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Our top choices for Winchendon hotels

The Maguire House Bed & Breakfast

The Maguire House Bed & Breakfast
3.5 star property
Ashburnham
10.0 out of 10, Exceptional, (36 reviews)
"Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. "
United States
Ranjit
The price is SAR 1,011
SAR 1,011 total
includes taxes & fees
21 Jan - 22 Jan
The Maguire House Bed & Breakfast

Gardner Inn

Gardner Inn
2.0 star property
Gardner
5.4 out of 10, (18 reviews)
"The property needs work but hte staff was pleasant and the facility was quiet. "
United States
Lou
The price is SAR 413
SAR 461 total
includes taxes & fees
19 Jan - 20 Jan
Gardner Inn

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1,002 reviews)
"Well-kept hotel with a great restaurant."
United States
Adam
The Colonial Hotel

Motel 6 Leominster, MA

Motel 6 Leominster, MA
2.0 star property
Leominster
8.2 out of 10, Very Good, (1,002 reviews)
"Clean room and friendly staff!"
United States
Ralph
The price is SAR 304
SAR 347 total
includes taxes & fees
25 Jan - 26 Jan
Motel 6 Leominster, MA

Chocksett Inn and Restaurant

Chocksett Inn and Restaurant
3.5 star property
Sterling
8.8 out of 10, Excellent, (148 reviews)
"The staff was very accommodating and friendly. Quaint place to stay. "
United States
Helen
The price is SAR 634
SAR 708 total
includes taxes & fees
19 Jan - 20 Jan
Chocksett Inn and Restaurant

Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster
4.0 star property
Leominster
8.6 out of 10, Excellent, (1,004 reviews)
"Clean room nice area close to shopping and plenty of restaurants "
United States
janine
The price is SAR 535
SAR 598 total
includes taxes & fees
1 Feb - 2 Feb
Doubletree by Hilton Hotel Leominster

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, (444 reviews)
"Room was clean, spacious and staff was pleasant. "
United States
Susan
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Centennial House

Centennial House
3.5 star property
Northfield
9.6 out of 10, Exceptional, (173 reviews)
"great proprietors beautiful vintage home excellent breakfast"
United States
JAMES
The price is SAR 706
SAR 746 total
includes taxes & fees
1 Feb - 2 Feb
Centennial House

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
2.0 star property
Keene
7.0 out of 10, Good, (1,001 reviews)
"Checkin was quick. I like the pre-check in process."
United States
Anthony
The price is SAR 335
SAR 363 total
includes taxes & fees
20 Jan - 21 Jan
Days Inn by Wyndham Keene NH

Howarth House B&B

Howarth House B&B
3.0 star property
Fitchburg
10.0 out of 10, Exceptional, (111 reviews)
"Wonderful hosts and cozy accommodations at an affordable price. Yummy, freshly prepared to order breakfast was a bonus! Will look forward to returning again in the near future."
United States
Leland
Howarth House B&B

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (167 reviews)
"Very helpful and welcoming host. "
United States
Bruce
The price is SAR 474
SAR 514 total
includes taxes & fees
1 Feb - 2 Feb
The Carriage Barn Inn

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (156 reviews)
"The building and room were very nice. The location is great, very walkable to the center of town. "
United States
Rochelle
The Burrell House

Monadnock Inn

Monadnock Inn
2.5 star property
Jaffrey
7.6 out of 10, Good, (278 reviews)
"The Inn was cozy, the room was clean and comfortable. The owner was engaging and helpful. Would definitely stay there again. "
United States
E S
Monadnock Inn

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, (759 reviews)
"Everything was clean, comfortable and the staff quite conversational"
United States
Diane
The price is SAR 656
SAR 712 total
includes taxes & fees
25 Jan - 26 Jan
Fairfield Inn & Suites 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, (1,001 reviews)
"Very comfortable and clean."
United States
Christina
The price is SAR 675
SAR 732 total
includes taxes & fees
25 Jan - 26 Jan
Courtyard by Marriott Keene Downtown

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, (978 reviews)
"Staff was very welcoming and the room was very clean. "
United States
Rebecca
The price is SAR 450
SAR 488 total
includes taxes & fees
19 Jan - 20 Jan
Keene Elm City Hotel, an Ascend Collection Hotel

The Birchwood Inn

The Birchwood Inn
3.5 star property
Temple
9.4 out of 10, Exceptional, (225 reviews)
"Very comfortable bed. Best out of the last 50 hotels we have stayed in."
United States
Rungnapha
The price is SAR 656
SAR 712 total
includes taxes & fees
19 Jan - 20 Jan
The Birchwood Inn

