Find hotels in Winchendon, MA from NT$2,895

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Compare 213 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Chocksett Inn and Restaurant

3.5 star property
Sterling
8.6 out of 10, Excellent, (144)
"Fine for an overnight stay. Seems to be one of the better options in the area. Room clean and spacious. "
United States
Ayah
The price is NT$4,978
NT$5,560 total
includes taxes & fees
Dec 7 - Dec 8
Chocksett Inn and Restaurant

Motel 6 Leominster, MA

2.0 star property
Leominster
8.0 out of 10, Very Good, (1020)
"Not like other Motel 6 hotels that I have stayed at. Room was clean and friendly staff. Restaurants nearby to walk to."
United States
Mike
The price is NT$2,536
NT$2,895 total
includes taxes & fees
Dec 8 - Dec 9
Motel 6 Leominster, MA

Doubletree by Hilton Hotel Leominster

4.0 star property
Leominster
8.6 out of 10, Excellent, (1001)
"Always a great place to stay! Friendly, clean and comfortable. "
United States
Lynn
The price is NT$3,954
NT$4,416 total
includes taxes & fees
Dec 21 - Dec 22
Doubletree by Hilton Hotel Leominster

Howarth House B&B

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

Great Wolf Lodge Boston / Fitchburg, MA

3.5 star property
Fitchburg
8.6 out of 10, Excellent, (1000)
"Everything about this place was incredible "
United States
Jaida
The price is NT$5,044
NT$5,634 total
includes taxes & fees
Jan 5 - 2026/1/6
Great Wolf Lodge Boston / Fitchburg, MA

The Birchwood Inn

3.5 star property
Temple
9.4 out of 10, Exceptional, (224)
"Great Spot!"
United States
Kialey
The price is NT$5,323
NT$5,775 total
includes taxes & fees
Dec 7 - Dec 8
The Birchwood Inn

The Colonial Hotel

3.0 star property
Gardner
8.8 out of 10, Excellent, (1000)
"Great hotel, fantastic restaurant, wonderful place!"
United States
Kate
The Colonial Hotel

Gardner Inn

2.0 star property
Gardner
5.6 out of 10, (16)
"The property needs work but hte staff was pleasant and the facility was quiet. "
United States
Lou
The price is NT$2,790
NT$3,116 total
includes taxes & fees
Jan 5 - 2026/1/6
Gardner Inn

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 star property
Peterborough
9.4 out of 10, Exceptional, (433)
"Super cute place! Would stay here again"
United States
Danielle
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Monadnock Inn

2.5 star property
Jaffrey
7.6 out of 10, Good, (277)
"It is a Beautiful Old Charm Inn. Everything was great. I would definitely come back and stay there again. "
United States
Sharon-Ann C
Monadnock Inn

The Carriage Barn Inn

3.0 star property
Keene
9.6 out of 10, Exceptional, (165)
"Excellent place!!!! Lovely room that had all I needed!!! The bed was comfortable and the stay was wonderful!!!!!!"
United States
natalia
The price is NT$3,990
NT$4,329 total
includes taxes & fees
Dec 29 - Dec 30
The Carriage Barn Inn

Courtyard by Marriott Keene Downtown

3.0 star property
Keene
8.8 out of 10, Excellent, (1001)
"Lovely hotel"
United States
ronald
The price is NT$5,636
NT$6,115 total
includes taxes & fees
Dec 12 - Dec 13
Courtyard by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown

2.5 star property
Keene
8.8 out of 10, Excellent, (755)
"Front desk pleasant and helpful Breakfast was good Room was spacious and clean Able to walk to shopping and dining. "
United States
Stephen
The price is NT$5,636
NT$6,115 total
includes taxes & fees
Dec 12 - Dec 13
Fairfield Inn & Suites by Marriott Keene Downtown

The Burrell House

2.5 star property
Keene
9.6 out of 10, Exceptional, (155)
"Very helpful, kind staff"
United States
Paitris
The Burrell House

Best Western Plus Keene Hotel

3.0 star property
Keene
8.4 out of 10, Very Good, (1000)
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is NT$4,352
NT$4,722 total
includes taxes & fees
Dec 7 - Dec 8
Best Western Plus Keene Hotel

Hampton Inn & Suites Keene

2.5 star property
Keene
8.8 out of 10, Excellent, (351)
"Nice place to stay, nice area, will stay again."
United States
Catherine
The price is NT$4,609
NT$5,000 total
includes taxes & fees
Dec 30 - Dec 31
Hampton Inn & Suites Keene

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 star property
Keene
8.4 out of 10, Very Good, (957)
"Enjoyed the breakfast options and the very comfortable bed. "
Canada
Nancy
The price is NT$3,410
NT$3,699 total
includes taxes & fees
Dec 25 - Dec 26
Keene Elm City Hotel, an Ascend Collection Hotel

Days Inn by Wyndham Keene NH

2.0 star property
Keene
7.0 out of 10, Good, (1001)
"Very professional people good service good staff "
United States
George
The price is NT$2,874
NT$3,118 total
includes taxes & fees
Dec 21 - Dec 22
Days Inn by Wyndham Keene NH

Centennial House

3.5 star property
Northfield
9.6 out of 10, Exceptional, (173)
"The house was cozy and inviting. Felt the history all around me and the breakfast made and served by Joan was great. We recommend this place for those looking for that historical b&b experience. "
United States
Paul
The price is NT$6,305
NT$6,664 total
includes taxes & fees
Dec 30 - Dec 31
Centennial House
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 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?
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 The Colonial Hotel and Doubletree by Hilton Hotel Leominster. 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?
The Colonial Hotel: Features a sauna, an indoor pool, and free self parking. Doubletree by Hilton Hotel Leominster and Great Wolf Lodge Boston / Fitchburg, MA are two additional hotels that offer an onsite pool. View all hotels with pools in Winchendon.
What's the best accommodation near Worcester Regional Airport (ORH)?
Hilton Garden Inn Worcester is one of the top choices for your stay and is a popular 3-star hotel featuring a restaurant and an indoor pool. It's located 3.7 mi (5.9 km) from Worcester Regional Airport. Other choices near the airport include Holiday Inn Express Worcester Downtown and AC Hotel by Marriott Worcester.
What is staying in Winchendon like?
Visitors can enjoy all that Winchendon has to offer including its parks. In Winchendon, there are 9 hotels and other accommodations to choose from. Find out more about Winchendon.
What should I see while I'm in Winchendon?
Natural beauty is on display at Wendall P. Clark Memorial, Militia Training Field, and Hyde Park. A couple of additional sights to add to your agenda are Lake Dennison State Recreation Area and Winchendon Town Hall. Check out what more to see and do in Expedia's Winchendon guide.
What's the weather like in Winchendon?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Winchendon are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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