Winchendon Holiday Rentals, Massachusetts: Private House Rentals

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Our top choices for Winchendon hotels

A grand lobby with a staircase, a piano, comfortable seating, and large windows.

1. The Colonial Hotel

Gardner

Mollie

฿5,429 total

includes taxes & fees

2 Nov - 3 Nov

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

2. Doubletree by Hilton Hotel Leominster

Leominster

louis

฿5,471 total

includes taxes & fees

15 Nov - 16 Nov

A spacious lobby with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

3. Best Western Plus Keene Hotel

Keene

Ruddy

฿5,186 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.

4. Hampton Inn & Suites Keene

Keene

Dayle

฿5,934 total

includes taxes & fees

19 Nov - 20 Nov

5. Fairfield Inn & Suites by Marriott Keene Downtown

Keene

Christopher

฿7,100 total

includes taxes & fees

2 Nov - 3 Nov

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

6. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

Lisa

฿4,874 total

includes taxes & fees

12 Nov - 13 Nov

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

7. Gardner Inn

Gardner

Leila

฿4,005 total

includes taxes & fees

1 Nov - 2 Nov

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

8. Great Wolf Lodge Boston / Fitchburg, MA

Fitchburg

Abderaouf

฿7,053 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.

9. The Maguire House Bed & Breakfast

Ashburnham

Jeffrey

฿9,964 total

includes taxes & fees

5 Nov - 6 Nov

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

10. Courtyard by Marriott Keene Downtown

Keene

Deborah

฿6,926 total

includes taxes & fees

2 Nov - 3 Nov

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

11. Riverhouse by Weekender (Formerly Jack Daniels Inn)

Peterborough

Kathleen

฿6,268 total

includes taxes & fees

1 Nov - 2 Nov

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

12. The Birchwood Inn

Temple

Karen

฿6,411 total

includes taxes & fees

2 Nov - 3 Nov

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

13. Howarth House B&B

Fitchburg

David

฿7,141 total

includes taxes & fees

3 Nov - 4 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.

14. Motel 6 Leominster, MA

Leominster

Ruth

฿3,650 total

includes taxes & fees

1 Nov - 2 Nov

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

15. Monadnock Inn

Jaffrey

Jim

฿5,021 total

includes taxes & fees

1 Nov - 2 Nov

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

16. Days Inn by Wyndham Keene NH

Keene

CHERYL

฿3,458 total

includes taxes & fees

29 Oct - 30 Oct

A room with a fireplace, a large mirror, and a window with a view of the outside.

17. Chocksett Inn and Restaurant

Sterling

Lisa

฿5,996 total

includes taxes & fees

29 Oct - 30 Oct

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

18. Centennial House

Northfield

Alan

฿6,405 total

includes taxes & fees

28 Oct - 29 Oct

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

19. The Carriage Barn Inn

Keene

Richard

฿5,889 total

includes taxes & fees

19 Nov - 20 Nov

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

20. The Burrell House

Keene

Carol

฿5,154 total

includes taxes & fees

28 Oct - 29 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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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

Keene Elm City Hotel, an Ascend Collection Hotel

8/10 Good

"."

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."

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."

More cheap stays in Winchendon

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH

฿3,187

฿3,458 total

29 Oct - 30 Oct

includes taxes & fees

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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Find hotels in Winchendon, MA from ฿3,458

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Our top choices for Winchendon hotels

1. The Colonial Hotel

2. Doubletree by Hilton Hotel Leominster

3. Best Western Plus Keene Hotel

4. Hampton Inn & Suites Keene

5. Fairfield Inn & Suites by Marriott Keene Downtown

6. Keene Elm City Hotel, an Ascend Collection Hotel

7. Gardner Inn

8. Great Wolf Lodge Boston / Fitchburg, MA

9. The Maguire House Bed & Breakfast

10. Courtyard by Marriott Keene Downtown

11. Riverhouse by Weekender (Formerly Jack Daniels Inn)

12. The Birchwood Inn

13. Howarth House B&B

14. Motel 6 Leominster, MA

15. Monadnock Inn

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

Learn more about Winchendon

Top Winchendon Hotel Reviews

Keene Elm City Hotel, an Ascend Collection Hotel

More cheap stays in Winchendon

Days Inn by Wyndham Keene NH

Frequently asked questions

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