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

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Chesapeake Beach holiday homes

Pool

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 HK$2,186
HK$4,889 total
includes taxes & fees
14 Jul - 15 Jul
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Exterior

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, (47 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 HK$684
HK$2,088 total
includes taxes & fees
12 Jul - 13 Jul
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
TV, fireplace

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, (1 review)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is HK$882
HK$1,948 total
includes taxes & fees
14 Jul - 15 Jul
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Fridge, microwave, oven, stovetop

Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (8 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is HK$1,841
HK$4,806 total
includes taxes & fees
16 Jul - 17 Jul
Renovated Bungalow | Walk to Beach | Dog-Friendly
Beach nearby

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)
"Although the house itself could use some maintenance, our stay was very comfortable. The rooms were spacious and it had all the amenities we needed. "
United States
Donovan B.
The price is HK$1,007
HK$3,032 total
includes taxes & fees
12 Jul - 13 Jul
Beachside Oasis with Beach Passes & King Suite by A Haven Away
Terrace/patio

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 HK$797
HK$2,204 total
includes taxes & fees
16 Jul - 17 Jul
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Property grounds

Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.6 out of 10, Exceptional, (20 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 HK$1,763
HK$2,949 total
includes taxes & fees
12 Jul - 13 Jul
Bright and airy waterfront getaway
Interior

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 HK$1,920
HK$4,904 total
includes taxes & fees
22 Jul - 23 Jul
Annapolis Retreat - 7 mins from downtown Annapolis!
TV, offices

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 HK$1,896
HK$5,431 total
includes taxes & fees
13 Jul - 14 Jul
Family Home on Mayo Peninsula | Deck | Sleeps 10
Beach nearby, sun-loungers, beach towels

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, (16 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is HK$2,786
HK$5,418 total
includes taxes & fees
13 Jul - 14 Jul
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Dining

Beach House w/TheaterRm, GameRm, Outdoor Shwr

Beach House w/TheaterRm, GameRm, Outdoor Shwr
Lusby
10.0 out of 10, Exceptional, (4 reviews)
"It was a beutiful spot!"
United States
Isaac T.
Beach House w/TheaterRm, GameRm, Outdoor Shwr
Fridge, microwave, oven, stovetop

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
Rose Haven
The price is HK$2,356
HK$3,070 total
includes taxes & fees
12 Jul - 13 Jul
Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
Exterior

Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is HK$2,135
HK$3,587 total
includes taxes & fees
12 Jul - 13 Jul
Plum Point Cottage #17
Beach

Londontowne Home | Beach | 3BR

Londontowne Home | Beach | 3BR
Edgewater
10.0 out of 10, Exceptional, (2 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 HK$1,896
HK$5,789 total
includes taxes & fees
12 Jul - 13 Jul
Londontowne Home | Beach | 3BR
Outdoor dining

Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (44 reviews)
"Comfortable, roomy, awesome views!"
United States
John C.
The price is HK$3,047
HK$3,839 total
includes taxes & fees
13 Jul - 14 Jul
Sunset Breezes - quiet waterfront retreat
Property grounds

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Lusby
9.6 out of 10, Exceptional, (13 reviews)
"The home was lovely and very quiet location. My sister and I were caring for our mom after discharge from hospital and it was very convenient. Would stay there again. "
United States
Tova A.
The price is HK$3,620
HK$6,711 total
includes taxes & fees
22 Jul - 23 Jul
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Smart TV

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, (15 reviews)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
The price is HK$3,056
HK$5,391 total
includes taxes & fees
13 Jul - 14 Jul
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Outdoor dining

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (73 reviews)
"We enjoyed our stay! The property has a beautiful view of the bay. It was a perfect set up for our family of four. "
United States
Jen M.
The price is HK$3,761
HK$6,825 total
includes taxes & fees
13 Jul - 14 Jul
Charming Annapolis WaterVIEW Home
Interior

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home for a girls weekend away. The view is spectacular, host was communicative, and lots of thoughtful small touches throughout the home and the experience. Thank you for a wonderful stay! "
United States
Katie K.
The price is HK$2,876
HK$5,079 total
includes taxes & fees
4 Aug - 5 Aug
Sunset Cottage - West River Access and Views!
Smart TV, fireplace, computer monitors, printers

Tranquil Modern Farmhouse

Tranquil Modern Farmhouse
Waldorf
9.2 out of 10, Wonderful, (10 reviews)
"The host communicated immediately if needed. The house has practically everything a family needs. Fully stocked kitchen for meal prep, wonderful towels and memory foam beds. A wonderful rental."
United States
Kymme
Tranquil Modern Farmhouse
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

Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"Great stay clean room and balcony"
Michael 1-night trip
Posted 1 hour ago
Rod 'N' Reel Resort

Find out more about Chesapeake Beach

Chesapeake Beach Vacation Homes information

Number of reviews
246
Accommodation
416 Vacation Homes
Lowest Price
HK$1,948
Highest Price
HK$6,825

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