Chesapeake Beach Holiday Rentals, Maryland: Private House Rentals

A harbor with boats docked, a pier, and a row of houses along the water.

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Our top choices for Chesapeake Beach hotels

A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.

A modern salon with multiple black salon chairs, a white reception desk, and large windows allowing natural light.

A bar area with multiple screens displaying sports content, a high ceiling with geometric patterns, and a view of the outside through large windows.

A modern bar area with a long counter and multiple bar stools.

1. Rod 'N' Reel Resort

Chesapeake Beach

3.749.667 ₫

4.162.130 ₫ total

includes taxes & fees

21 Oct - 22 Oct

A multi-story hotel with a central entrance, a landscaped garden with flowers, and a metal sculpture.

A marina with docked boats, a picnic area, and a grassy lawn with a tree.

A modern kitchen with a bar area, wooden flooring, and blue bar stools.

A modern kitchen with a large island, bar stools, and a wine rack.

2. Anchored Inn at Hidden Harbour Marina

Deale

Beverly

4.810.497 ₫

5.483.966 ₫ total

includes taxes & fees

11 Oct - 12 Oct

A hotel room with a large bed, bedside tables, a desk, a chair, a flat-screen TV, and a window with a view.

A gym with dumbbells, a bench, and a sign that says "USE AT YOUR OWN RISK".

A coffee station with two espresso machines, a coffee grinder, and various coffee-related items.

A modern hotel lobby with a blue carpet, seating areas, a reception desk, and a clock on the wall.

3. Holiday Inn Express Prince Frederick by IHG

Prince Frederick

John

3.065.640 ₫

3.691.238 ₫ total

includes taxes & fees

12 Oct - 13 Oct

A hotel lobby with a reception desk, a glass-top table with a bowl, potted plants, a vending machine, and a large window.

An indoor swimming pool with clear water, a tiled floor, and a few lounge chairs.

A lobby with two yellow armchairs, a glass-top coffee table, a lamp, and a decorative bamboo wall.

A hotel lobby with multiple seating areas, including tables and chairs, a television mounted on the wall, and a kitchen area in the background.

4. Springhill Suites by Marriott Prince Frederick

Prince Frederick

3.064.102 ₫

3.401.153 ₫ total

includes taxes & fees

18 Oct - 19 Oct

A hot tub in a grassy area with a building in the background.

A pool with two Adirondack chairs and a basket of items on the grass.

A room with a tufted armchair, a vase with white flowers, and a window with a view of the outdoors.

A cozy room with a brick fireplace, leather armchairs, and a rustic wooden table.

5. The Inn at Tacaro Estate

Tracys Landing

kristine

9.072.491 ₫

10.342.738 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A marina with boats docked at wooden piers, surrounded by greenery.

A waterfront property with houses, a dock, and a grassy area.

A building with a sign reading "The Inn."

A bed with two pillows, one with "HAPPY PLACE" text, and a framed picture above the bed.

6. Knapps Narrows Marina & Inn

Sherwood

BARBARA

2.598.000 ₫

2.857.800 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A two-story building with a brick facade, a covered entrance, and satellite dishes.

A reception area with a check-in counter, seating area, and a vending machine.

A hotel room with a large bed, two bedside tables with lamps, a window with curtains, and a wall-mounted heater.

A kitchen with a coffee station, a toaster, and a painting of a sunset on the wall.

7. SureStay by Best Western Prince Frederick

Prince Frederick

Greg

2.048.786 ₫

2.274.152 ₫ total

includes taxes & fees

11 Oct - 12 Oct

An outdoor seating area with tables and chairs, overlooking a body of water and greenery.

A modern lounge area with a fireplace, seating, and a view of the outdoors.

A waterfront property with a dock, a sailboat, and a building with a red roof.

A spacious indoor dining area with large windows, tables, and chairs.

