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

1. The Colonial Hotel

Gardner

Michele

Rp2.738.264

Rp3.058.728 total

includes taxes & fees

30 Sept - 1 Oct

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.

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

2. Doubletree by Hilton Hotel Leominster

Leominster

Jason

Rp2.994.814

Rp3.345.206 total

includes taxes & fees

25 Oct - 26 Oct

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 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.

3. Riverhouse by Weekender (Formerly Jack Daniels Inn)

Peterborough

Kathleen

Rp2.615.414

Rp3.031.793 total

includes taxes & fees

7 Oct - 8 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.

4. Chocksett Inn and Restaurant

Sterling

Brian

Rp2.846.577

Rp3.179.573 total

includes taxes & fees

29 Sept - 30 Sept

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.

5. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

Kristin

Rp2.237.875

Rp2.428.094 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 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 laundromat with multiple washing machines, a Coca-Cola refrigerator, and a snack vending machine.

6. Motel 6 Leominster, MA

Leominster

Linda

Rp1.858.132

Rp2.111.339 total

includes taxes & fees

4 Oct - 5 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.

7. The Carriage Barn Inn

Keene

Jonathan

Rp3.021.741

Rp3.278.589 total

includes taxes & fees

29 Sept - 30 Sept

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

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

8. Howarth House B&B

Fitchburg

David

Rp3.786.485

Rp3.786.485 total

includes taxes & fees

29 Sept - 30 Sept

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.

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.

9. Hampton Inn & Suites Keene

Keene

sheri

Rp2.466.317

Rp2.675.954 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

10. Fairfield Inn & Suites by Marriott Keene Downtown

Keene

Caroline

Rp3.469.601

Rp3.764.517 total

includes taxes & fees

25 Oct - 26 Oct

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 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.

11. Best Western Plus Keene Hotel

Keene

Ruddy

Rp2.488.517

Rp2.700.130 total

includes taxes & fees

25 Oct - 26 Oct

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

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.

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

Rp3.384.562

Rp3.672.250 total

includes taxes & fees

25 Oct - 26 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.

13. Gardner Inn

Gardner

Jesper

Rp1.772.397

Rp1.979.714 total

includes taxes & fees

18 Oct - 19 Oct

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.

14. The Birchwood Inn

Temple

Karen

Rp3.133.025

Rp3.399.422 total

includes taxes & fees

30 Sept - 1 Oct

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.

15. The Burrell House

Keene

Justin

Rp2.450.886

Rp2.732.738 total

includes taxes & fees

25 Oct - 26 Oct

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

A modern interior with a seating area, a kitchenette, and a reception desk.

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

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

16. Econo Lodge

Westminster

Sherry

Rp2.130.457

Rp2.337.058 total

includes taxes & fees

29 Sept - 30 Sept

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 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.

17. The Maguire House Bed & Breakfast

Ashburnham

Jeffrey

Rp5.818.475

Rp5.818.475 total

includes taxes & fees

28 Oct - 29 Oct

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

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.

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

18. Monadnock Inn

Jaffrey

Jed

Rp3.023.101

Rp3.280.009 total

includes taxes & fees

29 Sept - 30 Sept

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

A red building with white trim, surrounded by lush greenery and fruit trees.

19. Centennial House

Northfield

Alan

Rp3.213.194

Rp3.396.346 total

includes taxes & fees

29 Sept - 30 Sept

A water play area with children and adults.

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

A hotel with a prominent sign reading "Great Wolf Lodge."

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

Radcliff

Rp3.347.861

Rp3.739.561 total

includes taxes & fees

29 Sept - 30 Sept

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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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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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Beals Memorial Library

This historic library houses literary treasures and sensory-friendly programmes 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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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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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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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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Wetmore Trailhead

Wetmore Trailhead opens to miles of serene forest and wetland paths in Birch Hill Wildlife Management Area. Bring sturdy shoes and binoculars for spotting native birds along the well-maintained trails.

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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

Gardner Inn

8/10 Good

"It was a very good stay for the price. Very clean and the location was very good. I would definitely stay here again."