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1,000 reviews)
"Great stay pool was very nice"
United States
Patrick
The price is SAR 521
SAR 566 total
includes taxes & fees
19 Jan - 20 Jan
Best Western Plus Keene Hotel

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (364 reviews)
"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 SAR 651
SAR 706 total
includes taxes & fees
25 Jan - 26 Jan
Hampton Inn & Suites Keene

Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA
3.5 star property
Fitchburg
8.6 out of 10, Excellent, (1,002 reviews)
"The room was clean, the staff was very nice!"
United States
Entela
The price is SAR 671
SAR 750 total
includes taxes & fees
20 Jan - 21 Jan
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

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 skiing, hiking, and water activities at scenic spots like Lake Monomonac.
  • Charming New England Atmosphere: Explore picturesque hamlets and enjoy the quaint local culture.
  • Family-Friendly Attractions: Visit fun spots like mini-golf and water parks for an enjoyable family experience.
  • Cozy Accommodations: Choose from delightful bed & breakfasts and charming inns for a relaxing stay.
  • Scenic Beauty: Immerse yourself in the stunning landscapes that define this unique destination.

Find great hotels near Winchendon

Discover charming hotel accommodations in Winchendon, Massachusetts, where you can choose from delightful bed & breakfast options and cozy inns. Whether you're seeking adventure, a family-friendly atmosphere, or a historic-themed vacation experience, Winchendon has something for everyone. Explore the best hotels in Winchendon, read reviews, and find the perfect place to unwind during your visit to this quaint New England town.

  • The Colonial Hotel: Embrace a blend of tradition and modern comfort at The Colonial Hotel, a charming 3-star hotel located a mere 16.1km from Winchendon. This property is perfect for business travelers and pet owners alike, offering a welcoming atmosphere for furry friends with a pet-friendly policy. Guests can enjoy tasteful accommodations, along with essential amenities that cater to both work and leisure. The hotel's convenient location makes it an excellent base for exploring the surrounding area while providing a comfortable retreat after a day of activities.
  • Great Wolf Lodge Boston / Fitchburg, MA: Dive into a world of family fun at Great Wolf Lodge Boston, a lively 3.5-star resort located 22.5km from Winchendon. This destination is tailored for families and is proudly inclusive, welcoming LGBTQIA travelers. With an array of exciting amenities for children, including a water park, arcade game room, and supervised childcare, this resort guarantees an unforgettable experience for guests of all ages. Families can relax knowing that entertainment and comfort are at their fingertips, making it a fantastic choice for a joyous vacation.
  • Monadnock Inn: Experience a golfer’s paradise at Monadnock Inn, a delightful Bed & Breakfast located 16.1km from Winchendon. This charming inn invites guests to indulge in golf-themed adventures, offering easy access to picturesque courses nearby. With its cozy accommodations and warm hospitality, Monadnock Inn is an ideal retreat for golf enthusiasts looking to enjoy a relaxing getaway. Guests can unwind in a tranquil setting while still being close to local attractions, making it a perfect blend of leisure and recreation.

Where to stay near Winchendon

Your vacation in Winchendon, Massachusetts, promises a delightful blend of outdoor adventures and scenic beauty. Just a short drive from Worcester, you'll discover the tranquil Lake Monomonac, perfect for romantic strolls or family-friendly activities. Explore charming New England hamlets nearby and immerse yourself in the local atmosphere, rich with opportunities for recreation and relaxation. Whether you seek adventure or a peaceful getaway, Winchendon offers a convenient and inviting escape.

  • Fitchburg: Located 22.5km from Winchendon, Fitchburg is a city that offers a blend of family-friendly activities and entertainment. Whether you're looking for adventure at the local water park or hitting the slopes at nearby ski fields, there's something for everyone. The winter months from January to March see a peak in visitor numbers, making it a lively time to experience the city's attractions. Don't miss the iconic theme park and event conference venues that add to the city’s charm. Fitchburg is an ideal location for those seeking a fun-filled getaway.
  • Gardner: Just 12.9km away from Winchendon, Gardner is a vibrant city known for its sports and adventure experiences. Visitors often flock to the area during April, July, and September to take advantage of the outdoor activities, including skiing and local educational facilities. The city boasts venues like family beaches and event conference spaces, offering plenty of options for recreation and relaxation. Gardner's welcoming atmosphere and variety of attractions make it a must-visit for adventure enthusiasts looking to create unforgettable memories.
  • Rindge: A short 8.0km from Winchendon, Rindge is a picturesque city renowned for its stunning outdoor scenery and romantic ambiance. The peak travel season from July to September invites visitors to explore its recreational areas and historic sites. Experience the beauty of local lakes and mountains, perfect for hiking or a peaceful retreat. Rindge offers a blend of adventure and tranquility, making it an excellent choice for those seeking a scenic escape. Whether you’re looking to relax or explore, Rindge provides a beautiful backdrop for your vacation.