8. The Tilghman Island Inn

Tilghman

4.797.790 ₫

5.277.569 ₫ total

includes taxes & fees

12 Oct - 13 Oct

A room with a view of a wooden deck and a gazebo by the water.

A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.

A golf course with a water hazard and surrounding trees.

A living room with a fireplace, a sofa, a coffee table, and a television mounted on the wall.

9. Inn at Perry Cabin

Downtown St. Michaels

Virgilio

13.304.142 ₫

14.634.556 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A waterfront property with a covered patio, a dock, and a boat.

A waterfront hotel with a covered dock and a large building with multiple balconies.

A wooden pier extending into calm waters, a sandy beach with sparse vegetation, and a clear sky.

A swimming pool with lounge chairs and umbrellas, surrounded by a fence and trees.

10. Wylder Tilghman Island

Tilghman

Gary

6.313.140 ₫

8.243.454 ₫ total

includes taxes & fees

18 Oct - 19 Oct

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

A two-story building with a balcony on the upper floor, outdoor seating with wooden chairs and tables, and a clear view of the surrounding area.

A neatly made bed with white linens and a beige pillow, a straw hat on the bed, a wooden nightstand with a small plant and a glass, and a wall-mounted light fixture.

A restaurant with long tables set for dining, benches along the walls, and large windows allowing natural light.

11. The Wildset

Downtown St. Michaels

Sarah

5.938.886 ₫

7.181.125 ₫ total

includes taxes & fees

3 Nov - 4 Nov

A two-story building with a covered entrance and an American flag.

A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.

A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.

A hotel room with two beds, a chair, and a painting on the wall.

12. St Michaels Inn

St. Michaels

Lynn

2.310.719 ₫

2.541.790 ₫ total

includes taxes & fees

11 Oct - 12 Oct

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

A gym with treadmills, weight machines, and dumbbells.

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

A modern lobby with a reception desk, seating area, and a patterned rug.

13. Sonesta ES Suites Annapolis

Edgewater

Philip

2.359.994 ₫

2.690.394 ₫ total

includes taxes & fees

29 Oct - 30 Oct

A modern kitchen with grey cabinets, a white countertop, and various kitchen appliances.

A modern hotel with a flat roof and a sign reading "SPRINGHILL SUITES BY MARRIOTT".

A hotel pool area with two pools, chairs, and a sunshade.

A hotel reception area with a reception desk, a television, and seating area.

14. SpringHill Suites by Marriott Annapolis

Annapolis

Lisa

3.086.146 ₫

3.518.206 ₫ total

includes taxes & fees

9 Nov - 10 Nov

A lakeside view with sailboats, grassy areas, and white Adirondack chairs.

A beach with clear water, sandy shore, and some vegetation.

A large, two-story house with a balcony, situated on a grassy lawn with autumn leaves, near a body of water.

A waterfront bar with outdoor seating, a view of the water, and American flags.

15. Sandaway Suites & Beach

Oxford

Amber

7.779.163 ₫

8.557.183 ₫ total

includes taxes & fees

5 Nov - 6 Nov

A Courtyard Marriott hotel with a fire pit in the courtyard, outdoor seating, and a brick facade.

A hotel room with two beds, a desk, a chair, a large window with curtains, and a painting on the wall.

A reception area with two wooden reception desks, a green wall with a grass-like design, and a digital screen displaying information.

A Courtyard Marriott hotel entrance with a covered walkway, multiple windows, and a well-lit facade.

16. Courtyard Marriott Waldorf

Waldorf

Mitchell

2.601.699 ₫

2.887.886 ₫ total

includes taxes & fees

19 Oct - 20 Oct

A hotel room with a large bed, a bedside table with a phone, a nightstand, a wall-mounted TV, and a bathtub.

A hotel entrance with a sign indicating pet-friendly services.

A living room with a sofa, a coffee table, a dining table with chairs, a mirror, a window with curtains, a radiator, a magazine rack, and a television.

