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

I'm traveling for business

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Where to stay in Winchendon?

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

1. The Colonial Hotel

Gardner

$161 total

includes taxes & fees

Nov 1 - Nov 2

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

2. Gardner Inn

Gardner

$119 total

includes taxes & fees

Nov 1 - Nov 2

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

3. Doubletree by Hilton Hotel Leominster

Leominster

$162 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

$108 total

includes taxes & fees

Nov 1 - Nov 2

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

5. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

$144 total

includes taxes & fees

Nov 19 - Nov 20

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

6. Days Inn by Wyndham Keene NH

Keene

$102 total

includes taxes & fees

Oct 29 - Oct 30

A dining area with wooden tables and chairs, a mural on the wall, and large windows.

7. The Birchwood Inn

Temple

$190 total

includes taxes & fees

Oct 29 - Oct 30

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

8. Centennial House

Northfield

$190 total

includes taxes & fees

Oct 28 - Oct 29

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

9. Riverhouse by Weekender (Formerly Jack Daniels Inn)

Peterborough

$186 total

includes taxes & fees

Nov 1 - Nov 2

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

10. The Burrell House

Keene

$153 total

includes taxes & fees

Oct 28 - Oct 29

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

11. Monadnock Inn

Jaffrey

$149 total

includes taxes & fees

Nov 1 - Nov 2

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

12. Chocksett Inn and Restaurant

Sterling

$178 total

includes taxes & fees

Oct 28 - Oct 29

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

13. Hampton Inn & Suites Keene

Keene

$176 total

includes taxes & fees

Nov 19 - Nov 20

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

14. Best Western Plus Keene Hotel

Keene

$154 total

includes taxes & fees

Nov 1 - Nov 2

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

15. The Maguire House Bed & Breakfast

Ashburnham

$295 total

includes taxes & fees

Nov 5 - Nov 6

An indoor swimming pool with a spectator area and a stage.

16. Great Wolf Lodge Boston / Fitchburg, MA

Fitchburg

$209 total

includes taxes & fees

Oct 28 - Oct 29

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

17. Howarth House B&B

Fitchburg

$235 total

includes taxes & fees

Oct 28 - Oct 29

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

18. The Carriage Barn Inn

Keene

$196 total

includes taxes & fees

Nov 22 - Nov 23

19. Fairfield Inn & Suites by Marriott Keene Downtown

Keene

$210 total

includes taxes & fees

Nov 2 - Nov 3

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

20. Courtyard by Marriott Keene Downtown

Keene

$205 total

includes taxes & fees

Nov 2 - Nov 3

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

Riverhouse by Weekender (Formerly Jack Daniels Inn)

Peterborough

10/10 Exceptional

William and Susan

Doubletree by Hilton Hotel Leominster

Leominster

10/10 Exceptional

Paola

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

Keene Elm City Hotel, an Ascend Collection Hotel

Keene

10/10 Exceptional

Kristine

Hampton Inn & Suites Keene

Keene

10/10 Exceptional

kristin

Best Western Plus Keene Hotel

Keene

10/10 Exceptional

Susan

Chocksett Inn and Restaurant

Sterling

10/10 Exceptional

Bryan

Courtyard by Marriott Keene Downtown

Keene

10/10 Exceptional

Vic

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.