Winchendon Holiday Rentals, Massachusetts: Private House Rentals

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 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.

1. The Colonial Hotel

Gardner

John Timothy

฿4,848

฿5,416 total

includes taxes & fees

1 Nov - 2 Nov

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 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

Erick

฿5,358

฿5,985 total

includes taxes & fees

1 Nov - 2 Nov

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.

3. Best Western Plus Keene Hotel

Keene

Ruddy

฿4,750

฿5,154 total

includes taxes & fees

1 Nov - 2 Nov

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.

4. Fairfield Inn & Suites by Marriott Keene Downtown

Keene

Caroline

฿6,527

฿7,082 total

includes taxes & fees

25 Oct - 26 Oct

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

5. Hampton Inn & Suites Keene

Keene

Rebecca

฿4,724

฿5,125 total

includes taxes & fees

1 Nov - 2 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 modern kitchen with wooden cabinets, a coffee machine, a fruit juice dispenser, and a refrigerator.

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

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

6. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

Angelo

฿4,008

฿4,349 total

includes taxes & fees

2 Nov - 3 Nov

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

7. The Maguire House Bed & Breakfast

Ashburnham

Jeffrey

฿9,936

฿9,936 total

includes taxes & fees

5 Nov - 6 Nov

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.

8. Great Wolf Lodge Boston / Fitchburg, MA

Fitchburg

Radcliff

฿6,276

฿7,010 total

includes taxes & fees

7 Oct - 8 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 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.

9. Gardner Inn

Gardner

Leila

฿3,322

฿3,711 total

includes taxes & fees

20 Oct - 21 Oct

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.

10. Courtyard by Marriott Keene Downtown

Keene

Deborah

฿6,367

฿6,908 total

includes taxes & fees

25 Oct - 26 Oct

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 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.

11. The Birchwood Inn

Temple

Karen

฿5,873

฿6,372 total

includes taxes & fees

8 Oct - 9 Oct

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

฿7,098

฿7,098 total

includes taxes & fees

7 Oct - 8 Oct

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

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

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

13. Econo Lodge

Westminster

Ashleigh

฿3,407

฿3,737 total

includes taxes & fees

4 Nov - 5 Nov

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

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

14. Riverhouse by Weekender (Formerly Jack Daniels Inn)

Peterborough

Kathleen

฿5,000

฿5,788 total

includes taxes & fees

8 Oct - 9 Oct

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 porch with a wooden bench and a bench with cushions.

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

15. Monadnock Inn

Jaffrey

Jed

฿4,598

฿4,988 total

includes taxes & fees

6 Nov - 7 Nov

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

A Days Inn with a brick facade, a central entrance, and a parking lot.

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

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

฿3,092

฿3,355 total

includes taxes & fees

27 Oct - 28 Oct

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.

17. Motel 6 Leominster, MA

Leominster

Bruce

฿3,188

฿3,628 total

includes taxes & fees

4 Nov - 5 Nov

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.

18. Chocksett Inn and Restaurant

Sterling

Lisa

฿5,336

฿5,960 total

includes taxes & fees

20 Oct - 21 Oct

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.

19. Centennial House

Northfield

Alan

฿6,023

฿6,366 total

includes taxes & fees

20 Oct - 21 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 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.

20. The Carriage Barn Inn

Keene

Richard

฿5,664

฿6,146 total

includes taxes & fees

25 Oct - 26 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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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 amphitheatre 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 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

Hampton Inn & Suites Keene

10/10 Excellent

"5"

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"

Econo Lodge

10/10 Excellent

"Very clean very nice room . Ac worked great features are update . Friendly staff"

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"

Gardner Inn

8/10 Good

"It didn’t look very good from the entrance but when we pulled into the back which was really the front it looked simple but nice. The staff or owners were lovely and the room and halls were immaculate."

More cheap stays in Winchendon

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH

฿3,092

฿3,355 total

27 Oct - 28 Oct

includes taxes & fees

7/10 Good! (1,003 reviews)

Motel 6 Leominster, MA

48 Commercial Rd Leominster MA

฿3,188

฿3,628 total

4 Nov - 5 Nov

includes taxes & fees

8.2/10 Very good! (1,004 reviews)

Gardner Inn

22 Pearson Blvd Gardner MA

฿3,322

฿3,711 total

20 Oct - 21 Oct

includes taxes & fees

7.6/10 Good! (74 reviews)

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

฿4,008

฿4,349 total

2 Nov - 3 Nov

includes taxes & fees

Hampton Inn & Suites Keene

126 Key Rd Keene NH

฿4,724

฿5,125 total

1 Nov - 2 Nov

includes taxes & fees

8.8/10 Excellent! (417 reviews)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

80 Concord Street Peterborough NH

฿5,000

฿5,788 total

8 Oct - 9 Oct

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 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

Find hotels in Winchendon, MA from ฿3,355

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. Best Western Plus Keene Hotel

4. Fairfield Inn & Suites by Marriott Keene Downtown

5. Hampton Inn & Suites Keene

6. Keene Elm City Hotel, an Ascend Collection Hotel

7. The Maguire House Bed & Breakfast

8. Great Wolf Lodge Boston / Fitchburg, MA

9. Gardner Inn

10. Courtyard by Marriott Keene Downtown

11. The Birchwood Inn

12. Howarth House B&B

13. Econo Lodge

14. Riverhouse by Weekender (Formerly Jack Daniels Inn)

15. Monadnock Inn

16. Days Inn by Wyndham Keene NH

17. Motel 6 Leominster, MA

18. Chocksett Inn and Restaurant

19. Centennial House

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

Hampton Inn & Suites Keene

Doubletree by Hilton Hotel Leominster

Chocksett Inn and Restaurant

Econo Lodge

The Carriage Barn Inn

Centennial House

Fairfield Inn & Suites by Marriott Keene Downtown

Days Inn by Wyndham Keene NH

Gardner Inn

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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