A hilly landscape with a tower on top, dense forest, and a cloudy sky.

Find hotels in Winchendon, MA from £74

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Save instantly and earn perks with One Key
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Filter by

Property class

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Our top choices for Winchendon hotels

1. Gardner Inn

Gardner Inn
2.0 star property
Gardner
7.8 out of 10, Good, (96 reviews)
"It was a very good stay for the price. Very clean and the location was very good. I would definitely stay here again."
United States
Leila
The price is £74
includes taxes & fees
8 Dec - 9 Dec
Gardner Inn

2. The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
9.0 out of 10, Wonderful, (1,002 reviews)
"We love this hotel! We stay every year when we go to Wachusett Mountain"
United States
Mollie
The price is £117
includes taxes & fees
7 Dec - 8 Dec
The Colonial Hotel

3. Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster
4.0 star property
Leominster
8.8 out of 10, Excellent, (1,000 reviews)
"Good customer service and great location"
United States
louis
The price is £126
includes taxes & fees
15 Nov - 16 Nov
Doubletree by Hilton Hotel Leominster

4. Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
2.0 star property
Keene
7.0 out of 10, Good, (1,002 reviews)
"convenient and safe place to stay while on a drivng vacation through New England"
United States
CHERYL
The price is £75
includes taxes & fees
12 Nov - 13 Nov
Days Inn by Wyndham Keene NH

5. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1,004 reviews)
"Great place to go"
United States
Ruddy
The price is £115
includes taxes & fees
10 Nov - 11 Nov
Best Western Plus Keene Hotel

6. Motel 6 Leominster, MA

Motel 6 Leominster, MA
2.0 star property
Leominster
8.4 out of 10, Very good, (1,013 reviews)
"Clean room, staff was helpful and even tho I only stayed 2 nights I felt safe and comfortable. Would stay again when in the area."
United States
Ruth
The price is £79
includes taxes & fees
2 Dec - 3 Dec
Motel 6 Leominster, MA

7. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.6 out of 10, Excellent, (1,003 reviews)
"Excellent stay"
United States
Lisa
The price is £108
includes taxes & fees
8 Nov - 9 Nov
Keene Elm City Hotel, an Ascend Collection Hotel

8. Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)
2.5 star property
Peterborough
9.2 out of 10, Wonderful, (482 reviews)
"Very clean and convenient. Staff were lovely, big rooms."
United States
Kathleen
The price is £139
includes taxes & fees
10 Nov - 11 Nov
Riverhouse by Weekender (Formerly Jack Daniels Inn)

9. Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA
3.5 star property
Fitchburg
8.6 out of 10, Excellent, (1,006 reviews)
"Great place for a Family vacation"
United States
Josefa
The price is £132
includes taxes & fees
29 Nov - 30 Nov
Great Wolf Lodge Boston / Fitchburg, MA

10. The Maguire House Bed & Breakfast

The Maguire House Bed & Breakfast
3.5 star property
Ashburnham
10.0 out of 10, Exceptional, (41 reviews)
"Terry and Paul are wonderful warm Innkeepers. The inn is classically New England charming. The lake view is stunning. Appreciated the little touches like nighty cookies, water and snacks in the room."
United States
Jeffrey
The price is £210
includes taxes & fees
2 Dec - 3 Dec
The Maguire House Bed & Breakfast

11. The Birchwood Inn

The Birchwood Inn
3.5 star property
Temple
9.4 out of 10, Exceptional, (243 reviews)
"The host was absolutely wonderful in making recommendations for a future visit with our extended familyā£ļø We were pleasantly surprised by all that the surrounding smaller towns had to offer and cannot wait to return🌹"
United States
Karen
The price is £141
includes taxes & fees
2 Dec - 3 Dec
The Birchwood Inn

12. Monadnock Inn

Monadnock Inn
2.5 star property
Jaffrey
7.8 out of 10, Good, (296 reviews)
"The building and interior was big on ambiance and charm. The staff was very cordial and helpful. I would suggest the addition of an ice machine"
United States
Jim
The price is £119
includes taxes & fees
10 Nov - 11 Nov
Monadnock Inn

13. Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (431 reviews)
"Comfortable, clean, friendly staff, great breakfast"
United States
Dayle
The price is £128
includes taxes & fees
28 Nov - 29 Nov
Hampton Inn & Suites Keene

14. The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (177 reviews)
"Clean,quiet, beautiful inn in the heart of downtown Keene,NH. Joe was friendly and accommodating and a hell of a great guy. A+++++++"
United States
Richard
The price is £88
includes taxes & fees
16 Nov - 17 Nov
The Carriage Barn Inn

15. Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.6 out of 10, Excellent, (1,000 reviews)
"Comfortable, clean room. Helpful and friendly staff. Convenient location."
United States
Deborah
The price is £136
includes taxes & fees
15 Nov - 16 Nov
Courtyard by Marriott Keene Downtown

16. The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (189 reviews)
"The Burrell House is a lovely historic home convenient to downtown Keene. The room was very clean and the bed super comfortable. There is no staff but it worked fine for my stay."
United States
Carol
The price is £123
includes taxes & fees
16 Nov - 17 Nov
The Burrell House

17. Chocksett Inn and Restaurant

Chocksett Inn and Restaurant
3.5 star property
Sterling
8.8 out of 10, Excellent, (194 reviews)
"Good for one night stopover."
United States
Lisa
The price is £132
includes taxes & fees
10 Nov - 11 Nov
Chocksett Inn and Restaurant

18. Centennial House

Centennial House
3.5 star property
Northfield
9.8 out of 10, Exceptional, (193 reviews)
"Excellent host making us feel very welcome. Very nice room and really lovely breakfast. Would certainly stay again if we are in the area."
United Kingdom
Alan
The price is £138
includes taxes & fees
8 Dec - 9 Dec
Centennial House

19. Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (808 reviews)
"Looking for a quite stay there perfect"
United States
Christopher
The price is £156
includes taxes & fees
22 Nov - 23 Nov
Fairfield Inn & Suites by Marriott Keene Downtown

20. Howarth House B&B

Howarth House B&B
3.0 star property
Fitchburg
10.0 out of 10, Exceptional, (124 reviews)
"We needed somewhere near Mt. Wachusett to stay and this was a perfect spot. Very cozy and well decorated. The breakfast was such a nice touch."
United States
Maddy
The price is £157
includes taxes & fees
30 Nov - 1 Dec
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.
Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Winchendon attractions

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.

A river reflecting autumn trees and a dense forest.

Top Winchendon Hotel Reviews

More cheap stays in Winchendon

Find out more about Winchendon

Top reasons to visit Winchendon

  • Outdoor Adventures: Winchendon is a paradise for nature lovers, offering various outdoor activities in its picturesque landscapes and nearby state parks.
  • Winter Sports: The Easton Ski Area provides thrilling winter sports opportunities, perfect for adventure seekers.
  • Charming Accommodations: Enjoy a range of delightful bed and breakfasts and guesthouses that reflect the town's quaint charm.
  • Scenic Tours: Immerse yourself in scenic tours that showcase the natural beauty and captivating landscapes of New England.
  • Local Attractions: Explore unique local attractions, including nature reserves and historic sites, for a well-rounded experience.

Find great hotels near Winchendon

Discover the charming accommodations of Winchendon, Massachusetts, where a variety of lodging options await. From delightful bed and breakfasts to inviting guesthouses, this quaint town offers something for everyone. Perfect for adventurous families or those seeking a historic themed getaway, Winchendon’s hotels provide a warm and welcoming atmosphere. Whether you're searching for the best hotels or unique local stays, you'll find an array of options to make your visit memorable.

  • The Colonial Hotel: A charming 3-star hotel that caters to business travellers while also offering a pet-friendly experience. Located 6.2km from Winchendon, The Colonial Hotel features multiple meeting rooms and a well-equipped business centre, making it an ideal choice for those combining work and leisure. Guests appreciate the welcoming atmosphere and the ability to bring their furry friends along, thanks to its flexible pet policy. The hotel’s blend of professional amenities and homely comforts provides an inviting retreat for business and leisure guests alike.
  • Great Wolf Lodge Boston / Fitchburg, MA: A vibrant 3.5-star resort that promises an unforgettable family adventure. Situated 8.7km from Winchendon, this property is designed with families in mind, featuring a vast indoor water park, a dedicated children's pool, and an arcade game room. Its LGBTQIA-friendly environment ensures a welcoming experience for all guests. Parents can relax while their children enjoy supervised childcare activities or mini-golf onsite, making it a perfect getaway for families seeking fun, safety, and inclusivity during their stay.
  • Monadnock Inn: A delightful Bed and Breakfast located 6.2km from Winchendon, ideal for golf enthusiasts. The Monadnock Inn offers a unique golf-themed experience, encouraging travellers to indulge in their passion for the sport. Guests can enjoy easy access to golf facilities and a peaceful atmosphere that complements a relaxing retreat. With its quaint charm and personalised service, this inn is perfect for those looking to combine leisure with their love for golf in a picturesque setting.

