Chesapeake Beach Holiday House Rentals from AU$363: Search Holiday Homes

Chesapeake Beach Holiday Homes
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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 holiday homes

1. Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Chesapeak beach

9.2 out of 10, Wonderful, (7 reviews)

9.2/10

Wonderful

(7 reviews)

"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."

Bryan P.

The price is AU$623

AU$623

includes taxes & fees

23 Sept - 24 Sept

Beach Front, Bay View, Fishing, chesapeake,Family Getaway

A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

A shelf with various potted plants and storage boxes.

A living room with a blue sofa, a round mirror, and a coffee table.

A dining table set with pink bowls and glasses, surrounded by chairs, with a large plant and a window in the background.

2. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away

North Beach

10.0 out of 10, Exceptional, (23 reviews)

10/10

Exceptional

(23 reviews)

"Cute, family friendly home. Had everything we needed for a comfortable stay."

Johanna S.

The price is AU$504

AU$504

includes taxes & fees

28 Sept - 29 Sept

Beachside Oasis with Beach Passes & King Suite by A Haven Away

An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

A pier with a wooden walkway, a sandy beach, and a dog on a leash.

A dining area with a wooden table and chairs, a patterned rug, and a staircase leading to another level.

A two-story house with a porch, a white picket fence, and blooming pink trees.

3. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

North Beach

10.0 out of 10, Exceptional, (37 reviews)

10/10

Exceptional

(37 reviews)

"We enjoyed our stay in North Beach at this lovely residence. It was spacious, clean, nicely furnished and only a few minutes walk to the bay. The beds were so comfortable too!!"

Penny N.

The price is AU$642

AU$642

includes taxes & fees

28 Sept - 29 Sept

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

A laundry room with a washing machine and dryer, wooden cabinets above, and a shelf with a bottle.

A living room with a grey sofa, a flat-screen TV, a white console table, and a potted plant.

A room with a wooden floor, a white dresser, a window with blinds, and a view of a balcony with greenery.

A sign for Herrington Harbour with a clear sky and parked cars in the background.

4. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage

North Beach

"Great place to stay! Location was nice and close to water views. House was charming and CLEAN. Owners went above and beyond to make the stay welcoming and convenient. Price was reasonable until additional Vrbo fees were added."

Sharon t.

The price is AU$598

AU$598

includes taxes & fees

23 Sept - 24 Sept

Rose Haven Coastal Cottage

A single-story house with a gabled roof, a front porch, and a small front yard with a flag.

A living room with a sofa, TV, and a patterned rug.

A compact kitchen with a sink, a window, and a built-in shelf with dishes.

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

5. Plum Point Cottage #17

Plum Point Cottage #17

Huntingtown

The price is AU$643

AU$643

includes taxes & fees

23 Sept - 24 Sept

Plum Point Cottage #17

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

A park with swings, a bench, and a view of a body of water.

A kitchen with a stove, sink, and dining area with chairs and a table.

A dining area with a table, chairs, a chandelier, and a view through a window.

6. 3-bedroom house in Deale located on Bay many amenities and great views

3-bedroom house in Deale located on Bay many amenities and great views

Deale

The price is AU$704

AU$704

includes taxes & fees

30 Sept - 1 Oct

3-bedroom house in Deale located on Bay many amenities and great views

A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

A spacious living area with a white sofa, a dining table, and a kitchen with white cabinets.

A modern kitchen with white cabinetry, a built-in oven, a microwave, and a coffee maker.

A bedroom with a bed, a ceiling fan, a window, and a view of the outdoors.

7. WATERFRONT!! HOT TUB 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Cambridge

10.0 out of 10, Exceptional, (16 reviews)

10/10

Exceptional

(16 reviews)

"very serene, peaceful home on the bay! Amazing getaway! "

Jill C.

The price is AU$859

AU$859

includes taxes & fees

23 Sept - 24 Sept

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

A modern kitchen with a large window, a dishwasher, and a ceiling fan.

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

A calm lake with a wooden dock extending into the water, surrounded by trees and buildings in the background.

