Chesapeake Beach, MD Vacation Homes from ￥41,599

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.

￥72,968 total

includes taxes & fees

Sep 1 - Sep 2

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

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

North Beach

Stephanie V.

￥72,020 total

includes taxes & fees

Aug 31 - Sep 1

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

Stevensville

Dawn G.

￥46,037 total

includes taxes & fees

Aug 30 - Aug 31

5. Plum Point Cottage #17

Huntingtown

￥73,412 total

includes taxes & fees

Aug 29 - Aug 30

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

Shady Side

Joshua T.

￥41,599 total

includes taxes & fees

Aug 30 - Aug 31

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

8. Sunset Cottage - West River Access and Views!

Shady Side

Marci M.

￥89,028 total

includes taxes & fees

Sep 7 - Sep 8

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

Deale

￥81,651 total

includes taxes & fees

Sep 9 - Sep 10

10. Bright and airy waterfront getaway

Benedict

William N.

￥60,195 total

includes taxes & fees

Sep 11 - Sep 12

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

Annapolis

William

￥81,250 total

includes taxes & fees

Aug 30 - Aug 31

Coffee/tea maker, fridge, microwave, oven

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

Edgewater

Diane D.

￥92,962 total

includes taxes & fees

Sep 2 - Sep 3

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

Edgewater

Kristin G.

￥112,772 total

includes taxes & fees

Aug 29 - Aug 30

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

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

17. Charming Annapolis WaterVIEW Home

Arundel on the Bay

Whitney M.

￥110,938 total

includes taxes & fees

Sep 21 - Sep 22

18. Sunset Breezes - quiet waterfront retreat

Dorchester County

John C.

￥84,799 total

includes taxes & fees

Sep 27 - Sep 28

19. Londontowne Home | Beach | 3BR

Edgewater

Sam A.

￥123,354 total

includes taxes & fees

Aug 31 - Sep 1

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

Towneplace Suites by Marriott Clinton at Joint Base Andrews

10/10 Excellent

"The room was clean, staff were nice, and there was a good variety of food for breakfast."

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	￥41,599
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