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Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

Featured Cottages in Annapolis

Exterior detail
Secluded Cozy Cottage in Historic Downtown
Secluded Cozy Cottage in Historic Downtown
9.6 out of 10, Exceptional, (15)
"Very Annapolis! "
United States
Shannon G.
The price is AU$1,064
includes taxes & fees
3 Nov - 4 Nov
Secluded Cozy Cottage in Historic Downtown
Interior
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
2.0 star property
The price is AU$431
includes taxes & fees
2 Nov - 3 Nov
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Terrace/patio
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
2.0 star property
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
United States
shannan t.
The price is AU$1,399
includes taxes & fees
1 Nov - 2 Nov
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Outdoor dining
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Chesapeake Cottages- 2 Quaint Waterfront Retreats
9.6 out of 10, Exceptional, (22)
"Excellent Property"
United States
Buu T.
The price is AU$1,026
includes taxes & fees
21 Oct - 22 Oct
Chesapeake Cottages- 2 Quaint Waterfront Retreats
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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Top Annapolis Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Loved everything. Perfect location right on the main drag "
Timothy 1-night trip
Posted 19 hours ago
Historic Inns of Annapolis

Find out more about Annapolis

Annapolis Cottages information

Number of reviews
15
Accommodation
15 Cottages
Lowest Price
AU$431
Highest Price
AU$1,399

Frequently asked questions

How much do cottages in Annapolis cost?
You can expect to pay between AU$431 and AU$1,399 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.