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

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Oct 14 - Oct 15
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Our top choices for Winchendon hotels

1. The Colonial Hotel

The Colonial Hotel
Gardner
United States
John Timothy
NT$4,595
NT$5,133 total
includes taxes & fees
Nov 2 - Nov 3
The Colonial Hotel

2. Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster
Leominster
United States
louis
NT$5,078
NT$5,673 total
includes taxes & fees
Nov 12 - Nov 13
Doubletree by Hilton Hotel Leominster

3. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
Keene
United States
Ruddy
NT$4,519
NT$4,903 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Plus Keene Hotel

4. Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
Keene
United States
Caroline
NT$6,187
NT$6,713 total
includes taxes & fees
Oct 25 - Oct 26
Fairfield Inn & Suites by Marriott Keene Downtown

5. Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
Keene
United States
Rebecca
NT$4,939
NT$5,358 total
includes taxes & fees
Oct 25 - Oct 26
Hampton Inn & Suites Keene

6. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
Keene
United States
Mary
NT$3,799
NT$4,122 total
includes taxes & fees
Nov 2 - Nov 3
Keene Elm City Hotel, an Ascend Collection Hotel

7. The Maguire House Bed & Breakfast

The Maguire House Bed & Breakfast
Ashburnham
United States
Jeffrey
NT$9,488
NT$9,488 total
includes taxes & fees
Nov 5 - Nov 6
The Maguire House Bed & Breakfast

8. Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA
Fitchburg
United States
michael
NT$5,970
NT$6,668 total
includes taxes & fees
Oct 18 - Oct 19
Great Wolf Lodge Boston / Fitchburg, MA

9. Gardner Inn

Gardner Inn
Gardner
United States
Leila
NT$3,390
NT$3,787 total
includes taxes & fees
Nov 6 - Nov 7
Gardner Inn

10. Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
Keene
United States
Deborah
NT$6,035
NT$6,548 total
includes taxes & fees
Oct 25 - Oct 26
Courtyard by Marriott Keene Downtown

11. The Birchwood Inn

The Birchwood Inn
Temple
United States
Karen
NT$5,628
NT$6,107 total
includes taxes & fees
Oct 18 - Oct 19
The Birchwood Inn

12. Howarth House B&B

Howarth House B&B
Fitchburg
United States
David
NT$6,752
NT$6,752 total
includes taxes & fees
Oct 18 - Oct 19
Howarth House B&B

13. Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)
Peterborough
United States
Kathleen
NT$5,045
NT$5,823 total
includes taxes & fees
Oct 18 - Oct 19
Riverhouse by Weekender (Formerly Jack Daniels Inn)

14. Econo Lodge

Econo Lodge
Westminster
United States
isabel
NT$3,229
NT$3,542 total
includes taxes & fees
Nov 12 - Nov 13
Econo Lodge

15. Monadnock Inn

Monadnock Inn
Jaffrey
United States
Jed
NT$4,408
NT$4,783 total
includes taxes & fees
Nov 1 - Nov 2
Monadnock Inn

16. Motel 6 Leominster, MA

Motel 6 Leominster, MA
Leominster
United States
Ruth
NT$3,055
NT$3,477 total
includes taxes & fees
Nov 1 - Nov 2
Motel 6 Leominster, MA

17. Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
Keene
United States
CHERYL
NT$2,958
NT$3,209 total
includes taxes & fees
Oct 26 - Oct 27
Days Inn by Wyndham Keene NH

18. Centennial House

Centennial House
Northfield
United Kingdom
Alan
NT$5,730
NT$6,056 total
includes taxes & fees
Oct 25 - Oct 26
Centennial House

19. Chocksett Inn and Restaurant

Chocksett Inn and Restaurant
Sterling
United States
Lisa
NT$5,076
NT$5,670 total
includes taxes & fees
Oct 20 - Oct 21
Chocksett Inn and Restaurant

20. The Carriage Barn Inn

The Carriage Barn Inn
Keene
United States
Richard
NT$5,388
NT$5,846 total
includes taxes & fees
Oct 15 - Oct 16
The Carriage Barn 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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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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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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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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Militia Training Field

This historic field once served as training ground for local militia in colonial times. Today, the open green space offers a quiet retreat from the bustle of town life.
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Old Centre Historic District

