Top 10 Hotels in Winchendon, MA from ￥15,947 - 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 wooden pergola structure in a garden setting with a paved walkway leading to it.

A pool area with lounge chairs and potted plants.

1. The Colonial Hotel

Gardner

John Timothy

￥22,789

￥25,457 total

includes taxes & fees

Nov 11 - Nov 12

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

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

2. Gardner Inn

Gardner

Leila

￥15,705

￥17,543 total

includes taxes & fees

Nov 2 - Nov 3

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

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

3. Best Western Plus Keene Hotel

Keene

Ruddy

￥22,455

￥24,363 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 spacious hotel lobby with a central island, seating areas, and large windows.

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.

4. Doubletree by Hilton Hotel Leominster

Leominster

louis

￥25,236

￥28,189 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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 compact kitchen with a refrigerator, coffee maker, and a small sink. There is a wooden counter and a clock on the wall.

5. Econo Lodge

Westminster

isabel

￥16,046

￥17,603 total

includes taxes & fees

Nov 11 - Nov 12

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

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.

6. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

Mary

￥18,878

￥20,483 total

includes taxes & fees

Nov 2 - Nov 3

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.

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

7. Fairfield Inn & Suites by Marriott Keene Downtown

Keene

Caroline

￥30,744

￥33,358 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.

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

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

￥24,542

￥26,628 total

includes taxes & fees

Oct 25 - Oct 26

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.

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

9. Great Wolf Lodge Boston / Fitchburg, MA

Fitchburg

michael

￥29,604

￥33,069 total

includes taxes & fees

Oct 14 - Oct 15

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 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.

10. The Maguire House Bed & Breakfast

Ashburnham

Jeffrey

￥42,119

￥42,119 total

includes taxes & fees

Nov 5 - Nov 6

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

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.

11. Motel 6 Leominster, MA

Leominster

Ruth

￥15,069

￥17,150 total

includes taxes & fees

Nov 1 - Nov 2

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

12. Monadnock Inn

Jaffrey

Jed

￥21,743

￥23,591 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

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

13. Riverhouse by Weekender (Formerly Jack Daniels Inn)

Peterborough

Kathleen

￥24,834

￥28,661 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 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.

14. The Birchwood Inn

Temple

Karen

￥27,704

￥30,060 total

includes taxes & fees

Oct 28 - Oct 29

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

A modern hotel lobby with a central bar area, multiple seating arrangements, and a reception desk.

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

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

15. Courtyard by Marriott Keene Downtown

Keene

Deborah

￥29,991

￥32,540 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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

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

16. Howarth House B&B

Fitchburg

David

￥33,552

￥33,552 total

includes taxes & fees

Oct 18 - Oct 19

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.

17. Days Inn by Wyndham Keene NH

Keene

CHERYL

￥14,698

￥15,947 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 spacious living room with a staircase, a chandelier, a console table with decorative items, and a large abstract painting on the wall.

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

18. Chocksett Inn and Restaurant

Sterling

Lisa

￥25,224

￥28,175 total

includes taxes & fees

Oct 14 - Oct 15

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

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

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.

19. Centennial House

Northfield

Alan

￥25,625

￥27,086 total

includes taxes & fees

Oct 26 - Oct 27

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

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

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

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

20. The Carriage Barn Inn

Keene

Richard

￥22,178

￥24,063 total

includes taxes & fees

Oct 20 - Oct 21

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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.

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

"The facility is great. I was able to get handicapped parking this time which is always a plus. The room was great, very clean. The waterpark was fun. The food was delicious. Specifically at the Fireside restaurant. The staff at the restaurant was fast and efficient. We definitely will be going back."

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent

"It is a charming inn with very lovely staff & family attending the guests. I highly recommend staying here if you appreciate history & charm! The building was built in 1788 I believe they said. We stayed inPikes Suite and were comfortable and happy. Yes, the beautiful old floors creak, but it’s all part of the charm of this lovely still family owned hideaway! I hope to return again!"

