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
29 July - 30 July
Tomorrow
30 July - 31 July
This weekend
1 Aug - 3 Aug
Next weekend
8 Aug - 10 Aug

Filter by

Guest rating
Guest rating
Property class

Top hotels and accommodation in Winchendon

Chocksett Inn and Restaurant
Fireplace

Chocksett Inn and Restaurant

3.5 star property
8.8 out of 10, Excellent, (132)
"Great atmosphere. Spacious room. Colonial setting"
The price is AU$322
includes taxes & fees
30 July - 31 July
Chocksett Inn and Restaurant
Motel 6 Leominster, MA
Lobby

Motel 6 Leominster, MA

2.0 star property
8.0 out of 10, Very good, (1005)
"As always a great place to rest at."
The price is AU$165
includes taxes & fees
3 Aug - 4 Aug
Motel 6 Leominster, MA
Doubletree by Hilton Hotel Leominster
Reception

Doubletree by Hilton Hotel Leominster

4.0 star property
8.6 out of 10, Excellent, (1005)
"Enjoyed the pool. "
The price is AU$278
includes taxes & fees
17 Aug - 18 Aug
Doubletree by Hilton Hotel Leominster
Howarth House B&B
Garden

Howarth House B&B

3.0 star property
10.0 out of 10, Exceptional, (104)
"Beautiful gardens"
Howarth House B&B
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, (1016)
"The staffs are friendly, the rooms are clean nice and spacious."
The price is AU$306
includes taxes & fees
4 Aug - 5 Aug
Great Wolf Lodge Boston / Fitchburg, MA
The Birchwood Inn
Lunch, dinner, brunch served; farm to table cuisine

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 AU$281
includes taxes & fees
4 Aug - 5 Aug
The Birchwood 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$390
includes taxes & fees
7 Aug - 8 Aug
The Maguire House Bed & Breakfast
The Colonial Hotel
Interior

The Colonial Hotel

3.0 star property
8.8 out of 10, Excellent, (1017)
"We have stayed at this property a few times and it is always a pleasant experience. "
The Colonial Hotel
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, (408)
"Clean, comfortable, easy check in/check out. Beautiful location, staff was friendly and efficient. "
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Monadnock Inn
Exterior

Monadnock Inn

2.5 star property
7.6 out of 10, Good, (265)
"It was very personable. They were very flexible with check-in. Quiet and homie. "
Monadnock Inn
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$290
includes taxes & fees
26 Aug - 27 Aug
The Carriage Barn Inn
Courtyard by Marriott Keene Downtown
Reception

Courtyard by Marriott Keene Downtown

3.0 star property
8.8 out of 10, Excellent, (1005)
"Spacious, comfortable room in easy waking distance to many restaurants and shopping. Staff is warm and welcoming. "
The price is AU$312
includes taxes & fees
3 Aug - 4 Aug
Courtyard by Marriott Keene Downtown
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, (726)
"Friendly, helpful staff. Old hotel in good condition. "
The price is AU$258
includes taxes & fees
17 Aug - 18 Aug
Fairfield Inn & Suites by Marriott Keene Downtown
The Burrell House
Exterior

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
1 bedroom, premium bedding, individually decorated

Best Western Plus Keene Hotel

3.0 star property
8.2 out of 10, Very good, (1007)
"Nice hotel "
The price is AU$223
includes taxes & fees
30 July - 31 July
Best Western Plus Keene Hotel
Hampton Inn & Suites Keene
Reception

Hampton Inn & Suites Keene

2.5 star property
9.0 out of 10, Wonderful, (318)
"Keene NH Hampton was probaly the nicest Hampton I ever stayed at. Clean & friendly "
The price is AU$275
includes taxes & fees
10 Aug - 11 Aug
Hampton Inn & Suites Keene
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, (863)
"Good place to stop "
The price is AU$195
includes taxes & fees
31 July - 1 Aug
Keene Elm City Hotel, Ascend Hotel Collection
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, (1007)
"Great stay"
The price is AU$182
includes taxes & fees
31 July - 1 Aug
Days Inn by Wyndham Keene NH
Centennial House
Free daily full breakfast

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (157)
"Great breakfast, friendly staff"
The price is AU$263
includes taxes & fees
31 July - 1 Aug
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.
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

Escape to Winchendon! Enjoy its parks.

See all hotels in Winchendon

Top Winchendon Hotel Reviews

Motel 6 Leominster, MA

Motel 6 Leominster, MA

10/10 Excellent
"Staff are always great. Every room I have booked is not worth the amount of money to go into a dirty room. They need to inspect the rooms before booking floor is always dirty the tub and sink are always clogged. "
Jialyn 1-night trip
Posted 2 days ago
Motel 6 Leominster, MA

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: Offers 4 indoor swimming pools, a children's pool and free water park access. The Colonial Hotel 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 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.