Find hotels in Winchendon, MA from AED 340

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Compare 212 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Doubletree by Hilton Hotel Leominster

4.0 star property
Leominster
8.6 out of 10, Excellent, (1000)
"Always a great place to stay! Friendly, clean and comfortable. "
United States
Lynn
The price is AED 479
AED 535 total
includes taxes & fees
30 Dec - 31 Dec
Doubletree by Hilton Hotel Leominster

Great Wolf Lodge Boston / Fitchburg, MA

3.5 star property
Fitchburg
8.6 out of 10, Excellent, (1006)
"Everything about this place was incredible "
United States
Jaida
The price is AED 460
AED 514 total
includes taxes & fees
4 Dec - 5 Dec
Great Wolf Lodge Boston / Fitchburg, MA

The Colonial Hotel

3.0 star property
Gardner
8.8 out of 10, Excellent, (1013)
"Great hotel, fantastic restaurant, wonderful place!"
United States
Kate
The Colonial Hotel

Motel 6 Leominster, MA

2.0 star property
Leominster
8.0 out of 10, Very Good, (1015)
"This was pretty nice for a motel. It was clean and safe with several places to eat within walking distance. The people at the front desk were very friendly. If you're looking for a good deal for basic accommodations then this is the place."
United States
Jonathan
The price is AED 297
AED 340 total
includes taxes & fees
7 Dec - 8 Dec
Motel 6 Leominster, MA

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
The price is AED 511
AED 554 total
includes taxes & fees
3 Dec - 4 Dec
Best Western Plus Keene Hotel

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 AED 584
AED 652 total
includes taxes & fees
3 Dec - 4 Dec
Chocksett Inn and Restaurant

Days Inn by Wyndham Keene NH

2.0 star property
Keene
7.0 out of 10, Good, (1006)
"Very professional people good service good staff "
United States
George
The price is AED 337
AED 366 total
includes taxes & fees
21 Dec - 22 Dec
Days Inn by Wyndham Keene NH

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 star property
Peterborough
9.4 out of 10, Exceptional, (433)
"Super cute place! Would stay here again"
United States
Danielle
The price is AED 460
AED 539 total
includes taxes & fees
7 Dec - 8 Dec
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Gardner Inn

2.0 star property
Gardner
5.6 out of 10, (16)
"The property needs work but hte staff was pleasant and the facility was quiet. "
United States
Lou
The price is AED 364
AED 406 total
includes taxes & fees
9 Dec - 10 Dec
Gardner Inn

Hampton Inn & Suites Keene

2.5 star property
Keene
8.8 out of 10, Excellent, (351)
"Nice place to stay, nice area, will stay again."
United States
Catherine
The price is AED 541
AED 587 total
includes taxes & fees
23 Dec - 24 Dec
Hampton Inn & Suites Keene

Fairfield Inn & Suites by Marriott Keene Downtown

2.5 star property
Keene
8.8 out of 10, Excellent, (755)
"Front desk pleasant and helpful Breakfast was good Room was spacious and clean Able to walk to shopping and dining. "
United States
Stephen
The price is AED 606
AED 657 total
includes taxes & fees
21 Dec - 22 Dec
Fairfield Inn & Suites by Marriott Keene Downtown

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 star property
Keene
8.4 out of 10, Very Good, (957)
"Enjoyed the breakfast options and the very comfortable bed. "
Canada
Nancy
The price is AED 400
AED 434 total
includes taxes & fees
22 Dec - 23 Dec
Keene Elm City Hotel, an Ascend Collection Hotel

Howarth House B&B

3.0 star property
Fitchburg
10.0 out of 10, Exceptional, (110)
"Beautiful gardens"
United States
Christine
Howarth House B&B

Courtyard by Marriott Keene Downtown

3.0 star property
Keene
8.8 out of 10, Excellent, (1008)
"Lovely hotel"
United States
ronald
The price is AED 590
AED 640 total
includes taxes & fees
7 Dec - 8 Dec
Courtyard by Marriott Keene Downtown

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 AED 710
AED 751 total
includes taxes & fees
28 Dec - 29 Dec
Centennial House

The Birchwood Inn

3.5 star property
Temple
9.4 out of 10, Exceptional, (224)
"Great Spot!"
United States
Kialey
The price is AED 624
AED 677 total
includes taxes & fees
3 Dec - 4 Dec
The Birchwood 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 AED 459
AED 498 total
includes taxes & fees
31 Dec - 1 January 2026
The Carriage Barn Inn

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

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
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

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 offers various outdoor activities, including skiing, hiking, and water sports at Lake Monomonac.
  • Charming New England Atmosphere: Experience the quaint, vibrant culture of local hamlets and scenic views.
  • Family-Friendly Activities: Enjoy mini golf, water parks, and nature reserves suitable for all ages.
  • Romantic Getaways: Perfect for couples seeking a peaceful retreat surrounded by stunning landscapes.
  • Diverse Accommodations: Choose from cozy inns and charming bed & breakfasts tailored to various preferences.

