All of the desk staff were friendly and helpful. However, housekeeping not so nice. I stayed there for 6 nights. They only do a complete cleaning and sheet change after 4 nights. Ok. Two days, nothing - no clean towels, bed not made. One of those days I had asked for a shower cap ..."

Reviewed on Jul 30, 2025

Doubletree by Hilton Hotel Leominster
Keene Elm City Hotel, Ascend Hotel Collection

Keene Elm City Hotel, Ascend Hotel Collection

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 ...
8.2/10 Very Good! (864 reviews)
"Dillon, your front desk associate was amazing. Easy to work with and extremely accommodating. A real asset to the hotel."

Reviewed on Jul 26, 2025

Keene Elm City Hotel, Ascend Hotel Collection
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
Stay at this 3-star 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! (1,005 reviews)
"Great place!"

Reviewed on Jul 31, 2025

Best Western Plus Keene Hotel
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
Stay at this 3-star 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! (1,001 reviews)
"Property in good condition, clean, well located in Keene."

Reviewed on Aug 1, 2025

Courtyard by Marriott Keene Downtown
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! (321 reviews)
Comfortable but not anything special
"Overall the stay was just OK. The room was clean and well equipped. The only thing not working as expected in the room was the sink stopper was broken. The free breakfast was mediocre. The front desk was understaffed but when you finally got attention it was good. The lobby microwave that I used ..."

Reviewed on Jul 18, 2025

Hampton Inn & Suites Keene
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! (1,001 reviews)
"Lots of shopping and chain restaurants nearby, close to downtown, good breakfast"

Reviewed on Jul 31, 2025

Days Inn by Wyndham Keene NH
Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown

2.5 out of 5
30 Main Street, 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. ...
8.8/10 Excellent! (726 reviews)
"Friendly, helpful staff. Old hotel in good condition."

Reviewed on Jul 16, 2025

Fairfield Inn & Suites 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 3.5-star hotel in Sterling. Enjoy free WiFi, free parking, and room service. Popular attractions Mary Had a Little Lamb Statue and Davis' Farmland ...
8.6/10 Excellent! (132 reviews)
Short Stay
"Everything went smoothly, but for the noisy air conditioning system and the very noisy toilet!!! Other than that nice, clean, no disturbances at all."

Reviewed on Jun 25, 2025

Chocksett Inn and Restaurant
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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