Search Winchendon hotels

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
17 Aug - 18 Aug
Tomorrow
18 Aug - 19 Aug
Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug

Filter by

Guest rating
Guest rating
Property class

Top hotels and accommodation in Winchendon

Doubletree by Hilton Hotel Leominster
Reception

Doubletree by Hilton Hotel Leominster

4.0 star property
8.6 out of 10, Excellent, (1002)
"Nice place "
The price is AU$239
includes taxes & fees
24 Aug - 25 Aug
Doubletree by Hilton Hotel Leominster
Great Wolf Lodge Boston / Fitchburg, MA
4 indoor pools, seasonal outdoor pool, pool cabanas (surcharge)

Great Wolf Lodge Boston / Fitchburg, MA

3.5 star property
8.6 out of 10, Excellent, (1003)
"The staffs are friendly, the rooms are clean nice and spacious."
The price is AU$376
includes taxes & fees
25 Aug - 26 Aug
Great Wolf Lodge Boston / Fitchburg, MA
The Colonial Hotel
Interior

The Colonial Hotel

3.0 star property
8.8 out of 10, Excellent, (1000)
"We have stayed at this property a few times and it is always a pleasant experience. "
The Colonial Hotel
Best Western Plus Keene Hotel
1 bedroom, premium bedding, individually decorated

Best Western Plus Keene Hotel

3.0 star property
8.4 out of 10, Very good, (1008)
"Really enjoyed everything about my stay"
The price is AU$248
includes taxes & fees
24 Aug - 25 Aug
Best Western Plus Keene Hotel
Days Inn by Wyndham Keene NH
In-room safe, desk, blackout curtains, iron/ironing board

Days Inn by Wyndham Keene NH

2.0 star property
7.2 out of 10, Good, (1002)
"Would stay again"
The price is AU$186
includes taxes & fees
31 Aug - 1 Sept
Days Inn by Wyndham Keene NH
Motel 6 Leominster, MA
Lobby

Motel 6 Leominster, MA

2.0 star property
8.0 out of 10, Very good, (1001)
"As always a great place to rest at."
The price is AU$173
includes taxes & fees
21 Aug - 22 Aug
Motel 6 Leominster, MA
Chocksett Inn and Restaurant
Fireplace

Chocksett Inn and Restaurant

3.5 star property
8.8 out of 10, Excellent, (133)
"Wonderful room and excellent staff throughout the event. Servers, bartenders etc all excellent."
The price is AU$324
includes taxes & fees
18 Aug - 19 Aug
Chocksett Inn and Restaurant
Keene Elm City Hotel, Ascend Hotel Collection
Indoor pool

Keene Elm City Hotel, Ascend Hotel Collection

2.5 star property
8.4 out of 10, Very good, (878)
"Staff were friendly, room clean and comfortable "
The price is AU$209
includes taxes & fees
24 Aug - 25 Aug
Keene Elm City Hotel, Ascend Hotel Collection
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Free daily on-the-go breakfast

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 star property
9.4 out of 10, Exceptional, (417)
"Highly recommend PEARL restaurant nearby! Always comfortable accommodations. "
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Fairfield Inn & Suites by Marriott Keene Downtown
Exterior

Fairfield Inn & Suites by Marriott Keene Downtown

2.5 star property
8.8 out of 10, Excellent, (730)
"Loved our stay from the seamless staff checkin to the large, quiet room, to the ease of the parking lot to a great breakfast. Who could ask for more. Keene is a sweet area to window shop & find great dining & cocktail experiences. "
The price is AU$290
includes taxes & fees
1 Sept - 2 Sept
Fairfield Inn & Suites by Marriott Keene Downtown
Hampton Inn & Suites Keene
Reception

Hampton Inn & Suites Keene

2.5 star property
9.0 out of 10, Wonderful, (328)
"Great hotel with friendly staff"
The price is AU$262
includes taxes & fees
1 Sept - 2 Sept
Hampton Inn & Suites Keene
Centennial House
Free daily full breakfast

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (160)
"Lovely property and innkeepers, I was in the area for an event and hope to come back. "
The price is AU$327
includes taxes & fees
25 Aug - 26 Aug
Centennial House
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (153)
"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 AU$287
includes taxes & fees
2 Sept - 3 Sept
The Carriage Barn Inn
Howarth House B&B
Garden

Howarth House B&B

3.0 star property
10.0 out of 10, Exceptional, (105)
"Beautiful gardens"
Howarth House B&B
Courtyard by Marriott Keene Downtown
Reception

Courtyard by Marriott Keene Downtown

3.0 star property
8.8 out of 10, Excellent, (1002)
"Spacious, comfortable room in easy waking distance to many restaurants and shopping. Staff is warm and welcoming. "
The price is AU$315
includes taxes & fees
21 Aug - 22 Aug
Courtyard by Marriott Keene Downtown
The Burrell House
Exterior

The Burrell House

2.5 star property
9.6 out of 10, Exceptional, (134)
"Very nice property. Highly recommend. "
The Burrell House
The Birchwood Inn
Lunch, dinner, brunch served; farm to table cuisine

The Birchwood Inn

3.5 star property
9.4 out of 10, Exceptional, (207)
"Great Spot!"
The price is AU$283
includes taxes & fees
19 Aug - 20 Aug
The Birchwood Inn
Gardner Inn
Exterior

Gardner Inn

2.0 star property
4.8 out of 10, (3)
"Mold on bathroom ceiling. Water not hot in shower, Didnt drain very well. No coffee maker in room . Ice machine out of order. Floor in room was sticky. Had to get key in door just right to open. Bed and TV were good. "
The price is AU$179
includes taxes & fees
18 Aug - 19 Aug
Gardner Inn
Monadnock Inn
Exterior

Monadnock Inn

2.5 star property
7.6 out of 10, Good, (267)
"It was very personable. They were very flexible with check-in. Quiet and homie. "
Monadnock Inn
The Maguire House Bed & Breakfast
Property grounds

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 AU$423
includes taxes & fees
10 Sept - 11 Sept
The Maguire House Bed & Breakfast
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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.

See all hotels in Winchendon

Top Winchendon Hotel Reviews

Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown

10/10 Excellent
"Perfect spot, right downtown, "
Daniel 2-night trip
Posted 2 days ago
Fairfield Inn & Suites by Marriott Keene Downtown

Frequently asked questions

What's the best place to stay in Winchendon?

The Colonial Hotel, located 9.6 mi (15.4 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 Great Wolf Lodge Boston / Fitchburg, MA and Doubletree by Hilton Hotel Leominster. 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?

The Colonial Hotel: Offers a sauna, an indoor pool and free self parking. Great Wolf Lodge Boston / Fitchburg, MA and Doubletree by Hilton Hotel Leominster are two additional hotels with an on-site pool. 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 Blueberry Island and Wetmore Trailhead. 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.