Find hotels in Winchendon, MA from $92

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Our top choices for Winchendon hotels

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
$129 nightly
The price is $141
Dec 31 - Jan 1, 2026
Total with taxes and fees
The Carriage Barn Inn

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, (970)
"Staff was very welcoming and the room was very clean. "
United States
Rebecca
$114 nightly
The price is $124
Jan 1 - Jan 2, 2026
Total with taxes and fees
Keene Elm City Hotel, an Ascend Collection Hotel

Motel 6 Leominster, MA

Motel 6 Leominster, MA
2.0 star property
Leominster
8.2 out of 10, Very Good, (1002)
"Always satisfied with Motel 6 ."
United States
Allan A
$83 nightly
The price is $92
Jan 6 - Jan 7, 2026
Total with taxes and fees
Motel 6 Leominster, MA

Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster
4.0 star property
Leominster
8.6 out of 10, Excellent, (1000)
"The hotel was very nice and the restaurant was a nice establishment. "
United States
Dina
$143 nightly
The price is $159
Jan 4 - Jan 5, 2026
Total with taxes and fees
Doubletree by Hilton Hotel Leominster

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1000)
"Great staff, clean room, nice breakfast"
United States
DORTHY
$129 nightly
The price is $140
Dec 31 - Jan 1, 2026
Total with taxes and fees
Best Western Plus Keene Hotel

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1003)
"Easy checkin, pleasant staff and clean room. "
United States
Susan
$160 nightly
The price is $179
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Colonial Hotel

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
$180 nightly
The price is $195
Jan 6 - Jan 7, 2026
Total with taxes and fees
Fairfield Inn & Suites by Marriott Keene Downtown

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
2.0 star property
Keene
7.0 out of 10, Good, (1000)
"Checkin was quick. I like the pre-check in process."
United States
Anthony
$99 nightly
The price is $107
Dec 31 - Jan 1, 2026
Total with taxes and fees
Days Inn by Wyndham Keene NH

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
$186 nightly
The price is $197
Jan 15 - Jan 16, 2026
Total with taxes and fees
Centennial House

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (360)
"Clean comfy nice staff "
United States
Katherine
$170 nightly
The price is $184
Jan 25 - Jan 26, 2026
Total with taxes and fees
Hampton Inn & Suites Keene

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (156)
"The building and room were very nice. The location is great, very walkable to the center of town. "
United States
Rochelle
$131 nightly
The price is $142
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Burrell House

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (1005)
"Very comfortable and clean."
United States
Christina
$180 nightly
The price is $195
Jan 6 - Jan 7, 2026
Total with taxes and fees
Courtyard by Marriott Keene Downtown

Chocksett Inn and Restaurant

Chocksett Inn and Restaurant
3.5 star property
Sterling
8.6 out of 10, Excellent, (144)
"Staff was wonderful. Would highly recommend this hotel."
United States
Paul
$169 nightly
The price is $189
Jan 1 - Jan 2, 2026
Total with taxes and fees
Chocksett Inn and Restaurant

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, (438)
"Rooms were clean. Pillows were very soft and the lighting they had outside added a nice touch. "
United States
Tracy
$169 nightly
The price is $183
Jan 4 - Jan 5, 2026
Total with taxes and fees
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA
3.5 star property
Fitchburg
8.6 out of 10, Excellent, (1006)
"The room was clean, the staff was very nice!"
United States
Entela
$179 nightly
The price is $200
Jan 5 - Jan 6, 2026
Total with taxes and fees
Great Wolf Lodge Boston / Fitchburg, MA

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 traveler
$175 nightly
The price is $190
Jan 2 - Jan 3, 2026
Total with taxes and fees
The Birchwood Inn

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
$245 nightly
The price is $245
Jan 22 - Jan 23, 2026
Total with taxes and fees
The Maguire House Bed & Breakfast

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
$235 nightly
The price is $235
Dec 31 - Jan 1, 2026
Total with taxes and fees
Howarth House B&B

Monadnock Inn

Monadnock Inn
2.5 star property
Jaffrey
7.6 out of 10, Good, (277)
"The room was comfortable and clean wwhen we arrived "
United States
Peter
$148 nightly
The price is $161
Dec 31 - Jan 1, 2026
Total with taxes and fees
Monadnock 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
$99 nightly
The price is $111
Jan 1 - Jan 2, 2026
Total with taxes and fees
Gardner Inn
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Stay near popular Winchendon attractions

Learn more about Winchendon

Toy Town's charm comes alive at the Old Murdock Senior Center, 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.

The Millers River in Winchendon, Massachusetts

Top Winchendon Hotel Reviews

More cheap stays in Winchendon

Hotels in Winchendon with star-rating

Find out more about Winchendon

Top reasons to visit Winchendon

  • Outdoor Adventures: Winchendon is a paradise for outdoor lovers, offering activities like skiing, hiking, and water sports at scenic locations such as Lake Monomonac.
  • Family-Friendly Fun: Enjoy exciting attractions like mini golf and water parks, perfect for families looking for a day of adventure.
  • Charming Accommodations: Stay in cozy bed and breakfasts or quaint guesthouses that enhance the region's charm.
  • Rich Scenic Beauty: Experience the picturesque landscapes and serene environments that make Winchendon a romantic getaway.
  • Cultural Exploration: Discover historical New England hamlets and local colleges while immersing yourself in the area's rich heritage.

