Chesapeake Beach Holiday Homes from €259: Search Top 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 holiday homes

A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

1. The Cozy Crab- Your Charming Haven in Lovely North Beach!

North Beach

James L.

includes taxes & fees

28 Oct - 29 Oct

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

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

North Beach

Johanna S.

includes taxes & fees

1 Nov - 2 Nov

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

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

North Beach

Sarah

includes taxes & fees

30 Oct - 31 Oct

A dining area with a wooden spiral staircase, a round table with chairs, a chandelier, and a clock on the wall.

4. Rose Haven Coastal Cottage

North Beach

Sodbileg

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

5. 3-bedroom house in Deale located on Bay many amenities and great views

Deale

"Everything at this location was as shown on the listing and it was very clean. We were very satisfied with all elements of this stay. We were there for a weekend and did not use the place heavily, but it suited our needs. It's a quiet location. They had all the major points covered. The only negative comment I have is that the water out of the tap was smelly. I suggest bringing a couple of bottles of water and not drinking the water out of the taps. This is obviously a well maintained home...

Amelia

includes taxes & fees

28 Oct - 29 Oct

A spacious living room with a grey sectional sofa, a round wooden coffee table, and a patterned rug.

6. Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Prince Frederick

Sean B.

includes taxes & fees

2 Nov - 3 Nov

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

7. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

Shady Side

David S.

includes taxes & fees

28 Oct - 29 Oct

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

8. Sunset Cottage - West River Access and Views!

Shady Side

Michelle H.

includes taxes & fees

10 Nov - 11 Nov

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

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

Stevensville

Anthony P.

includes taxes & fees

1 Nov - 2 Nov

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

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

Edgewater

Diane D.

includes taxes & fees

28 Oct - 29 Oct

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

11. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

Saint Leonard

Nancy P.

includes taxes & fees

2 Nov - 3 Nov

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

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

Edgewater

Kristin G.

includes taxes & fees

28 Oct - 29 Oct

A beach with chairs and a pier in the background.

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

Arundel on the Bay

Ryan C.

includes taxes & fees

3 Nov - 4 Nov

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

14. Bright and airy waterfront getaway

Benedict

George

includes taxes & fees

2 Nov - 3 Nov

A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

15. Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere

Paul C.

includes taxes & fees

10 Nov - 11 Nov

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

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

Cambridge

Jill C.

includes taxes & fees

28 Oct - 29 Oct

A calm lake with a sandy shore, surrounded by trees and houses.

17. Londontowne Home | Beach | 3BR

Edgewater

Sam A.

includes taxes & fees

28 Oct - 29 Oct

A spacious living room with a sofa set, a coffee table, and a chair. There is a painting on the wall and a window providing natural light.

18. Londontowne Rancher | 3BR | Near Waterfront

Edgewater

"The house was much smaller then it originally appeared to be in the listing photos and what they had available was the bare minimum. The neighborhood was rowdy and there was screaming late into the night. The shower also sprayed water all over the floor and caused a massive puddle. The house was overall nice and clean but not worth the price that it was listed for. A hotel would have much better accommodated our needs. "

rebekah h.

includes taxes & fees

2 Nov - 3 Nov

Three birds perched on a wooden structure by the water.

19. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Stevensville

barbara s.

includes taxes & fees

28 Oct - 29 Oct

A modern living room with a grey sofa, a dining table with chairs, and large windows with autumn foliage views.

20. Tranquil Modern Farmhouse

Waldorf

Jay W.

includes taxes & fees

2 Nov - 3 Nov

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Top Chesapeake Beach Hotel Reviews

Residence Inn by Marriott Waldorf

8/10 Good

"Didn't like the one hour wait to get the room...it was well after 5 to be assigned a room....the television in the common area of the room didn't work and staff was notified but no one came to fix it. The fire alarm went off early am and had to get up and the rowdy guess...well the police was there for them several times throughout the night."

Springhill Suites by Marriott Prince Frederick

10/10 Excellent

"The only think I would change is the coffee to one of the more modern automatic types and maybe add flavored creamer. The room coffee maker is older and they only provide a powder packet. I brought my own but the hotel was nice and I would sty again."

Hilton Garden Inn Solomons

8/10 Good

"The room was clean and away from the elevators with no issues for the specific room. The only reason this is not a 5 star review is that there is no accommodation for customers / guests that need a nightstand on both sides of the bed. In our situation both customers have a CPAP machine. The reservation was for 2 guests and the room was a queen bed and upon arrival we had to decide who was going to sleep without their CPAP machine because the room has no bedside table or electrical outlets on the outer edge of the bed. Regardless of the medical need when will Hotels learn that both sides of the bed need a place to hold their CPAP or book or tea."

Find out more about Chesapeake Beach

Chesapeake Beach Holiday Homes information

Number of reviews	285
Accommodation	410 Holiday Homes
Lowest Price	€259
Highest Price	€1,169

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Check prices for these dates

Our top choices for Chesapeake Beach holiday homes

1. The Cozy Crab- Your Charming Haven in Lovely North Beach!

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