A river reflecting autumn trees and a dense forest.

Hotels in Winchendon

Q: What accommodations do travelers recommend in Winchendon?

Guests like The Colonial Hotel , Gardner Inn and Monadnock Inn .

Where to?

Dates

November 2026

December 2026

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Where to stay in Winchendon?

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

1. Gardner Inn

Gardner

$119 total

includes taxes & fees

Nov 9 - Nov 10

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

2. The Colonial Hotel

Gardner

$179 total

includes taxes & fees

Nov 9 - Nov 10

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

3. Doubletree by Hilton Hotel Leominster

Leominster

$169 total

includes taxes & fees

Nov 15 - Nov 16

A modern hotel room with a large bed, a bedside table, a nightstand, a mirror, and a bathroom with a sink and towel rack.

4. Motel 6 Leominster, MA

Leominster

$106 total

includes taxes & fees

Nov 22 - Nov 23

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

5. Days Inn by Wyndham Keene NH

Keene

$100 total

includes taxes & fees

Nov 10 - Nov 11

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

$144 total

includes taxes & fees

Nov 9 - Nov 10

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

7. The Maguire House Bed & Breakfast

Ashburnham

$285 total

includes taxes & fees

Dec 2 - Dec 3

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

8. Best Western Plus Keene Hotel

Keene

$154 total

includes taxes & fees

Nov 10 - Nov 11

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

9. Monadnock Inn

Jaffrey

$160 total

includes taxes & fees

Nov 9 - Nov 10

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

10. Great Wolf Lodge Boston / Fitchburg, MA

Fitchburg

$208 total

includes taxes & fees

Nov 17 - Nov 18

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

11. The Birchwood Inn

Temple

$190 total

includes taxes & fees

Nov 9 - Nov 10

A modern dining area with a central seating area, a kitchen in the background, and large windows providing natural light.

12. Hampton Inn & Suites Keene

Keene

$171 total

includes taxes & fees

Nov 28 - Nov 29

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

13. Riverhouse by Weekender (Formerly Jack Daniels Inn)

Peterborough

$186 total

includes taxes & fees

Nov 10 - Nov 11

A dining area with wooden tables and chairs, large windows with a view of trees, and a bench along the wall.

14. The Carriage Barn Inn

Keene

$165 total

includes taxes & fees

Nov 16 - Nov 17

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

15. The Burrell House

Keene

$166 total

includes taxes & fees

Nov 16 - Nov 17

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

16. Chocksett Inn and Restaurant

Sterling

$178 total

includes taxes & fees

Nov 9 - Nov 10

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

17. Centennial House

Northfield

$190 total

includes taxes & fees

Nov 9 - Nov 10

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

18. Courtyard by Marriott Keene Downtown

Keene

$184 total

includes taxes & fees

Nov 15 - Nov 16

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

19. Howarth House B&B

Fitchburg

$235 total

includes taxes & fees

Nov 9 - Nov 10

20. Fairfield Inn & Suites by Marriott Keene Downtown

Keene

$210 total

includes taxes & fees

Nov 16 - Nov 17

View all properties

Go beyond your typical stay in Winchendon

Top landmarks in Winchendon

Lake Dennison State Recreation Area

10.0/10 (1 review)

Lake Dennison State Recreation Area is 3.5 mi (5.6 km) from central Winchendon, why not stop by during your stay.

See properties

Learn more about Winchendon

Winchendon is well-known for its attractions such as Lake Dennison State Recreation Area and Beals Memorial Library.

See all hotels in Winchendon

Check out reviews of Winchendon hotels guests love

The Colonial Hotel

Gardner

10/10 Exceptional

Robin

Howarth House B&B

Fitchburg

10/10 Exceptional

For the wedding we stayed at our very first B&B. Howarth House Bed and Breakfast in Fitchburg, Mass. It is a beautiful house built in 1910. The current owners, Sarah and Ryan purchased the house in 2020. The owners were friendly, kind, accommodating and Ryan can sure cook a great breakfast. Sarah presented us with a departing gift of her homemade Blueberry and white chocolate scones. Delicious! The room was comfortable, the location quiet and we will definitely be back. I wish I had taken more...

Darleen

The Maguire House Bed & Breakfast

Ashburnham

10/10 Exceptional

Anonymous traveler

The Birchwood Inn

Temple

10/10 Exceptional

Anonymous traveler

Doubletree by Hilton Hotel Leominster

Leominster

10/10 Exceptional

Paola

Keene Elm City Hotel, an Ascend Collection Hotel

Keene

10/10 Exceptional

Kristine

Centennial House

Northfield

10/10 Exceptional

My husband and I have never stayed at a B&B. We were looking for a nearby weekend get-away and found The Centennial House on an on-line search. The Hosts Joan & Steve were very hospitable and knowledgable of the area and it's history and attractions. The surrounding area, the room and the breakfast were beautiful, comfortable and delicious!! Our first B&B experience was excellent, thank you Joan & Steve. Until we meet again, Bill & Anne

Anonymous traveler

The Carriage Barn Inn

Keene

10/10 Exceptional

William

Best Western Plus Keene Hotel

Keene

10/10 Exceptional

Susan

Hampton Inn & Suites Keene

Keene

10/10 Exceptional

kristin

Courtyard by Marriott Keene Downtown

Keene

10/10 Exceptional

Vic

Chocksett Inn and Restaurant

Sterling

10/10 Exceptional

Bryan

Gardner Inn

Gardner

10/10 Exceptional

Grace

Monadnock Inn

Jaffrey

10/10 Exceptional

On a Foliage tour through New England in October, my wife and I stayed at The Monadnock Inn following a hike of the nearby Mt. Monadnock. Arrival mid-week was simple and the Inn is full of centuries-old charm and comfort. Check-in was very simple and we were handed a key and walked up the stairs to the 3rd Floor Pauline Room. The room was very cozy with an antique soak tub and shower (great after a long hike), beautiful bay windows, steam radiator, comfortable bed, and warmly lit. There was no...

Todd

Frequently Asked Questions

What accommodations do travelers recommend in Winchendon?

Guests like The Colonial Hotel, Gardner Inn and Monadnock Inn.

Can I book a refundable hotel in Winchendon?

If you're looking for the flexibility to change your travel plans to Winchendon, most accommodations provide refundable* bookable rates. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Winchendon if I want a vacation home instead of a traditional hotel?

Browse 6 vacation homes on our site.

What will the weather in Winchendon be like during my vacation?

The warmest months in Winchendon are usually July and August with an average temp of 66°F. January and February are the chilliest months when the average temp is 28°F. The rainiest months are July and October.

Why should I book my Winchendon hotel through Hotels.com?

There are plenty of reasons to book your Winchendon travel with us: our free cancellations on selected hotels* gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.