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Compare 1 B&B in Annapolis with updated reviews, rates, and availability.

Old Caledonian Bed and Breakfast
Front of property

Old Caledonian Bed and Breakfast

4.0 star property
9.8 out of 10, Exceptional, (30)
"This is a beautiful property, and the hosts (Jon and Penny) are wonderful. Jon is a chef who prepares really tasty vegan meals. Highly recommended for a weekend getaway!"
Old Caledonian Bed and 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 Annapolis

Small Town Lodge - Black River

Small Town Lodge - Black River

4.0 out of 10, (1)
"The bathroom was broken and unusable, we had to skiddaddle first thing in the morning to use the bathroom at the gas station...which was kinda far! OOF. No compensation was made :("
The price is AED 463
AED 907 total
includes taxes & fees
5 Dec - 6 Dec
Small Town Lodge - Black River
Hillside Cabin #2 Annapolis, MO Black River

Hillside Cabin #2 Annapolis, MO Black River

9.4 out of 10, Exceptional, (56)
"My husband and I came here with the hopes of escaping and just enjoying a peaceful weekend. The cabin is perfect for what we needed. Cozy and comfy and just what we needed. Yes the couch is broken, LOL. But if a broken couch is going to ruin your vacay maybe this isn’t the place for you. Just saying that just added to the character and provided some laughter. "
The price is AED 436
AED 793 total
includes taxes & fees
30 Nov - 1 Dec
Hillside Cabin #2 Annapolis, MO Black River
Hillside Cabin #3 Annapolis, MO Black River

Hillside Cabin #3 Annapolis, MO Black River

7.8 out of 10, Good, (26)
"Really a nice and clean and cozy stay."
The price is AED 377
AED 715 total
includes taxes & fees
27 Nov - 28 Nov
Hillside Cabin #3 Annapolis, MO Black River
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 Annapolis?
Whether you’re traveling with your family and want a friendly place to stay, or you’re traveling solo and hoping to meet fellow tourists, B&Bs can be a great choice for many travelers. If your ideal vacation to Annapolis includes spending lots of time outside, Taum Sauk Mountain State Park and Mark Twain National Forest are good spots to enjoy the scenery.
Are you thinking about B&Bs over traditional hotel rooms?
Every B&B has its own unique feel. Whether it’s a comfy common area with a fireplace or a beautiful dining room, the little details are what make bed and breakfasts the perfect escape.
What's the best time of year to book my B&B in Annapolis?
When you’re planning your stay in Annapolis, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 76°F, while the coldest months are January and February with an average of 40°F. Average annual precipitation for Annapolis is 52 inches.
What is there to do in Annapolis?
When you want to spend some time in the great outdoors, Taum Sauk Mountain State Park and Mark Twain National Forest are some notable spots. You might put K Bridge Recreation Area and Walnut Hollow Lake on your list if you want to see more of the area.