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

Find hotels in Winchendon, MA from AED 376

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19 Sep - 20 Sep
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20 Sep - 21 Sep
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25 Sep - 27 Sep
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2 Oct - 4 Oct

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Our top choices for Winchendon hotels

1. The Colonial Hotel

The Colonial Hotel
Gardner
United States
Michele
AED 562
AED 628 total
includes taxes & fees
21 Sep - 22 Sep
The Colonial Hotel

2. Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster
Leominster
United States
Jason
AED 584
AED 653 total
includes taxes & fees
4 Oct - 5 Oct
Doubletree by Hilton Hotel Leominster

3. Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA
Fitchburg
United States
Roman
AED 687
AED 767 total
includes taxes & fees
20 Sep - 21 Sep
Great Wolf Lodge Boston / Fitchburg, MA

4. Gardner Inn

Gardner Inn
Gardner
United States
Vicki
AED 390
AED 436 total
includes taxes & fees
20 Sep - 21 Sep
Gardner Inn

5. Motel 6 Leominster, MA

Motel 6 Leominster, MA
Leominster
United States
Linda
AED 348
AED 396 total
includes taxes & fees
22 Sep - 23 Sep
Motel 6 Leominster, MA

6. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
Keene
United States
David
AED 492
AED 534 total
includes taxes & fees
20 Sep - 21 Sep
Keene Elm City Hotel, an Ascend Collection Hotel

7. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
Keene
United States
Ruddy
AED 547
AED 594 total
includes taxes & fees
20 Sep - 21 Sep
Best Western Plus Keene Hotel

8. Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
Keene
United States
sheri
AED 584
AED 634 total
includes taxes & fees
27 Sep - 28 Sep
Hampton Inn & Suites Keene

9. Centennial House

Centennial House
Northfield
United States
Lauren
AED 620
AED 655 total
includes taxes & fees
20 Sep - 21 Sep
Centennial House

10. The Birchwood Inn

The Birchwood Inn
Temple
United States
Karen
AED 643
AED 697 total
includes taxes & fees
22 Sep - 23 Sep
The Birchwood Inn

11. Howarth House B&B

Howarth House B&B
Fitchburg
United States
David
AED 777
AED 777 total
includes taxes & fees
27 Sep - 28 Sep
Howarth House B&B

12. The Maguire House Bed & Breakfast

The Maguire House Bed & Breakfast
Ashburnham
United States
Ranjit
AED 1,122
AED 1,122 total
includes taxes & fees
23 Sep - 24 Sep
The Maguire House Bed & Breakfast

13. Monadnock Inn

Monadnock Inn
Jaffrey
United States
Jed
AED 620
AED 673 total
includes taxes & fees
20 Sep - 21 Sep
Monadnock Inn

14. Econo Lodge

Econo Lodge
Westminster
United States
Sherry
AED 403
AED 442 total
includes taxes & fees
18 Oct - 19 Oct
Econo Lodge

15. Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
Keene
United States
Caroline
AED 799
AED 867 total
includes taxes & fees
27 Sep - 28 Sep
Fairfield Inn & Suites by Marriott Keene Downtown

16. Chocksett Inn and Restaurant

Chocksett Inn and Restaurant
Sterling
United States
Brian
AED 584
AED 652 total
includes taxes & fees
20 Sep - 21 Sep
Chocksett Inn and Restaurant

17. Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)
Peterborough
United States
Kathleen
AED 537
AED 622 total
includes taxes & fees
7 Oct - 8 Oct
Riverhouse by Weekender (Formerly Jack Daniels Inn)

18. The Carriage Barn Inn

The Carriage Barn Inn
Keene
United States
Jonathan
AED 561
AED 609 total
includes taxes & fees
20 Sep - 21 Sep
The Carriage Barn Inn

19. The Burrell House

The Burrell House
Keene
United States
Justin
AED 503
AED 561 total
includes taxes & fees
21 Sep - 22 Sep
The Burrell House

20. Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
Keene
United States
Alex
AED 347
AED 376 total
includes taxes & fees
22 Sep - 23 Sep
Days Inn by Wyndham Keene NH
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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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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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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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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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Wendall P. Clark Memorial

After visiting Wendall P. Clark Memorial, make a plan to see the other sights and activities in Winchendon. While you're in the area, wander around the parks.
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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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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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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