Explore the great outdoors at Old Centre Historic District, 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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The Robinson-Broadhurst Foundation Performing Arts Ampitheater

Enjoy an outing to The Robinson-Broadhurst Foundation Performing Arts Ampitheater during your stay in Winchendon. 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

Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

10/10 Excellent
"The facility is great. I was able to get handicapped parking this time which is always a plus. The room was great, very clean. The waterpark was fun. The food was delicious. Specifically at the Fireside restaurant. The staff at the restaurant was fast and efficient. We definitely will be going back."
Barbara 1-night trip
Posted 16 hours ago
Great Wolf Lodge Boston / Fitchburg, MA
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"It is a charming inn with very lovely staff & family attending the guests. I highly recommend staying here if you appreciate history & charm! The building was built in 1788 I believe they said. We stayed inPikes Suite and were comfortable and happy. Yes, the beautiful old floors creak, but it’s all part of the charm of this lovely still family owned hideaway! I hope to return again!"
Diane 1-night trip
Posted 17 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel
Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown

10/10 Excellent
"Breakfast was very good. The staff friendly and very helpful. Room clean and comfortable. My area was a bit noisy though. Very convenient. Overall an excellent place to stay. I would return and also recommend!"
Shirley 5-night trip
Posted 17 hours ago
Fairfield Inn & Suites by Marriott Keene Downtown
Monadnock Inn

Monadnock Inn

8/10 Good
"The building and interior was big on ambiance and charm. The staff was very cordial and helpful. I would suggest the addition of an ice machine"
Jim 2-night trip
Posted 18 hours ago
Monadnock Inn
Motel 6 Leominster, MA

Motel 6 Leominster, MA

10/10 Excellent
"There are few things to be concerned about. You can here your next door neighbor when they speaking loud and there were some cigarettes smoke in the room eventhough we had a non smoking room. It wasn't strong. Overall, the property surprised me how clean it is and how white the sheets and towels are. Very convenient locati I need to shopping area and to the soccer tournament location."
Marina 2-night trip
Posted 23 hours ago
Motel 6 Leominster, MA
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

10/10 Excellent
"I got a quiet room to stay. That was great. Staff was very nice and helpful. Cleaners came every day to clean room"
Vandana 3-night trip
Posted 2 days ago
Days Inn by Wyndham Keene NH
Econo Lodge

Econo Lodge

10/10 Excellent
"We were there for 1 night and everything so perfect. The room was extremely clean. The service is excellent the area was quiet and around really local restaurants. Will book again"
isabel 1-night trip
Posted 2 days ago
Econo Lodge
Centennial House

Centennial House

10/10 Excellent
"Everything was great. Highly recommended."
Neil 1-night trip
Posted 2 days ago
Centennial House
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

8/10 Good
"The hotel needs some updating, and could be a little cleaner. Bathroom door looked like it had not been cleaned in a long time. The staff was friendly, and breakfast was good."
Teresa D 1-night trip
Posted 3 days ago
Best Western Plus Keene Hotel

More cheap stays in Winchendon

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH
NT$2,958
NT$3,209 total
Oct 26 - Oct 27
includes taxes & fees
7/10 Good! (1,005 reviews)
Days Inn by Wyndham Keene NH
Motel 6 Leominster, MA

Motel 6 Leominster, MA

48 Commercial Rd Leominster MA
NT$3,055
NT$3,477 total
Nov 1 - Nov 2
includes taxes & fees
8.2/10 Very Good! (1,005 reviews)
Motel 6 Leominster, MA
Gardner Inn

Gardner Inn

22 Pearson Blvd Gardner MA
NT$3,390
NT$3,787 total
Nov 6 - Nov 7
includes taxes & fees
7.6/10 Good! (78 reviews)
Gardner Inn
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH
NT$3,799
NT$4,122 total
Nov 2 - Nov 3
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
Keene Elm City Hotel, an Ascend Collection Hotel
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

126 Key Rd Keene NH
NT$4,939
NT$5,358 total
Oct 25 - Oct 26
includes taxes & fees
8.8/10 Excellent! (419 reviews)
Hampton Inn & Suites Keene
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

