Top 10 Hotels in Winchendon, MA from ₩134,125 - 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

₩192,065

₩214,547 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.

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

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

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

2. Doubletree by Hilton Hotel Leominster

Leominster

louis

₩179,430

₩200,423 total

includes taxes & fees

Nov 15 - Nov 16

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

A water play area with children and adults.

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

3. Great Wolf Lodge Boston / Fitchburg, MA

Fitchburg

Abderaouf

₩249,505

₩278,698 total

includes taxes & fees

Oct 19 - Oct 20

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

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

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.

4. The Maguire House Bed & Breakfast

Ashburnham

Jeffrey

₩380,261

₩380,261 total

includes taxes & fees

Nov 18 - Nov 19

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

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

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.

5. Gardner Inn

Gardner

Leila

₩132,091

₩147,546 total

includes taxes & fees

Oct 19 - Oct 20

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

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

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

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

₩188,863

₩204,917 total

includes taxes & fees

Nov 1 - Nov 2

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.

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.

7. Hampton Inn & Suites Keene

Keene

Rebecca

₩206,408

₩223,952 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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

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

8. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

Lisa

₩169,450

₩183,854 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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

9. Fairfield Inn & Suites by Marriott Keene Downtown

Keene

Christopher

₩258,578

₩280,557 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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

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

10. The Birchwood Inn

Temple

Karen

₩233,494

₩253,348 total

includes taxes & fees

Oct 26 - Oct 27

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 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.

11. Riverhouse by Weekender (Formerly Jack Daniels Inn)

Peterborough

Kathleen

₩214,948

₩247,681 total

includes taxes & fees

Nov 1 - Nov 2

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

12. Howarth House B&B

Fitchburg

David

₩282,194

₩282,194 total

includes taxes & fees

Oct 20 - Oct 21

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 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.

13. Monadnock Inn

Jaffrey

Jim

₩182,872

₩198,416 total

includes taxes & fees

Nov 1 - Nov 2

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.

14. Courtyard by Marriott Keene Downtown

Keene

Deborah

₩252,240

₩273,680 total

includes taxes & fees

Oct 25 - Oct 26

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

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.

15. Motel 6 Leominster, MA

Leominster

Ruth

₩126,740

₩144,239 total

includes taxes & fees

Nov 1 - Nov 2

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

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.

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

16. Days Inn by Wyndham Keene NH

Keene

CHERYL

₩123,618

₩134,125 total

includes taxes & fees

Oct 25 - Oct 26

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

17. Chocksett Inn and Restaurant

Sterling

Lisa

₩212,146

₩236,963 total

includes taxes & fees

Oct 20 - Oct 21

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

A bedroom with a bed, a nightstand, a lamp, a chair, and a door leading to another room.

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.

18. Centennial House

Northfield

Alan

₩239,468

₩253,118 total

includes taxes & fees

Oct 19 - Oct 20

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

A bench in front of an apple tree with ripe apples.

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.

19. The Carriage Barn Inn

Keene

Richard

₩225,200

₩244,342 total

includes taxes & fees

Oct 19 - Oct 20

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

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

20. The Burrell House

Keene

Carol

₩182,657

₩203,663 total

includes taxes & fees

Oct 22 - Oct 23

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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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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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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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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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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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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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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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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.

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A river reflecting autumn trees and a dense forest.

Top Winchendon Hotel Reviews

Best Western Plus Keene Hotel

10/10 Excellent

"Friendly staff"

Econo Lodge

10/10 Excellent

"We got a bigger room than we expected which was nice. The only thing we found issue with is that the water in the shower didn’t get hot."

Motel 6 Leominster, MA

10/10 Excellent

"Stayed for 2 nights. Room was very clean. Beds could have been more comfortable. Staff were very nice. Location was great.. lots of choices for food to eat even within walking distance"

Hampton Inn & Suites Keene

8/10 Good

"Clean room and comfortable"

Doubletree by Hilton Hotel Leominster

10/10 Excellent

"The room was very clean, staff were fantastic. On the negative side, for the amount paid for one night (over $300), breakfast should be included. But they did give a chocolate chip cookie."

Gardner Inn

10/10 Excellent

"The room was clean. They have made improvements. There are now hair dryers in the room and they have installed a coat rack. We had a very enjoyable stay for my class reunion. The only real amenity is 24 hr coffee in the lobby and the ice machine. Restaurants and laundry are within walking distance . Thus was our 2nd time staying at this hotel and I will definitely stay here again."

Days Inn by Wyndham Keene NH

8/10 Good

"I arrived late and exhausted. Young man at front counter was friendly and efficient. Carpet in hallway slightly warn. Room and bath very clean, no complaints. Bed was large and soft. I slept well. Parking lot safe and quiet. Free breakfast was… nothing special. Other businesses close by. Would definitely stay there again. Thank you."

Great Wolf Lodge Boston / Fitchburg, MA

8/10 Good

"Overall our stay was good and our son loved the trip. Really the only con I can say is that one of the queen beds made a really large noise when moving in the bed to the point you thought it would break. That obviously didn’t happen but it made us slightly concerned. Other than that, it was a great trip!"

Centennial House

10/10 Excellent

"We arrived and immediately were shown to our quaint room. The property has a small orchard/garden in the back and David allowed us to go pick apples and raspberries. We were served an amazing breakfast in the morning. David was also helpful with local recommendations. Everything was clean. We had a wonderful stay!"

More cheap stays in Winchendon