Winchendon Hotels

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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)
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 P16,187
P16,187 total
includes taxes & fees
Jan 14 - Jan 15
The Maguire House Bed & Breakfast

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 P5,827
P6,509 total
includes taxes & fees
Jan 7 - Jan 8
Gardner Inn

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

Motel 6 Leominster, MA

Motel 6 Leominster, MA
2.0 star property
Leominster
8.2 out of 10, Very Good, (1011)
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 P4,767
P5,443 total
includes taxes & fees
Jan 11 - Jan 12
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, (1006)
"The hotel was very nice and the restaurant was a nice establishment. "
United States
Dina
The price is P8,398
P9,381 total
includes taxes & fees
Jan 25 - Jan 26
Doubletree by Hilton Hotel Leominster

Chocksett Inn and Restaurant

Chocksett Inn and Restaurant
3.5 star property
Sterling
8.8 out of 10, Excellent, (146)
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 P9,948
P11,111 total
includes taxes & fees
Jan 21 - Jan 22
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, (441)
"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)
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 P11,191
P11,829 total
includes taxes & fees
Feb 1 - Feb 2
Centennial House

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

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 P4,753
P5,157 total
includes taxes & fees
Jan 9 - Jan 10
Days Inn by Wyndham Keene NH

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (166)
This cozy 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 P7,501
P8,139 total
includes taxes & fees
Jan 7 - Jan 8
The Carriage Barn Inn

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

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 Center.

"The room was comfortable and clean wwhen we arrived "
United States
Peter
Monadnock Inn

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (1006)
Stylish accommodations in Keene Downtown, 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 P9,456
P10,260 total
includes taxes & fees
Jan 17 - Jan 18
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, (975)
Escape to this quiet retreat with an indoor pool and fitness center 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 travelers.

"Staff was very welcoming and the room was very clean. "
United States
Rebecca
The price is P7,888
P8,558 total
includes taxes & fees
Jan 11 - Jan 12
Keene Elm City Hotel, an Ascend Collection 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
The price is P10,831
P11,751 total
includes taxes & fees
Jan 22 - Jan 23
Fairfield Inn & Suites by Marriott Keene Downtown

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 center make this Keene hotel a great choice. Swim in the indoor pool or request room service after exploring nearby Cheshire Children's Museum. Travelers 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 P10,162
P11,026 total
includes taxes & fees
Jan 25 - Jan 26
Hampton Inn & Suites Keene

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 center or unwind with a drink at the bar after exploring nearby attractions.

"Great stay pool was very nice"
United States
Patrick
The price is P8,182
P8,878 total
includes taxes & fees
Jan 11 - Jan 12
Best Western Plus Keene Hotel

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 traveler
The price is P10,301
P11,177 total
includes taxes & fees
Jan 8 - Jan 9
The Birchwood Inn

Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA
3.5 star property
Fitchburg
8.6 out of 10, Excellent, (1015)
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 P9,522
P10,636 total
includes taxes & fees
Feb 4 - Feb 5
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

Find out more about Winchendon

Top reasons to visit Winchendon

  • Outdoor Adventures: Winchendon offers a range of outdoor activities such as skiing, mini golf, and access to tranquil lakes, perfect for nature lovers.
  • Romantic Getaways: The picturesque scenery and serene atmosphere make it an ideal spot for couples seeking a romantic escape.
  • Charming Accommodations: Visitors can choose from delightful bed and breakfasts and guesthouses, enhancing their stay with unique amenities.
  • Local Shopping: Explore a variety of shops at the local shopping centre for a taste of the community.
  • Eco-Friendly Experiences: Winchendon offers eco-friendly adventures, ideal for those who appreciate nature's beauty.

Find great hotels near Winchendon

Explore the charming town of Winchendon, Massachusetts, where you can find an array of delightful lodging options, including bed and breakfasts and guesthouses. Ideal for adventurous families and those seeking a historic vacation experience, the local hotels offer unique amenities and services to enhance your stay. Delve into hotel reviews to discover the best accommodations in Winchendon, ensuring a memorable getaway in this picturesque setting.