80 Concord Street Peterborough NH
NT$5,045
NT$5,823 total
Oct 18 - Oct 19
includes taxes & fees
9.2/10 Wonderful! (480 reviews)
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Hotels in Winchendon with star-rating

Find out more about Winchendon

Top reasons to visit Winchendon

  • Outdoor Adventures: Winchendon offers a range of outdoor activities, including hiking, skiing, and exploring serene lakes like Lake Monomonac.
  • Scenic Beauty: Enjoy picturesque landscapes and charming New England hamlets that enhance the vacation experience.
  • Family-Friendly Activities: Engage in fun activities such as mini golf and water parks, perfect for visitors of all ages.
  • Cozy Accommodations: Stay in inviting bed & breakfasts and inns that provide a warm, welcoming atmosphere.
  • Romantic Getaways: Winchendon is ideal for couples seeking a romantic escape in a serene setting.

Find great hotels near Winchendon

Explore the charming accommodations in Winchendon, Massachusetts, where you'll find a variety of options including cozy bed & breakfasts and inviting inns. Perfect for adventurous families and LGBTQIA travelers, these hotels offer a warm, welcoming atmosphere. With an array of amenities tailored to enhance your stay, you can easily discover the best hotels in Winchendon, MA, along with genuine reviews to help guide your choice.

  • The Colonial Hotel: The Colonial Hotel embodies charm and comfort with a distinct focus on business travelers and pet-friendly experiences. Located 16.1km from Winchendon, this 3-star hotel welcomes guests with its warm atmosphere and thoughtful amenities. The property allows pets, making it a fantastic choice for those traveling with furry companions. With a range of business facilities and a serene environment, it is perfect for both work and leisure. Guests appreciate the welcoming staff and the convenience of being close to local attractions.
  • Great Wolf Lodge Boston / Fitchburg, MA: A family-friendly haven, Great Wolf Lodge Boston / Fitchburg is a 3.5-star resort located 22.5km from Winchendon. Tailored for families and LGBTQIA travelers, this vibrant resort features a vast array of amenities including an exciting indoor water park, arcade game room, and mini-golf. Kids will love the supervised childcare services, while parents can enjoy relaxation and fun in a welcoming environment. The lodge’s commitment to inclusivity and family experiences creates a memorable getaway for guests of all ages.
  • Monadnock Inn: The Monadnock Inn offers a cozy bed and breakfast experience with a unique golf theme, located 16.1km from Winchendon. Perfect for golf enthusiasts, the inn provides access to beautiful golf courses and a relaxed atmosphere for unwinding after a day on the greens. Guests can enjoy personalized service, comfortable accommodations, and a hearty breakfast to start their day. The inn’s charm and focus on golf make it an appealing choice for travelers seeking a laid-back vacation with a sporty twist.

Where to stay near Winchendon

Experience the charm of Winchendon, Massachusetts, where outdoor adventures and romantic getaways await. Just a short drive from Worcester, explore the serene beauty of Lake Monomonac or wander through picturesque New England hamlets. With family-friendly activities and recreational opportunities nearby, Winchendon offers a perfect blend of relaxation and adventure for every traveler. Discover the quaint atmosphere and the scenic landscapes that make this region a hidden gem.

  • Fitchburg: Located 22.5km from Winchendon, Fitchburg is a vibrant city known for its family-friendly atmosphere and adventurous spirit. Visitors flock here primarily for entertainment-themed experiences, with peak travel occurring from January to March. The city boasts attractions such as a thrilling water park and ski fields, providing ample opportunities for fun year-round. Don't miss the local theme park and event conference venues that often host exciting activities. Whether you're looking for a day of skiing or family-friendly entertainment, Fitchburg has something for everyone.
  • Gardner: Just 12.9km away from Winchendon, Gardner is a dynamic city popular for sports and adventure. Its visitor numbers peak in April, July, and September, drawing outdoor enthusiasts eager to explore the local ski fields and educational opportunities. Gardner is home to several event conference venues and family-friendly beaches, making it a great spot for both relaxation and action. Whether you want to hit the slopes or enjoy a day at the beach, Gardner is your go-to destination for an exciting getaway.
  • Rindge: Situated only 8.0km from Winchendon, Rindge offers a picturesque escape perfect for those seeking outdoor adventures and romantic scenery. With peak travel from July to September, visitors can explore its stunning lakes and mountains while enjoying recreational activities. Rindge is also home to historic sites, providing a mix of education and exploration. Whether you're hiking, picnicking, or simply taking in the beautiful views, Rindge is an ideal locale for a serene yet adventurous vacation.

