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Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 Jun

Compare 5 B&B in Winchendon with updated reviews, rates, and availability.

The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (146)
"This is a great place to stay. Host, Joe, was very friendly and helpful. The room was clean and cozy , and nicely furnished. Common areas were very comfortable and welcoming. We will definitely come back! "
The price is AED 625
AED 678 total
includes taxes & fees
5 May - 6 May
The Carriage Barn Inn
Monadnock Inn
Exterior

Monadnock Inn

2.5 star property
7.6 out of 10, Good, (264)
"owners are very nice "
The price is AED 559
AED 607 total
includes taxes & fees
25 Apr - 26 Apr
Monadnock Inn
Centennial House
Exterior detail

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (150)
"We had a great stay at Centennial House! Myself and my 14 year old son stayed for one night -- the bed was very comfortable and breakfast was fabulous!!"
The price is AED 710
AED 751 total
includes taxes & fees
27 Apr - 28 Apr
Centennial House
Howarth House B&B
Front of property - evening/night

Howarth House B&B

3.0 star property
10.0 out of 10, Exceptional, (96)
"I thought it was great."
The price is AED 790
AED 790 total
includes taxes & fees
15 Apr - 16 Apr
Howarth House B&B
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 price is AED 1,010
AED 1,010 total
includes taxes & fees
16 Apr - 17 Apr
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.
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Other property types in Winchendon

Modern Waterfront Gem w/ Dock on Lake Monomonac
Fridge, coffee/tea maker, toaster, cookware/dishes/utensils

Modern Waterfront Gem w/ Dock on Lake Monomonac

10.0 out of 10, Exceptional, (2)
"We couldn’t have had a better experience! Such a beautiful cottage—immaculate, gorgeous decor, spectacular deck w/exquisite lake view, super-cozy beds, outstanding communication with hosts! We actually had local plans canceled due to a late March “wintry” ice storm, but couldn’t imagine a better place to hunker down! Hope to return! "
Modern Waterfront Gem w/ Dock on Lake Monomonac
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski
Exterior

Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

9.4 out of 10, Exceptional, (13)
"We drove from Wisconsin to bring one child back to The Winchendon School and to tour Curry College for another. We planned to be back and forth a lot and found the location of this property decent. Our goal with renting a property is to prepare our own meals and to have a comfortable space. The kitchen had basic supplies/equipment. The pans could be updated due to heavily scratched coating, although they worked ok. I found some of the utensils to be dirty, especially the pizza cutter. I am...
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski
Relaxing Retreat
Interior

Relaxing Retreat

9.8 out of 10, Exceptional, (27)
"We had a great stay at this location. It was clean, spacious and quiet nice neighborhood. Very good location to visit our family who live nearby. The owner is very easy to communicate and is friendly. We would recommend this to any family or friends wanting to visit Central MA. Good restaurants, state parks, rail trail and MT Washussett to visit.nearby. 5star location! "
Relaxing Retreat
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.

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, Lake Dennison State Recreation Area and Wendall P. Clark Memorial 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 B&Bs in the surrounding area: Monadnock Inn: 11 rooms. 9.7 mi (15.7 km) from the heart of Winchendon.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, Lake Dennison State Recreation Area and Millers River are some notable spots. You might put Wetmore Trailhead and Beals Memorial Library 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.