Find great hotels near Winchendon

Explore a variety of lodging options in Winchendon, Massachusetts, including charming bed & breakfasts and cozy inns. Whether you're seeking an adventurous getaway, a family-friendly environment, or an LGBTQIA-welcoming experience, you'll find hotels that cater to your needs. Dive into hotel reviews and discover the best accommodations for your vacation in this unique New England town.

  • The Colonial Hotel: Experience the charm of The Colonial Hotel, a welcoming 3-star property situated 16.1km from Winchendon. This hotel is perfect for travelers seeking a blend of business convenience and a pet-friendly atmosphere. With amenities that cater to both professionals and pet owners, guests can enjoy a stress-free stay with their furry friends. The hotel features well-appointed rooms, complimentary Wi-Fi, and a business center, making it an ideal choice for business travelers. Additionally, the pet policy allows certain pets on-site, ensuring that no family member is left behind. The friendly staff is dedicated to providing exemplary service, ensuring a comfortable and enjoyable stay.
  • Great Wolf Lodge Boston / Fitchburg, MA: A magical retreat for families, Great Wolf Lodge Boston / Fitchburg, MA is a 3.5-star resort located 22.5km from Winchendon. Renowned for its family-friendly atmosphere, this lodge offers an array of amenities designed to entertain and engage children of all ages. Guests can take advantage of the on-site water park, mini-golf, and arcade game room, along with free supervised childcare services. The lodge is also committed to inclusivity, welcoming LGBTQIA travelers with open arms. With spacious family suites and a vibrant atmosphere, it’s a perfect destination for creating unforgettable family memories.
  • Monadnock Inn: Step into the serene ambiance of Monadnock Inn, a cozy Bed & Breakfast located 16.1km from Winchendon. This charming inn is ideal for golf enthusiasts, offering a unique golf-themed experience with easy access to local courses. Guests can unwind in tastefully decorated rooms and enjoy a complimentary breakfast each morning, fueling their adventures. The inn's tranquil setting and personalized service create a home-away-from-home feeling, making it a favorite for travelers seeking a peaceful getaway centered around their passion for golf.

Where to stay near Winchendon

Winchendon, Massachusetts, is a hidden gem for travelers seeking outdoor adventures and romantic getaways. Just a short drive from Worcester, this charming city offers scenic views and family-friendly activities. Explore the beautiful Lake Monomonac, perfect for recreation and relaxation. Don’t miss the quaint New England hamlets nearby, where the atmosphere is vibrant with local culture and charm. Whether you're looking for adventure or a peaceful retreat, Winchendon has something for everyone.

  • Fitchburg: Located 22.5km from Winchendon, Fitchburg is a vibrant city that attracts visitors year-round, with a peak in winter months. Known for its family-friendly atmosphere, adventure opportunities, and entertainment options, Fitchburg offers a variety of experiences. Engage in thrilling activities at the local water park, or hit the slopes at nearby ski fields. Don’t miss the chance to explore exciting local landmarks such as the theme park and event conference venue, making it a perfect spot for a fun-filled day.
  • Gardner: Just 12.9km away from Winchendon, Gardner is a charming city that sees a steady stream of visitors, especially during the spring and summer months. Famous for its sports and adventure experiences, Gardner offers ample opportunities for skiing and other outdoor activities. Discover its local attractions like the family-friendly beach and event conference venue, which cater to both relaxation and entertainment. Whether you're looking to challenge yourself with outdoor sports or enjoy a leisurely day by the water, Gardner has something for everyone.
  • Rindge: A mere 8.0km from Winchendon, Rindge is a picturesque city known for its stunning outdoor scenery and romantic ambiance. With a moderate seasonal visitor flow, the summer months are particularly popular for those seeking outdoor adventures. Explore the breathtaking landscapes at local lakes and mountains, or visit historical sites that tell the story of the area. Rindge is perfect for those who appreciate nature and want to indulge in recreational activities, making it a delightful escape.

Things to do in and around Winchendon

Winchendon, Massachusetts, is perfect for outdoor and romantic getaways, offering scenic views and various activities. Visitors can enjoy skiing at nearby ski fields, play mini golf, and have fun at a water park. For those looking to shop, the local shopping center provides a variety of options. Experience the charm and leisurely pace of this lovely town during your vacation.

Shopping

In Winchendon, visit the 1761 Old Mill Gift Shop for unique gifts. Ava Marie Handmade Chocolates, located nearby, offers delicious treats. If you're up for a drive, The Mall at Whitney Field, 30.6km away, features a variety of shops and entertainment options for a fun day out.

Recreation

Lake Dennison State Recreation Area offers a tranquil setting for relaxation and outdoor activities, perfect for unwinding in nature. For golf enthusiasts, Shattuck Golf Course and Ellinwood Country Club provide scenic courses just 10 and 19.3km away, respectively, blending sports with beautiful landscapes.

Adventure

Embark on an adventure along the Wapack Trail, a picturesque hiking route 22.5km from Winchendon, offering breathtaking scenery. Closer to town, explore the Wetmore Trailhead and the Towline Trailhead, both providing thrilling outdoor experiences that immerse you in Winchendon's natural beauty.

