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Check prices for these dates

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18 Jul - 19 Jul
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19 Jul - 20 Jul
This weekend
18 Jul - 20 Jul
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25 Jul - 27 Jul

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Top 10 trending Winchendon hotels

Chocksett Inn and Restaurant
Cozy up by the traditional fireplace, complete with a mantel and mirror.

Chocksett Inn and Restaurant

3.5 star property
8.8 out of 10, Excellent, (132)
"Great atmosphere. Spacious room. Colonial setting"
The price is €181
includes taxes & fees
31 Jul - 1 Aug
Chocksett Inn and Restaurant
Motel 6 Leominster, MA
Guests can wait comfortably in the lobby area with a table and chairs.

Motel 6 Leominster, MA

2.0 star property
8.0 out of 10, Very good, (1011)
"Best motel around "
The price is €119
includes taxes & fees
23 Jul - 24 Jul
Motel 6 Leominster, MA
Doubletree by Hilton Hotel Leominster
Welcome to our lobby, featuring a central reception desk, comfortable seating areas, and framed artworks on the walls.

Doubletree by Hilton Hotel Leominster

4.0 star property
8.6 out of 10, Excellent, (1000)
"Very well maintained property. Will stay again."
The price is €165
includes taxes & fees
17 Aug - 18 Aug
Doubletree by Hilton Hotel Leominster
Howarth House B&B
Sit and unwind in a serene outdoor space surrounded by lush greenery and vibrant flowers.

Howarth House B&B

3.0 star property
10.0 out of 10, Exceptional, (103)
"Such a beautiful property with so much charm. We will be back!"
Howarth House B&B
Great Wolf Lodge Boston / Fitchburg, MA
Relax by the pool surrounded by hotel buildings with rectangular windows.

Great Wolf Lodge Boston / Fitchburg, MA

3.5 star property
8.6 out of 10, Excellent, (1000)
"Great time for family kids had a wonderful time "
The price is €191
includes taxes & fees
30 Jul - 31 Jul
Great Wolf Lodge Boston / Fitchburg, MA
The Birchwood Inn
Enjoy dining in this beautifully designed space with a large mural and comfortable seating.

The Birchwood Inn

3.5 star property
9.4 out of 10, Exceptional, (204)
"What a beautiful Inn! Amy was so nice and helpful, we had a wonderful stay. "
The price is €159
includes taxes & fees
20 Jul - 21 Jul
The Birchwood Inn
The Maguire House Bed & Breakfast
Relax in a serene garden setting surrounded by lush foliage and vibrant flowers.

The Maguire House Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (34)
"Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. "
The price is €236
includes taxes & fees
30 Jul - 31 Jul
The Maguire House Bed & Breakfast
The Colonial Hotel
Experience the grandeur of our lobby, featuring a beautifully patterned carpet, a comfortable seating area, and a stunning staircase.

The Colonial Hotel

3.0 star property
8.8 out of 10, Excellent, (1004)
"Very good hotel "
The Colonial Hotel
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Enjoy cooking and brewing in this well-equipped kitchen with a coffee machine, coffee grinder, and refrigerator.

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 star property
9.4 out of 10, Exceptional, (406)
"Clean, comfortable, easy check in/check out. Beautiful location, staff was friendly and efficient. "
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Monadnock Inn
Stroll up to this charming residence, featuring a covered porch with white columns and a small railing, surrounded by lush greenery.

Monadnock Inn

2.5 star property
7.6 out of 10, Good, (265)
"Hi it’s a beautiful inn and very comfortable "
Monadnock Inn
The Carriage Barn Inn
Enjoy a meal with a view from this dining table near a window.

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (152)
"Loved our stay. Beautifully decorated and I was able to play the house guitar in common room which was a unique touch I really enjoyed. Would gladly stay here again."
The price is €169
includes taxes & fees
31 Jul - 1 Aug
The Carriage Barn Inn
Courtyard by Marriott Keene Downtown
Check-in and check-out services are available at the central counter, with additional assistance offered at the smaller counters.

Courtyard by Marriott Keene Downtown

3.0 star property
8.8 out of 10, Excellent, (1002)
"Hotel itself clean and nice but surrounding area has homeless people, or seems a little sketchy, which made us a little nervous walking around town "
The price is €158
includes taxes & fees
22 Jul - 23 Jul
Courtyard by Marriott Keene Downtown
Fairfield Inn & Suites by Marriott Keene Downtown
Classic architecture meets modern comfort at this inviting hotel entrance.