A spacious living room with a fireplace, a round wooden dining table with chairs, a sofa, and a large window offering a view of a lake.

8. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!

Shady Side

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."

Michelle H.

The price is AU$803

AU$803

includes taxes & fees

6 Oct - 7 Oct

Sunset Cottage - West River Access and Views!

A lakeside view with chairs and a table, a rainbow, and trees.

A compact kitchen with white cabinets, a stainless steel oven, a black stove, and a sink.

A living room with a black leather sofa, a brown armchair, a flat-screen TV, a tall floor-standing speaker, and a sliding glass door leading to a balcony with a view of a body of water.

A compact kitchen with a white countertop, a stainless steel refrigerator, and a dining area with a table and chairs.

9. Bright and airy waterfront getaway

Bright and airy waterfront getaway

Benedict

9.8 out of 10, Exceptional, (24 reviews)

9.8/10

Exceptional

(24 reviews)

"Amazing host and home, great view with the water right there, and short drive to any shopping needs. It was the serene getaway I needed to recharge from city life and corporate burnout."

George

The price is AU$484

AU$484

includes taxes & fees

23 Sept - 24 Sept

Bright and airy waterfront getaway

A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

A spacious living room with a ceiling fan, a staircase, and a view of the outdoors.

A modern kitchen with wooden cabinets, stainless steel appliances, and a large island with a sink.

An aerial view of a marina with numerous boats docked, surrounded by residential and commercial buildings.

10. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Stevensville

9.8 out of 10, Exceptional, (55 reviews)

9.8/10

Exceptional

(55 reviews)

"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."

Dawn G.

The price is AU$402

AU$402

includes taxes & fees

23 Sept - 24 Sept

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

A beach with chairs and a pier in the background.

An aerial view of a marina with boats docked, surrounded by residential buildings and lush greenery.

A restaurant interior with tables, chairs, and a green dinosaur-shaped salt shaker.

A living room with a sofa, coffee table, and a ceiling fan. There is a staircase with a railing leading to an upper level.

11. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Arundel on the Bay

9.6 out of 10, Exceptional, (19 reviews)

9.6/10

Exceptional

(19 reviews)

"Almost everything that you might need is provided, but if not there is shopping close by. Hot tub was nice. Very clean home."

Sharon Z.

The price is AU$646

AU$646

includes taxes & fees

23 Sept - 24 Sept

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

A deck with outdoor furniture, a red door, and a house with windows.

A hallway with a framed map on the left, a door leading to a bedroom with a patterned bedspread, and a light fixture on the ceiling.

A bedroom with a bed, a nightstand, a lamp, a guitar, a window with curtains, and a ceiling fan.

A modern kitchen with wooden cabinets, stainless steel appliances, a round dining table with stools, and a ceiling fan.

12. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

Shady Side

9.0 out of 10, Wonderful, (2 reviews)

9.0/10

Wonderful

(2 reviews)

"The location was spectacular, the host was communicative, and we had a great time! A beautiful and clean home with everything needed to make a trip a success. One small issue with some needed essentials meant a quick run to the store (TP!) but otherwise a great location, great stay, and would stay again!"

David S.

The price is AU$540

AU$540

includes taxes & fees

30 Sept - 1 Oct

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

A single-story house with a front porch, a small window above the door, and a front yard with a bush.

A wooden staircase with a white console table beside it, a window with blinds, and decorative wall hangings.

A room with three large windows, wicker furniture, a small table with a plant, and a patterned rug.

13. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

3-bedroom house in soothing Saint Leonard with AC for relaxing stays

Saint Leonard

10.0 out of 10, Exceptional, (8 reviews)

10/10

Exceptional

(8 reviews)

"Loved the location and the hosts' kindness and care."

Nancy P.

The price is AU$363

AU$363

includes taxes & fees

23 Sept - 24 Sept

3-bedroom house in soothing Saint Leonard with AC for relaxing stays

A covered outdoor area with a view of the water, a wicker chair, a table with a plant, and a sofa with pillows.