A building with a sign reading "The Inn of the Hills" and a staircase leading to the entrance.

17. Executive Inn And Suites

Upper Marlboro

Towanda

2.289.712 ₫

2.587.375 ₫ total

includes taxes & fees

29 Oct - 30 Oct

A covered outdoor seating area with wicker furniture and large windows.

A modern living room with a fireplace, sofas, and a large window.

A hotel reception area with a self-service beverage station, snack vending machines, and a minibar.

A spacious hotel lobby with multiple seating areas, large windows offering views of the outdoors, and a modern interior design.

18. Hilton Garden Inn Solomons

Solomons

3.284.541 ₫

3.645.841 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A modern hotel lobby with a reception desk, seating area, and a large window.

A modern kitchen with a green accent wall, a sign reading 'Delight in the day,' and a window with a view of trees.

A hotel room with a bed, bedside tables, a desk, a flat-screen TV, and a lamp.

A self-service coffee station with dispensers for regular coffee, hot water, and decaf coffee, a coffee machine, and a bottle of coffee creamer.

19. Spark by Hilton Waldorf

Waldorf

Tanaysia

2.072.127 ₫

2.300.061 ₫ total

includes taxes & fees

9 Nov - 10 Nov

20. Laurel Grove Inn on the South

Annapolis

Ruth

4.668.120 ₫

5.321.657 ₫ total

includes taxes & fees

9 Nov - 10 Nov

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Stay near popular Chesapeake Beach attractions

A coastal residential area with houses along the beach and a lighthouse in the distance.

Breezy Point Beach

8.4/10 (61 reviews)

Stroll this half-mile Chesapeake Bay shoreline where gentle waves meet fossil-hunting adventures. Relax in shaded picnic areas after swimming in the netted area or trying your luck at the 200-foot fishing pier.

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A water park with a large pool, a yellow slide, and a lookout tower.

Chesapeake Beach Water Park

8.2/10 (88 reviews)

This family-friendly water park offers water slides, a lazy river, and pools for all ages. Currently closed for renovations until 2027, it will reopen with modernised facilities and new attractions.

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Chesapeake Beach Railway Museum

8.0/10 (34 reviews)

Housed in the original 1898 railway station, this museum chronicles Chesapeake Beach Resort's golden era. View authentic artefacts and a restored vintage railway car while exploring early 20th century coastal tourism.

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Bruce Gabrielson's Surf Art Gallery and Museum

7.8/10 (19 reviews)

Maryland's only surfing museum showcases Bruce Gabrielson's 50-year collection of historic boards and rare artefacts. Visitors can arrange private tours to see Duke Kahanamoku exhibits and Dale Velzy's shaping equipment.

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Brownies Beach

Why not spend a lazy afternoon at Brownies Beach during your trip to Chesapeake Beach? Stroll along this relaxing area's beaches or simply enjoy its restaurants.

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Learn more about Chesapeake Beach

Stroll the half-mile boardwalk at sunset, where fishing boats return with the day's catch and locals gather for crab feasts. Families splash in the water park's eight slides by day, then hunt for fossilised shark teeth along the Bay's ancient shoreline.

See all hotels in Chesapeake Beach

A coastal town with a marina, residential buildings, and a clear sky.

Top Chesapeake Beach Hotel Reviews

Residence Inn by Marriott Waldorf

10/10 Excellent

"Clean & comfy room. Nice staff."

Rod 'N' Reel Resort

10/10 Excellent

"Great local getaway on the water."

Spark by Hilton Waldorf

10/10 Excellent

"Short stay, but a clean and relaxing stay! Would definitely recommend"

St Michaels Inn

10/10 Excellent

"Late night manager was extremely helpful!"

