Chesapeake Beach, MD Vacation Homes from ￥39,804

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 vacation homes

1. Family Beach House: Spacious Deck, Grill & Views

Chesapeak beach

Bryan P.

￥73,009 total

includes taxes & fees

Sep 1 - Sep 2

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

Ellen B.

￥57,294 total

includes taxes & fees

Aug 30 - Aug 31

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

Stephanie V.

￥72,061 total

includes taxes & fees

Aug 30 - Aug 31

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

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

Stevensville

Dawn G.

￥43,744 total

includes taxes & fees

Aug 30 - Aug 31

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

5. Plum Point Cottage #17

Huntingtown

￥73,919 total

includes taxes & fees

Sep 25 - Sep 26

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

6. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

Shady Side

Joshua T.

￥39,804 total

includes taxes & fees

Aug 31 - Sep 1

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

7. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

Saint Leonard

Nancy P.

￥41,639 total

includes taxes & fees

Sep 2 - Sep 3

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

8. Sunset Cottage - West River Access and Views!

Shady Side

Marci M.

￥85,229 total

includes taxes & fees

Sep 8 - Sep 9

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

9. 3-bedroom house in Deale located on Bay many amenities and great views

Deale

￥81,697 total

includes taxes & fees

Sep 9 - Sep 10

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

10. Bright and airy waterfront getaway

Benedict

William N.

￥57,434 total

includes taxes & fees

Aug 30 - Aug 31

A waterfront town with historic buildings, a dock with boats, and a prominent white dome structure in the background.

11. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Annapolis

William

￥81,250 total

includes taxes & fees

Sep 9 - Sep 10

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

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

Edgewater

￥92,962 total

includes taxes & fees

Sep 2 - Sep 3

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

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

Edgewater

Kristin G.

￥112,836 total

includes taxes & fees

Aug 29 - Aug 30

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

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

Cambridge

Jill C.

￥94,739 total

includes taxes & fees

Sep 2 - Sep 3

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.

￥96,594 total

includes taxes & fees

Sep 9 - Sep 10

16. 3-bedroom house in serene Lusby with refreshing AC, heat, outdoor fireplace

Lusby

￥64,308 total

includes taxes & fees

Sep 23 - Sep 24

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

17. Charming Annapolis WaterVIEW Home

Arundel on the Bay

Whitney M.

￥113,363 total

includes taxes & fees

Sep 1 - Sep 2

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

18. Sunset Breezes - quiet waterfront retreat

Dorchester County

John C.

￥84,799 total

includes taxes & fees

Sep 27 - Sep 28

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

19. Londontowne Home | Beach | 3BR

Edgewater

Sam A.

￥123,354 total

includes taxes & fees

Aug 31 - Sep 1

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.

20. 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.

￥112,836 total

includes taxes & fees

Aug 30 - Aug 31

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Top Chesapeake Beach Hotel Reviews

St Michaels Inn

8/10 Good

"The rooms, though dated, are clean. I did bring to the attention of the manager that the towel bar in my bathroom was coming off. The handrail to walk down the steps into the pool was also loose, which I think is a safety hazard. The manager acknowledged he knew about it, but despite tons of cosmetic work being done outside, which was a bit inconvenient, the hand rail was not tightened Staff was nice, especially Tamia at the front desk and Helena in the breakfast room. The rooms are spacious and the A/C works fine!"

SpringHill Suites by Marriott Annapolis

8/10 Good

"The property, including the room, was clean. The staff was friendly and attentive. Breakfast was okay (continental) and staff will accommodate if needed for dietary restrictions. The dining area is small but does have tables with seats/high chairs to sit. There are two computers, a laundry room, ice room, and an exercise room. Based on a window peep, there is a disabled accessible pool/jaccuzi, but it was closed for maintenance during our stay and reopened on our check-out day so we didn't get to use it. One of the issues we experienced was getting a parking citation everyday even though we paid at check-in. The desk clerk assured we wouldn't be towed and the company would be notified by email regarding the error, but it still was frustrating. Parking is $9.50/day via third party scan code or text to pay through a website. The second issue was our microwave did not work properly but we used the common one downstairs. The final issue was our mini-fridge was loud if not closed a certain way yet, it did work to keep our items cold. The location is quiet and felt safe. You have to use your key card to enter the lobby after 12am. Overall, we would choose to book this hotel again if available in the future."

Springhill Suites by Marriott Prince Frederick

10/10 Excellent

"I loved the hotel however, the bathroom shower curtain bar was leaning forward and needs to be adjusted. Water from the shower kept getting all over the floor and we had to use the towels to soak up the floor water. So I called and they never brought new ones. I went to the front desk and they never brought new ones. On my way out I mentioned it and got points on my Marriott account. Did not do me any good. Thank goodness we had access to the pool towels. I gave a low rating on maintenance because the wallpaper seams in the bathrooms are starting to separate and look cruddy. The bed was comfortable and the food was decent. Staff are friendly except the guy who swore because I asked him where the ice machine was. All else good."

Find out more about Chesapeake Beach

Chesapeake Beach Vacation Homes information

Number of reviews	210
Accommodation	409 Vacation Homes
Lowest Price	￥39,804
Highest Price	￥123,354

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chesapeake Beach vacation homes

1. Family Beach House: Spacious Deck, Grill & Views

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