Find great hotels near Winchendon

Discover the charm of Winchendon, Massachusetts, where a variety of cozy accommodations await you. Choose from inviting bed and breakfasts or quaint guesthouses that promise a memorable stay. Whether you're seeking adventure, a family-friendly atmosphere, or a touch of history, Winchendon hotels offer something for every traveler. Check out reviews and find the perfect spot to unwind after exploring the beautiful surroundings and local attractions.

  • The Colonial Hotel: Embracing a charming blend of historic elegance and modern amenities, The Colonial Hotel is a 3-star lodging located 10 miles from Winchendon, perfect for both business and leisure travelers. Its pet-friendly policy allows furry companions, making it a welcoming choice for all. With dedicated facilities for business needs, including multiple meeting rooms and a business center, it caters to corporate guests. The Colonial Hotel features cozy accommodations with a touch of classic style, ensuring a comfortable stay for its visitors.
  • Great Wolf Lodge Boston / Fitchburg, MA: This 3.5-star resort, situated 14 miles from Winchendon, is a family-friendly haven that embraces inclusivity and fun for everyone. With a focus on LGBTQIA welcoming, Great Wolf Lodge offers an array of engaging amenities for children, including a free water park, supervised childcare, and an arcade game room. Families can enjoy quality time together with onsite mini-golf and a dedicated children's pool. The vibrant atmosphere and diverse activities make it an ideal destination for a memorable family vacation.
  • Monadnock Inn: Located 10 miles from Winchendon, the Monadnock Inn offers a unique bed and breakfast experience ideal for golf enthusiasts. Nestled in a picturesque setting, this charming inn allows guests to indulge in their love for golf with nearby golfing opportunities. The inn combines rustic charm with comfortable accommodations, ensuring a relaxing stay. Guests appreciate the cozy ambiance and personalized service, making it a perfect retreat for those seeking a tranquil getaway while enjoying their favorite sport.

Where to stay near Winchendon

Winchendon, Massachusetts, offers a charming blend of outdoor adventures and romantic getaways. Just a short drive from Worcester, this picturesque city is perfect for family-friendly fun and scenic exploration. Visit the serene Lake Monomonac for recreational activities, or wander through New England hamlets rich in history. With its convenient location and beautiful surroundings, Winchendon is an ideal base for discovering the natural beauty and cultural treasures of the region.

  • Fitchburg: Located 14 miles from Winchendon, Fitchburg is a vibrant city that attracts visitors year-round, especially from January to March. This destination is perfect for families and adventure seekers, offering a range of entertainment options. Popular activities include skiing and enjoying the local water park. Notable attractions nearby include a theme park and event conference venue, making it an ideal spot for both fun and gatherings. The city's combination of outdoor adventures and family-friendly venues ensures a memorable travel experience.
  • Gardner: Just 8 miles away from Winchendon, Gardner is a lively city known for its sports and adventure offerings. Visitors are drawn to this area particularly in April, July, and September. With access to ski fields and educational opportunities, Gardner caters to active tourists and families alike. The city is also home to beautiful beaches and serene lakes, perfect for a day of relaxation or recreational activities. Gardner's welcoming atmosphere and variety of local attractions make it a great addition to your itinerary.
  • Rindge: A mere 5 miles from Winchendon, Rindge is a charming city that offers scenic views and outdoor experiences. This destination sees a peak in visitors from July to September, as people flock to enjoy its beautiful landscapes and romantic settings. Rindge is an outdoor enthusiast’s paradise, featuring lakes and beaches that are perfect for a day of exploration. Additionally, the presence of a modern college university adds a youthful energy to the area. Rindge's picturesque environment and outdoor activities create a perfect getaway for nature lovers.

Things to do in and around Winchendon

Winchendon offers a charming getaway perfect for outdoor lovers and couples seeking romance. Enjoy the scenic beauty while engaging in activities like skiing at the local ski field or relaxing in recreational areas. Families can have a blast at the water park or challenge each other to a round of mini golf, ensuring a delightful vacation experience filled with fun and adventure.

Shopping

In Winchendon, explore the 1761 Old Mill Gift Shop for unique souvenirs. If you're up for a drive, head to Ava Marie Handmade Chocolates, located 14 miles away, for delicious treats. The Mall at Whitney Field, 19 miles from Winchendon, offers a more extensive shopping experience with various shops and entertainment.

Recreation

At Lake Dennison State Recreation Area, immerse yourself in nature with hiking, fishing, and picnicking, all set against serene lake views. For golf enthusiasts, Shattuck Golf Course and The Driving Range offer excellent outdoor sports experiences, surrounded by beautiful landscapes ideal for relaxation and recreation.

Adventure

Embark on an exhilarating hike along the Wapack Trail, 14 miles from Winchendon, where stunning scenery awaits. Explore the Wetmore Trailhead, located in Winchendon, for a thrilling outdoor experience. Don't miss the Towline Trailhead, only 4 miles away, offering more breathtaking views and adventure vibes.

