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

Winchendon Hotels

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Aug 21 - Aug 22
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Aug 22 - Aug 23
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Aug 21 - Aug 23
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Aug 28 - Aug 30

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Our top choices for Winchendon hotels

1. Centennial House

Centennial House
Northfield
United States
Amy
P11,066
P11,697 total
includes taxes & fees
Aug 26 - Aug 27
Centennial House

2. The Colonial Hotel

The Colonial Hotel
Gardner
United States
Mark
P9,431
P10,534 total
includes taxes & fees
Aug 23 - Aug 24
The Colonial Hotel

3. Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA
Fitchburg
Canada
Brynna
P11,283
P12,604 total
includes taxes & fees
Aug 24 - Aug 25
Great Wolf Lodge Boston / Fitchburg, MA

4. Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster
Leominster
United Kingdom
Elizabeth
P9,809
P10,956 total
includes taxes & fees
Aug 30 - Aug 31
Doubletree by Hilton Hotel Leominster

5. Gardner Inn

Gardner Inn
Gardner
United States
Vicki
P6,104
P6,818 total
includes taxes & fees
Aug 30 - Aug 31
Gardner Inn

6. Howarth House B&B

Howarth House B&B
Fitchburg
United States
David
P13,041
P13,041 total
includes taxes & fees
Aug 23 - Aug 24
Howarth House B&B

7. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
Keene
United States
Karen
P9,187
P9,968 total
includes taxes & fees
Aug 24 - Aug 25
Best Western Plus Keene Hotel

8. Motel 6 Leominster, MA

Motel 6 Leominster, MA
Leominster
United States
Linda
P4,901
P5,598 total
includes taxes & fees
Aug 26 - Aug 27
Motel 6 Leominster, MA

9. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
Keene
United States
James
P7,067
P7,668 total
includes taxes & fees
Sep 3 - Sep 4
Keene Elm City Hotel, an Ascend Collection Hotel

10. The Maguire House Bed & Breakfast

The Maguire House Bed & Breakfast
Ashburnham
United States
Ranjit
P17,573
P17,573 total
includes taxes & fees
Aug 26 - Aug 27
The Maguire House Bed & Breakfast

11. Monadnock Inn

Monadnock Inn
Jaffrey
United States
Saif
P10,147
P11,010 total
includes taxes & fees
Aug 26 - Aug 27
Monadnock Inn

12. Econo Lodge

Econo Lodge
Westminster
United States
Chauncey
P6,761
P7,417 total
includes taxes & fees
Sep 20 - Sep 21
Econo Lodge

13. The Birchwood Inn

The Birchwood Inn
Temple
United States
Karen
P10,790
P11,708 total
includes taxes & fees
Aug 25 - Aug 26
The Birchwood Inn

14. Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
Keene
United States
Brian
P11,071
P12,012 total
includes taxes & fees
Aug 30 - Aug 31
Fairfield Inn & Suites by Marriott Keene Downtown

15. Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
Keene
United States
Deborah
P11,071
P12,012 total
includes taxes & fees
Aug 30 - Aug 31
Courtyard by Marriott Keene Downtown

16. Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
Keene
United States
Christopher
P9,125
P9,900 total
includes taxes & fees
Aug 30 - Aug 31
Hampton Inn & Suites Keene

17. The Carriage Barn Inn

The Carriage Barn Inn
Keene
United States
Jonathan
P9,010
P9,776 total
includes taxes & fees
Aug 23 - Aug 24
The Carriage Barn Inn

18. Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
Keene
United States
Michael
P5,975
P6,483 total
includes taxes & fees
Sep 16 - Sep 17
Days Inn by Wyndham Keene NH

19. Chocksett Inn and Restaurant

Chocksett Inn and Restaurant
Sterling
United States
Beth
P9,804
P10,950 total
includes taxes & fees
Aug 27 - Aug 28
Chocksett Inn and Restaurant

20. Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)
Peterborough
United States
Tracy
P9,378
P10,844 total
includes taxes & fees
Aug 23 - Aug 24
Riverhouse by Weekender (Formerly Jack Daniels Inn)
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Stay near popular Winchendon attractions

Lake Dennison State Recreation Area

10.0/10 (1 review)
This serene 85-acre lake offers swimming, fishing, and access to 50+ miles of mountain biking trails. Reserve one of the 150 wooded campsites early for a prime lakeside spot to fully experience this natural retreat.
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Blueberry Island

Blueberry Island sits privately in Lake Monomonac, spanning the NH-MA border. While enjoying the lake's recreational offerings, respect the island's residential nature and focus on surrounding public areas instead.
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Winchendon Community Park

Winchendon Community Park offers a picturesque amphitheater for concerts and community events during warmer months. Enjoy dog-friendly trails before settling in for performances under the stars.
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Winchendon Town Hall

The Winchendon Municipal Building serves as the town's administrative center. Visitors can observe civic operations during business hours and occasionally attend public meetings.
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Hyde Park

Explore the great outdoors at Hyde Park, a lovely green space in Winchendon. While you're in the area, wander around the parks.
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Beals Memorial Library

This historic library houses literary treasures and sensory-friendly programs for neurodivergent visitors. Browse the collection, join a book club, or borrow unique items from their "Library of Things" like telescopes.
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Wetmore Trailhead

Wetmore Trailhead opens to miles of serene forest and wetland paths in Birch Hill Wildlife Management Area. Bring sturdy shoes and binoculars for spotting native birds along the well-maintained trails.
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Monument Park

Monument Park is just one of the places to see in Winchendon, so why not enjoy the other things to explore during your travels? While you're in the area, wander around the parks.
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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.