Things to do in and around Winchendon

Winchendon, Massachusetts, is perfect for outdoor and romantic getaways, offering a variety of activities. Visitors can enjoy skiing at local ski fields, explore shopping centers, and engage in fun activities like mini golf and a water park. The beautiful scenery enhances the experience, making it an ideal destination for those looking to relax and unwind in nature.

Shopping

For shopping in Winchendon, visit the 1761 Old Mill Gift Shop for unique gifts. If you're up for a drive, check out The Mall at Whitney Field for diverse shops and entertainment, or stop by Ava Marie Handmade Chocolates for delicious treats, located 22.5km away.

Recreation

Explore Lake Dennison State Recreation Area for serene walks and nature relaxation, perfect for unwinding amidst scenic beauty. For a more active experience, head to Shattuck Golf Course or Ellinwood Country Club, both offering fantastic golfing opportunities surrounded by picturesque landscapes.

Adventure

The Wapack Trail, located 22.5km from Winchendon, offers breathtaking views and invigorating hikes through stunning landscapes. For a more local adventure, visit the Wetmore Trailhead within Winchendon, where you can explore scenic trails. The Towline Trailhead, only 6.4km away, also invites outdoor enthusiasts to discover its natural beauty.

Nightlife

In Winchendon, nightlife thrives with cultural experiences at nearby theaters. The Peterborough Players, 27.4km away, and Wilton Town Hall Theatre, 30.6km away, offer captivating performances, while the Colonial Theatre, 33.8km away, provides a charming atmosphere for romance and entertainment.

*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 for lower accommodation rates, as prices soar in summer and October. Booking your stay on a Monday rather than a Saturday can also cut costs. Use Expedia to compare room rates, find cheap hotel deals, and take advantage of package savings by bundling flights and activities. Don’t forget to filter your search by price to find the best offers, and explore free activities around town to further stretch 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 Monday. The most expensive day to stay in Winchendon is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia's search tool to customize your options based on your budget, desired location, and preferred hotel type. To discover the best prices and available deals, arrange the price filter from lowest to highest.
  • Consider bundling your trip: By booking an Expedia package, you can save money by combining your Winchendon hotel stay with your flights and activities.

Find the best attractions in and around Winchendon

Winchendon, Massachusetts, is perfect for tourists seeking outdoor adventures, beautiful scenery, and romantic getaways. Visitors can explore local attractions such as modern colleges and universities, nature reserves, and serene lakes, offering eco-friendly experiences and opportunities for adventure. Whether you enjoy hiking, picnicking, or simply appreciating nature, Winchendon has something for everyone to enjoy during their vacation.

  • The Winchendon School: Experience the vibrant atmosphere of The Winchendon School, a modern college that combines academic excellence with a dynamic community. Engage with students and faculty who foster a rich educational environment in the heart of Winchendon.
  • Cathedral of the Pines: Just 11.3km from Winchendon, this beautiful church offers a serene and culturally rich experience. The stunning architecture and peaceful surroundings make it an ideal spot for reflection and appreciation of the arts.
  • Jacobs Hill: Located 9.7km away, Jacobs Hill is a wonderful recreational area known for its friendly locals and relaxing vibe. This secluded spot is perfect for hiking, picnicking, or simply unwinding in nature.

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 have convenient access to three major airports. Boston Logan International Airport (BOS) is 91.7km away, with nearby hotels like the 5-star InterContinental Boston and Encore Boston Harbor, both 2-4.8km from the airport. Manchester-Boston Regional Airport (MHT) is closer at 56.3km, with excellent options such as the 5-star Grand at Bedford Village Inn, located 6.4km from the airport. Lastly, Worcester Regional Airport (ORH) is just 48.3km away, featuring hotels like the 4-star Beechwood Hotel, 8.0km from the airport. Each hotel provides easy access 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 Motel 6 Leominster, 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.
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: Offers 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'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 10 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 Hyde Park, V F W Park, and Militia Training Field. 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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