Top 10 Hotels in Winchendon, MA from ₩134,704 - Competitive Prices

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

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Our top choices for Winchendon hotels

A grand lobby with a staircase, a piano, comfortable seating, and large windows.

A formal dining room with round tables, dark wooden chairs, and white tablecloths.

A pool area with lounge chairs and potted plants.

A wooden pergola structure in a garden setting with a paved walkway leading to it.

1. The Colonial Hotel

Gardner

John Timothy

₩192,893

₩215,472 total

includes taxes & fees

Nov 1 - Nov 2

A bar area with a long counter, multiple bar stools, hanging pendant lights, and a bar stocked with bottles.

A gym with treadmills, a television, and weightlifting equipment.

A modern living room with two sofas, a coffee table, and a dining area with chairs and a table.

A spacious hotel lobby with a central island, seating areas, and large windows.

2. Doubletree by Hilton Hotel Leominster

Leominster

louis

₩213,167

₩238,108 total

includes taxes & fees

Nov 1 - Nov 2

A hotel lobby with a check-in counter, a reception desk, a clock, a potted plant, and seating areas.

A hotel room with two beds, a desk, a chair, a window with curtains, and two wall-mounted lamps.

A reception area with a check-in counter, a waiting area with seating, a tiled floor, and a clock on the wall.

A hotel hallway with red doors, numbered room signs, and a patterned carpet.

3. Gardner Inn

Gardner

Leila

₩132,660

₩148,181 total

includes taxes & fees

Oct 18 - Oct 19

A covered porch with Adirondack chairs and a table with wine glasses, overlooking a lake and lush greenery.

A cozy living room with two grey sofas, a red patterned rug, and a view of a lake and forest through large windows.

A bedroom with a large bed, a view of a lake, and a table with flowers.

A large, two-story house with a well-maintained lawn and a stone fountain.

4. The Maguire House Bed & Breakfast

Ashburnham

Jeffrey

₩395,300

₩395,300 total

includes taxes & fees

Nov 5 - Nov 6

A water play area with children and adults.

A hotel with a prominent sign reading "Great Wolf Lodge."

A rustic interior with wooden tables, a barrel, and a wall displaying colorful items.

5. Great Wolf Lodge Boston / Fitchburg, MA

Fitchburg

Radcliff

₩250,300

₩279,585 total

includes taxes & fees

Oct 12 - Oct 13

A bar area with a high ceiling and stained glass windows, bar stools, and a checkered floor.

A covered outdoor area with a wooden deck, white railings, and string lights.

A spacious lobby with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

A hotel room with a large bed, two smaller beds, a desk with a TV, a chair, and a view of the outdoors.

6. Best Western Plus Keene Hotel

Keene

Ruddy

₩189,677

₩205,799 total

includes taxes & fees

Nov 1 - Nov 2

A living room with a brick wall, two armchairs, a sofa, a coffee table, and a patterned rug.

A bar area with a dark wooden bar, multiple bar stools, and a large screen displaying the hotel name.

A bar area with a fireplace, seating, and a TV.

7. Fairfield Inn & Suites by Marriott Keene Downtown

Keene

Caroline

₩232,356

₩252,106 total

includes taxes & fees

Oct 25 - Oct 26

A modern dining area with a central seating area, a kitchen in the background, and large windows providing natural light.

A modern hotel with a clear entrance, a parking area, and a sign indicating a 11' clearance.

A reception area with a 'Welcome to the Granite State' sign, a reception desk, and a well-organized suite shop.

A hotel suite shop with shelves stocked with snacks and sundries, a refrigerated display case, and a sign indicating 24-hour availability.

8. Hampton Inn & Suites Keene

Keene

Rebecca

₩187,935

₩203,910 total

includes taxes & fees

Nov 1 - Nov 2

A hotel reception area with two counters labeled 'Choice Hotels' and 'Ascend Hotel Collection'. There are vending machines and a refrigerator with beverages.

A hotel room with a bed, a desk, a chair, a wooden door, and a window.

A modern kitchen with wooden cabinets, a coffee machine, a fruit juice dispenser, and a refrigerator.

An indoor swimming pool with clear blue water, a lifebuoy, and a few lounge chairs.

9. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

Angelo

₩159,460

₩173,014 total

includes taxes & fees

Nov 2 - Nov 3

A wooden picnic table with a bottle and two glasses, surrounded by lush greenery and a wooden fence.

A room with a wooden coffee table, two chairs, a bookshelf, and a large mirror on the wall.

A hotel with a snow-covered driveway, Christmas lights, and a large tree in front.

A kitchen with a coffee machine, coffee pods, a fruit basket, and a refrigerator.

