Cottages in Hillsmere Shores
Annapolis
Maryland
United States of America
Cottages
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Search Hillsmere Shores Cottage Rentals from CA $316

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your current months are November, 2026 and December, 2026.

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Our top choices for Hillsmere Shores cottages

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

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

A dock with a boat and a house in the background.

1. 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 CA $508

CA $508

CA $892 total

includes taxes & fees

Nov 11 - Nov 12

Chesapeake Cottages- 2 Quaint Waterfront Retreats

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

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

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

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

2. Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown

Historic District

9.6 out of 10, Exceptional, (24 reviews)

9.6/10

Exceptional

(24 reviews)

"The cottage was perfectly located in the heart of Annapolis. It has many eclectic decorations throughout out it. We enjoyed our stay."

Bridget C.

The price is CA $635

CA $635

CA $1,004 total

includes taxes & fees

Nov 11 - Nov 12

Secluded Cozy Cottage in Historic Downtown

A two-story house with a wooden deck, a garage, and a shed in the backyard.

A living room with a sofa, coffee table, and dining area.

A two-story house with a covered porch, a small garden, and a wooden staircase leading to the upper level.

A modern living room with a sofa, a coffee table with cushions, a piano, a TV, and a staircase leading to another room.

3. Lakefront Home Firepit BWI Marleycreek River

Lakefront Home Firepit BWI Marleycreek River

3.0 star property

Marley

The price is CA $384

CA $384

CA $457 total

includes taxes & fees

Nov 11 - Nov 12

Lakefront Home Firepit BWI Marleycreek River

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.

View all properties

Top reviews in Hillsmere Shores

A multi-story hotel with a brick facade, large windows, and an American flag.

A hotel lobby with a bar area, seating arrangements, and a patterned carpet.

A modern living room with a fireplace, two armchairs, a coffee table, and decorative items.

A swimming pool with a clear blue water, surrounded by lounge chairs and a glass wall.

Crowne Plaza Annapolis by IHG

Annapolis

10/10 Excellent

Nice for family

Tarun

Reviewed September 3, 2024Reviewed September 3, 2024

Crowne Plaza Annapolis by IHG

A historic brick building with a red roof, multiple windows, and a central staircase.

A spacious indoor area with brick walls, multiple tables and chairs, and string lights.

An aerial view of a coastal town with a marina, houses, and a bridge in the background.

A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.

Historic Inns of Annapolis

Historic District

10/10 Excellent

Great hotel great location. Friendly staff

Kelly

Reviewed April 29, 2026Reviewed April 29, 2026

Historic Inns of Annapolis

A DoubleTree by Hilton hotel entrance with a brick facade, a gated driveway, and a clear sky.

A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.

A restaurant with wooden tables and chairs, a bar area, and a tiled floor.

A spacious lobby with a high ceiling, a central seating area with sofas and tables, and large windows with curtains.

DoubleTree by Hilton Hotel Annapolis

Annapolis

10/10 Excellent

Bon emplacement et aux standards des Doubletree

Jean

Reviewed October 25, 2026Reviewed October 25, 2026

DoubleTree by Hilton Hotel Annapolis

A multi-story Microtel by Wyndham hotel with a parking lot and a landscaped area in front.

A hotel room with a bed, bedside tables, a desk with a chair, a microwave, a refrigerator, and a window with curtains.

A modern hotel lobby with a sofa area, a flat-screen TV, and a dining area.

A snack and beverage vending area with various snacks and drinks.

Microtel Inn & Suites by Wyndham Gambrills/Odenton

Gambrills

10/10 Excellent

Super clean

Mario

Reviewed May 12, 2026Reviewed May 12, 2026

Microtel Inn & Suites by Wyndham Gambrills/Odenton

A Sonesta ES Suites hotel with a brick facade, large windows, and a red awning.

A patio area with a stone fire pit, outdoor furniture, and a covered seating area.

A hotel room with a sofa, a desk, a television, a chair, a bed, and a fireplace.

A modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.

Sonesta ES Suites Annapolis

Edgewater

10/10 Excellent

Clean. Very nice. Courteous staff.

karen

Reviewed November 11, 2025Reviewed November 11, 2025

Sonesta ES Suites Annapolis

A modern Courtyard by Marriott hotel with a well-lit entrance, landscaped garden, and a clear sky.

A courtyard with a stone fire pit surrounded by wicker furniture and a grassy lawn.

A section of a hotel with a wall labeled "the market" and two refrigerated display cases filled with beverages and snacks.

An indoor swimming pool with clear glass walls, lounge chairs, and a view of the outside.

Courtyard by Marriott Annapolis

Annapolis

10/10 Excellent

Okay

Shirley

Reviewed July 16, 2026Reviewed July 16, 2026

Courtyard by Marriott Annapolis

A Comfort Inn hotel with a parking lot and a covered entrance.

A hotel lobby with a reception desk, seating area, and artwork on the walls.

An outdoor seating area with tables and chairs, blue umbrellas, and a brick building in the background.

A hotel lobby with a long bar area, seating, and a projection screen.

