𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Winchendon (2026)

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Winchendon

Pet friendly

Apartment

Pool

Condo

Family friendly

Waterpark

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for Winchendon hotels

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

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

1. Gardner Inn

Gardner

Leila

S$142

includes taxes & fees

18 Oct - 19 Oct

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

A pool area with lounge chairs and potted plants.

A brick building with a steeple, arched windows, and flags.

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

2. The Colonial Hotel

Gardner

John Timothy

S$206

includes taxes & fees

1 Nov - 2 Nov

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.

3. Econo Lodge

Westminster

Ashleigh

S$142

includes taxes & fees

9 Nov - 10 Nov

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.

An indoor swimming pool with clear blue water, surrounded by brick walls and large windows.

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

4. Doubletree by Hilton Hotel Leominster

Leominster

louis

S$228

includes taxes & fees

1 Nov - 2 Nov

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

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

A bedroom with a large bed, a bedside table, a chair, and a dresser.

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

5. The Birchwood Inn

Temple

Karen

S$243

includes taxes & fees

18 Oct - 19 Oct

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 modern bedroom with a large bed, a nightstand, a lamp, and a stone pillar.

6. Riverhouse by Weekender (Formerly Jack Daniels Inn)

Peterborough

Kathleen

S$232

includes taxes & fees

18 Oct - 19 Oct

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.

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

A modern fitness center with cardio machines, weightlifting equipment, and a large mirror.

7. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

Angelo

S$165

includes taxes & fees

2 Nov - 3 Nov

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

A laundromat with multiple washing machines, a Coca-Cola refrigerator, and a snack vending machine.

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

8. Motel 6 Leominster, MA

Leominster

Ruth

S$138

includes taxes & fees

1 Nov - 2 Nov

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

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

A dining area with two tables, chairs, and a radiator.

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.

9. Monadnock Inn

Jaffrey

Jed

S$190

includes taxes & fees

1 Nov - 2 Nov

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

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

10. Days Inn by Wyndham Keene NH

Keene

CHERYL

S$129

includes taxes & fees

25 Oct - 26 Oct

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

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.

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

11. The Carriage Barn Inn

Keene

Richard

S$220

includes taxes & fees

20 Oct - 21 Oct

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

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

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

A gazebo with a white fence and a blue roof, surrounded by a well-maintained lawn, with a brick building in the background.

12. Best Western Plus Keene Hotel

Keene

Ruddy

S$197

includes taxes & fees

1 Nov - 2 Nov

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

An indoor swimming pool with lounge chairs and a sign indicating no lifeguard on duty and no diving.

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

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

13. Hampton Inn & Suites Keene

Keene

Rebecca

S$204

includes taxes & fees

11 Nov - 12 Nov

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

A grand chandelier with multiple light fixtures hanging from the ceiling, a large arched window above a set of double doors with an exit sign, and a patterned floor.

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

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

14. Chocksett Inn and Restaurant

Sterling

Lisa

S$227

includes taxes & fees

12 Oct - 13 Oct

A historic brick building with a porch and a sign reading "Burrell House."

A hallway with a white radiator, a wooden staircase, and a door with decorative glass panels.

A kitchen with a microwave, coffee maker, and a KUPPST refrigerator. There are two stools and a small shelf with a vase.

A covered outdoor seating area with tables and chairs, overlooking a residential street with houses and a road.

15. The Burrell House

Keene

Justin

S$195

includes taxes & fees

21 Oct - 22 Oct

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

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

A table with a plate of strawberries, a mug, and binoculars, set against a window with a view of greenery and a body of water.

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

16. The Maguire House Bed & Breakfast

Ashburnham

Jeffrey

S$340

includes taxes & fees

5 Nov - 6 Nov

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

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

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

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

17. Centennial House

Northfield

Alan

S$219

includes taxes & fees

26 Oct - 27 Oct

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.

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

18. Fairfield Inn & Suites by Marriott Keene Downtown

Keene

Caroline

S$241

includes taxes & fees

25 Oct - 26 Oct

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

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

A spacious living room with two patterned sofas, a coffee table, and a fireplace.

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

19. Howarth House B&B

Fitchburg

David

S$271

includes taxes & fees

12 Oct - 13 Oct

A water play area with children and adults.

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

A group of people engaged in a craft activity at a table with various colored markers and papers.

20. Great Wolf Lodge Boston / Fitchburg, MA

Fitchburg

michael

S$267

includes taxes & fees

12 Oct - 13 Oct

View all properties

Save an average of 15% on thousands of hotels when you're signed in

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

V F W Park

This tranquil community park honours veterans with thoughtful memorials and well-maintained green spaces. Bring a picnic to enjoy in the open areas while reflecting on local military service.

See properties

Learn more about Winchendon

Toy Town's charm comes alive at the Old Murdock Senior Centre, 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

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent

"I was specially impressed by the employee who walked extra miles to provide the information I asked for and more to make my staying and continuing travel easy and accessible. Shema, I really thank you for your help. God bless you!"