A modern kitchen with a central island, stainless steel appliances, wooden cabinets, and a large window.

A bedroom with a large bed, a view of the sea, and a wooden window frame.

A sandy beach with a calm water body, wooden piers, and a distant shoreline with buildings and trees.

14. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home

Arundel on the Bay

9.8 out of 10, Exceptional, (78 reviews)

9.8/10

Exceptional

(78 reviews)

"Our family had a wonderful stay at your beautiful home! The views are to die for! House was very clean with all equipment and kitchen appliances all available! Very happy with our stay! "

Whitney M.

The price is AU$1,081

AU$1,081

includes taxes & fees

28 Sept - 29 Sept

Charming Annapolis WaterVIEW Home

A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

A living room with a sofa, ottoman, and a coffee table. There is a ladder leaning against the wall and a door leading to a balcony.

A kitchen with white cabinets, a granite countertop, and three stools.

A calm waterfront with docked boats, a clear sky, and houses in the background.

15. Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly

Edgewater

9.8 out of 10, Exceptional, (13 reviews)

9.8/10

Exceptional

(13 reviews)

"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "

Diane D.

The price is AU$876

AU$876

includes taxes & fees

20 Oct - 21 Oct

Renovated Bungalow | Walk to Beach | Dog-Friendly

A covered outdoor dining area with a table and chairs, overlooking a body of water and trees.

A modern kitchen with white cabinets, a marble island, and wooden bar stools.

A dining area with a table and chairs, a bookshelf, and a view of the outdoors.

A multi-story building with a central staircase, outdoor seating area, and potted plants.

16. Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat

Dorchester County

10.0 out of 10, Exceptional, (45 reviews)

10/10

Exceptional

(45 reviews)

"Comfortable, roomy, awesome views!"

John C.

The price is AU$668

AU$668

includes taxes & fees

27 Sept - 28 Sept

Sunset Breezes - quiet waterfront retreat

A spacious cabin with a wooden interior, a fireplace, a television, and a dining area.

A cozy cabin interior with a wooden ceiling, a dining area with chairs, a bicycle, and a bookshelf with books.

A rocky beach with clear blue water and a distant boat.

A wooden deck with rocking chairs, a table with a plant, and a dining area with chairs and a table.

17. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub

Lusby

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Very much enjoyed our stay. The host was very kind and responsive and the property very comfortable. Hot tub and quiet location were great!"

Tanya S.

The price is AU$1,650

AU$1,650

includes taxes & fees

17 Oct - 18 Oct

Lakefront Cabin Near Solomons Island w/ Hot Tub

A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

A modern living room with a sofa, a coffee table with flowers, a kitchen area with a refrigerator, and a dining table with chairs.

A room with a window, two chairs, a desk, and a lamp.

A house with a red door, a small front yard with a pathway, and a bush with pink flowers.

18. Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10

Edgewater

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"House was clean and comfortable. Great layout. "

Kristin G.

The price is AU$1,062

AU$1,062

includes taxes & fees

6 Oct - 7 Oct

Family Home on Mayo Peninsula | Deck | Sleeps 10

A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

A dining area with a white table, a vase of flowers, and a staircase.

A kitchen with white cabinets, a central island with stools, a dining area with a table and chairs, and a view through the glass doors.

A spacious living room with a large window, a ceiling fan, and a sofa.

19. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Stevensville

10.0 out of 10, Exceptional, (43 reviews)

10/10

Exceptional

(43 reviews)

"Fantastic, property, location and positive interaction with owner."

David R.

The price is AU$1,981

AU$1,981

includes taxes & fees

23 Sept - 24 Sept

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

A two-story house with a red roof, a brick chimney, and a small porch.

A hallway with wooden flooring, a colorful rug, a potted plant, a wall-mounted wooden art piece, and a door leading to another room.

A modern kitchen with a stainless steel refrigerator, a sink with a faucet, wooden cabinets, and a patterned rug.

A spacious living room with a sectional sofa, a fireplace, and a sliding glass door leading to a balcony.

20. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

Stevensville

7.6 out of 10, Good, (4 reviews)

7.6/10

Good

(4 reviews)

"The place was very clean and Host was ok the shopping was six miles away, not in walking distance, we had no pets on this trip."

Anonymous traveller

The price is AU$1,414

AU$1,414

includes taxes & fees

23 Sept - 24 Sept

5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

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 Chesapeake Beach Hotel Reviews

Candlewood Suites Annapolis by IHG

8/10 Good

"Couldn’t figure out how to use cook top. Turned the knob on wall and appeared to give power to cook top, but as soon as we tried to touch hot plate buttons it switched off. No instructions."

Colleen 2-night trip

Posted 8 hours ago

Candlewood Suites Annapolis by IHG

Rod 'N' Reel Resort

10/10 Excellent

"Top notch resort with lots to offer. We willl definitely go back!"

Nancy 2-night trip

Posted 1 day ago

Rod 'N' Reel Resort

Inn at Perry Cabin

10/10 Excellent

"Fantastic place; one of those that you don’t want to leave the property until the very sad time to go. Lovely staff, all of them, amazing food."

Virgilio 1-night trip

Posted 1 day ago

Inn at Perry Cabin

Springhill Suites by Marriott Prince Frederick

8/10 Good

"The property was ok. The room was clean and served its purpose. They do offer free breakfast. I would not call what I had breakfast. Cold eggs and a stale muffin. So for the price you it was not worth it."

David 1-night trip

Posted 1 day ago

Springhill Suites by Marriott Prince Frederick

Executive Inn And Suites

10/10 Excellent

"It clean an queit"

Micheal 1-night trip

Posted 2 days ago

Executive Inn And Suites

SpringHill Suites by Marriott Annapolis

10/10 Excellent

"Breakfast and pool were awesome"

FRANK 3-night trip

Posted 3 days ago

SpringHill Suites by Marriott Annapolis

Hilton Garden Inn Solomons

8/10 Good

"No Continental Breakfast ! No 24/7 Coffee Bar ! And Pay for Parking is No Way to greet your customers !!"

Kathy 3-night trip

Posted 3 days ago

Hilton Garden Inn Solomons

Holiday Inn Express Waldorf by IHG

10/10 Excellent

"Perfect! No complaints"

Valerie 1-night trip

Posted 7 days ago

Holiday Inn Express Waldorf by IHG

Find out more about Chesapeake Beach

Chesapeake Beach Holiday Homes information

Number of reviews	289
Accommodation	404 Holiday Homes
Lowest Price	AU$363
Highest Price	AU$1,981

Explore a world of travel with Expedia

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Book Holiday Homes in Chesapeake Beach on Expedia.com

Holiday Homes in Chesapeake Beach

Check prices for these dates

Our top choices for Chesapeake Beach holiday homes

1. Beach Front, Bay View, Fishing, chesapeake,Family Getaway

2. Beachside Oasis with Beach Passes & King Suite by A Haven Away

3. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

4. Rose Haven Coastal Cottage

5. Plum Point Cottage #17

6. 3-bedroom house in Deale located on Bay many amenities and great views

7. WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

8. Sunset Cottage - West River Access and Views!

9. Bright and airy waterfront getaway

10. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

11. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

12. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

13. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

14. Charming Annapolis WaterVIEW Home

15. Renovated Bungalow | Walk to Beach | Dog-Friendly

16. Sunset Breezes - quiet waterfront retreat

17. Lakefront Cabin Near Solomons Island w/ Hot Tub

18. Family Home on Mayo Peninsula | Deck | Sleeps 10

19. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

20. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

Find holiday rentals that suit your style

Top Chesapeake Beach Hotel Reviews

Candlewood Suites Annapolis by IHG

Find out more about Chesapeake Beach

Chesapeake Beach Holiday Homes information

Explore a world of travel with Expedia

7. WATERFRONT!! HOT TUB 3 bedroom Oasis on 2+ acres - Sleeps 8