Fairfield Inn & Suites by Marriott Keene Downtown

10/10 Excellent

"Breakfast was very good. The staff friendly and very helpful. Room clean and comfortable. My area was a bit noisy though. Very convenient. Overall an excellent place to stay. I would return and also recommend!"

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"

Motel 6 Leominster, MA

10/10 Excellent

"There are few things to be concerned about. You can here your next door neighbor when they speaking loud and there were some cigarettes smoke in the room eventhough we had a non smoking room. It wasn't strong. Overall, the property surprised me how clean it is and how white the sheets and towels are. Very convenient locati I need to shopping area and to the soccer tournament location."

Days Inn by Wyndham Keene NH

10/10 Excellent

"I got a quiet room to stay. That was great. Staff was very nice and helpful. Cleaners came every day to clean room"

Econo Lodge

10/10 Excellent

"We were there for 1 night and everything so perfect. The room was extremely clean. The service is excellent the area was quiet and around really local restaurants. Will book again"

Centennial House

10/10 Excellent

"Everything was great. Highly recommended."

Best Western Plus Keene Hotel

8/10 Good

"The hotel needs some updating, and could be a little cleaner. Bathroom door looked like it had not been cleaned in a long time. The staff was friendly, and breakfast was good."

More cheap stays in Winchendon

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH

￥14,698

￥15,947 total

Oct 25 - Oct 26

includes taxes & fees

7/10 Good! (1,005 reviews)

Motel 6 Leominster, MA

48 Commercial Rd Leominster MA

￥15,069

￥17,150 total

Nov 1 - Nov 2

includes taxes & fees

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

Gardner Inn

22 Pearson Blvd Gardner MA

￥15,705

￥17,543 total

Nov 2 - Nov 3

includes taxes & fees

7.6/10 Good! (78 reviews)

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

￥18,878

￥20,483 total

Nov 2 - Nov 3

includes taxes & fees

8.6/10 Excellent! (1,007 reviews)

Hampton Inn & Suites Keene

126 Key Rd Keene NH

￥24,542

￥26,628 total

Oct 25 - Oct 26

includes taxes & fees

8.8/10 Excellent! (419 reviews)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

80 Concord Street Peterborough NH

￥24,834

￥28,661 total

Oct 18 - Oct 19

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 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 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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Massachusetts Vacation Rentals

Book Hotels in Winchendon on Expedia.com

Find hotels in Winchendon, MA from ￥15,947

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Winchendon

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for Winchendon hotels

1. The Colonial Hotel

2. Gardner Inn

3. Best Western Plus Keene Hotel

4. Doubletree by Hilton Hotel Leominster

5. Econo Lodge

6. Keene Elm City Hotel, an Ascend Collection Hotel

7. Fairfield Inn & Suites by Marriott Keene Downtown

8. Hampton Inn & Suites Keene

9. Great Wolf Lodge Boston / Fitchburg, MA

10. The Maguire House Bed & Breakfast

11. Motel 6 Leominster, MA

12. Monadnock Inn

13. Riverhouse by Weekender (Formerly Jack Daniels Inn)

14. The Birchwood Inn

15. Courtyard by Marriott Keene Downtown

16. Howarth House B&B

17. Days Inn by Wyndham Keene NH

18. Chocksett Inn and Restaurant

19. Centennial House

20. The Carriage Barn Inn

Stay near popular Winchendon attractions

Lake Dennison State Recreation Area

Hyde Park

Blueberry Island

Monument Park

Militia Training Field

Old Centre Historic District

Beals Memorial Library

The Robinson-Broadhurst Foundation Performing Arts Ampitheater

Learn more about Winchendon

Top Winchendon Hotel Reviews

Great Wolf Lodge Boston / Fitchburg, MA

Keene Elm City Hotel, an Ascend Collection Hotel

Fairfield Inn & Suites by Marriott Keene Downtown

Monadnock Inn

Motel 6 Leominster, MA

Days Inn by Wyndham Keene NH

Econo Lodge

Centennial House

Best Western Plus Keene Hotel

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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