𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Winchendon (2026)

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 pool area with lounge chairs and potted plants.

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

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

1. The Colonial Hotel

Gardner

Mollie

₹11,754

₹13,129 total

includes taxes & fees

3 Nov - 4 Nov

A hotel lobby with a central circular skylight, a reception desk, and a seating area with sofas.

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

A hotel with a modern design, featuring a prominent tree in the foreground and a clear view of the sky.

A self-service snack area with various packaged snacks and a refrigerator stocked with beverages.

2. Doubletree by Hilton Hotel Leominster

Leominster

louis

₹13,684

₹15,285 total

includes taxes & fees

15 Nov - 16 Nov

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.

3. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

Lisa

₹12,343

₹13,392 total

includes taxes & fees

29 Oct - 30 Oct

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

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

4. Best Western Plus Keene Hotel

Keene

Ruddy

₹13,439

₹14,581 total

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.

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

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

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

5. Hampton Inn & Suites Keene

Keene

Neil

₹15,373

₹16,680 total

includes taxes & fees

19 Nov - 20 Nov

A hotel room with a brick wall, a large bed with white bedding, a flat-screen TV, and a desk with a lamp.

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

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

6. Fairfield Inn & Suites by Marriott Keene Downtown

Keene

Christopher

₹16,463

₹17,862 total

includes taxes & fees

1 Nov - 2 Nov

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 living room with a chessboard, a glass of beer, a sofa, and a chair.

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.

7. The Maguire House Bed & Breakfast

Ashburnham

Jeffrey

₹26,608

₹26,608 total

includes taxes & fees

5 Nov - 6 Nov

An indoor swimming pool with a spectator area and a stage.

A spacious lobby with a fireplace, a large chandelier, and a view of the surrounding area.

An indoor recreational area with a pool, seating, and a bar area labeled 'The Watering Hole.'

A hotel with a prominent rock sculpture in the foreground, a well-maintained garden, and a clear view of the building's entrance.

8. Great Wolf Lodge Boston / Fitchburg, MA

Fitchburg

Abderaouf

₹17,754

₹19,832 total

includes taxes & fees

26 Oct - 27 Oct

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

A hotel lobby with a coffee machine, a Coca-Cola refrigerator, and a map on the wall.

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.

9. Gardner Inn

Gardner

Leila

₹9,023

₹10,079 total

includes taxes & fees

3 Nov - 4 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 hallway with white walls, a mirror, and a door leading to a bathroom with a bathtub and a window.

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

10. The Birchwood Inn

Temple

Karen

₹16,615

₹18,028 total

includes taxes & fees

26 Oct - 27 Oct

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

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

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

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

11. Riverhouse by Weekender (Formerly Jack Daniels Inn)

Peterborough

Kathleen

₹15,295

₹17,625 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

12. Courtyard by Marriott Keene Downtown

Keene

Deborah

₹16,060

₹17,425 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

13. Howarth House B&B

Fitchburg

David

₹20,080

₹20,080 total

includes taxes & fees

26 Oct - 27 Oct

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

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.

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

14. Monadnock Inn

Jaffrey

Jim

₹13,013

₹14,119 total

includes taxes & fees

1 Nov - 2 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 hallway with a vending machine, a laundry area, and a door with a sign.

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

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

15. Motel 6 Leominster, MA

Leominster

Ruth

₹9,019

₹10,264 total

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 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.

16. Days Inn by Wyndham Keene NH

Keene

CHERYL

₹8,796

₹9,544 total

includes taxes & fees

28 Oct - 29 Oct

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 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.

17. Chocksett Inn and Restaurant

Sterling

Lisa

₹15,096

₹16,862 total

includes taxes & fees

26 Oct - 27 Oct

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

A wooden gazebo with a peaked roof, surrounded by a gravel area with potted plants.

A room with a built-in bench, a window with curtains, and a wooden railing.

A dining area with round tables, chairs, and a kitchen counter with a refrigerator.

18. Centennial House

Northfield

Alan

₹15,847

₹16,751 total

includes taxes & fees

28 Oct - 29 Oct

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 bench in front of an apple tree with ripe apples.

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.

19. The Carriage Barn Inn

Keene

Richard

₹13,583

₹14,737 total

includes taxes & fees

23 Nov - 24 Nov

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

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

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

A bedroom with a large bed, a wooden desk, and three chairs. There are three windows with shutters.

20. The Burrell House

Keene

Carol

₹12,997

₹14,492 total

includes taxes & fees

26 Oct - 27 Oct

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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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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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Millers River Wildlife Management Area

This serene wildlife reserve along the Millers River offers diverse habitats perfect for nature enthusiasts. Explore woodland trails while watching for wildlife, or cast a line for native trout in the pristine waters.