Centennial House

Centennial House

10/10 Excellent
"Excellent host making us feel very welcome. Very nice room and really lovely breakfast. Would certainly stay again if we are in the area."
Alan 1-night trip
Posted 1 hour ago
Centennial House
Econo Lodge

Econo Lodge

10/10 Excellent
"Not what I expected . Room was updated and clean . Would stay here again if needed for the night"
Sabrina 1-night trip
Posted 3 hours ago
Econo Lodge
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

10/10 Excellent
"Great place to go"
Ruddy 6-night trip
Posted 3 days ago
Best Western Plus Keene Hotel
Gardner Inn

Gardner Inn

8/10 Good
"Great staff. The challenge is the location...road noise from the highway but that's what makes it convenient."
victoria 1-night trip
Posted 6 days ago
Gardner Inn
Cozy Lakefront Cottage

Cozy Lakefront Cottage

10/10 Excellent
"What a wonderful way to bring the summer to a close. Our host was truly remarkable and so very quick to respond to each and every contact. Our stay was peaceful and relaxing which is exactly what I needed. The cottage is warm, comfortable and roomy. The lake is just beautiful and seeing a Loon up close was a real bonus!"
Christine L. 1-night trip
Posted 3 weeks ago
Cozy Lakefront Cottage
Monadnock Inn

Monadnock Inn

10/10 Excellent
"Very nice, clean, and a good vibe. An older building but very charming. Would certainly stay again."
Jed 1-night trip
Posted 3 weeks ago
Monadnock Inn
Modern Waterfront Gem w/ Dock on Lake Monomonac

Modern Waterfront Gem w/ Dock on Lake Monomonac

10/10 Excellent
"The cottage was very cute and the lot was nice with a bit of elbow room between the cottage and the neighbors. Situated right on the lake it was a nice setting for relaxing which was exactly what we were looking for."
Melanie C. 4-night trip
Posted 4 months ago
Modern Waterfront Gem w/ Dock on Lake Monomonac

More cheap stays in Winchendon

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH
AED 347
AED 376 total
22 Sep - 23 Sep
includes taxes & fees
7/10 Good! (1,001 reviews)
Days Inn by Wyndham Keene NH
Motel 6 Leominster, MA

Motel 6 Leominster, MA

48 Commercial Rd Leominster MA
AED 348
AED 396 total
22 Sep - 23 Sep
includes taxes & fees
Motel 6 Leominster, MA
Gardner Inn

Gardner Inn

22 Pearson Blvd Gardner MA
AED 390
AED 436 total
20 Sep - 21 Sep
includes taxes & fees
7.6/10 Good! (62 reviews)
Gardner Inn
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH
AED 492
AED 534 total
20 Sep - 21 Sep
includes taxes & fees
Keene Elm City Hotel, an Ascend Collection Hotel
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

80 Concord Street Peterborough NH
AED 537
AED 622 total
7 Oct - 8 Oct
includes taxes & fees
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

126 Key Rd Keene NH
AED 584
AED 634 total
27 Sep - 28 Sep
includes taxes & fees
Hampton Inn & Suites Keene

Find out more about Winchendon

Top reasons to visit Winchendon

  • Outdoor Adventures: Winchendon offers various outdoor activities, including skiing, hiking, and water sports at Lake Monomonac.
  • Charming New England Atmosphere: Experience the quaint, vibrant culture of local hamlets and scenic views.
  • Family-Friendly Activities: Enjoy mini golf, water parks, and nature reserves suitable for all ages.
  • Romantic Getaways: Perfect for couples seeking a peaceful retreat surrounded by stunning landscapes.
  • Diverse Accommodations: Choose from cozy inns and charming bed & breakfasts tailored to various preferences.

Find great hotels near Winchendon

Explore a variety of lodging options in Winchendon, Massachusetts, including charming bed & breakfasts and cozy inns. Whether you're seeking an adventurous getaway, a family-friendly environment, or an LGBTQIA-welcoming experience, you'll find hotels that cater to your needs. Dive into hotel reviews and discover the best accommodations for your vacation in this unique New England town.

