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Our top choices for Winchendon hotels

Property grounds
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 NZ$429
includes taxes & fees
7 Jan - 8 Jan
The Maguire House Bed & Breakfast
Double Room
Gardner Inn

Gardner Inn

Gardner Inn
2.0 star property
Gardner
5.4 out of 10, (18)
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 NZ$192
includes taxes & fees
6 Jan - 7 Jan
Gardner Inn
Interior
The Colonial Hotel

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1003)
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
Lobby
Motel 6 Leominster, MA

Motel 6 Leominster, MA

Motel 6 Leominster, MA
2.0 star property
Leominster
8.2 out of 10, Very good, (1009)
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.
"I always have a great stay."
United States
alice
The price is NZ$160
includes taxes & fees
11 Jan - 12 Jan
Motel 6 Leominster, MA
Reception
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, (1006)
"The hotel was very nice and the restaurant was a nice establishment. "
United States
Dina
The price is NZ$276
includes taxes & fees
11 Jan - 12 Jan
Doubletree by Hilton Hotel Leominster
Fireplace
Chocksett Inn and Restaurant

Chocksett Inn and Restaurant

Chocksett Inn and Restaurant
3.5 star property
Sterling
8.6 out of 10, Excellent, (145)
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.
"Staff was wonderful. Would highly recommend this hotel."
United States
Paul
The price is NZ$327
includes taxes & fees
6 Jan - 7 Jan
Chocksett Inn and Restaurant
Breakfast 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, (440)
"Room was clean, spacious and staff was pleasant. "
United States
Susan
Riverhouse by Weekender (Formerly Jack Daniels Inn)
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.
"great proprietors beautiful vintage home excellent breakfast"
United States
JAMES
The price is NZ$341
includes taxes & fees
1 Feb - 2 Feb
Centennial House
Garden
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
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)
"Checkin was quick. I like the pre-check in process."
United States
Anthony
The price is NZ$152
includes taxes & fees
7 Jan - 8 Jan
Days Inn by Wyndham Keene NH
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, (166)
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 NZ$235
includes taxes & fees
6 Jan - 7 Jan
The Carriage Barn Inn
Exterior
The Burrell House

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (156)
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.
"The building and room were very nice. The location is great, very walkable to the center of town. "
United States
Rochelle
The Burrell House
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.
"The room was comfortable and clean wwhen we arrived "
United States
Peter
Monadnock Inn
Reception
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, (1006)
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 NZ$302
includes taxes & fees
16 Jan - 17 Jan
Courtyard by Marriott Keene Downtown
Indoor pool
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, (974)
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.
"Staff was very welcoming and the room was very clean. "
United States
Rebecca
The price is NZ$243
includes taxes & fees
6 Jan - 7 Jan
Keene Elm City Hotel, an Ascend Collection Hotel
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 NZ$346
includes taxes & fees
22 Jan - 23 Jan
Fairfield Inn & Suites by Marriott Keene Downtown
Reception
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (362)
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.
"Room is very clean , breakfast is good and fresh .coffee serve well all time . Will back to stay again . "
United States
Raymond
The price is NZ$320
includes taxes & fees
1 Feb - 2 Feb
Hampton Inn & Suites Keene
Premium bedding, individually decorated, individually furnished, desk
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, (1002)
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 stay pool was very nice"
United States
Patrick
The price is NZ$280
includes taxes & fees
6 Jan - 7 Jan
Best Western Plus Keene Hotel
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 NZ$329
includes taxes & fees
8 Jan - 9 Jan
The Birchwood Inn
4 indoor pools, seasonal outdoor pool, pool cabanas (surcharge)
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, (1013)
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 NZ$312
includes taxes & fees
3 Feb - 4 Feb
Great Wolf Lodge Boston / Fitchburg, MA
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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Winchendon Town Hall

The Winchendon Municipal Building serves as the town's administrative centre. Visitors can observe civic operations during business hours and occasionally attend public meetings.
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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
"Great "
Domingos 1-night trip
Posted 2 days ago
Great Wolf Lodge Boston / Fitchburg, MA

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 NZ$152 per night from 7 Jan to 8 Jan
NZ$152
7 Jan - 8 Jan
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 The Colonial Hotel. 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. 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 11 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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