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1 Dec - 2 Dec
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5 Dec - 7 Dec
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12 Dec - 14 Dec

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Top hotels and accommodation in Winchendon

Reception
Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster

4.0 star property
Leominster
8.6 out of 10, Excellent, (1006)
"Always a great place to stay! Friendly, clean and comfortable. "
United States
Lynn
The price is AU$222
includes taxes & fees
23 Dec - 24 Dec
Doubletree by Hilton Hotel Leominster
4 indoor pools, seasonal outdoor pool, pool cabanas (surcharge)
Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

3.5 star property
Fitchburg
8.6 out of 10, Excellent, (1005)
"Everything about this place was incredible "
United States
Jaida
The price is AU$214
includes taxes & fees
7 Dec - 8 Dec
Great Wolf Lodge Boston / Fitchburg, MA
Interior
The Colonial Hotel

The Colonial Hotel

3.0 star property
Gardner
8.8 out of 10, Excellent, (1013)
"Great hotel, fantastic restaurant, wonderful place!"
United States
Kate
The Colonial Hotel
Lobby
Motel 6 Leominster, MA

Motel 6 Leominster, MA

2.0 star property
Leominster
8.0 out of 10, Very good, (1015)
"Was very nice "
United States
Laurie
The price is AU$141
includes taxes & fees
7 Dec - 8 Dec
Motel 6 Leominster, MA
Fireplace
Chocksett Inn and Restaurant

Chocksett Inn and Restaurant

3.5 star property
Sterling
8.6 out of 10, Excellent, (144)
"Fine for an overnight stay. Seems to be one of the better options in the area. Room clean and spacious. "
United States
Ayah
The price is AU$271
includes taxes & fees
2 Dec - 3 Dec
Chocksett Inn and Restaurant
Premium bedding, individually decorated, individually furnished, desk
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3.0 star property
Keene
8.4 out of 10, Very good, (1006)
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is AU$230
includes taxes & fees
2 Dec - 3 Dec
Best Western Plus Keene Hotel
In-room safe, desk, blackout curtains, iron/ironing board
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2.0 star property
Keene
7.0 out of 10, Good, (1005)
"Very professional people good service good staff "
United States
George
The price is AU$152
includes taxes & fees
16 Dec - 17 Dec
Days Inn by Wyndham Keene NH
Breakfast area
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 star property
Peterborough
9.4 out of 10, Exceptional, (433)
"Super cute place! Would stay here again"
United States
Danielle
The price is AU$224
includes taxes & fees
2 Dec - 3 Dec
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Double Room
Gardner Inn

Gardner Inn

2.0 star property
Gardner
5.6 out of 10, (16)
"The property needs work but hte staff was pleasant and the facility was quiet. "
United States
Lou
The price is AU$169
includes taxes & fees
2 Dec - 3 Dec
Gardner Inn
Exterior
Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown

2.5 star property
Keene
8.8 out of 10, Excellent, (754)
"Front desk pleasant and helpful Breakfast was good Room was spacious and clean Able to walk to shopping and dining. "
United States
Stephen
The price is AU$273
includes taxes & fees
21 Dec - 22 Dec
Fairfield Inn & Suites by Marriott Keene Downtown
Reception
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

2.5 star property
Keene
8.8 out of 10, Excellent, (351)
"Nice place to stay, nice area, will stay again."
United States
Catherine
The price is AU$244
includes taxes & fees
23 Dec - 24 Dec
Hampton Inn & Suites Keene
Indoor pool
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 star property
Keene
8.4 out of 10, Very good, (956)
"Enjoyed the breakfast options and the very comfortable bed. "
Canada
Nancy
The price is AU$180
includes taxes & fees
21 Dec - 22 Dec
Keene Elm City Hotel, an Ascend Collection Hotel
Garden
Howarth House B&B

Howarth House B&B

3.0 star property
Fitchburg
10.0 out of 10, Exceptional, (110)
"Beautiful gardens"
United States
Christine
Howarth House B&B
Free daily full breakfast
Centennial House

Centennial House

3.5 star property
Northfield
9.6 out of 10, Exceptional, (173)
"The house was cozy and inviting. Felt the history all around me and the breakfast made and served by Joan was great. We recommend this place for those looking for that historical b&b experience. "
United States
Paul
The price is AU$312
includes taxes & fees
26 Dec - 27 Dec
Centennial House
Reception
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

3.0 star property
Keene
8.8 out of 10, Excellent, (1007)
"Lovely hotel"
United States
ronald
The price is AU$266
includes taxes & fees
5 Dec - 6 Dec
Courtyard by Marriott Keene Downtown
Exterior
The Burrell House

The Burrell House

2.5 star property
Keene
9.6 out of 10, Exceptional, (155)
"Very helpful, kind staff"
United States
Paitris
The Burrell House
Farm to table cuisine
The Birchwood Inn

The Birchwood Inn

3.5 star property
Temple
9.4 out of 10, Exceptional, (224)
"Great Spot!"
United States
Kialey
The price is AU$282
includes taxes & fees
2 Dec - 3 Dec
The Birchwood Inn
Free daily continental breakfast
The Carriage Barn Inn

The Carriage Barn Inn

3.0 star property
Keene
9.6 out of 10, Exceptional, (165)
"Excellent place!!!! Lovely room that had all I needed!!! The bed was comfortable and the stay was wonderful!!!!!!"
United States
natalia
The price is AU$207
includes taxes & fees
31 Dec - 1 Jan 2026
The Carriage Barn Inn
Exterior
Monadnock Inn

Monadnock Inn

2.5 star property
Jaffrey
7.6 out of 10, Good, (277)
"It is a Beautiful Old Charm Inn. Everything was great. I would definitely come back and stay there again. "
United States
Sharon-Ann C
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.
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Stay near popular Winchendon attractions

Lake Dennison State Recreation Area

You can take time to visit Lake Dennison State Recreation Area during your travels to Winchendon. Discover the area's waterfalls and mountain views.
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Winchendon Town Hall

After visiting Winchendon Town Hall, make a plan to see the other sights and activities in Winchendon. While you're in the area, wander around the parks.
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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
The Millers River in Winchendon, Massachusetts

Top Winchendon Hotel Reviews

Recent Reviews in Winchendon

The Colonial Hotel

The Colonial Hotel

10/10 Excellent
"Staff was very polite, the restaurant was lovely the service was amazing the room was comfortable and relaxing we loved it :)"
Lily 2-night trip
Posted 5 days ago
The Colonial Hotel

More cheap accommodation in Winchendon

More cheap accommodation in Winchendon

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH
The price is AU$152 per night from 16 Dec to 17 Dec
AU$152
16 Dec - 17 Dec
includes taxes & fees
7/10 Good! (1,002 reviews)

Frequently asked questions

What's the best place to stay in Winchendon?
Based on Expedia's traveller preferences, Cozy Lakefront Cottage is a top place to stay in Winchendon. Other good choices for your stay in the area are The Colonial Hotel 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?
Cozy Lakefront Cottage: This highly rated holiday home rental in Winchendon is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a selection of books. 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: Features a sauna, an indoor pool and free self parking. Doubletree by Hilton Hotel Leominster and Great Wolf Lodge Boston / Fitchburg, MA 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 Wendall P. Clark Memorial, Militia Training Field and Hyde Park. A couple of additional sights to add to your itinerary are Lake Dennison State Recreation Area 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.

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