  • The Colonial Hotel: Experience the charm of The Colonial Hotel, a welcoming 3-star property situated 16.1km from Winchendon. This hotel is perfect for travelers seeking a blend of business convenience and a pet-friendly atmosphere. With amenities that cater to both professionals and pet owners, guests can enjoy a stress-free stay with their furry friends. The hotel features well-appointed rooms, complimentary Wi-Fi, and a business center, making it an ideal choice for business travelers. Additionally, the pet policy allows certain pets on-site, ensuring that no family member is left behind. The friendly staff is dedicated to providing exemplary service, ensuring a comfortable and enjoyable stay.
  • Great Wolf Lodge Boston / Fitchburg, MA: A magical retreat for families, Great Wolf Lodge Boston / Fitchburg, MA is a 3.5-star resort located 22.5km from Winchendon. Renowned for its family-friendly atmosphere, this lodge offers an array of amenities designed to entertain and engage children of all ages. Guests can take advantage of the on-site water park, mini-golf, and arcade game room, along with free supervised childcare services. The lodge is also committed to inclusivity, welcoming LGBTQIA travelers with open arms. With spacious family suites and a vibrant atmosphere, it’s a perfect destination for creating unforgettable family memories.
  • Monadnock Inn: Step into the serene ambiance of Monadnock Inn, a cozy Bed & Breakfast located 16.1km from Winchendon. This charming inn is ideal for golf enthusiasts, offering a unique golf-themed experience with easy access to local courses. Guests can unwind in tastefully decorated rooms and enjoy a complimentary breakfast each morning, fueling their adventures. The inn's tranquil setting and personalized service create a home-away-from-home feeling, making it a favorite for travelers seeking a peaceful getaway centered around their passion for golf.

Where to stay near Winchendon

Winchendon, Massachusetts, is a hidden gem for travelers seeking outdoor adventures and romantic getaways. Just a short drive from Worcester, this charming city offers scenic views and family-friendly activities. Explore the beautiful Lake Monomonac, perfect for recreation and relaxation. Don’t miss the quaint New England hamlets nearby, where the atmosphere is vibrant with local culture and charm. Whether you're looking for adventure or a peaceful retreat, Winchendon has something for everyone.

  • Fitchburg: Located 22.5km from Winchendon, Fitchburg is a vibrant city that attracts visitors year-round, with a peak in winter months. Known for its family-friendly atmosphere, adventure opportunities, and entertainment options, Fitchburg offers a variety of experiences. Engage in thrilling activities at the local water park, or hit the slopes at nearby ski fields. Don’t miss the chance to explore exciting local landmarks such as the theme park and event conference venue, making it a perfect spot for a fun-filled day.
  • Gardner: Just 12.9km away from Winchendon, Gardner is a charming city that sees a steady stream of visitors, especially during the spring and summer months. Famous for its sports and adventure experiences, Gardner offers ample opportunities for skiing and other outdoor activities. Discover its local attractions like the family-friendly beach and event conference venue, which cater to both relaxation and entertainment. Whether you're looking to challenge yourself with outdoor sports or enjoy a leisurely day by the water, Gardner has something for everyone.
  • Rindge: A mere 8.0km from Winchendon, Rindge is a picturesque city known for its stunning outdoor scenery and romantic ambiance. With a moderate seasonal visitor flow, the summer months are particularly popular for those seeking outdoor adventures. Explore the breathtaking landscapes at local lakes and mountains, or visit historical sites that tell the story of the area. Rindge is perfect for those who appreciate nature and want to indulge in recreational activities, making it a delightful escape.

Things to do in and around Winchendon

Winchendon, Massachusetts, is perfect for outdoor and romantic getaways, offering scenic views and various activities. Visitors can enjoy skiing at nearby ski fields, play mini golf, and have fun at a water park. For those looking to shop, the local shopping center provides a variety of options. Experience the charm and leisurely pace of this lovely town during your vacation.

Shopping

In Winchendon, visit the 1761 Old Mill Gift Shop for unique gifts. Ava Marie Handmade Chocolates, located nearby, offers delicious treats. If you're up for a drive, The Mall at Whitney Field, 30.6km away, features a variety of shops and entertainment options for a fun day out.

Recreation

Lake Dennison State Recreation Area offers a tranquil setting for relaxation and outdoor activities, perfect for unwinding in nature. For golf enthusiasts, Shattuck Golf Course and Ellinwood Country Club provide scenic courses just 10 and 19.3km away, respectively, blending sports with beautiful landscapes.

