Find hotels in Winchendon, MA from ฿2,840

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25 Dec - 26 Dec
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26 Dec - 27 Dec
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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)
Escape to this quiet retreat with an indoor pool and fitness centre near Ashuelot River. Just minutes from local shops and eateries, this hotel offers free breakfast, WiFi, and parking. The helpful staff ensures a comfortable stay for business or leisure travellers.
"The room was perfect, and the food was great "
United States
Paul
The price is ฿3,664
฿3,976 total
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 ฿4,081
฿4,559 total
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)
This cosy Carriage Barn Inn provides complimentary continental breakfast, WiFi, and parking. Located near Thorne-Sagendorph Art Gallery, the bed and breakfast creates a perfect base for exploring Keene's cultural attractions.
"Excellent place!!!! Lovely room that had all I needed!!! The bed was comfortable and the stay was wonderful!!!!!!"
United States
natalia
The price is ฿3,960
฿4,297 total
includes taxes & fees
8 Jan - 9 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, (1005)
Situated just a 14-minute walk from North Leominster Station, this motel offers easy access to The Mall at Whitney Field and Doyle Community Park. Enjoy free WiFi and daily housekeeping while the friendly 24-hour front desk ensures a comfortable stay.
"Very clean room and helpful, friendly staff !"
United States
Ralph
The price is ฿2,517
฿2,874 total
includes taxes & fees
4 Jan - 5 Jan 2026
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, (1000)
Set in picturesque Gardner with stunning countryside views, this hotel offers Swedish massages and facials. Guests enjoy the quiet atmosphere, convenient highway access, and thoughtful amenities like an on-site restaurant and bar.
"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)
This hotel offers quiet rooms and a peaceful environment near the Ashuelot River. Enjoy complimentary breakfast, WiFi, and parking. Guests love the helpful staff and convenient location. Visit the 24-hour fitness centre or unwind with a drink at the bar after exploring nearby attractions.
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is ฿4,320
฿4,687 total
includes taxes & fees
29 Dec - 30 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, (1001)
"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 ฿2,618
฿2,840 total
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)
Free breakfast, parking, and 24-hour fitness centre make this Keene hotel a great choice. Swim in the indoor pool or request room service after exploring nearby Cheshire Children's Museum. Travellers praise the helpful staff and morning meal.
"Clean comfy nice staff "
United States
Katherine
The price is ฿5,123
฿5,558 total
includes taxes & fees
25 Jan - 26 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 ฿5,594
฿6,069 total
includes taxes & fees
8 Jan - 9 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)
Charming hotel with an on-site restaurant serving dinner. Enjoy convenient amenities like free WiFi and parking while exploring nearby Mary Had a Little Lamb Statue and Davis' Farmland & Mega Maze. North Leominster Station is just a short drive away.
"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 ฿4,946
฿5,524 total
includes taxes & fees
28 Dec - 29 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)
Walking distance to Central Square, this inviting guesthouse offers complimentary WiFi and self parking. Enjoy the outdoor picnic area after exploring nearby attractions like CC&H Framing and Pepper Pete's Hot Shop.
"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)
Stylish accommodation in Keene City centre, close to Colonial Theatre and Central Square. Enjoy a refreshing swim in the indoor pool, grab a bite at the coffee shop, then unwind at the bar. Free WiFi and parking make exploring the area convenient.
"Very comfortable and clean."
United States
Christina
The price is ฿5,594
฿6,069 total
includes taxes & fees
8 Jan - 9 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)
Escape to this charming Colonial inn offering Porters restaurant with farm-to-table cuisine. Guest rooms include refrigerators and microwaves, while a bar and terrace provide relaxation spaces. Near Solon Mansfield Memorial Library and Temple Mountain with free breakfast, WiFi and parking.
"A wonderful historic Inn. Great resturant and lovely accommodations . A very gracious host."
United States
Anonymous traveller
The price is ฿5,288
฿5,738 total
includes taxes & fees
29 Dec - 30 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)
Located near Wachusett Mountain Ski Area, this family-friendly resort offers a lazy river and poolside bar. Enjoy American cuisine at Lodge Wood Fired Grill or order room service. Each accommodation includes convenient refrigerators and microwaves for added comfort.
"The room was clean, the staff was very nice!"
United States
Entela
The price is ฿5,011
฿5,597 total
includes taxes & fees
25 Jan - 26 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)
Discover Centennial House, a charming colonial B&B adjacent to Northfield Golf Club. Enjoy free full breakfast, WiFi, and parking. Explore nearby hiking trails, cross-country skiing routes, or relax in the garden and terrace after visiting local attractions.
"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 ฿6,258
฿6,615 total
includes taxes & fees
8 Jan - 9 Jan 2026
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)
Set in scenic Ashburnham, this charming B&B offers complimentary daily breakfast and outdoor adventures like rowing, cross-country skiing, and sledding. The peaceful property features a garden, terrace, and snack bar, all near Stevens Memorial Library and Ashburnham State Forest.
"Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. "
United States
Ranjit
The price is ฿8,546
฿8,546 total
includes taxes & fees
8 Jan - 9 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)
Set beside Shattuck Golf Course, this charming B&B provides the perfect base for hiking and mountain biking adventures. Enjoy complimentary WiFi and parking while exploring nearby Jaffrey Civic Centre.
"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)
Explore attractions like Dunn State Park from this convenient lodging in Gardner. Free parking, WiFi, and 24-hour front desk make your visit seamless. Worcester Regional Airport is 44 minutes away.
"The property needs work but hte staff was pleasant and the facility was quiet. "
United States
Lou
The price is ฿3,077
฿3,436 total
includes taxes & fees
21 Jan - 22 Jan 2026
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)
Unwind in a tranquil setting with jetted tubs and plush pillows at this relaxing B&B. Just a 16-minute walk from Fitchburg Station, guests enjoy free breakfast, WiFi, and parking while exploring nearby trails or visiting the Fitchburg Art Museum.
"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

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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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

Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

10/10 Excellent
"Everything "
Karen 1-night trip
Posted 3 days ago
Great Wolf Lodge Boston / Fitchburg, 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 ฿2,618 per night from 31 Dec to 1 Jan
฿2,618
฿2,840 total
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, 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 Great Wolf Lodge Boston / Fitchburg, MA and Doubletree by Hilton Hotel Leominster. See all available top hotels, or 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.