Things to do in and around Winchendon

Winchendon is perfect for outdoor and romantic getaways, offering a variety of activities. You can enjoy skiing at local ski fields, shop at nearby centers, and have fun at attractions like a water park and mini golf. The scenic beauty of the area enhances the experience, making it an ideal destination for those looking to relax and explore the great outdoors.

Shopping

For unique gifts, visit 1761 Old Mill Gift Shop, located 17.7km away from Winchendon. If you're up for a drive, check out The Mall at Whitney Field, 30.6km away, for a wider selection and lively atmosphere. Don’t miss Ava Marie Handmade Chocolates, 22.5km from Winchendon.

Recreation

Explore Lake Dennison State Recreation Area for serene hiking trails and peaceful picnic spots surrounded by nature. For golf enthusiasts, Shattuck Golf Course and Ellinwood Country Club offer beautiful landscapes and a chance to unwind while enjoying a round of golf just a short drive away.

Adventure

Explore the Wapack Trail, a stunning hiking experience 22.5km from Winchendon, offering breathtaking scenery and outdoor adventure vibes. For a convenient outing, visit Wetmore Trailhead and Towline Trailhead, both located in Winchendon, where you can immerse yourself in nature and enjoy thrilling outdoor activities.

Nightlife

Experience the vibrant nightlife in Winchendon by visiting the nearby Peterborough Players, Colonial Theatre, and Wilton Town Hall Theatre. Each venue, located within 17 to 33.8km, offers a charming blend of romance, entertainment, and culture, perfect for an enjoyable 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, consider visiting between November and January when hotel prices are lower. Book your stay for a Monday to take advantage of lower rates, avoiding the more expensive Saturdays. Use Expedia to compare hotel rates and refine your search based on your budget and preferences, like eco-friendly options. Additionally, look for package deals that combine flights, hotels, and activities for extra savings. Lastly, explore free local attractions and utilize public transport for affordable travel around the area.

  • 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 hotel type. For instance, selecting the Eco-certified option will showcase sustainable and environmentally-friendly hotels that are currently available. To find the best prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by booking a package with Expedia that combines your hotel in Winchendon with your flights and activities.

Find the best attractions in and around Winchendon

Winchendon, Massachusetts, is perfect for outdoor and romantic getaways, featuring stunning scenery and a range of attractions. Visitors can explore local points of interest, including modern colleges and universities, serene nature reserves, and picturesque lakes. These sites provide opportunities for adventure and eco-friendly experiences, making it an ideal destination for travelers seeking to connect with nature while enjoying the charm of New England.

  • The Winchendon School: Experience the vibrant city atmosphere at The Winchendon School, a modern college that blends education with contemporary living. Engage with students and enjoy the dynamic campus life.
  • Cathedral of the Pines: Located 11.3km from Winchendon, this unique church offers a serene setting surrounded by nature. With its rich cultural vibes, it's a perfect spot for reflection and appreciation of artistry in a tranquil environment.
  • Jacobs Hill: Just 9.7km away, Jacobs Hill is a hidden gem offering a secluded escape. Enjoy recreational activities and the friendly local community, making it an ideal place to relax and unwind.

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 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

Traveling to Winchendon, Massachusetts, you can choose from three major airports. BOSton Logan International Airport (BOS) is 91.7km away and offers nearby hotels like Encore Boston Harbor and InterContinental Boston, both 3 and 3.2km from the airport, respectively. Manchester-Boston Regional Airport (MHT) is 56.3km away, with top hotels such as The Grand at Bedford Village Inn and DoubleTree by Hilton Manchester Downtown, located just 6.4km from the airport. Lastly, Worcester Regional Airport (ORH) is 48.3km away, with options like Beechwood Hotel and AC Hotel by Marriott Worcester, both within 8.0km. Each airport provides convenient access to nearby accommodations.

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 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 vacation rentals in Winchendon?
Cozy Lakefront Cottage: Visitors give good reviews to this Winchendon vacation home rental, which 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. Another good choice for your trip to Winchendon is Spacious lakeside 4-bedroom house in beautiful Ashburnham. 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?
Great Wolf Lodge Boston / Fitchburg, MA: Resort steps from Great Wolf Lodge Waterpark. Offers 4 indoor pools, a children's pool, and free water-park access. Spacious lakeside 4-bedroom house in beautiful Ashburnham and The Colonial Hotel 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 11 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, Hyde Park, and Militia Training Field. A couple of additional sights to add to your agenda are Lake Dennison State Recreation Area and Otter River State Forest. 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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