See all hotels in Winchendon
A river reflecting autumn trees and a dense forest.

Top Winchendon Hotel Reviews

Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

10/10 Excellent
"The location was good and walkable to the downtown restaurants and shops. The room was clean and comfortable and the staff was very helpful with advising on area hikes. The only negative was the outside of the property could have more attention to detail. Will definitely go back next time in Peterborough NH."
William and Susan 2-night trip
Posted 3 hours ago
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"Staff was great. Room was fine. Besides the small bathroom set up and basic continental breakfast, stay was great."
Krystal 1-night trip
Posted 2 days ago
Keene Elm City Hotel, an Ascend Collection Hotel
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

10/10 Excellent
"Comfortable, clean room. Helpful and friendly staff. Convenient location."
Deborah 3-night trip
Posted 2 days ago
Courtyard by Marriott Keene Downtown
Chocksett Inn and Restaurant

Chocksett Inn and Restaurant

10/10 Excellent
"Nice quiet location with spacious clean rooms. Reasonable rates and pet friendly too. Easy access to highways. Chocksett Inn is a great choice for visitors to Central Massachusetts."
Beth 4-night trip
Posted 2 days ago
Chocksett Inn and Restaurant
Motel 6 Leominster, MA

Motel 6 Leominster, MA

10/10 Excellent
"Fantastic stay"
Megan 6-night trip
Posted 3 days ago
Motel 6 Leominster, MA
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

8/10 Good
"It was a very pleasant stay"
Joseph 1-night trip
Posted 5 days ago
Days Inn by Wyndham Keene NH
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

10/10 Excellent
"Quiet place and clean. Efficient and helpful staff."
William 1-night trip
Posted 6 days ago
Hampton Inn & Suites Keene
Monadnock Inn

Monadnock Inn

10/10 Excellent
"Very easy and friendly check in. The owner was helpful about info on things to do and explained a detour in the area. Enjoyed our time and would definitely stay again!"
William 1-night trip
Posted 11 days ago
Monadnock Inn
The Carriage Barn Inn

The Carriage Barn Inn

10/10 Excellent
"A charming little inn Nice and quiet, easy and easy out. It was immaculate the owner Joe was very responsive very professional. Truly enjoyed our short stay"
William 1-night trip
Posted 2 weeks ago
The Carriage Barn Inn

More cheap stays in Winchendon

Motel 6 Leominster, MA

Motel 6 Leominster, MA

48 Commercial Rd Leominster MA
P4,901
P5,598 total
Aug 26 - Aug 27
includes taxes & fees
8.2/10 Very Good! (1,013 reviews)
Motel 6 Leominster, MA
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH
P5,975
P6,483 total
Sep 16 - Sep 17
includes taxes & fees
7/10 Good! (1,003 reviews)
Days Inn by Wyndham Keene NH
Gardner Inn

Gardner Inn

22 Pearson Blvd Gardner MA
P6,104
P6,818 total
Aug 30 - Aug 31
includes taxes & fees
Gardner Inn
Econo Lodge

Econo Lodge

183 Main St Westminster MA
P6,761
P7,417 total
Sep 20 - Sep 21
includes taxes & fees
6.4/10 (325 reviews)
Econo Lodge
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH
P7,067
P7,668 total
Sep 3 - Sep 4
includes taxes & fees
8.6/10 Excellent! (1,009 reviews)
Keene Elm City Hotel, an Ascend Collection Hotel
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

126 Key Rd Keene NH
P9,125
P9,900 total
Aug 30 - Aug 31
includes taxes & fees
8.8/10 Excellent! (406 reviews)
Hampton Inn & Suites Keene

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?
Great Wolf Lodge Boston / Fitchburg, MA, located 13.6 mi (21.9 km) from the heart of Winchendon, is a top choice for your stay based on our traveler data. Other good choices for your trip to the area are The Colonial Hotel and Keene Elm City Hotel, an Ascend Collection 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 steps from Great Wolf Lodge Waterpark. Provides 4 indoor pools, a children's pool, and free water-park access. The Colonial Hotel and Keene Elm City Hotel, an Ascend Collection Hotel 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 Blueberry Island, Millers River, and Hyde Park. A couple of additional sights to add to your agenda are Lake Dennison State Recreation Area and Beals Memorial Library. 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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