Top Cottages in Anne Arundel County in 2026

Anne Arundel County Cottages
Maryland
United States of America
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An aerial view of a coastal town with a prominent church, dense residential area, and a marina with boats.

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Top Cities in Anne Arundel County

A pier extending into calm waters at sunset with a cloudy sky.

Pasadena

A wooden boardwalk along a sandy beach with buildings and a pier in the background.

North Beach

Our top choices for Anne Arundel County cottages

A small, single-story house with a green roof and a covered porch.

A living room with a grey sectional sofa, a grey ottoman, a wooden coffee table, and a rustic fireplace.

A poolside area with lounge chairs and umbrellas, a pool, and a view of the ocean.

A living room with a grey sofa, a small table, and a ladder leaning against the wall. There are framed pictures on the wall and a window with a view of the outdoors.

1. The Heron's Nest at Atlantic Marina

The Heron's Nest at Atlantic Marina

Pasadena

9.8 out of 10, Exceptional, (327 reviews)

9.8/10

Exceptional

(327 reviews)

"Perfect little cottage for our weekend getaway! We will definitely be back."

Brian R.

The Heron's Nest at Atlantic Marina

A two-story house with a front porch and a small garden area.

A sunset over a calm body of water with a distant bridge, a tree on the right, and a rocky shoreline.

A modern kitchen with white cabinets, stainless steel appliances, and a wooden table.

A modern kitchen with white cabinets, stainless steel appliances, and a wooden dining table.

2. Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly

Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly

Annapolis

9.8 out of 10, Exceptional, (45 reviews)

9.8/10

Exceptional

(45 reviews)

"Very nice property, everything was as expected and the entire process was easy. Great, quiet spot to enjoy the Bay close to everything fun in Annapolis. I’d go back."

Brian R.

Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly

A wooden deck with benches overlooking a beach.

A dining table with four chairs, each with a checkered cushion. A decorative coral centerpiece is on the table.

A beach with a wooden pier extending into calm waters, surrounded by greenery and a clear sky.

A single-story house with a stone chimney, a front porch, and a well-maintained garden with various plants and flowers.

3. Firefly Cottage at the Cape, Hot Tub, Community beach, Boat Show, USNA Football.

Firefly Cottage at the Cape, Hot Tub, Community beach, Boat Show, USNA Football.

Cape Saint Claire

10.0 out of 10, Exceptional, (124 reviews)

10/10

Exceptional

(124 reviews)

"We stay here three times each year when we visit Annapolis. Great for a small family with a large back yard and many outdoor amenities."

Nancy A.

Firefly Cottage at the Cape, Hot Tub, Community beach, Boat Show, USNA Football.

A hot tub in a backyard with a view of a lake and trees.

A dining area with a wooden table, chairs, and a ceiling fan. There are large windows with blinds, a bookshelf, and a television.

A modern kitchen with dark cabinetry, a central island, and a dining area with a table set for four.

The spacious remodeled kitchen makes it easy to cook and connect while enjoying views toward the water.

4. Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Deale

9.8 out of 10, Exceptional, (91 reviews)

9.8/10

Exceptional

(91 reviews)

"We are a party of 3 generations and a dog. Everyone had a great time and had something fun to do at the Chesapeake Paradise cottage. Shawn was always available and ready to assist. The cottage was cozy and clean, had all the amenities and household items we needed. Would love to revisit!"

grace d.

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

A two-story building with a covered outdoor area, a staircase, and trees with autumn leaves.

A bedroom with a bed, a chair, a bedside table with a lamp, a picture on the wall, and a window with curtains.

A riverside view with a bridge, boats, and a grassy area with chairs.

A dining table with a wine bottle, glasses, and a red bowl with a leaf pattern.

5. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!

West Annapolis

10.0 out of 10, Exceptional, (94 reviews)

10/10

Exceptional

(94 reviews)

"Lovely location and Jim was very helpful all the way around!"

Jill R.

The price is AED 1,125

AED 1,125

AED 1,672 total

includes taxes & fees

5 Oct - 6 Oct

Your Annapolis Waterfront retreat for a weekend or any-day getaway!

A two-story house with a front porch, a chimney, and a small garden area.

A spacious living area with a stone fireplace, wooden furniture, and a large TV.

A kitchen with wooden cabinets, a dining table with chairs, a built-in bench, and a refrigerator.

A wooden dock extending into a calm body of water, surrounded by lush green trees and two houses with a well-maintained lawn.