Doubletree by Hilton Hotel Leominster

10/10 Excellent

"Everything was as you would expect when entering a well keep hotel"

The Burrell House

8/10 Good

"This is a no-contact property. I didn't receive my entry information and was too busy working/travelling to be able to contact the property until quite late. I was rather panicked, but I received a quick response. The property is old and has a charm. Unfortunately I found the property quite noisy, with others staying in the property talking/shouting and creaking floor boards. I imagine that's just luck of the draw."

Best Western Plus Keene Hotel

10/10 Excellent

"Great"

Days Inn by Wyndham Keene NH

10/10 Excellent

"I booked at the last minute for an unplanned visit and was pleasantly surprised by the accommodations for the price."

The Colonial Hotel

10/10 Excellent

"Our stay was nice, king size bed was very comfortable and warm. Carpet in the rooms were well maintained, and bathrooms look new. Overall, a comfortable night!"

Riverhouse by Weekender (Formerly Jack Daniels Inn)

8/10 Good

"I have stayed here many times but now there seems to be no staff on site ever. This is disconcerting for a woman traveling alone. I get thet not all small hotels have staff 24/7 but I am not sure what anyone would even do if they had an issue getting into their room or some sort of emergency."

Centennial House

10/10 Excellent

"Excellent host making us feel very welcome. Very nice room and really lovely breakfast. Would certainly stay again if we are in the area."

Monadnock Inn

10/10 Excellent

"Very nice, clean, and a good vibe. An older building but very charming. Would certainly stay again."

More cheap stays in Winchendon

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH

Rp1.612.881

Rp1.749.976 total

27 Oct - 28 Oct

includes taxes & fees

7/10 Good! (1,007 reviews)

Gardner Inn

22 Pearson Blvd Gardner MA

Rp1.772.397

Rp1.979.714 total

18 Oct - 19 Oct

includes taxes & fees

7.6/10 Good! (72 reviews)

Motel 6 Leominster, MA

48 Commercial Rd Leominster MA

Rp1.858.132

Rp2.111.339 total

4 Oct - 5 Oct

includes taxes & fees

8.2/10 Very good! (1,010 reviews)

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

Rp2.237.875

Rp2.428.094 total

27 Oct - 28 Oct

includes taxes & fees

Hampton Inn & Suites Keene

126 Key Rd Keene NH

Rp2.466.317

Rp2.675.954 total

25 Oct - 26 Oct

includes taxes & fees

Riverhouse by Weekender (Formerly Jack Daniels Inn)

80 Concord Street Peterborough NH

Rp2.615.414

Rp3.031.793 total

7 Oct - 8 Oct

includes taxes & fees

9.2/10 Wonderful! (479 reviews)

Hotels in Winchendon with star rating

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 Rp1.749.976

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. Riverhouse by Weekender (Formerly Jack Daniels Inn)

4. Chocksett Inn and Restaurant

5. Keene Elm City Hotel, an Ascend Collection Hotel

6. Motel 6 Leominster, MA

7. The Carriage Barn Inn

8. Howarth House B&B

9. Hampton Inn & Suites Keene

10. Fairfield Inn & Suites by Marriott Keene Downtown

11. Best Western Plus Keene Hotel

12. Courtyard by Marriott Keene Downtown

13. Gardner Inn

14. The Birchwood Inn

15. The Burrell House

16. Econo Lodge

17. The Maguire House Bed & Breakfast

18. Monadnock Inn

19. Centennial House

20. Great Wolf Lodge Boston / Fitchburg, MA

Stay near popular Winchendon attractions

Lake Dennison State Recreation Area

Hyde Park

Monument Park

Beals Memorial Library

Winchendon Community Park

Blueberry Island

Wendall P. Clark Memorial

Wetmore Trailhead

Learn more about Winchendon

Top Winchendon Hotel Reviews

Gardner Inn

Doubletree by Hilton Hotel Leominster

The Burrell House

Best Western Plus Keene Hotel

Days Inn by Wyndham Keene NH

The Colonial Hotel

Riverhouse by Weekender (Formerly Jack Daniels Inn)

Centennial House

Monadnock 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

Riverhouse by Weekender (Formerly Jack Daniels Inn)

Hotels in Winchendon with star rating

Frequently asked questions

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