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Compare 15 Cottages in Annapolis with updated reviews, rates, and availability.

Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,
Exterior detail
Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,
10.0 out of 10, Exceptional, (80)
"My husband and son really loved their stay at Pat & Ken's VRBO house! They enjoyed going on walks around the neighborhood, visiting the local restaurants, and sitting in the hot tub. It was perfect for our family. Pat & Ken are such gracious hosts, and we will definitely stay here again!"
Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Room
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
10.0 out of 10, Exceptional, (24)
"Great location and very clean property. Cyndi was responsive and a great host. Would definitely stay again."
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Pet-friendly Annapolis Home: Walk to Beach!
Property grounds
Pet-friendly Annapolis Home: Walk to Beach!
3.0 star property
Pet-friendly Annapolis Home: Walk to Beach!
Amazing views, short walks to great dining!
"The cottage is lovely—vintage charm in perfect combination with the best modern updates. I was comfortable every minute I spent there..." Darcy - June 2021
Amazing views, short walks to great dining!
10.0 out of 10, Exceptional, (73)
"Perfect for a romantic weekend away!"
Amazing views, short walks to great dining!
The Yellow Cottage on Harness Creek
The Yellow Cottage on Harness Creek
The Yellow Cottage on Harness Creek
10.0 out of 10, Exceptional, (156)
"This was a great place to relax, have time to disconnect, and time to enjoy the company of my good friend. Loved the location and walked to the winery for a fabulous afternoon picnic. "
The Yellow Cottage on Harness Creek
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Regularly cleaned and maintained hot tub perfect for cool nights
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
9.8 out of 10, Exceptional, (22)
"My husband and I stayed here for 3 nights while I recovered from a surgery. It was a perfect, peaceful cottage and beautiful neighborhood. "
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Waterfront dog-friendly home with beach just mins to Downtown Annapolis
Welcome to the renovated kitchen at Oh Happy Bay!
Waterfront dog-friendly home with beach just mins to Downtown Annapolis
9.8 out of 10, Exceptional, (29)
"My stay was wonderful, listing just as described. Beautiful water views and enjoyed the local area. Highly recommend and plan to return. Thank you so much for a lovely stay!"
Waterfront dog-friendly home with beach just mins to Downtown Annapolis
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Terrace/patio
Waterfront Annapolis Home: Fire Pit & Fishing Pier
3.0 star property
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Eastport Cozy Charmer
Living area
Eastport Cozy Charmer
9.6 out of 10, Exceptional, (5)
"This property was cute, clean and the neighborhood was friendly. Close enough to walk everywhere!"
Eastport Cozy Charmer
Cozy Maryland Retreat Near Sandy Pointe State Park
Living area
Cozy Maryland Retreat Near Sandy Pointe State Park
3.0 star property
Cozy Maryland Retreat Near Sandy Pointe State Park
Secluded Cozy Cottage in Historic Downtown
Room
Secluded Cozy Cottage in Historic Downtown
10.0 out of 10, Exceptional, (2)
"We had a great time. Easy walk to everything. House was perfect and clean. The whole process was easy."
The price is AED 1,469
AED 2,328 total
includes taxes & fees
25 Nov - 26 Nov
Secluded Cozy Cottage in Historic Downtown
Cozy Nautical Cottage in Annapolis w/ Beautiful Outdoor Space
Terrace/patio
Cozy Nautical Cottage in Annapolis w/ Beautiful Outdoor Space
8.8 out of 10, Excellent, (3)
"The most lovely and completely outfitted and furnished with the latest tech and very nice amenities. The owner William answers any and all questions within minutes. The perfect spot to get away from it all yet near the Naval Academy very close by. Our first trip to this region and will not be our last."
Cozy Nautical Cottage in Annapolis w/ Beautiful Outdoor Space
Walk to Everything - Historic Art’s District
Exterior
Walk to Everything - Historic Art’s District
2.0 star property
Walk to Everything - Historic Art’s District
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
Living area
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.
Terrace/patio
Cozy cottage, Bayridge neighborhood for rent. 2 bedrooms, 1 1/2 bathrooms.
Cozy cottage, Bayridge neighborhood for rent. 2 bedrooms, 1 1/2 bathrooms.
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

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Private rear courtyard
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
10.0 out of 10, Exceptional, (202)
"This cozy home was perfect for my coaches & I that were in town for a lacrosse tourney @ the Naval Academy. This home is literally less than 100 steps from the gate of the Naval Base and same distance to dowtown Annapolis city docks, diming, shopping and sight-seeing. We will defintely be back! Thanks John!!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Annapolis Coastal Gem w/ Hot Tub, Dock, Close to Everything & Sleeps 5
Main room lounge area. Sectional has a new pull out sofa bed (double).
Annapolis Coastal Gem w/ Hot Tub, Dock, Close to Everything & Sleeps 5
10.0 out of 10, Exceptional, (12)
"Fantastic! Clean, spacious and welcoming. We had an amazing weekend as a family."
Annapolis Coastal Gem w/ Hot Tub, Dock, Close to Everything & Sleeps 5
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Miscellaneous
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (20)
"Our group had an amazing time staying on this property. There are many areas inside the house as well as outside the house where you can gather with family and friends. It was very quick and easy to order Ubers/lyfts to the downtow Annapolis area whenever we needed. The house is also convientely located near a small shaping center less than a mile away. We would highly recommend this property!"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
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

How much do cottages in Annapolis cost?
Prices for cottages in Annapolis range between AED 1,730 and AED 1,730 per night. Whatever your budget, you’ll find the perfect place to reconnect with nature. These prices were 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.
How many cottages are there in Annapolis?
Take advantage of your vacation days and choose from 15 cottages in Annapolis. Picturing a place where you can get in touch with nature? Expedia can help you find the ideal stay in a few simple clicks.
Why book your cottage in Annapolis with Expedia?
We think that traveling should be stress-free, so if you’re after cottages in Annapolis at a great price, Expedia has got your back. Keep costs down and opt for a thrifty option far from the downtown buzz, or book a 5-star cottage to treat your loved ones.
How can I find cheap cottages in Annapolis?
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