SpringHill Suites by Marriott Annapolis

10/10 Excellent

"Nice room and bed. Love that they had continental breakfast"

Inn at Perry Cabin

10/10 Excellent

"Outstanding experience in every way. Staff was superior — everyone greeted us by name and was eager to ensure we had everything we needed. Meals at Stars were excellent — and the gorgeous views of the water and property enhanced the dining experience. The lit firepits and comfy seating outside were a welcome retreat in the early evening so we could sit and take in the views. We strolled the grounds via the walking paths and enjoyed the lush gardens and plantings. All in all, an amazing getaway."

More cheap stays in Chesapeake Beach

Econo Lodge Andrews Air Force Base

7851 Malcolm Road Clinton MD

1.542.814 ₫

1.743.380 ₫ total

8 Nov - 9 Nov

includes taxes & fees

SureStay by Best Western Prince Frederick

75 Main St Prince Frederick MD

2.048.786 ₫

2.274.152 ₫ total

11 Oct - 12 Oct

includes taxes & fees

7.4/10 Good! (310 reviews)

St Michaels Inn

1228 S Talbot Street St. Michaels MD

2.310.719 ₫

2.541.790 ₫ total

11 Oct - 12 Oct

includes taxes & fees

8/10 Very good! (1,001 reviews)

Executive Inn And Suites

2901 Crain Highway Upper Marlboro MD

2.289.712 ₫

2.587.375 ₫ total

29 Oct - 30 Oct

includes taxes & fees

Candlewood Suites Annapolis by IHG

1 Womack Dr Annapolis MD

2.416.140 ₫

2.882.741 ₫ total

1 Nov - 2 Nov

includes taxes & fees

Holiday Inn Express Waldorf by IHG

11370 Days Ct Waldorf MD

2.727.900 ₫

3.027.969 ₫ total

20 Oct - 21 Oct

includes taxes & fees

8.2/10 Very good! (1,001 reviews)

Hotels in Chesapeake Beach with star rating

Frequently asked questions

What's the seasonal weather in Chesapeake Beach?

The hottest months are usually July and August, with an average temperature of 24°C, while the coldest months are January and February, with an average of 5°C. Average annual precipitation for Chesapeake Beach is 1331 mm.

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Book Hotels in Chesapeake Beach on Expedia.com

Find hotels in Chesapeake Beach, MD from 1.743.380 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chesapeake Beach

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Chesapeake Beach hotels

1. Rod 'N' Reel Resort

2. Anchored Inn at Hidden Harbour Marina

3. Holiday Inn Express Prince Frederick by IHG

4. Springhill Suites by Marriott Prince Frederick

5. The Inn at Tacaro Estate

6. Knapps Narrows Marina & Inn

7. SureStay by Best Western Prince Frederick

8. The Tilghman Island Inn

9. Inn at Perry Cabin

10. Wylder Tilghman Island

11. The Wildset

12. St Michaels Inn

13. Sonesta ES Suites Annapolis

14. SpringHill Suites by Marriott Annapolis

15. Sandaway Suites & Beach

16. Courtyard Marriott Waldorf

17. Executive Inn And Suites

18. Hilton Garden Inn Solomons

19. Spark by Hilton Waldorf

20. Laurel Grove Inn on the South

Stay near popular Chesapeake Beach attractions

Breezy Point Beach

Chesapeake Beach Water Park

Chesapeake Beach Railway Museum

Bruce Gabrielson's Surf Art Gallery and Museum

Brownies Beach

Learn more about Chesapeake Beach

Top Chesapeake Beach Hotel Reviews

Residence Inn by Marriott Waldorf

Rod 'N' Reel Resort

Spark by Hilton Waldorf

St Michaels Inn

SpringHill Suites by Marriott Annapolis

Inn at Perry Cabin

More cheap stays in Chesapeake Beach

Econo Lodge Andrews Air Force Base

SureStay by Best Western Prince Frederick

St Michaels Inn

Executive Inn And Suites

Candlewood Suites Annapolis by IHG

Holiday Inn Express Waldorf by IHG

Hotels in Chesapeake Beach with star rating

Frequently asked questions

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