Adventure

Embark on an adventure along the Wapack Trail, a picturesque hiking route 22.5km from Winchendon, offering breathtaking scenery. Closer to town, explore the Wetmore Trailhead and the Towline Trailhead, both providing thrilling outdoor experiences that immerse you in Winchendon's natural beauty.

Nightlife

In Winchendon, you can enjoy vibrant nightlife options like the Peterborough Players, Colonial Theatre, and Wilton Town Hall Theatre, all offering captivating performances within a short drive. Each venue radiates romance and culture, creating an enchanting atmosphere for an unforgettable evening out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Winchendon

To save money on your trip to Winchendon, visit during the off-peak months of November to January when accommodation prices are lower. Book your stay on a Monday for the best rates, avoiding the pricier Saturdays. Use Expedia to compare hotel rates and consider package deals that combine flights and activities for added savings. Look for free local attractions and utilize public transport for budget-friendly travel options. Sorting prices from lowest to highest can help you find affordable accommodations tailored to your preferences.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Winchendon are November to January, where the prices are slightly lower. This is in comparison to June to July and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Winchendon is Monday. The most expensive day to stay in Winchendon is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia's search tool to refine your preferences, such as your budget, desired location, and preferred type of accommodation. To find the most affordable options and best deals, 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, Massachusetts, is perfect for outdoor enthusiasts and romantic getaways, featuring stunning natural scenery. Visitors can explore a variety of attractions, including modern colleges, nature reserves, and picturesque lakes. Whether you're seeking adventure or an eco-friendly experience, Winchendon offers a range of activities that cater to all types of travelers looking to enjoy the great outdoors.

  • The Winchendon School: Experience the vibrant atmosphere of The Winchendon School, a modern college that combines academic rigor with a lively community. The school’s innovative approach to education creates an engaging environment, perfect for visitors interested in contemporary campus life.
  • Cathedral of the Pines: Nestled 11.3km from Winchendon, this stunning church offers a unique cultural experience surrounded by nature. The serene setting and beautiful architecture make it a perfect spot for reflection, contemplation, and appreciating the local artistry.
  • Jacobs Hill: Located 9.7km away, Jacobs Hill is a secluded haven ideal for recreation and relaxation. Enjoy friendly interactions with locals while exploring trails and taking in the tranquil natural beauty that this hidden gem offers.

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

To visit Winchendon, Massachusetts, you can fly into three major airports. Boston Logan International Airport (BOS) is 91.7km away, with luxurious hotels like the InterContinental Boston, Boston Harbor Hotel, and Encore Boston Harbor, all within 4.8km. Manchester-Boston Regional Airport (MHT) is 56.3km away, offering nearby accommodations such as The Grand at Bedford Village Inn and DoubleTree by Hilton Manchester Downtown, both 6.4km from the airport. Worcester Regional Airport (ORH) is the closest at 48.3km, featuring hotels like Beechwood Hotel and AC Hotel by Marriott, both just a few miles away. Each airport provides convenient access to these excellent lodging options.

Frequently asked questions

What's the best place to stay in Winchendon?
Great Wolf Lodge Boston / Fitchburg, MA, located 2.4 mi (3.9 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.
What are some of the best vacation rentals in Winchendon?
Cozy Lakefront Cottage: Visitors like this Winchendon vacation home rental. It is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of books. See all vacation rentals in Winchendon.
If I need to cancel my hotel reservation in Winchendon, will I receive a refund?
Yes! You'll find that most hotel room reservations are fully refundable if cancelled prior to the hotel's cancellation deadline, which often is within 24-48 hours of your check-in date. If you booked a non-refundable reservation, it may still be possible to cancel it and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchendon.
Where can I learn more about changing or cancelling my trip to Winchendon?
To access more information about updating your trip to Winchendon or cancelling it, click here.
What's the best place to stay near Lake Dennison State Recreation Area?
The Colonial Hotel is one of the top choices for your stay based on our traveler data, and this 3-star hotel offers a restaurant and an indoor pool. You'll find it 9 mi (14.5 km) from Lake Dennison State Recreation Area. Other good options in the area include Super 8 by Wyndham Gardner and The Maguire House Bed & Breakfast.
What are some hotels with pools in Winchendon?
Great Wolf Lodge Boston / Fitchburg, MA: 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 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 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.