Nightlife

In Winchendon, the nearby Peterborough Players offers captivating theater performances, just 17 miles away, while the Colonial Theatre, 21 miles away, provides a charming atmosphere for entertainment. The Wilton Town Hall Theatre, located 19 miles from Winchendon, also features delightful shows, perfect for a romantic night out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Winchendon

To save money on your trip to Winchendon, plan your visit between November and January for lower accommodation rates, particularly on Wednesdays. Avoid Saturdays for the best savings. Use Expedia to compare hotel prices and consider booking package deals that include flights and activities for additional discounts. Join Expedia's One Key membership for exclusive offers and earn OneKeyCash for future bookings. Look for flexible booking options and be aware of any additional fees to maximize your savings. Enjoy free local attractions to enhance your experience without straining your budget.

  • 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 Wednesday. The most expensive day to stay in Winchendon is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia's search tool to narrow down your options based on your budget, desired location, and preferred type of accommodation. To find the most affordable rates and special offers, be sure to sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your Winchendon hotel reservations with your flights and activities through an Expedia package deal.
  • Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions in and around Winchendon

Winchendon, Massachusetts, is perfect for outdoor enthusiasts and romantic getaways, offering a blend of scenic beauty and adventure. Explore local attractions such as colleges, nature reserves, and pristine lakes, all catering to eco-friendly travelers seeking a memorable experience. Whether you're looking for relaxation or outdoor activities, Winchendon has something to offer everyone.

  • The Winchendon School: Experience the vibrant atmosphere of The Winchendon School, a modern college that embraces a dynamic learning environment. With its contemporary facilities and engaging community, this institution offers a unique glimpse into the educational landscape of America.
  • Cathedral of the Pines: Located 7 miles away, the Cathedral of the Pines is a serene church that blends nature with spirituality. This tranquil setting features beautiful architecture and hosts various cultural events, making it a perfect spot for reflection and appreciation of the arts.
  • Laurel Lake: Just 7 miles from Winchendon, Laurel Lake is an idyllic destination for outdoor enthusiasts. With its picturesque scenery, sandy beach, and romantic ambiance, it's ideal for swimming, picnicking, or simply enjoying nature's beauty.

Best time to go to Winchendon

The best time to visit Winchendon is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January23.0°F (-5.0°C)Light RainMostly SunnyAverageSlightly Low
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 CloudyAverageAverage
May56.3°F (13.5°C)Light RainMostly SunnyAverageAverage
June64.4°F (18.0°C)Light RainMostly SunnySlightly HighSlightly High
July70.9°F (21.6°C)Light RainMostly SunnySlightly HighSlightly High
August68.9°F (20.5°C)Light RainMostly SunnySlightly HighAverage
September61.7°F (16.5°C)Light RainMostly SunnyAverageAverage
October50.4°F (10.2°C)Light RainMostly SunnySlightly LowSlightly High
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

For your trip to Winchendon, Massachusetts, you have several airport options. Boston Logan International Airport (BOS) is 57 miles away, with nearby hotels like Encore Boston Harbor, The Langham, and The Liberty, all 2-3 miles from the airport. Manchester-Boston Regional Airport (MHT) is 35 miles from Winchendon, offering hotels such as The Grand at Bedford Village Inn and DoubleTree by Hilton Manchester Downtown, both 4 miles away. Lastly, Worcester Regional Airport (ORH) is 30 miles from Winchendon, with accommodations like Beechwood Hotel and AC Hotel by Marriott Worcester, both within 5 miles. Each hotel provides easy 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 center, particularly around Central Street and Front Street, which offers easy access to local amenities and the town's main attractions.

This central area provides convenience for travelers looking to explore Winchendon on foot. You'll find a selection of local shops, eateries, and public spaces within a short walk. The proximity to the Millers River and Lake Monomonac also offers pleasant natural surroundings.

Families often find this area ideal due to its accessibility to parks and outdoor activities. The Winchendon Community Park, for example, is a popular spot for recreation and is easily reachable from the town center. The convenience of having dining options and other services nearby makes planning family outings straightforward.

Couples looking for a relaxing getaway will appreciate the blend of local charm and natural beauty. Strolling along the river or enjoying a quiet meal in one of the local restaurants provides a pleasant experience.
When is the best time to go to Winchendon?
The best time to go to Winchendon is during the summer months, from June to August, or in the fall, from September to October.

Summer offers warm weather, with average temperatures in the 70s Fahrenheit, making it ideal for outdoor activities. The Winchendon State Forest provides opportunities for hiking, fishing, and picnicking, and the nearby Lake Monomonac is great for boating and swimming. Families will find this a great time to visit for outdoor recreation.

Fall brings cooler temperatures and the renowned New England foliage. The landscape transforms with vibrant reds, oranges, and yellows, especially in areas like Otter River State Forest.
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 can I save on a Winchendon hotel booking with Expedia?
With Expedia, you earn OneKeyCash™* on eligible Winchendon hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
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 $92 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.

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