Winchendon Hotels

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Check prices for these dates

Tonight
24 Dec - 25 Dec
Tomorrow
25 Dec - 26 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

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Our top choices for Winchendon hotels

Lobby
Keene Elm City Hotel, an Ascend Collection Hotel

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, (967)
"The room was perfect, and the food was great "
United States
Paul
The price is €108
includes taxes & fees
28 Dec - 29 Dec
Keene Elm City Hotel, an Ascend Collection Hotel
Lobby
Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster
4.0 star property
Leominster
8.6 out of 10, Excellent, (1001)
"The hotel was very nice and the restaurant was a nice establishment. "
United States
Dina
The price is €124
includes taxes & fees
30 Dec - 31 Dec
Doubletree by Hilton Hotel Leominster
Free daily continental breakfast
The Carriage Barn Inn

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 €117
includes taxes & fees
31 Dec - 1 Jan 2026
The Carriage Barn Inn
Free WiFi, bed sheets
Motel 6 Leominster, MA

Motel 6 Leominster, MA

Motel 6 Leominster, MA
2.0 star property
Leominster
8.2 out of 10, Very good, (1004)
"Very clean room and helpful, friendly staff !"
United States
Ralph
The price is €78
includes taxes & fees
28 Dec - 29 Dec
Motel 6 Leominster, MA
Interior
The Colonial Hotel

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1002)
"Easy checkin, pleasant staff and clean room. "
United States
Susan
The Colonial Hotel
Restaurant
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1001)
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is €128
includes taxes & fees
25 Dec - 26 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

Days Inn by Wyndham Keene NH
2.0 star property
Keene
7.0 out of 10, Good, (1000)
"Not exactly spotless by the experience was better than at the Courtyard by Marriott on Railroad St. in Keene NH."
United States
Miroslaw
The price is €77
includes taxes & fees
31 Dec - 1 Jan 2026
Days Inn by Wyndham Keene NH
Free daily buffet breakfast
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (358)
"Clean comfy nice staff "
United States
Katherine
The price is €157
includes taxes & fees
11 Jan - 12 Jan 2026
Hampton Inn & Suites Keene
Exterior
Fairfield Inn & Suites by Marriott Keene Downtown

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, (758)
"Room spacious, breakfast good, poor directions to parking, snow covered disability ramp."
United States
Stephanie
The price is €166
includes taxes & fees
1 Jan - 2 Jan 2026
Fairfield Inn & Suites by Marriott Keene Downtown
Fireplace
Chocksett Inn and Restaurant

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 €151
includes taxes & fees
25 Dec - 26 Dec
Chocksett Inn and Restaurant
BBQ/picnic Area
Riverhouse by Weekender (Formerly Jack Daniels Inn)

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, (437)
"Super cute place! Would stay here again"
United States
Danielle
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Exterior
The Burrell House

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
Pub
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (1001)
"Very comfortable and clean."
United States
Christina
The price is €166
includes taxes & fees
31 Dec - 1 Jan 2026
Courtyard by Marriott Keene Downtown
Farm to table cuisine
The Birchwood Inn

The Birchwood Inn

The Birchwood Inn
3.5 star property
Temple
9.4 out of 10, Exceptional, (225)
"A wonderful historic Inn. Great resturant and lovely accommodations . A very gracious host."
United States
Anonymous traveller
The price is €156
includes taxes & fees
25 Dec - 26 Dec
The Birchwood Inn
Water park
Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA
3.5 star property
Fitchburg
8.6 out of 10, Excellent, (1006)
"Nice place "
United States
Daniel
The price is €153
includes taxes & fees
22 Jan - 23 Jan 2026
Great Wolf Lodge Boston / Fitchburg, MA
Free daily full breakfast
Centennial House

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 €180
includes taxes & fees
28 Dec - 29 Dec
Centennial House
Terrace/patio
The Maguire House Bed & Breakfast

The Maguire House Bed & Breakfast

The Maguire House Bed & Breakfast
3.5 star property
Ashburnham
10.0 out of 10, Exceptional, (36)
"Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. "
United States
Ranjit
The price is €233
includes taxes & fees
7 Jan - 8 Jan 2026
The Maguire House Bed & Breakfast
Exterior
Monadnock Inn

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
Lobby
Gardner Inn

Gardner Inn

Gardner Inn
2.0 star property
Gardner
5.6 out of 10, (17)
"The property needs work but hte staff was pleasant and the facility was quiet. "
United States
Lou
The price is €94
includes taxes & fees
28 Dec - 29 Dec
Gardner Inn
Front of property – evening/night
Howarth House B&B

Howarth House B&B

Howarth House B&B
3.0 star property
Fitchburg
10.0 out of 10, Exceptional, (110)
"Beautiful place, great hospitality! "
United States
andrew
Howarth House B&B
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

This serene 85-acre lake offers swimming, fishing, and access to 50+ miles of mountain biking trails. Reserve one of the 150 wooded campsites early for a prime lakeside spot to fully experience this natural retreat.
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Wendall P. Clark Memorial

After visiting Wendall P. Clark Memorial, 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

Motel 6 Leominster, MA

Motel 6 Leominster, MA

10/10 Excellent
"Perfect...they let me check in early too at no charge "
PAUL 1-night trip
Posted 2 days ago
Motel 6 Leominster, MA

More cheap stays in Winchendon

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH
The price is €77 per night from 31 Dec to 1 Jan
€77
31 Dec - 1 Jan 2026
includes taxes & fees
7/10 Good! (999 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 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?
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?
Great Wolf Lodge Boston / Fitchburg, MA: Resort, 9-minute walk from Great Wolf Lodge Waterpark. Features 4 indoor swimming pools, a children's pool and free water park access. Doubletree by Hilton Hotel Leominster and The Colonial Hotel 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, Millers River 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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