A hilly landscape with a tower on top, dense forest, and a cloudy sky.

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Our top choices for Winchendon hotels

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.6 out of 10, Excellent, (1,006 reviews)
"Good stay everything you could ask for from a budget friendly hotel."
United States
Stephen
The price is NZ$226
includes taxes & fees
6 July - 7 July
Keene Elm City Hotel, an Ascend Collection Hotel

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1,003 reviews)
"Best place to stay the food was good and we had a wonderful stay. Swimming pool was fun and safe for kids"
United States
Nidia Ruby
The price is NZ$242
includes taxes & fees
8 July - 9 July
Best Western Plus Keene Hotel

Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA
3.5 star property
Fitchburg
8.6 out of 10, Excellent, (1,005 reviews)
"This place is awesome"
United States
Deserie
The price is NZ$291
includes taxes & fees
19 July - 20 July
Great Wolf Lodge Boston / Fitchburg, MA

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (172 reviews)
"Self check-in and checkout. Room was very clean but a bit too much potpourri for my allergies. Will stay here again when in Keene. "
United States
Charles
The price is NZ$249
includes taxes & fees
6 July - 7 July
The Burrell House

Gardner Inn

Gardner Inn
2.0 star property
Gardner
7.4 out of 10, Good, (33 reviews)
"Great for a quick stay while passing through!"
United States
Cristen
The price is NZ$201
includes taxes & fees
6 July - 7 July
Gardner Inn

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
2.0 star property
Keene
7.0 out of 10, Good, (1,001 reviews)
"Great breakfast, friendly staff and good place to stay."
United States
Michael
The price is NZ$168
includes taxes & fees
29 July - 30 July
Days Inn by Wyndham Keene NH

Chocksett Inn and Restaurant

Chocksett Inn and Restaurant
3.5 star property
Sterling
8.8 out of 10, Excellent, (169 reviews)
"Beautiful inn, nice room, friendly staff."
United States
Annemarie
The price is NZ$311
includes taxes & fees
7 July - 8 July
Chocksett Inn and Restaurant

Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster
4.0 star property
Leominster
8.6 out of 10, Excellent, (1,001 reviews)
"Best place in central mass to stay!"
United States
Linda
The price is NZ$327
includes taxes & fees
19 July - 20 July
Doubletree by Hilton Hotel Leominster

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (174 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
The price is NZ$304
includes taxes & fees
9 July - 10 July
The Carriage Barn Inn

The Birchwood Inn

The Birchwood Inn
3.5 star property
Temple
9.4 out of 10, Exceptional, (231 reviews)
"A true old inn, private bathrooms, sitting room and a comfortable bed. Coffee, snacks and breakfast items in each room. The food in the restaurant was exceptional. Friendly staff."
United States
Mark
The price is NZ$332
includes taxes & fees
6 July - 7 July
The Birchwood Inn

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1,007 reviews)
"Good place to stay "
United States
Glenn
The price is NZ$284
includes taxes & fees
8 July - 9 July
The Colonial Hotel

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (390 reviews)
"Clean rooms, good location, easy parking, excellent service!"
United States
Kerry
The price is NZ$355
includes taxes & fees
7 July - 8 July
Hampton Inn & Suites Keene

Econo Lodge

Econo Lodge
2.0 star property
Westminster
6.4 out of 10, (319 reviews)
"Clean rooms and friendly staff "
United States
Steven
The price is NZ$286
includes taxes & fees
6 July - 7 July
Econo Lodge

Motel 6 Leominster, MA

Motel 6 Leominster, MA
2.0 star property
Leominster
8.2 out of 10, Very good, (1,000 reviews)
"Once again it was another great stay"
United States
alice
The price is NZ$215
includes taxes & fees
2 Aug - 3 Aug
Motel 6 Leominster, MA

Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (783 reviews)
"My favorite hotel!!!!"
United States
Brian
The price is NZ$313
includes taxes & fees
26 July - 27 July
Fairfield Inn & Suites by Marriott Keene Downtown