6. Waterfront Annapolis Cottage: Fire Pit & Pier

Waterfront Annapolis Cottage: Fire Pit & Pier

Annapolis

9.4 out of 10, Exceptional, (49 reviews)

9.4/10

Exceptional

(49 reviews)

"The place worked well for us. It must be a great place in the warmer months."

John R.

Waterfront Annapolis Cottage: Fire Pit & Pier

A wooden dock leading to a small red cabin by a calm water body, surrounded by lush greenery and a white fence.

A row of brick buildings with storefronts, a bicycle parked outside, and a sidewalk.

A porch with two wicker chairs and a small table, a red house with white shutters, and a green door.

A backyard with a fire pit, outdoor seating, and a view of a lake.

7. Waterfront River Cottage for 2, dog-friendly

Waterfront River Cottage for 2, dog-friendly

Severna Park

9.2 out of 10, Wonderful, (14 reviews)

9.2/10

Wonderful

(14 reviews)

"Excellent stay for a couple as a getaway after boatshow"

Anonymous traveler

Waterfront River Cottage for 2, dog-friendly

A small, single-story house with a front porch, a wooden deck, and a stone pathway leading to the door.

A modern kitchen with white cabinets, a stainless steel stove, and a dining area with a wooden table and chairs.

A bathroom with a glass-enclosed shower, a toilet, and a sink.

A living room with a gray sofa, a wooden coffee table, a lamp, and a view through a window.

8. Charming 1-bedroom cottage with AC in cozy Harwood

Charming 1-bedroom cottage with AC in cozy Harwood

Harwood

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"Very quiet area, cute house for two. Lots of open area for our small dogs to play."

Susan S.

Charming 1-bedroom cottage with AC in cozy Harwood

A wooden deck with wicker furniture, a glass-top table, and a view of a body of water and trees.

A neatly made bed with a quilted blanket and pillows, a bedside table with a lamp, and a small nightstand with a tissue box.

A living room with a fireplace, a Christmas tree, a sofa, and a book on a coffee table.

9. Cozy and serene one bedroom waterfront guest cottage

Cozy and serene one bedroom waterfront guest cottage

Herald Harbor

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"The place is super cute and right on the water. Thanks for a great stay. We hope to come back again as we have friends in Herald Harbor"

Jill M.

Cozy and serene one bedroom waterfront guest cottage

A wooden deck with wicker furniture, a round table, and a fire pit.

A modern kitchen with white cabinets, a wooden dining table, stainless steel appliances, and a window providing natural light.

A modern kitchen with a built-in refrigerator, a dining area with a wooden table and chairs, a television mounted on the wall, and a large window offering a view of the outdoors.

A house with a large lawn, a dock, and a tree.

10. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Pasadena

9.6 out of 10, Exceptional, (24 reviews)

9.6/10

Exceptional

(24 reviews)

"Excellent Property"

Buu T.

The price is AED 1,322

AED 1,322

AED 2,441 total

includes taxes & fees

5 Oct - 6 Oct

Chesapeake Cottages- 2 Quaint Waterfront Retreats

A house with a front porch surrounded by a garden with various flowers.

A wooden desk with a lamp, a framed picture, and a wicker basket.

A living room with a wooden floor, a sofa, a coffee table, a television, and a bookshelf.

A living room with a white sofa, black and white patterned pillows, a wooden coffee table, a dining table with chairs, and framed artwork on the walls.

11. The Yellow Cottage on Harness Creek

The Yellow Cottage on Harness Creek

Hillsmere

10.0 out of 10, Exceptional, (182 reviews)

10/10

Exceptional

(182 reviews)

"Charming and cozy, pretty view and has everything you need"

Laura K.

The Yellow Cottage on Harness Creek

A marina with multiple boats docked, a building with a distinctive yellow roof, and a clear sky.

A building with a black metal gate, a brick pathway, and greenery.

A two-story white building with dark shutters, a wooden door, and a small porch with a white railing.

A kitchen with white cabinets, a granite countertop, and two black bar stools.

12. Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown

Historic District

9.6 out of 10, Exceptional, (22 reviews)

9.6/10

Exceptional

(22 reviews)

"The host was amazing, the house was perfect and well equipped, and the location was amazing!!! "

Tim G.

The price is AED 1,928

AED 1,928

AED 3,111 total

includes taxes & fees

2 Nov - 3 Nov

Secluded Cozy Cottage in Historic Downtown

A shower with a metal door, a white curtain, and a framed artwork on the wall.

A parking area with trees, a body of water, and a distant view of houses.

A modern kitchen with stainless steel appliances, white cabinetry, and a granite countertop.