10. Riverhouse by Weekender (Formerly Jack Daniels Inn)

Peterborough

Kathleen

₩210,206

₩242,600 total

includes taxes & fees

Oct 18 - Oct 19

A dining area with wooden tables and chairs, a mural on the wall, and large windows.

A bar with wooden chairs and shelves stocked with liquor bottles.

A staircase with wooden steps and a blue handrail leading to a white door with a blackboard.

A hallway with white walls, a mirror, and a door leading to a bathroom with a bathtub and a window.

11. The Birchwood Inn

Temple

Karen

₩234,238

₩254,155 total

includes taxes & fees

Nov 2 - Nov 3

A well-lit garden area with a gazebo, a small house, and a large tree in the background.

A white wooden pergola with a lattice design, surrounded by lush greenery and flowering plants.

A bedroom with a fireplace, a bed, a chair, and a table with a lamp.

A swimming pool surrounded by lush greenery and a white fence.

12. Howarth House B&B

Fitchburg

David

₩283,410

₩283,410 total

includes taxes & fees

Oct 12 - Oct 13

A modern hotel room with a large bed, a desk, and a chair. There are two bedside tables with lamps.

A living room with a sofa, coffee table, and a rug. There is a door leading outside, a window with a view of the outside, and a small table with a lamp.

A modern interior with a seating area, a kitchenette, and a reception desk.

A modern kitchen with a dining area, built-in appliances, and a view of trees.

13. Econo Lodge

Westminster

Ashleigh

₩135,541

₩148,689 total

includes taxes & fees

Nov 8 - Nov 9

A bar area with a dark tiled backsplash, multiple stools, and a variety of bottles and glasses on the counter.

An indoor swimming pool with clear water, a glass railing, and a seating area with tables and chairs.

A multi-story brick building with a sign reading "COURTYARD BY MARRIOTT".

A hotel room with two beds, a desk, an orange chair, and a view of buildings through the window.

14. Courtyard by Marriott Keene Downtown

Keene

Deborah

₩253,327

₩274,859 total

includes taxes & fees

Oct 25 - Oct 26

A two-story building with a white facade and green shutters, a covered front porch, and a sign for the "M" Inn.

A porch with a wooden bench and a bench with cushions.

A cozy living room with a sofa, armchairs, a coffee table, and a dining table. There is a large window with curtains, a fireplace, and a lamp.

A staircase with a patterned carpet, a wooden table with a lamp, and a wall with floral wallpaper.

15. Monadnock Inn

Jaffrey

Jed

₩183,660

₩199,271 total

includes taxes & fees

Nov 1 - Nov 2

A modern hotel room with a large bed, a bedside table, a nightstand, a mirror, and a bathroom with a sink and towel rack.

A hallway with a vending machine, a laundry area, and a door with a sign.

A motel lobby with two red chairs, a reception desk, and a large window offering a view of parked cars and trees outside.

A motel with a prominent '6' sign, a balcony, and a 'Welcome' entrance.

16. Motel 6 Leominster, MA

Leominster

Allan

₩127,287

₩144,860 total

includes taxes & fees

Nov 1 - Nov 2

A hotel room with two beds, a TV, a desk, and a window with curtains.

A conference room with a black table, wooden chairs, a mounted TV, and a decorative mirror.

A hotel gym with treadmills, an elliptical, dumbbells, and a stationary bike.

A reception area with a black marble counter, wooden cabinets, and a 'Staff Only' door.

17. Days Inn by Wyndham Keene NH

Keene

CHERYL

₩124,151

₩134,704 total

includes taxes & fees

Oct 25 - Oct 26

A two-story house with a red door, green shutters, and a snow-covered front yard.

A kitchenette with a refrigerator, a coffee station, and a fruit basket.

A group of women in formal attire standing in a garden with a house in the background.

A golf course with a brick pathway, wooden boxes, and a tee box.

18. Centennial House

Northfield

Alan

₩240,232

₩253,925 total

includes taxes & fees

Oct 13 - Oct 14

A room with a fireplace, a large mirror, and a window with a view of the outside.

A spacious living room with a staircase, a chandelier, a console table with decorative items, and a large abstract painting on the wall.

A spacious hallway with large windows, chandeliers, and classic furniture.

A banquet hall with round tables set for a formal event, featuring chandeliers and table settings.

19. Chocksett Inn and Restaurant

Sterling

Lisa

₩212,822

₩237,718 total

includes taxes & fees

Oct 12 - Oct 13

A wooden table set with plates, cutlery, and a folded napkin.

A two-story building with a porch, a sign indicating guest rooms, and an American flag.

A corner room with wooden flooring, a wooden table, and four chairs. Large windows with curtains are visible, offering a view of a green landscape and a red deck outside.

A cozy room with a wooden floor, a rocking chair, a blue armchair, a bookshelf, and a globe on a table.

