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Featured Cottages in Annapolis

Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun
10.0 out of 10, Exceptional, (61)
"We had a great time at this very cute cottage and really appreciated the extra touches of the hosts, who were very helpful. The yard is truly a great place to hangout but there were also lots of places to enjoy close by."
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun
Waterfront home with beach on the Chesapeake Dog-Friendly
9.8 out of 10, Exceptional, (20)
"The home was beautiful, the setting was stunning, and the check-in and check-out process was a breeze! Our group of 6 cousins had a fantastic time together enjoying the beautiful views and all that Annapolis has to offer. We are already planning a return trip next year!"
Waterfront home with beach on the Chesapeake Dog-Friendly
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
9.8 out of 10, Exceptional, (17)
"This was the perfect space for our family of five. Check-in was a breeze and Isaac even went as far as to leave the lights on for us knowing we were getting in late. Isaac let us know he was available if we needed anything, but we did not. Despite the rain, we were able to enjoy the hot tub overlooking the creek. The view was stunning! If you are looking for a peaceful stay, this is it!"
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
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Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
10.0 out of 10, Exceptional, (20)
"Beautiful house in peaceful West Annapolis, a short distance from the local shops and restaurants and the Naval College. Well equipped, everything you need, a real home from home and a very friendly, helpful and accommodating host. Highly recommended place to stay!"
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Amazing views, short walks to great dining!
10.0 out of 10, Exceptional, (65)
"Extremely responsive host and beautiful cottage. Incredible location with tranquil views of the water. 5 minute walk to ice cream and nice restaurants. Easy walk (20-25 mins) otherwise into more bustling downtown Annapolis."
Amazing views, short walks to great dining!
Waterfront Annapolis Home: Fire Pit & Fishing Pier
3.5 star property
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Eastport Cozy Charmer
9.4 out of 10, Exceptional, (3)
"We really enjoyed our stay. We felt very comfortable there, and it worked well for us. Especially liked that there was space to park the boat on the street next to the house."
Eastport Cozy Charmer
Cozy Maryland Retreat Near Sandy Pointe State Park
3.0 star property
Cozy Maryland Retreat Near Sandy Pointe State Park
Cozy Nautical Cottage in Annapolis w/ Beautiful Outdoor Space
Cozy Nautical Cottage in Annapolis w/ Beautiful Outdoor Space
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
3.0 star property
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
Cozy cottage, Bayridge neighborhood for rent. 2 bedrooms, 1 1/2 bathrooms.
Cozy cottage, Bayridge neighborhood for rent. 2 bedrooms, 1 1/2 bathrooms.
Secluded Cozy Cottage in Historic Downtown
Secluded Cozy Cottage in Historic Downtown
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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.

Other property types in Annapolis

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (4)
"Incredibly beautiful home! The house is a perfect place to host your family for commissioning week or for any stay. The pool and river offer a great places to relax. The views are gorgeous and the property is located in a very peaceful neighborhood. The property has amazing amount space to accommodate our large family. We enjoyed eating on the patio, swimming in the pool, kayaking and playing pickle ball. We hope to come back just to vacation here!"
The price is AU$2,184
includes taxes & fees
4 June - 5 June
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (180)
"Charming spot in the heart of Annapolis, just a few moments walk from anything you might need."
Directly Across from Gate One & Steps from the Waterfront
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun
10.0 out of 10, Exceptional, (61)
"We had a great time at this very cute cottage and really appreciated the extra touches of the hosts, who were very helpful. The yard is truly a great place to hangout but there were also lots of places to enjoy close by."
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun
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.

Annapolis Cottages information

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Frequently asked questions

How much do cottages in Annapolis cost?
You can expect to pay between and per night for cottages in Annapolis. Whatever your budget, an epic stay is a click away on Expedia. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What is there to do in Annapolis near my cottage?
There are tons of superb things to sink your teeth into in Annapolis. Drop by top attractions like Sandy Point State Park, Sandy Point Beach and Triton Beach. Matapeake State Park, Bay Ridge Beach and Annapolis Bowl are other must-see’s.

Recent Reviews in Annapolis
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