Search B&B in Winchendon

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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Winchendon bed & breakfast

Free daily continental breakfast
The Carriage Barn Inn

The Carriage Barn Inn

3.0 star property
Keene
9.6 out of 10, Exceptional, (165)
"Excellent place!!!! Lovely room that had all I needed!!! The bed was comfortable and the stay was wonderful!!!!!!"
United States
natalia
The price is AED 463
AED 503 total
includes taxes & fees
31 Dec - 1 January 2026
The Carriage Barn Inn
Free daily full breakfast
Centennial House

Centennial House

3.5 star property
Northfield
9.6 out of 10, Exceptional, (173)
"The house was cozy and inviting. Felt the history all around me and the breakfast made and served by Joan was great. We recommend this place for those looking for that historical b&b experience. "
United States
Paul
The price is AED 732
AED 774 total
includes taxes & fees
28 Dec - 29 Dec
Centennial House
Garden
Howarth House B&B

Howarth House B&B

3.0 star property
Fitchburg
10.0 out of 10, Exceptional, (110)
"Beautiful gardens"
United States
Christine
Howarth House B&B
Property grounds
The Maguire House Bed & Breakfast

The Maguire House Bed & Breakfast

3.5 star property
Ashburnham
10.0 out of 10, Exceptional, (36)
"Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. "
United States
Ranjit
The price is AED 939
AED 939 total
includes taxes & fees
7 Jan - 8 January 2026
The Maguire House Bed & Breakfast
Exterior
Monadnock Inn

Monadnock Inn

2.5 star property
Jaffrey
7.6 out of 10, Good, (277)
"It is a Beautiful Old Charm Inn. Everything was great. I would definitely come back and stay there again. "
United States
Sharon-Ann C
Monadnock Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winchendon Hotel Reviews

The Colonial Hotel

The Colonial Hotel

10/10 Excellent
"Clean, courteous. "
Suzanne 1-night trip
Posted 18 hours ago
The Colonial Hotel

Frequently asked questions

Searching for B&Bs in Winchendon?
If you're looking for something a little different than your standard hotel experience, a stay at a bed and breakfast might be the perfect option for your getaway. While you're enjoying your trip to Winchendon, Wendall P. Clark Memorial and Hyde Park are perfect spots to get in some fresh air and greenery.
Are you thinking about B&Bs over traditional hotel rooms?
With attentive service, opportunities to interact with the owner, and top-rated breakfasts, B&Bs offer a unique setting.
What are the top B&Bs in Winchendon?
Here are some well-liked B&Bs in the surrounding area: Monadnock Inn: 11 rooms. 9.7 mi (15.7 km) from the downtown core. Howarth House B&B: 3 rooms. Situated 14.5 mi (23.3 km) from the heart of Winchendon. Enjoy the free full breakfast and in-room pools. The Maguire House Bed & Breakfast: 3 rooms. Located 6.7 mi (10.8 km) from the core of Winchendon. Enjoy the free full breakfast and deli.
What's the best time of year to stay at a B&B in Winchendon?
When you're dreaming of a getaway to Winchendon, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Winchendon are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Winchendon?
When you want to spend some time in the great outdoors, Wendall P. Clark Memorial and Hyde Park are some notable spots. You might put Lake Dennison State Recreation Area and Winchendon Town Hall on your list if you want to see more of the area.
How can I get to and around Winchendon?
Planning your excursions in and around Winchendon is easier with these transportation options. Fly into Nashua, NH (ASH-Nashua Municipal), which is located 28 mi (45.1 km) away from the city center. Otherwise, look for flights into Worcester, MA (ORH-Worcester Regional), which is 30.1 mi (48.5 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.