Book Winchendon Bed & Breakfast

Start date: Check-in selected.
To Date
End date: Check-out

    Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

    OneKeyCash

    Earn OneKeyCash on all your eligible bookings

    Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

B&B in Winchendon

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (157)
"Very quiet and peaceful but at the same time it's right down the street from Main Street. Joe the owner was so nice! "
$200 nightly
The price is $218
Oct 13 - Oct 14
Total with taxes and fees
The Carriage Barn Inn

Howarth House B&B

3.0 star property
10.0 out of 10, Exceptional, (107)
"Beautiful gardens"
$235 nightly
The price is $235
Oct 14 - Oct 15
Total with taxes and fees
Howarth House B&B

Monadnock Inn

2.5 star property
7.6 out of 10, Good, (271)
"It is a Beautiful Old Charm Inn. Everything was great. I would definitely come back and stay there again. "
$152 nightly
The price is $165
Nov 2 - Nov 3
Total with taxes and fees
Monadnock Inn

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (168)
"The property was wonderful and the hosts exceptional❤️"
$208 nightly
The price is $220
Oct 26 - Oct 27
Total with taxes and fees
Centennial House

The Maguire House Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (34)
"Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. "
$275 nightly
The price is $275
Nov 6 - Nov 7
Total with taxes and fees
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winchendon Hotel Reviews

Find out more about Winchendon

Winchendon B&B information

Number of reviews
597
Accommodation
5 B&B
Lowest Price
$165
Highest Price
$275

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Winchendon?
Prices for B&Bs in Winchendon often vary, but you can find a great deal from $165 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Winchendon B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a B&B in Winchendon?
The best time to book a B&B in Winchendon is during the vibrant fall months of September and October. This period draws travelers looking to immerse themselves in the stunning autumn foliage that blankets the region. With crisp air and temperatures ranging from the upper 40s to mid-60s Fahrenheit, it's an ideal time for outdoor activities like hiking and apple picking, allowing visitors to fully enjoy the natural beauty that Winchendon has to offer.

As the leaves change, local festivals and events celebrate the season, providing a unique cultural experience that complements the breathtaking scenery. Whether you're wandering through charming downtown shops or exploring nearby parks, the inclusive setting of fall in Winchendon makes it a delightful destination for those who appreciate quality and convenience in their travel plans.

For those considering a visit during the quieter months, November offers a more budget-friendly option while still showcasing the tail end of the fall colors. This time allows for peaceful nature walks and a chance to explore the area's rich history without the hustle and bustle of peak tourist activity.
What is the difference between a Winchendon Bed and Breakfast and a hotel?
Every Winchendon B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Winchendon B&Bs.

Explore a world of travel with Expedia