  • The Colonial Hotel: Nestled 16.1km from Winchendon, The Colonial Hotel offers a charming retreat with a blend of modern convenience and classic elegance. This 3-star property is ideal for business travellers and those seeking a pet-friendly environment, with amenities that include a waiver for service animals and a welcome for pets. Guests appreciate the hotel's sophisticated decor and comfortable accommodations, making it a perfect choice for both work and leisure. The Colonial Hotel is equipped with meeting spaces, ensuring that it caters to professional needs while still providing a relaxing atmosphere for a well-rounded stay.
  • Great Wolf Lodge Boston / Fitchburg, MA: Located 22.5km from Winchendon, this 3.5-star resort is a family-friendly haven that embraces a vibrant atmosphere. Great Wolf Lodge is renowned for its welcoming approach to LGBTQIA guests and offers numerous amenities designed specifically for children. Families can enjoy a complimentary water park, mini golf, and an arcade game room, ensuring entertainment for all ages. The resort’s supervised childcare services allow parents to unwind, making it an ideal choice for those looking to create lasting family memories in a fun and inclusive environment.
  • Monadnock Inn: Situated 16.1km from Winchendon, Monadnock Inn presents a delightful bed and breakfast experience infused with a golf-themed charm. This inviting property caters to golf enthusiasts, offering guests the opportunity to indulge in their passion for the sport. The inn's warm hospitality and picturesque surroundings create a serene atmosphere, perfect for relaxation after a day on the greens. Travellers can enjoy a hearty breakfast each morning, setting the tone for a day of adventure in the beautiful Massachusetts countryside.

Where to stay near Winchendon

Winchendon, Massachusetts, offers a charming blend of outdoor adventures and romantic scenery, making it an ideal destination for tourists. Just a short drive from Worcester, visitors can enjoy the serene beauty of Lake Monomonac and explore the quaint New England hamlets nearby. The city's family-friendly atmosphere, coupled with opportunities for recreation and relaxation, ensures a memorable holiday experience for all who venture here.

  • Fitchburg: Located 22.5km from Winchendon, Fitchburg is a vibrant city that offers a mix of family-friendly adventures and entertainment. With visitor numbers peaking from January to March, this city is ideal for those seeking thrills at its popular water park and ski fields. Enjoy various attractions, including a theme park and a conference venue, making it a perfect spot for both relaxation and excitement. Whether you're enjoying a day on the slopes or splashing about in water attractions, Fitchburg promises a delightful experience for all.
  • Gardner: Just 12.9km away from Winchendon, Gardner is a lively city known for its sports and adventurous spirit. With visitors flocking in April, July, and September, it’s a great destination for outdoor enthusiasts looking to hit the ski slopes or enjoy recreational activities. The presence of family-friendly beaches and educational venues adds to its charm, making it a well-rounded destination for families and sports lovers alike. Discover the local conference venues and soak in the community vibe while enjoying the beautiful surroundings Gardner has to offer.
  • Rindge: Situated a mere 8.0km from Winchendon, Rindge is a picturesque city perfect for those who appreciate the great outdoors. With seasonal visitors peaking from July to September, you can expect stunning scenery and romantic getaways amidst lakes and mountains. Rindge is ideal for outdoor activities and offers numerous recreational areas for hiking, picnicking, and exploring historic sites. Whether you’re seeking a peaceful retreat or an adventurous day out, Rindge is a lovely destination that will captivate your heart and soul.

Things to do in and around Winchendon

Winchendon is perfect for outdoor and romantic getaways, offering a range of activities and scenic views. Visitors can enjoy skiing at local ski fields, partake in mini golf, or unwind at a nearby water park. For those looking to shop, the local shopping centre provides a variety of options to explore. Whether you're seeking adventure or relaxation, Winchendon has something for everyone.