Where to stay near Winchendon

Winchendon, Massachusetts, offers a delightful blend of outdoor adventures and scenic beauty, perfect for a romantic getaway or a family-friendly holiday. Explore the charming landscapes and vibrant atmosphere of nearby towns, where you can indulge in recreation and discover hidden gems. The area's picturesque views and welcoming communities make it an ideal destination for those seeking both adventure and relaxation, ensuring an unforgettable travel experience.

  • Fitchburg: Located a mere 8.7km from Winchendon, Fitchburg is a vibrant city that offers a variety of attractions for visitors seeking family-friendly adventures and entertainment. With a bustling ski field and a thrilling water park, your time here can be filled with excitement, especially during the winter months. Notable landmarks include a lively theme park and an event conference venue, making Fitchburg a great destination for fun-filled activities year-round.
  • Gardner: Just 5.0km from Winchendon, Gardner is a charming city that attracts sports enthusiasts and adventure seekers alike. The city is particularly popular during the warmer months, with visitors flocking to enjoy its ski fields and engaging educational experiences. Gardner boasts lovely local attractions, including scenic beaches and tranquil lakes, perfect for a day of relaxation or family outings. The city's welcoming atmosphere ensures a delightful experience for all who visit.
  • Rindge: A short 3.1km from Winchendon, Rindge is a picturesque city celebrated for its stunning outdoor scenery and romantic spots. This destination is particularly enticing from July to September, when the beauty of nature truly shines. Enjoy a myriad of outdoor activities, from exploring serene lakes and sandy beaches to engaging in educational pursuits at the modern college university. Rindge's enchanting landscapes make it an ideal location for those seeking a blend of adventure and tranquility.

Things to do in and around Winchendon

Winchendon, Massachusetts, offers a charming escape for outdoor enthusiasts and couples alike, with its picturesque scenery and recreational opportunities. Visitors can explore the local educational attractions and enjoy activities at the Easton Ski Area, perfect for those seeking winter sports. Whether you're indulging in scenic tours or simply soaking in the natural beauty, Winchendon promises a delightful vacation experience.

Shopping

Discover the charming 1761 Old Mill Gift Shop, perfect for unique souvenirs, located 6.8km from Winchendon. If you're up for a drive, indulge in delightful treats at Ava Marie Handmade Chocolates, 8.7km away, or enjoy a broader shopping experience at The Mall at Whitney Field, 11.8km away.

Recreation

At Lake Dennison State Recreation Area, immerse yourself in nature with serene trails and tranquil waters, ideal for relaxation. Shattuck Golf Course offers invigorating outdoor sports amidst beautiful landscapes, while Winchendon Community Park provides peaceful spaces for unwinding and enjoying leisurely strolls amidst greenery.

Adventure

Explore Wetmore Trailhead for an invigorating hike amidst nature's charm, offering a true outdoor adventure. The Wapack Trail, located 8.7km away, boasts stunning scenery and thrilling hiking experiences. For a shorter trek, Towline Trailhead, only 2.5km distant, provides an excellent outdoor escapade.

Nightlife

In Winchendon, the Robinson-Broadhurst Foundation Performing Arts Amphitheater offers a charming blend of culture and entertainment. Nearby, the Peterborough Players and Colonial Theatre, both within 13.0km, provide captivating performances in a romantic atmosphere, perfect for a delightful evening out.

Booking tips and Expedia advantages for Winchendon

To save money on your visit to Winchendon, consider travelling between November and January when prices are lower. Aim to book your stay on a Monday, the cheapest day, and avoid Saturdays, which are the priciest. Use Expedia’s search tool to filter by budget and location, and sort results from lowest to highest price. Additionally, save further by bundling your hotel, flights, and activities into a package deal. Don’t forget to explore free activities around town, as walking is a great way to discover Winchendon without spending a penny.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Winchendon are November to January, where the prices are slightly lower. This is in comparison to June to July and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Winchendon is Monday. The most expensive day to stay in Winchendon is Saturday.
  • Find cheap hotels on Expedia: Expedia's search tool enables you to specify your budget, preferred location, and additional criteria. You can organise your search results to display prices from lowest to highest, allowing you to view the most affordable hotels first. Furthermore, you have the option to refine your choices by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels available for booking.
  • Consider bundling your trip: You can save money by combining your hotel booking in Winchendon with your flights and activities through an Expedia package deal.

