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

Holiday Homes in Chesapeake Beach

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Chesapeake Beach holiday homes

Pool

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)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is AU$713
includes taxes & fees
2 Sept - 3 Sept
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Beach nearby

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, (22 reviews)
"Lovely ! "
United States
Ellen B.
The price is AU$614
includes taxes & fees
1 Sept - 2 Sept
Beachside Oasis with Beach Passes & King Suite by A Haven Away
Exterior

3. 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, (51 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is AU$460
includes taxes & fees
11 Aug - 12 Aug
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Coffee/tea maker, fridge, microwave, oven

4. Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
Rose Haven
The price is AU$1,028
includes taxes & fees
5 Aug - 6 Aug
Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
TV, fireplace

5. 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, (4 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is AU$392
includes taxes & fees
18 Aug - 19 Aug
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Exterior

6. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is AU$639
includes taxes & fees
17 Aug - 18 Aug
Plum Point Cottage #17
Outdoor dining

7. 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)
"Such a great house! "
United States
Stephanie V.
The price is AU$1,015
includes taxes & fees
30 Aug - 31 Aug
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Coffee/tea maker, fridge, microwave, oven

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

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (10 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
United States
Diane D.
The price is AU$871
includes taxes & fees
1 Sept - 2 Sept
Renovated Bungalow | Walk to Beach | Dog-Friendly
Terrace/patio

9. 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
The price is AU$496
includes taxes & fees
24 Aug - 25 Aug
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Marina

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

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is AU$674
includes taxes & fees
11 Aug - 12 Aug
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Property grounds

11. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (21 reviews)
"Sophia was an amazing host and the place was exactly as advertised. I couldn't recommend the place enough!"
United States
William N.
The price is AU$516
includes taxes & fees
6 Aug - 7 Aug
Bright and airy waterfront getaway
Dining

12. Chic retreat steps to Water, Piers & Waterfront Park

Chic retreat steps to Water, Piers & Waterfront Park
Deale
10.0 out of 10, Exceptional, (1 review)
"This place is beautiful, and big. The back yard is nice. We played games out back and had a cookout. Walking distance to the pier and a playground. The"
United States
Jamie C.
The price is AU$856
includes taxes & fees
5 Aug - 6 Aug
Chic retreat steps to Water, Piers & Waterfront Park
Interior

13. Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is AU$758
includes taxes & fees
25 Aug - 26 Aug
Annapolis Retreat - 7 mins from downtown Annapolis!
Interior

14. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 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."
United States
Michelle H.
The price is AU$895
includes taxes & fees
10 Aug - 11 Aug
Sunset Cottage - West River Access and Views!
TV, offices

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

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (4 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is AU$999
includes taxes & fees
1 Sept - 2 Sept
Family Home on Mayo Peninsula | Deck | Sleeps 10
Beach

16. Londontowne Home | Beach | 3BR

Londontowne Home | Beach | 3BR
Edgewater
9.4 out of 10, Exceptional, (3 reviews)
"The property was beautiful with plenty of space to have a getaway with friends. The host was super communicative when we had issues with check in. Would highly recommend staying here!"
United States
Sam A.
The price is AU$1,052
includes taxes & fees
9 Aug - 10 Aug
Londontowne Home | Beach | 3BR
TV

17. Londontowne Rancher | 3BR | Near Waterfront

Londontowne Rancher | 3BR | Near Waterfront
Edgewater
7.0 out of 10, Good, (2 reviews)
"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. "
United States
rebekah h.
The price is AU$989
includes taxes & fees
5 Aug - 6 Aug
Londontowne Rancher | 3BR | Near Waterfront
Living area

18. Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
The price is AU$990
includes taxes & fees
12 Aug - 13 Aug
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Outdoor dining

19. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (73 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! "
United States
Whitney M.
The price is AU$1,028
includes taxes & fees
1 Sept - 2 Sept
Charming Annapolis WaterVIEW Home
Dining

20. Beach House w/TheaterRm, GameRm, Outdoor Shwr

Beach House w/TheaterRm, GameRm, Outdoor Shwr
Lusby
10.0 out of 10, Exceptional, (5 reviews)
"This was a fantastic property and location for our stay in Lusby. The home is designed with families in mind, and there was plenty for everyone to do. The house is beautiful and in a quiet, residential community. You can walk to the beach less than two blocks away, and we found dozens of sharks teeth there! Josh was so helpful with advice throughout. We would definitely come again."
United States
Mollie O.
Beach House w/TheaterRm, GameRm, Outdoor Shwr
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

Towneplace Suites by Marriott Clinton at Joint Base Andrews

Towneplace Suites by Marriott Clinton at Joint Base Andrews

10/10 Excellent
"Super"
Visar 2-night trip
Posted 7 hours ago
Towneplace Suites by Marriott Clinton at Joint Base Andrews

Find out more about Chesapeake Beach

Chesapeake Beach Holiday Homes information

Number of reviews
217
Accommodation
404 Holiday Homes
Lowest Price
AU$392
Highest Price
AU$1,052