Shopping

In Winchendon, you can visit the 1761 Old Mill Gift Shop for unique souvenirs. If you're up for a drive, check out The Mall at Whitney Field for a variety of shops and entertainment, or indulge in delicious treats at Ava Marie Handmade Chocolates, located nearby.

Recreation

Lake Dennison State Recreation Area offers a tranquil escape with opportunities for hiking and picnicking amidst nature. For outdoor enthusiasts, Shattuck Golf Course provides a splendid golfing experience surrounded by scenic views. Winchendon Community Park invites relaxation with its open spaces, perfect for leisurely strolls and unwinding.

Adventure

Explore the Wapack Trail, a scenic hiking path 22.5km from Winchendon, where you can immerse yourself in nature's beauty. For a more immediate adventure, the Wetmore Trailhead and Towline Trailhead, both located in Winchendon, offer excellent trails for outdoor enthusiasts seeking excitement and stunning landscapes.

Nightlife

Experience the charm of Winchendon's nightlife at the Robinson-Broadhurst Foundation Performing Arts Amphitheater for captivating shows. Just 30.6km away, the Wilton Town Hall Theatre and Peterborough Players offer delightful performances, all infused with romance and cultural vibes, perfect for an enchanting 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 during your trip to Winchendon, plan to visit from November to January when accommodation prices are lower, particularly booking for a Monday. Use Expedia to filter for budget-friendly options, including eco-certified hotels. Consider combining your hotel, flights, and activities for better deals. Additionally, explore free local attractions and check for public transport options, which can be cost-effective for getting around. Always look for flexible booking options to avoid unexpected fees and maximise your savings.

  • 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: Utilise Expedia’s search tool to refine your preferences, such as your budget, desired location, and the type of accommodation you prefer. For instance, selecting the Eco-certified option will showcase sustainable and eco-friendly hotels that are currently available. To find the most economical prices and offers, 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 is an ideal destination for outdoor enthusiasts and couples seeking a romantic getaway. Visitors can explore local attractions such as modern universities, picturesque nature reserves, and tranquil lakes. The area offers a variety of eco-friendly experiences and adventures, making it perfect for those who appreciate the beauty of nature and seek an adventurous escape.

  • The Winchendon School: This modern institution offers a vibrant atmosphere, blending contemporary educational facilities with a welcoming community. Visitors can appreciate the school's commitment to academic excellence and diverse extracurricular activities.
  • Red Apple Farm: Located 14.5km from Winchendon, this charming farm invites you to experience rural life. Enjoy apple picking, seasonal produce, and picturesque views, making it a perfect spot for families and nature lovers.
  • Franklin Pierce University: Situated 9.7km away, this modern university boasts a lively campus with a focus on student engagement. Explore its beautiful grounds and learn about its innovative programs while soaking up the city vibes.

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

When visiting Winchendon, Massachusetts, you can fly into several major airports. Boston Logan International Airport (BOS) is 91.7km away and offers luxury hotels such as the 5-star InterContinental Boston and Boston Harbor Hotel, both 3.2km from the airport. Manchester-Boston Regional Airport (MHT), located 56.3km from Winchendon, has options like the 4-star DoubleTree by Hilton Manchester Downtown, 6.4km away. Worcester Regional Airport (ORH) is the closest at 48.3km, with hotels like the 4-star Beechwood Hotel, situated 8.0km from the airport. Each hotel provides convenient transportation services to their respective airports, ensuring a smooth travel experience.

Frequently asked questions

What's the best place to stay in Winchendon?
Based on Expedia's traveler preferences, Modern Waterfront Gem w/ Dock on Lake Monomonac 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.
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.
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 pools, a children's pool, and free water-park access. The Colonial Hotel and Doubletree by Hilton Hotel Leominster are two additional hotels that offer an onsite 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 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, Millers River, 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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