A living room with a sectional sofa, a small round table, and a door with a window.

13. Pet Friendly Water View Cottage

Pet Friendly Water View Cottage

Pasadena

10.0 out of 10, Exceptional, (38 reviews)

10/10

Exceptional

(38 reviews)

"Loved it, can't wait to come back. "

Marguerite H.

Pet Friendly Water View Cottage

A yellow house with a front porch, a garage, and a paved driveway.

A sunlit room with a wicker sofa and ottomans, a small round table, and a window overlooking a street.

A room with a hanging chair, wooden ceiling, large windows, and a staircase leading to another level.

A modern living room with a staircase, a flat-screen TV, and a dining area.

14. Updated North Beach Cottage: Pet Friendly!

Updated North Beach Cottage: Pet Friendly!

North Beach

9.6 out of 10, Exceptional, (28 reviews)

9.6/10

Exceptional

(28 reviews)

"Cozy cottage, beds were comfy and it was great to bring our dog. "

Chloe W.

Updated North Beach Cottage: Pet Friendly!

A deck with outdoor seating and a view of a lake.

A hallway with wooden flooring, light grey walls, and nautical-themed artwork.

A modern kitchen with dark cabinets, a central island, and a dining area with a gray sofa and a table.

A modern kitchen with dark cabinets, stainless steel appliances, and a bar area with stools.

15. Rock Creek Cottage, Waterfront, Serene Views

Rock Creek Cottage, Waterfront, Serene Views

Riviera Beach

10.0 out of 10, Exceptional, (17 reviews)

10/10

Exceptional

(17 reviews)

"We always stay at Rock Creek cottage when we come to visit family. It’s impeccably clean and comfortable place to call home for our visit. The water views are beautiful and relaxing. We look forward to our next visit!"

Thea S.

Rock Creek Cottage, Waterfront, Serene Views

A deck with a pergola, barbecue grill, and outdoor furniture.

A white house with a porch and a large tree in front.

A cozy living room with a sofa, armchairs, a coffee table, and a bookshelf.

A kitchen with wooden cabinets, a white countertop, and a dining area with a table and chairs.

16. Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

Edgewater

10.0 out of 10, Exceptional, (235 reviews)

10/10

Exceptional

(235 reviews)

"Awesome location and very nice, we had a great stay! "

Megan B.

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

A light blue house with a porch, white railings, and a flag.

A spacious hallway with a light blue wall, wooden flooring, and a seating area with a chair and ottoman.

A spacious living room with a light blue wall, wooden flooring, and a large window. There are two sofas, a coffee table, and a side table with a vase.

A rocky shoreline with a wooden pier extending into calm waters.

17. Bayfront Maryland Retreat w/ Deck, Near Beaches!

Bayfront Maryland Retreat w/ Deck, Near Beaches!

3.0 star property

North Beach

Bayfront Maryland Retreat w/ Deck, Near Beaches!

A pathway leading to a house with a garden, a fence, and hanging flower baskets.

A front porch with a white door, a porch light, a plaque, a wicker chair, and a 'peace' doormat.

A porch with wicker furniture, a glass-top table, and potted plants.

A living room with a sectional sofa, a patterned rug, and a small side table with a lamp.

18. Walk to Everything - Historic Art’s District

Walk to Everything - Historic Art’s District

Annapolis

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"As advertised. Very cute, walk to everything. Fantastic place to stay."

James S.

Walk to Everything - Historic Art’s District

A modern kitchen with white cabinets, stainless steel appliances, and a wooden countertop.

A bedroom with a bed, a nightstand, a ceiling fan, and a window with blinds.

A living room with a sofa, a coffee table, a leather chair, and a ceiling fan.

19. Updated North Beach Cottage: Pet Friendly!

Updated North Beach Cottage: Pet Friendly!

3.0 star property

North Beach

6.0 out of 10, (1 review)

6.0/10

(1 review)

"The property needs a severe cleaning. The floors were filthy. "

Lacy

Updated North Beach Cottage: Pet Friendly!

A single-story house with a red door, a front porch, and a small front yard.

A modern bathroom with white tiles, a shower, a bathtub, and a shelf with toiletries.

A wooden deck with wicker chairs and a table, a covered porch, and a view of neighboring houses.

A spacious dining area with a wooden table and chairs, a large pendant light, and a view into the kitchen.

20. The Red Door Cottage in Eastport - Pet-Friendly!

The Red Door Cottage in Eastport - Pet-Friendly!

Eastport

The Red Door Cottage in Eastport - Pet-Friendly!

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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