Find the best attractions in and around Winchendon

Winchendon, Massachusetts, offers a charming escape for those seeking outdoor adventures and romantic scenery. Visitors can explore local attractions such as nature reserves and state parks, perfect for eco-friendly experiences. Highlights include popular sites in Winchendon, captivating castles, and various outdoor activities that showcase the area's natural beauty. This quaint town is an ideal destination for travellers looking to immerse themselves in nature while enjoying the quaint charm of New England.

  • The Winchendon School: Immerse yourself in the vibrant atmosphere of The Winchendon School, a modern educational institution that blends contemporary architecture with a lively campus life. Experience the local community and engage in various cultural activities.
  • Paradise Island: Only 1.9km from Winchendon, Paradise Island offers a serene escape with its stunning beaches and lush outdoor spaces. Enjoy a relaxing day soaking up the sun, swimming, or picnicking in this idyllic setting.
  • Monadnock State Park: Situated 6.8km from Winchendon, Monadnock State Park is perfect for adventure seekers. Explore its scenic trails, enjoy breathtaking views, and experience the great outdoors in a picturesque environment.

Best time to go to Winchendon

The best time to visit Winchendon can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Winchendon falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Winchendon falls in January, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January23.0°F (-5.0°C)Light RainMostly SunnyAverageAverage
February25.0°F (-3.9°C)Light RainMostly CloudyAverageAverage
March32.5°F (0.3°C)Light RainMostly CloudyAverageAverage
April44.4°F (6.9°C)Light RainMostly CloudyAverageSlightly High
May56.3°F (13.5°C)Light RainMostly SunnyAverageSlightly Low
June64.4°F (18.0°C)Light RainMostly SunnySlightly HighAverage
July70.9°F (21.6°C)Light RainMostly SunnySlightly HighSlightly High
August68.9°F (20.5°C)Light RainMostly SunnySlightly HighSlightly High
September61.7°F (16.5°C)Light RainMostly SunnyAverageAverage
October50.4°F (10.2°C)Light RainMostly SunnySlightly LowAverage
November38.5°F (3.6°C)Light RainMostly SunnySlightly LowSlightly Low
December29.5°F (-1.4°C)Light RainMostly CloudySlightly LowSlightly Low

The nearest major airports for your trip to Winchendon

When planning your visit to Winchendon, Massachusetts, you have several major airports to consider. Boston Logan International Airport (BOS) is 35.4km away, with luxurious hotels like Encore Boston Harbor, The Langham, and Boston Harbor Hotel all within 1.9km. Manchester-Boston Regional Airport (MHT) is closer at 21.7km, featuring nearby accommodations such as The Grand at Bedford Village Inn and DoubleTree by Hilton Manchester Downtown, both 2.5km from the airport. Worcester Regional Airport (ORH) is the nearest at 18.6km, with excellent options like Beechwood Hotel and AC Hotel by Marriott, just 2.5km away. Each hotel offers convenient access to its respective airport.

Frequently asked questions

What is the best area to stay in Winchendon?
The best area to stay in Winchendon is near the town centre, particularly around Central Street and Front Street.

This area is the heart of Winchendon, offering easy access to local amenities and a sense of community. You'll find a selection of local shops, eateries, and public spaces, including the beautiful Winchendon Common, which often hosts community events. The town centre is quite walkable, making it convenient to explore on foot.

For families, staying in this central area is ideal. It provides close proximity to attractions like the Murdock-Whitney House Museum and the Beals Memorial Library, which often has children's programmes. The nearby Winchendon Community Park offers green space for kids to play.

Couples looking for a relaxed retreat will also appreciate the town centre. It offers a quieter pace with access to local dining options and the opportunity to enjoy strolls around the Common or along the Millers River, which runs through town.
When is the best time to go to Winchendon?
The best time to go to Winchendon is during the autumn months, specifically from September to October.

This period offers the most pleasant weather for outdoor activities, with mild temperatures and less humidity than the summer. The main draw, however, is the spectacular New England foliage, which transforms the landscape into a canvas of reds, oranges, and yellows. The Winchendon State Forest and the surrounding rural areas are particularly picturesque during this time.

Couples looking for a relaxing getaway will appreciate the scenic drives and opportunities for hiking or leisurely walks through the colourful forests. Many local farms also offer seasonal activities like apple picking and pumpkin patches, adding to the charm of an autumn visit.

Families will find autumn an excellent time for a visit, too. The cooler weather is ideal for exploring Winchendon's outdoor spaces without the intense heat of summer.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Winchendon.
How much is the nightly rate at a Winchendon hotel?
Prices for hotels in Winchendon often vary, but you can find a great deal from £74 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

Explore a world of travel with Expedia