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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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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

The Colonial Hotel

8/10 Good

"This is a dated, solid 3-star hotel. The interior finishes all need a serious refresh. I was on the ground floor in a nice room, but the Wi-Fi was terrible and they stuck me down by the mechanical plant and housekeeping offices. Normally not a bid deal but they left the doors open to the mechanical room the entire time I was in my room. They also need to update the quality and number of WAPs. They were confused when I asked if they had a "business center" because they don't. Given the quality of the Wi-Fi in my room, it would've been nice if they had one.😊 The Colonial Grille is awesome; it is a shining star for this somewhat tired hotel. The restuarant/bar staff are awesome, and the food is good American fare. The bar is a lot of fun, and it's big. This is a local destination for weddings. I was there from Friday to Sunday in late October and I think there were not less than 3 weddings."

Fairfield Inn & Suites by Marriott Keene Downtown

8/10 Good

"Not sure why room was so warm. Turned heat off still warm. Had to turn ac on when it's 28 degrees outside. Staff was excellent. Breakfast was good."

Best Western Plus Keene Hotel

8/10 Good

"Breakfast Convenient location"

Great Wolf Lodge Boston / Fitchburg, MA

10/10 Excellent

"Super volvería una y otra ves"

Days Inn by Wyndham Keene NH

8/10 Good

"Clean comfortable room with a comfortable bed. I didn’t like the smell of whatever cleaning product they used, it was a bit bit strong let the kind you used to cover up something. Was this recently a smoking hotel? Also I missed an cycle in the fitness center, although the machines that were there seemed to work well. All in all it’s about what you would expect for a moderately priced hotel in New Hampshire during leaf peeper season."

Chocksett Inn and Restaurant

10/10 Excellent

"We are happy with our stay. Room was clean, bed comfortable, quiet for sleep. Staff very friendly. I did find locating the inn a bit confusing, but once I found it OK."

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"

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."

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+++++++"

More cheap stays in Winchendon

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH

₹8,796

₹9,544 total

28 Oct - 29 Oct

includes taxes & fees

Gardner Inn

22 Pearson Blvd Gardner MA

₹9,023

₹10,079 total

3 Nov - 4 Nov

includes taxes & fees

Motel 6 Leominster, MA

48 Commercial Rd Leominster MA

₹9,019

₹10,264 total

1 Nov - 2 Nov

includes taxes & fees

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

₹12,343

₹13,392 total

29 Oct - 30 Oct

includes taxes & fees

8.6/10 Excellent! (1,006 reviews)

Hampton Inn & Suites Keene

126 Key Rd Keene NH

₹15,373

₹16,680 total

19 Nov - 20 Nov

includes taxes & fees

Econo Lodge

183 Main St Westminster MA

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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.

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Book Hotels in Winchendon on Expedia.com

Winchendon Hotels from ₹9,544

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. Keene Elm City Hotel, an Ascend Collection Hotel

4. Best Western Plus Keene Hotel

5. Hampton Inn & Suites Keene

6. Fairfield Inn & Suites by Marriott Keene Downtown

7. The Maguire House Bed & Breakfast

8. Great Wolf Lodge Boston / Fitchburg, MA

9. Gardner Inn

10. The Birchwood Inn

11. Riverhouse by Weekender (Formerly Jack Daniels Inn)

12. Courtyard by Marriott Keene Downtown

13. Howarth House B&B

14. Monadnock Inn

15. Motel 6 Leominster, MA

16. Days Inn by Wyndham Keene NH

17. Chocksett Inn and Restaurant

18. Centennial House

19. The Carriage Barn Inn

20. The Burrell House

Stay near popular Winchendon attractions

Lake Dennison State Recreation Area

Blueberry Island

Hyde Park

Monument Park

Militia Training Field

Millers River Wildlife Management Area

The Robinson-Broadhurst Foundation Performing Arts Ampitheater

Old Centre Historic District

Learn more about Winchendon

Top Winchendon Hotel Reviews

The Colonial Hotel

Fairfield Inn & Suites by Marriott Keene Downtown

Best Western Plus Keene Hotel

Great Wolf Lodge Boston / Fitchburg, MA

Days Inn by Wyndham Keene NH

Chocksett Inn and Restaurant

Monadnock Inn

Riverhouse by Weekender (Formerly Jack Daniels Inn)

The Carriage Barn Inn

More cheap stays in Winchendon

Days Inn by Wyndham Keene NH

Gardner Inn

Motel 6 Leominster, MA

Keene Elm City Hotel, an Ascend Collection Hotel

Hampton Inn & Suites Keene

Econo Lodge

Frequently asked questions

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