Fairfield Inn & Suites by Marriott Keene Downtown

2.5 star property
8.8 out of 10, Excellent, (725)
"Friendly, helpful staff. Old hotel in good condition. "
The price is €136
includes taxes & fees
10 Aug - 11 Aug
Fairfield Inn & Suites by Marriott Keene Downtown
The Burrell House
Traditional home with a covered front porch and garage, set amidst a beautifully landscaped yard.

The Burrell House

2.5 star property
9.6 out of 10, Exceptional, (131)
"Beautiful Inn!! Very happy customer ! I’ll be back !"
The Burrell House
Best Western Plus Keene Hotel
Welcome to Best Western PLUS, featuring a clean and modern exterior with a prominent logo and inviting entrance.

Best Western Plus Keene Hotel

3.0 star property
8.2 out of 10, Very good, (1001)
"Nice hotel "
The price is €125
includes taxes & fees
21 Jul - 22 Jul
Best Western Plus Keene Hotel
Hampton Inn & Suites Keene
Welcome to the Granite State hotel, featuring a reception area and suite shop.

Hampton Inn & Suites Keene

2.5 star property
9.0 out of 10, Wonderful, (315)
"Keene NH Hampton was probaly the nicest Hampton I ever stayed at. Clean & friendly "
The price is €138
includes taxes & fees
27 Jul - 28 Jul
Hampton Inn & Suites Keene
Keene Elm City Hotel, Ascend Hotel Collection
Relax by the pool surrounded by a spacious deck and lounge chairs.

Keene Elm City Hotel, Ascend Hotel Collection

2.5 star property
8.4 out of 10, Very good, (857)
"Good place to stop "
The price is €104
includes taxes & fees
24 Jul - 25 Jul
Keene Elm City Hotel, Ascend Hotel Collection
Days Inn by Wyndham Keene NH
Two double beds with blue bedding and a blue accent wall create a cozy atmosphere.

Days Inn by Wyndham Keene NH

2.0 star property
7.2 out of 10, Good, (1002)
"Great stay"
The price is €90
includes taxes & fees
3 Aug - 4 Aug
Days Inn by Wyndham Keene NH
Centennial House
Enjoy meals in a beautifully lit dining area with arched windows and a view of the outdoors.

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (155)
"Elegant 200-year-old home updated with an en suite BR, AC. Wonderful hosts, Joan & Steve; excellent gourmet breakfast served in their historic dining area. Highly recommend for a quiet, historic, picturesque, comfortable, friendly stay."
The price is €158
includes taxes & fees
20 Jul - 21 Jul
Centennial House
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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Learn more about Winchendon

Escape to Winchendon! Enjoy its parks.

See all hotels in Winchendon

Top Winchendon Hotel Reviews

The Colonial Hotel

The Colonial Hotel

10/10 Excellent
"Very nice place"
Brice 1-night trip
Posted 2 days ago
The Colonial Hotel

Frequently asked questions

What's the best place to stay in Winchendon?

Great Wolf Lodge Boston / Fitchburg, MA, located 13.8 mi (22.2 km) from the heart of Winchendon, is a top choice for your stay, based on our traveller data. Other good choices for your stay in the area are The Colonial Hotel and Motel 6 Leominster, MA. See all available top hotels, or vacation rentals in Winchendon.

What are some of the best holiday rentals that Winchendon has to offer?

Modern Waterfront Gem w/ Dock on Lake Monomonac: This highly rated holiday home rental in Winchendon is located on a lake, and has a selection of games, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, kitchenware and a coffee maker. See all vacation rentals in Winchendon.

If I need to cancel my hotel reservation in Winchendon, will I receive a refund?

Yes, you'll find most room reservations are fully refundable if you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a reservation that's non-refundable, you might be able to cancel it and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchendon.

What are some hotels with pools in Winchendon?

Great Wolf Lodge Boston / Fitchburg, MA: Provides 4 indoor swimming pools, a children's pool and free water park access. Also, another option that offers an on-site pool is The Colonial Hotel. View all hotels with pools in Winchendon.

What is staying in Winchendon like?

Visitors can enjoy all that Winchendon has to offer, including its parks. In Winchendon, there are 9 hotels and other accommodation options to choose from. Find out more about Winchendon.

What are the top places to visit in Winchendon?

Natural beauty is on display at Lake Dennison State Recreation Area, Millers River and V F W Park. A couple of additional sights to add to your itinerary are Beals Memorial Library and Militia Training Field. Take a look at what more there is to see and do in Expedia's Winchendon guide.

What's the seasonal weather in Winchendon?

The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Winchendon are January, March, February and November, with each month seeing an average of 19 cm of snowfall.