Howarth House B&B

Howarth House B&B
3.0 star property
Fitchburg
10.0 out of 10, Exceptional, (115 reviews)
"Ryan and Sarah were so nice! They made our one night stay feel like we stayed at a friend's home. Their Bed and Breakfast was so quaint and charming. Our room was very comfortable with the jacuzzi bath. The breakfast was delicious. You get to choose what you prefer either an omelette, pancakes, waffles, or any egg style. It was so nice to wake up to a great breakfast. My wife and I were so impressed with everything they did, we highly recommend staying here if you are in the area of...
United States
Mark
The price is NZ$370
includes taxes & fees
12 July - 13 July
Howarth House B&B

Monadnock Inn

Monadnock Inn
2.5 star property
Jaffrey
7.8 out of 10, Good, (287 reviews)
"Lots of character and run by a great family!"
United States
Evan
The price is NZ$313
includes taxes & fees
6 July - 7 July
Monadnock Inn

Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)
2.5 star property
Peterborough
9.2 out of 10, Wonderful, (468 reviews)
"I love this place."
United States
Tracy
The price is NZ$358
includes taxes & fees
4 Aug - 5 Aug
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.6 out of 10, Excellent, (1,000 reviews)
"Na no breakfast parking easy no cost "
United States
John
The price is NZ$341
includes taxes & fees
13 July - 14 July
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.
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Stay near popular Winchendon attractions

Learn more about Winchendon

Toy Town's charm comes alive at the Old Murdock Senior Centre, where the town's unique toy-making history is celebrated. Lake Dennison Recreation Area offers perfect summer swimming, while winter visitors can explore nearby Wachusett Mountain for skiing in Princeton.

A river reflecting autumn trees and a dense forest.

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Frequently asked questions

What is the best area to stay in Winchendon?
The best area to stay in Winchendon is near the town centre, particularly around Central Street and Front Street.

This area is the heart of Winchendon, offering easy access to local amenities and a sense of community. You'll find a selection of local shops, eateries, and public spaces, including the beautiful Winchendon Common, which often hosts community events. The town centre is quite walkable, making it convenient to explore on foot.

For families, staying in this central area is ideal. It provides close proximity to attractions like the Murdock-Whitney House Museum and the Beals Memorial Library, which often has children's programmes. The nearby Winchendon Community Park offers green space for kids to play.

Couples looking for a relaxed retreat will also appreciate the town centre. It offers a quieter pace with access to local dining options and the opportunity to enjoy strolls around the Common or along the Millers River, which runs through town.
When is the best time to go to Winchendon?
The best time to go to Winchendon is during the autumn months, specifically from September to October.

This period offers the most pleasant weather for outdoor activities, with mild temperatures and less humidity than the summer. The main draw, however, is the spectacular New England foliage, which transforms the landscape into a canvas of reds, oranges, and yellows. The Winchendon State Forest and the surrounding rural areas are particularly picturesque during this time.

Couples looking for a relaxing getaway will appreciate the scenic drives and opportunities for hiking or leisurely walks through the colourful forests. Many local farms also offer seasonal activities like apple picking and pumpkin patches, adding to the charm of an autumn visit.

Families will find autumn an excellent time for a visit, too. The cooler weather is ideal for exploring Winchendon's outdoor spaces without the intense heat of summer.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, although it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24 to 48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to 'My Trips' and selecting your reservation. To find flexible deals, filter your search by 'Fully refundable property' for hotels in Winchendon.
How can I save on a hotel booking in Winchendon with Expedia?
One Keyā„¢ – Expedia's free travel rewards programme – gives you instant access to perks and Member Prices on Winchendon hotels. Plus, you'll earn OneKeyCashā„¢* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
How much is the nightly rate for a hotel in Winchendon?
Prices for hotels in Winchendon often vary, but you can find a great deal from NZ$168 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by 'Price: low to high' for our cheapest rates.

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