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
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Winchendon hotels

The Burrell House

2.5 star property
9.6 out of 10, Exceptional, (130)
"Well maintained property with beautifully decorated rooms. "
The Burrell House

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 €235
includes taxes & fees
17 Jul - 18 Jul
The Maguire House Bed & Breakfast

The Colonial Hotel

3.0 star property
8.8 out of 10, Excellent, (1005)
"Great place, location is nice, Restaurant is great."
The Colonial Hotel

Howarth House B&B

3.0 star property
10.0 out of 10, Exceptional, (98)
"Owners are friendly and welcoming. The facility is warm, cozy and beautiful. "
Howarth House B&B

Hampton Inn & Suites Keene

2.5 star property
9.0 out of 10, Wonderful, (308)
"We had a great time here! Clean rooms, polite staff and nice dinning area"
The price is €137
includes taxes & fees
6 Jul - 7 Jul
Hampton Inn & Suites Keene

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (150)
"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 €187
includes taxes & fees
1 Jul - 2 Jul
The Carriage Barn Inn

Doubletree by Hilton Hotel Leominster

4.0 star property
8.6 out of 10, Excellent, (1004)
"Clean, friendly, great location "
The price is €141
includes taxes & fees
2 Jul - 3 Jul
Doubletree by Hilton Hotel Leominster

Chocksett Inn and Restaurant

3.5 star property
8.8 out of 10, Excellent, (130)
"Great atmosphere. Spacious room. Colonial setting"
The price is €177
includes taxes & fees
30 Jun - 1 Jul
Chocksett Inn and Restaurant

The Birchwood Inn

3.5 star property
9.4 out of 10, Exceptional, (202)
"What a beautiful Inn! Amy was so nice and helpful, we had a wonderful stay. "
The price is €158
includes taxes & fees
30 Jun - 1 Jul
The Birchwood Inn

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (153)
"This historic property is very nice. Beds are comfortable. The hosts are very welcoming and communication was very good. Breakfast was outstanding! I highly recommend this property and hope to return for another visit someday. "
The price is €142
includes taxes & fees
29 Jun - 30 Jun
Centennial House

Fairfield Inn & Suites by Marriott Keene Downtown

2.5 star property
8.8 out of 10, Excellent, (722)
"We had a lovely stay. Decent breakfast, clean facilities. "
The price is €136
includes taxes & fees
13 Jul - 14 Jul
Fairfield Inn & Suites by Marriott Keene Downtown

Keene Elm City Hotel, Ascend Hotel Collection

2.5 star property
8.4 out of 10, Very good, (847)
"The hotel receptionist was very pleasant and helpful. "
The price is €108
includes taxes & fees
6 Jul - 7 Jul
Keene Elm City Hotel, Ascend Hotel Collection

Courtyard by Marriott Keene Downtown

3.0 star property
8.8 out of 10, Excellent, (1001)
"Great check in experience and clean, comfortable rooms. "
The price is €137
includes taxes & fees
2 Jul - 3 Jul
Courtyard by Marriott Keene Downtown

Motel 6 Leominster, MA

2.0 star property
8.0 out of 10, Very good, (1011)
"Clean, staff pleasant, food locations close by"
The price is €105
includes taxes & fees
30 Jun - 1 Jul
Motel 6 Leominster, MA

Days Inn by Wyndham Keene NH

2.0 star property
7.2 out of 10, Good, (1000)
"Convenient to places to eat in shopping, easy to find. Friendly staff, easy check in. Decent shape of the building and clean in the rooms. "
The price is €86
includes taxes & fees
30 Jun - 1 Jul
Days Inn by Wyndham Keene NH

Monadnock Inn

2.5 star property
7.6 out of 10, Good, (265)
"Hi it’s a beautiful inn and very comfortable "
Monadnock Inn
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

Pet-friendly hotels in Winchendon you'll enjoy

These apartments in Winchendon may fit your trip

Check out cottages in Winchendon

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.

Learn more about Winchendon

Escape to Winchendon! Enjoy its parks.

Frequently asked questions

What's the best place to stay in Winchendon?

Based on Expedia's traveller preferences, Modern Waterfront Gem w/ Dock on Lake Monomonac is a top place to stay in Winchendon. Other good choices for your stay in the area are The Colonial Hotel and Great Wolf Lodge Boston / Fitchburg, 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?

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 Beals Memorial Library and Winchendon Town Hall. 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.