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Barefoot Escapes on the Chesapeake

Thoughtfully curated retreats throughout Annapolis, each celebrating unique aspects of Chesapeake living. Distinctive. Curated. Pet Friendly.

4.96 average
Hand-picked homes
★ 4.96 guest rating
24/7 support
200+ stays hosted
30+ days Mid-Term Stays
Local Love

We love sharing this place we call home. Annapolis, MD is a vibrant maritime town filled with history, sailing, and delicious food! Let us introduce ourselves, David and Melanie, and we are your hosts here at Stay Barefoot Annapolis. Our goal for all our guest, is to have the getaway you envision. From relaxing, quiet retreats to weekend adventures on the Chesapeake, and days of food and exploring, we are here to help you see and do it all!

Featured Stays

Your Next Adventure

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Golden hour

The best seat in the house.

Golden hour, quiet water, and long evenings outside.

Experience Annapolis

Waterside dining. Sailing Adventures. Historic charms. Unforgettable moments.

Thomas Point Lighthouse
Steamed Crabs
Flags on Fleet Street
Cormarant on Piling
Our Story

Stay Barefoot Annapolis

Created from a love of home, hospitality , and the Chesapeake way of life. For us, Annapolis i smore than a destination. It is early mornings by the water, crab feasts in July, sailboats on the Bay, and the feeling of slowing down.
Local

Local

Hands-on hosts
4.96

4.96

Avg. rating
9

9

Years hosting
Sailboat on Severn River
Don't take our word for it

Loved by guests

Erin S.

Melanie's place was perfect for a quiet getaway with a few official events at the Naval Academy a short drive away. The neighborhood is beautiful--I had a great time walking around the perimeter exploring the various views of the Bay. The space is spotless and very comfy. Highly recommended.

Barefoot Cottage
Sheila O.

I needed a mid-week break and this was the perfect spot! I still had to work remotely (Wifi was perfect) but it felt like a mini-vacation. Went to the grocery store on my way and had no reason to leave. The community beach was a short walk through the neighborhoold and very peaceful. Melanie was communicative and available. Highly recommend.

Barefoot Cottage
Hannah F.

We had a wonderful stay! Very conveniently located close to everything we wanted to do. The community was very quiet and nice to walk around. We would definitely recommend if you're looking for a quiet getaway by the bay!

Barefoot Cottage
4.9 from 153 reviews
Good to Know

Questions, answered

Anything else, ask a human — we answer the phone, even at dinner.

Is Barefoot Cottage private?
Yes. Barefoot Cottage is considered an Accessory Dwelling Unit (ADU) and is private for our guests; there is no shared space. It is physically part of The Residence at Barefoot Cottage property via the garage, but there is no access between properties from inside.

Is there bay beach access?
Yes! Barefoot Cottage is a short walk from the Chesapeake Bay and our community has a private beach for your use. Take in a view of the lighthouse, sailboats dotting the bay, or spy a cruise passing through.

Ready to Stay Barefoot

Your Annapolis escape is waiting.