Search Bed and Breakfast in Winchendon

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Featured B&B in Winchendon

Centennial House
Exterior detail

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (145)
"Lovely bed & breakfast!!! We appreciate the hospitality and delicious breakfast. "
The price is S$255
includes taxes & fees
1 Dec - 2 Dec
Centennial House
Monadnock Inn
Exterior

Monadnock Inn

2.5 star property
7.6 out of 10, Good, (263)
"The place is over coming new ownership so it has work being done but the new owners seem nice and our room was nice a clean and the bed was super comfy. I would love to see it in a year to see all the renovations done. "
The price is S$241
includes taxes & fees
1 Dec - 2 Dec
Monadnock Inn
Howarth House B&B
Front of property – evening/night

Howarth House B&B

3.0 star property
10.0 out of 10, Exceptional, (95)
"Lovely, quaint bed and breakfast. The hosts were wonderful and friendly. Beautiful room with excellent bed. The jetted tub was great too! Would definitely recommend. Just off the Fitchburg State University Campus and a short drive from the John Adam’s Homestead. "
The price is S$290
includes taxes & fees
28 Nov - 29 Nov
Howarth House B&B
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (142)
"Lovely old BnB, easy to find, very convenient Very clean room Great continental breakfast Loved ease of walking to downtown, many stores and restaurants Informative and very friendly and helpful owner"
The price is S$267
includes taxes & fees
2 Dec - 3 Dec
The Carriage Barn Inn
The Maguire House Bed & Breakfast
Building design

The Maguire House Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (34)
"Terry was an amazing host. She was so hospitable and made my stay here that much more comfortable. She not only cooks really amazing breakfast but she was so helpful when I wanted to check out the town. Her house is really truly beautiful and the lake is a little walk away from the house. I highly recommend coming here."
The Maguire House Bed & Breakfast
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.
Don't see what you're looking for?
See all available properties in Winchendon
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Winchendon

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Frequently asked questions

Searching for B&Bs in Winchendon?
If you’re looking for something a little more offbeat than the traditional hotel experience, a stay at a bed and breakfast could be the perfect alternative for your holiday. While you’re enjoying your trip to Winchendon, Lake Dennison State Recreation Area and Wendall P. Clark Memorial are perfect spots to get in some fresh air and greenery.
Are you interested in an apartment instead of a traditional hotel?
With attentive service, opportunities to meet other guests and top-rated breakfasts, B&Bs all have a one-of-a-kind setting.
What are the top B&Bs in Winchendon?
Here are some B&Bs in the surrounding area: Monadnock Inn: 11 rooms. 9.7 mi (15.7 km) from the city centre. 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 snack bar/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 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.
What is there to do in Winchendon?
When you want to spend some time in the great outdoors, Lake Dennison State Recreation Area and Wendall P. Clark Memorial are some notable spots. You should put Beals Memorial Library and Winchendon Town Hall on your list if you want to see more of the area.
How can I get to and around Winchendon?
You can map out your trip in and around Winchendon ahead of time with these transportation options. Fly into Nashua, NH (ASH-Nashua Municipal), which is located 28 mi (45.1 km) from the city centre. You can also search 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, consider renting a car to explore more sights.