Nightlife

In Winchendon, you can enjoy vibrant nightlife options like the Peterborough Players, Colonial Theatre, and Wilton Town Hall Theatre, all offering captivating performances within a short drive. Each venue radiates romance and culture, creating an enchanting atmosphere for an unforgettable evening 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, visit during the off-peak months of November to January when accommodation prices are lower. Book your stay on a Monday for the best rates, avoiding the pricier Saturdays. Use Expedia to compare hotel rates and consider package deals that combine flights and activities for added savings. Look for free local attractions and utilize public transport for budget-friendly travel options. Sorting prices from lowest to highest can help you find affordable accommodations tailored to your preferences.

  • 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: Utilize Expedia's search tool to refine your preferences, such as your budget, desired location, and preferred type of accommodation. To find the most affordable options and best deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your Winchendon hotel reservation with your flights and activities through an Expedia package.

Find the best attractions in and around Winchendon

Winchendon, Massachusetts, is perfect for outdoor enthusiasts and romantic getaways, featuring stunning natural scenery. Visitors can explore a variety of attractions, including modern colleges, nature reserves, and picturesque lakes. Whether you're seeking adventure or an eco-friendly experience, Winchendon offers a range of activities that cater to all types of travelers looking to enjoy the great outdoors.

  • The Winchendon School: Experience the vibrant atmosphere of The Winchendon School, a modern college that combines academic rigor with a lively community. The school’s innovative approach to education creates an engaging environment, perfect for visitors interested in contemporary campus life.
  • Cathedral of the Pines: Nestled 11.3km from Winchendon, this stunning church offers a unique cultural experience surrounded by nature. The serene setting and beautiful architecture make it a perfect spot for reflection, contemplation, and appreciating the local artistry.
  • Jacobs Hill: Located 9.7km away, Jacobs Hill is a secluded haven ideal for recreation and relaxation. Enjoy friendly interactions with locals while exploring trails and taking in the tranquil natural beauty that this hidden gem offers.

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

To visit Winchendon, Massachusetts, you can fly into three major airports. Boston Logan International Airport (BOS) is 91.7km away, with luxurious hotels like the InterContinental Boston, Boston Harbor Hotel, and Encore Boston Harbor, all within 4.8km. Manchester-Boston Regional Airport (MHT) is 56.3km away, offering nearby accommodations such as The Grand at Bedford Village Inn and DoubleTree by Hilton Manchester Downtown, both 6.4km from the airport. Worcester Regional Airport (ORH) is the closest at 48.3km, featuring hotels like Beechwood Hotel and AC Hotel by Marriott, both just a few miles away. Each airport provides convenient access to these excellent lodging options.

Frequently asked questions

What's the best place to stay in Winchendon?
Based on Expedia's traveler preferences, Cozy Lakefront Cottage is a top place to stay in Winchendon. Other good choices for your trip to the area are The Colonial Hotel and Doubletree by Hilton Hotel Leominster. See all available top hotels, or vacation rentals in Winchendon.
What are some of the best vacation rentals in Winchendon?
Cozy Lakefront Cottage: Visitors like this Winchendon vacation home rental. It is located on a lake and has a patio, a garden, and a barbecue grill 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 vacation with amenities like 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 that most hotel room reservations are fully refundable if cancelled prior to the hotel's cancellation deadline, which often is within 24-48 hours of your check-in date. If you booked a non-refundable reservation, it may still be possible to cancel it and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchendon.
Where can I learn more about changing or cancelling my trip to Winchendon?
To access more information about updating your trip to Winchendon or cancelling it, click here.
What's the best place to stay near Lake Dennison State Recreation Area?
The Colonial Hotel is one of the top choices for your stay based on our traveler data, and this 3-star hotel offers a restaurant and an indoor pool. You'll find it 9 mi (14.5 km) from Lake Dennison State Recreation Area. Other good options in the area include Super 8 by Wyndham Gardner and The Maguire House Bed & Breakfast.
What are some hotels with pools in Winchendon?
The Colonial Hotel: Features a sauna, an indoor pool, and free self parking. Doubletree by Hilton Hotel Leominster and Great Wolf Lodge Boston / Fitchburg, MA are two additional hotels that offer an onsite pool. View all hotels with pools in Winchendon.
What's the best accommodation near Worcester Regional Airport (ORH)?
Hilton Garden Inn Worcester is one of the top choices for your stay and is a popular 3-star hotel featuring a restaurant and an indoor pool. It's located 3.7 mi (5.9 km) from Worcester Regional Airport. Other choices near the airport include Holiday Inn Express Worcester Downtown and AC Hotel by Marriott Worcester.
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 accommodations to choose from. Find out more about Winchendon.
What should I see while I'm in Winchendon?
Natural beauty is on display at Wendall P. Clark Memorial, Militia Training Field, and Hyde Park. A couple of additional sights to add to your agenda are Lake Dennison State Recreation Area and Winchendon Town Hall. Check out what more to see and do in Expedia's Winchendon guide.
What's the weather like in Winchendon?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Winchendon are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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