Best Western Plus Keene Hotel

10/10 Excellent

"Very clean, breakfast was very good. And the restaurant attached to the hotel was amazing"

Centennial House

10/10 Excellent

"I liked the style and decor of the house - historical but not fussy. The large yard and gazebo were a relaxing place to stroll around. (you can pick apples). The atmosphere/vibe was relaxed and welcoming. David, the host, was very pleasant. The breakfasts were quite good (omelets, meat, fruit, muffins) two of the three days of our stay. Mondays are continental breakfast, which was not the same caliber and angered some of the guests. They need a work around for this. The nearby businesses are a delightful throwback to an earlier era: the Creamie Ice cream shop, the IGA market, etc. The Four Star Brewery has a fantastic outdoor space/yard and excellent hard cider. Did not try the beer."

Riverhouse by Weekender (Formerly Jack Daniels Inn)

8/10 Good

"Nobody is at the reception if you arrive after 6 pm. You cannot open the window in the room anymore."

Gardner Inn

8/10 Good

"Our room was clean. Some things were outdated but it was a good place to stop for the night. No issues"

The Colonial Hotel

10/10 Excellent

"Absolutely loved our stay here with our two golden doodles! We were in town for our daughter’s hockey game. We stay in chain hotels most weekends snd leave our dogs home . We made a little trip out of this 2 game series and The Colonial Hotel was the perfect little getaway."

Motel 6 Leominster, MA

10/10 Excellent

"Clean room, staff was helpful and even tho I only stayed 2 nights I felt safe and comfortable. Would stay again when in the area."

Doubletree by Hilton Hotel Leominster

10/10 Excellent

"."

Hampton Inn & Suites Keene

10/10 Excellent

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

More cheap stays in Winchendon

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH

S$129

25 Oct - 26 Oct

includes taxes & fees

7/10 Good! (1,002 reviews)

Motel 6 Leominster, MA

48 Commercial Rd Leominster MA

S$138

1 Nov - 2 Nov

includes taxes & fees

8.2/10 Very good! (1,001 reviews)

Gardner Inn

22 Pearson Blvd Gardner MA

S$142

18 Oct - 19 Oct

includes taxes & fees

7.8/10 Good! (77 reviews)

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

S$165

2 Nov - 3 Nov

includes taxes & fees

8.6/10 Excellent! (1,004 reviews)

Hampton Inn & Suites Keene

126 Key Rd Keene NH

S$204

11 Nov - 12 Nov

includes taxes & fees

8.8/10 Excellent! (419 reviews)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

80 Concord Street Peterborough NH

S$232

18 Oct - 19 Oct

includes taxes & fees

9.2/10 Wonderful! (480 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 traveller data. Other good choices for your stay in 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 most room reservations are fully refundable if you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a reservation that's non-refundable, you might be able to cancel it and receive a refund within a 24-hour period 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: Offers 4 indoor swimming pools, a children's pool and free water park access. The Colonial Hotel and Doubletree by Hilton Hotel Leominster are two additional hotels with an on-site 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 10 hotels and other accommodation options to choose from. Find out more about Winchendon.

What are the top places to visit 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 itinerary are Lake Dennison State Recreation Area and Beals Memorial Library. Take a look at what more there is to see and do in Expedia's Winchendon guide.

What's the seasonal weather in Winchendon?

The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Winchendon are January, March, February and November, with each month seeing an average of 19 cm of snowfall.

Winchendon Hotels from S$129

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. Gardner Inn

2. The Colonial Hotel

3. Econo Lodge

4. Doubletree by Hilton Hotel Leominster

5. The Birchwood Inn

6. Riverhouse by Weekender (Formerly Jack Daniels Inn)

7. Keene Elm City Hotel, an Ascend Collection Hotel

8. Motel 6 Leominster, MA

9. Monadnock Inn

10. Days Inn by Wyndham Keene NH

11. The Carriage Barn Inn

12. Best Western Plus Keene Hotel

13. Hampton Inn & Suites Keene

14. Chocksett Inn and Restaurant

15. The Burrell House

16. The Maguire House Bed & Breakfast

17. Centennial House

18. Fairfield Inn & Suites by Marriott Keene Downtown

19. Howarth House B&B

20. Great Wolf Lodge Boston / Fitchburg, MA

Stay near popular Winchendon attractions

Lake Dennison State Recreation Area

Hyde Park

Blueberry Island

Monument Park

Militia Training Field

Old Centre Historic District

The Robinson-Broadhurst Foundation Performing Arts Ampitheater

V F W Park

Learn more about Winchendon

Top Winchendon Hotel Reviews

Keene Elm City Hotel, an Ascend Collection Hotel

Best Western Plus Keene Hotel

Centennial House

Riverhouse by Weekender (Formerly Jack Daniels Inn)

Gardner Inn

The Colonial Hotel

Motel 6 Leominster, MA

Doubletree by Hilton Hotel Leominster

Hampton Inn & Suites Keene

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

Explore a world of travel with Expedia

Go further with the Expedia app