Search for Cheap Deals on
Hotels in Winchendon

Check Last Minute Winchendon Hotel Deals

Tonight Oct 17 - Oct 18This weekend Oct 17 - Oct 19

Choose from 208 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 ...
8.8/10 Excellent! (1,010 reviews)
"The hotel was very nice outside and inside. I only stayed 1 night and we got in late. They did allow me to have a late checkout time at noon. (we did leave well before that) We had drinks and nachos in the Gardner grill. Very good drinks and the nachos were also very good. I do wish they provided ..."

Reviewed on Oct 12, 2025

The Colonial Hotel
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! (1,008 reviews)
"Good place to rest."

Reviewed on Oct 11, 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! (1,007 reviews)
"Room clean, breakfast very good, everyone was friendly and helpful if needed"

Reviewed on Oct 11, 2025

Doubletree by Hilton Hotel Leominster
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! (919 reviews)
"Room was clean and staff was friendly."

Reviewed on Oct 10, 2025

Keene Elm City Hotel, an Ascend Collection 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! (1,000 reviews)
"Everything about this place was incredible"

Reviewed on Sep 30, 2025

Great Wolf Lodge Boston / Fitchburg, MA
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! (1,013 reviews)
"Very nice place for the price. Breakfast area was very clean. Although we didn't eat there, it was nice to have a restaurant connected to the property for dinner. I would stay there again"

Reviewed on Oct 10, 2025

Best Western Plus Keene Hotel
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! (136 reviews)
"Staff was wonderful. Would highly recommend this hotel."

Reviewed on Sep 29, 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! (426 reviews)
"Stayed three nights in ground level room. Clean, nice bed and bedding, good shower, easy to sleep in. Staff good and always open to grab a coffee, water or piece of fruit. All in all a solid stay in a updated room at an older motel property. Would stay again in the future."

Reviewed on Oct 10, 2025

Riverhouse by Weekender (Formerly Jack Daniels Inn)
Gardner Inn

Gardner Inn

2 out of 5
22 Pearson Blvd, Gardner, MA
  • 18 min drive from The Winchendon School
Stay at this hotel in Gardner. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Dunn State Park and 1761 Old Mill Gift Shop are located ...
5.4/10 (9 reviews)
"Clean room"

Reviewed on Oct 14, 2025

Gardner Inn
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! (334 reviews)
"Great staff, great position. Stayed here whilst visiting friends in Keene. It was so easy to get around and close to Main Street."

Reviewed on Oct 3, 2025

Hampton Inn & Suites Keene
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)
"Friendly staff, clean rooms; a bit noisy (street, next room and appliances in the room)."

Reviewed on Sep 26, 2025

Courtyard by Marriott Keene Downtown
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.

Find cheap hotels in Winchendon

You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your Winchendon hotel with Hotwire to complete your one-of-a-kind travel checklist.

For you, intrepid voyager, Hotwire has a large selection of the best hotels in Winchendon.

Choosing the right hotel in Massachusetts has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Winchendon’s 208 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $103. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great Winchendon hotel deals at the last minute.

While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Winchendon. No matter your reason for visiting Winchendon, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.

Frequently Asked Questions About Winchendon hotels

Where can I find the best last-minute travel deals?

If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can unlock great deals on your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Winchendon for as low as $103.

How many hotels are there in Winchendon?

With over 208 hotels in Winchendon, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $103.

How to find cheap car rentals in Winchendon?

Finding a cheap car rental deal in Winchendon is as easy as scoring cheap hotels in Winchendon. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.