20. The Carriage Barn Inn

Keene

Richard

₩226,171

₩245,396 total

includes taxes & fees

Oct 11 - Oct 12

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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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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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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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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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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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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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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

10/10 Excellent

"Everything was perfect!!"

Motel 6 Leominster, MA

10/10 Excellent

"Always a great stay. The mgt and staff are always ready to assist you. To ensure a safe stay."

Hampton Inn & Suites Keene

10/10 Excellent

"Staff friendly and helpful. Clean and great breakfast!"

Doubletree by Hilton Hotel Leominster

8/10 Good

"Hotel was great, except for a leak coming through the light over the tub coming from the room above. We were compensated with free breakfast and some points. The hotel staff was great, and I would stay at this hotel again."

Chocksett Inn and Restaurant

10/10 Excellent

"Clean room, staff helpful and friendly"

The Carriage Barn Inn

10/10 Excellent

"Clean,quiet, beautiful inn in the heart of downtown Keene,NH. Joe was friendly and accommodating and a hell of a great guy. A+++++++"

Centennial House

10/10 Excellent

"The innkeeper was very nice and helpful. The inn is super charming and breakfast was delicious!!"

Fairfield Inn & Suites by Marriott Keene Downtown

10/10 Excellent

"Free parking included. Centrally located.Friendly staff. Large rooms"

Days Inn by Wyndham Keene NH

8/10 Good

"The staff was friendly and helpful when something was needed. Obviously every hotel has an odor and people who don’t follow rules so yes it smelled of smoke at times. But the sheets smelled fresh and the room was clean. Overall a good quiet stay"

More cheap stays in Winchendon

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH

₩124,151

₩134,704 total

Oct 25 - Oct 26

includes taxes & fees

Motel 6 Leominster, MA

48 Commercial Rd Leominster MA

₩127,287

₩144,860 total

Nov 1 - Nov 2

includes taxes & fees

8.2/10 Very Good! (1,005 reviews)

Gardner Inn

22 Pearson Blvd Gardner MA

₩132,660

₩148,181 total

Oct 18 - Oct 19

includes taxes & fees

7.6/10 Good! (74 reviews)

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

₩159,460

₩173,014 total

Nov 2 - Nov 3

includes taxes & fees

Hampton Inn & Suites Keene

126 Key Rd Keene NH

₩187,935

₩203,910 total

Nov 1 - Nov 2

includes taxes & fees

8.8/10 Excellent! (419 reviews)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

80 Concord Street Peterborough NH

₩210,206

₩242,600 total

Oct 18 - Oct 19

includes taxes & fees

9.2/10 Wonderful! (479 reviews)

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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Book Hotels in Winchendon on Expedia.com

Find hotels in Winchendon, MA from ₩134,704

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Winchendon

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Winchendon hotels

1. The Colonial Hotel

2. Doubletree by Hilton Hotel Leominster

3. Gardner Inn

4. The Maguire House Bed & Breakfast

5. Great Wolf Lodge Boston / Fitchburg, MA

6. Best Western Plus Keene Hotel

7. Fairfield Inn & Suites by Marriott Keene Downtown

8. Hampton Inn & Suites Keene

9. Keene Elm City Hotel, an Ascend Collection Hotel

10. Riverhouse by Weekender (Formerly Jack Daniels Inn)

11. The Birchwood Inn

12. Howarth House B&B

13. Econo Lodge

14. Courtyard by Marriott Keene Downtown

15. Monadnock Inn

16. Motel 6 Leominster, MA

17. Days Inn by Wyndham Keene NH

18. Centennial House

19. Chocksett Inn and Restaurant

20. The Carriage Barn Inn

Stay near popular Winchendon attractions

Lake Dennison State Recreation Area

Blueberry Island

Hyde Park

Monument Park

The Robinson-Broadhurst Foundation Performing Arts Ampitheater

Old Centre Historic District

Winchendon Community Park

Wendall P. Clark Memorial

Learn more about Winchendon

Top Winchendon Hotel Reviews

Great Wolf Lodge Boston / Fitchburg, MA

Motel 6 Leominster, MA

Hampton Inn & Suites Keene

Doubletree by Hilton Hotel Leominster

Chocksett Inn and Restaurant

The Carriage Barn Inn

Centennial House

Fairfield Inn & Suites by Marriott Keene Downtown

Days Inn by Wyndham Keene NH

More cheap stays in Winchendon

Days Inn by Wyndham Keene NH

Motel 6 Leominster, MA

Gardner Inn

Keene Elm City Hotel, an Ascend Collection Hotel

Hampton Inn & Suites Keene

Riverhouse by Weekender (Formerly Jack Daniels Inn)

Frequently asked questions

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