Comfort Inn Conference Center

Bowie

10/10 Excellent

I appreciate the location for my purposea. Comfortable, quiet, pleasant personnel.

Maureen

Reviewed September 10, 2024Reviewed September 10, 2024

Comfort Inn Conference Center

A hotel with a modern design, featuring a mix of brick and siding exteriors, a covered entrance, and a parking area.

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

A reception desk with a 'HELLO' sign and 'Annapolis' text, wooden paneling, and hanging pendant lights.

A compact hotel room with a kitchenette, a desk with two chairs, a sofa, and a bed.

TownePlace Suites by Marriott Annapolis

Annapolis

10/10 Excellent

All good great room suite all high end Staff eere the best i have experienced in a longtime

Steven

Reviewed April 18, 2026Reviewed April 18, 2026

TownePlace Suites by Marriott Annapolis

A marina with numerous boats docked, a prominent building with a dome in the background, and a clear view of the water.

A spacious atrium with a high ceiling, skylights, and a patterned floor.

A modern lounge area with a blue sofa, red chairs, and plaid armchairs. A coffee table with books and a vase of flowers is in the center. Large windows offer a view of a brick building with awnings.

A hotel lobby with a high ceiling, large windows, and a blue and white color scheme. Tables and chairs are arranged for dining or meetings.

Graduate by Hilton Annapolis

Annapolis

10/10 Excellent

Great burger in restaurant

JONATHAN

Reviewed September 15, 2026Reviewed September 15, 2026

Graduate by Hilton Annapolis

A patio with a barbecue grill, outdoor seating, and a small garden area with yellow flowers.

A hotel room with a bed, a desk with a chair, a television, a kitchenette, and a shower area.

A modern hotel kitchen with wooden cabinets, a buffet area, and a dining area with wooden tables and chairs.

A modern hotel room with a kitchenette, a dining area, a sofa, and a small round table.

TownePlace Suites Bowie Town Center

Bowie

10/10 Excellent

Everything was clean 😁

chantal

Reviewed March 17, 2026Reviewed March 17, 2026

TownePlace Suites Bowie Town Center

A Hilton Garden Inn with a prominent entrance, multiple flags, and a well-maintained parking area.

A modern lobby with a reception desk, seating area, and potted plants.

An outdoor patio with tables and chairs, a brick floor, and a building with a green roof in the background.

A hotel dining area with multiple tables and chairs, large windows, and a chandelier.

Hilton Garden Inn Annapolis

Annapolis

10/10 Excellent

Shane

Reviewed November 2, 2026Reviewed November 2, 2026

Hilton Garden Inn Annapolis

A modern hotel with a symmetrical facade, large windows, and a well-lit entrance.

An outdoor patio with tables, chairs, and a fire feature.

A modern dining area with multiple tables and chairs, large windows with a view of greenery, and decorative wall mirrors.

A modern lounge area with a sofa, round tables, and chairs, featuring geometric wall decor and large windows.

Fairfield Inn & Suites By Marriott Annapolis

Annapolis

10/10 Excellent

Rooms are clean, comfortable and give you a cool non-boxy vibe

Ben

Reviewed December 5, 2025Reviewed December 5, 2025

Fairfield Inn & Suites By Marriott Annapolis

A hotel with a modern design, featuring a mix of red and white facades, multiple windows, and a prominent entrance with arched doorways.

A bar area with multiple shelves of liquor bottles, a cash register, and bar stools.

A hotel room with two beds, a desk with a chair, a television, and a large window with a view of greenery.

Hilton Garden Inn Annapolis Downtown

Annapolis

10/10 Excellent

Nice hotel in a very central part of town

Francesco

Reviewed July 8, 2026Reviewed July 8, 2026

Hilton Garden Inn Annapolis Downtown

A Courtyard by Marriott hotel with a curved entrance, multiple floors, and a brick facade.

An outdoor patio area with seating arrangements and a fire feature.

A reception area with two wooden reception desks, a stone wall, and a modern ceiling design.

A modern bar area with a wooden counter, bar stools, a television screen, and a variety of beverages.

Courtyard by Marriott Bowie

Bowie

10/10 Excellent

Had a pleasant stay. Staff were very friendly.

Darko

Reviewed November 11, 2025Reviewed November 11, 2025

Courtyard by Marriott Bowie

A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.

A bar area with a circular seating arrangement, a central bar counter, and a hanging plant decoration.

A modern hotel lobby with a curved seating area, a bar, and a large bookshelf.

The Westin Annapolis

Annapolis

10/10 Excellent

Great last minute booking. All went smoothly

Kelly

Reviewed October 23, 2026Reviewed October 23, 2026

The Westin Annapolis

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Search Hillsmere Shores Cottage Rentals from CA $316

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Hillsmere Shores cottages

1. Chesapeake Cottages- 2 Quaint Waterfront Retreats

2. Secluded Cozy Cottage in Historic Downtown

3. Lakefront Home Firepit BWI Marleycreek River

Top reviews in Hillsmere Shores

Crowne Plaza Annapolis by IHG

10/10 Excellent

Explore a world of travel with Expedia