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

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Very clean and nice property"
United States
Ben W.
Family Beach House: Spacious Deck, Grill & Views

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, (25 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is AED 323
AED 1,137 total
includes taxes & fees
16 Nov - 17 Nov
Beachside Oasis with Beach Passes & King Suite by A Haven Away

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

The Cozy Crab- Your Charming Haven in Lovely North Beach!
North Beach
9.6 out of 10, Exceptional, (30 reviews)
"Wonderful place to visit "
United States
James L.
The price is AED 533
AED 1,145 total
includes taxes & fees
16 Nov - 17 Nov
The Cozy Crab- Your Charming Haven in Lovely North Beach!

4. 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, (41 reviews)
"This property and host were excellent. Property was as advertised. Lovely, clean, quiet and comfortable. Owner was super responsive and check in and check out was easy. 100% recommend."
United States
Sarah
The price is AED 405
AED 1,446 total
includes taxes & fees
16 Nov - 17 Nov
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

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

3-bedroom house in Deale located on Bay many amenities and great views
Deale
10.0 out of 10, Exceptional, (2 reviews)
"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...
United States
Amelia
The price is AED 661
AED 1,604 total
includes taxes & fees
16 Nov - 17 Nov
3-bedroom house in Deale located on Bay many amenities and great views

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

Relax on Kent Island in 4 Bedroom Home w/Waterview
Stevensville
9.8 out of 10, Exceptional, (57 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
The price is AED 375
AED 1,128 total
includes taxes & fees
23 Nov - 24 Nov
Relax on Kent Island in 4 Bedroom Home w/Waterview

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

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Prince Frederick
9.2 out of 10, Wonderful, (12 reviews)
"A great place to crash and explore the area."
United States
Sean B.
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

8. 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
9.4 out of 10, Exceptional, (3 reviews)
"the house was clean and fully stocked with all linens. there are some staples in the refrigerator and cabinets. All cookware and eatery are provided. there is only one grocery store in the area, so plan ahead. Fast food is not readily available. Nick responded quickly and thoroughly to all messages, that was great. It's a quiet neighborhood. It was the perfect place for a family and pet. we will return"
United States
Jenny A.
The price is AED 628
AED 1,323 total
includes taxes & fees
14 Dec - 15 Dec
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

9. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
9.8 out of 10, Exceptional, (6 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 AED 801
AED 1,645 total
includes taxes & fees
15 Dec - 16 Dec
Sunset Cottage - West River Access and Views!

10. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (26 reviews)
"Amazing host and home, great view with the water right there, and short drive to any shopping needs. It was the serene getaway I needed to recharge from city life and corporate burnout."
United States
George
The price is AED 845
AED 1,343 total
includes taxes & fees
16 Nov - 17 Nov
Bright and airy waterfront getaway

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

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (14 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 AED 707
AED 1,958 total
includes taxes & fees
16 Nov - 17 Nov
Renovated Bungalow | Walk to Beach | Dog-Friendly

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

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
9.8 out of 10, Exceptional, (7 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is AED 889
AED 2,471 total
includes taxes & fees
16 Nov - 17 Nov
Family Home on Mayo Peninsula | Deck | Sleeps 10

13. 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, (19 reviews)
"Super clean, well furnished and in a nice quiet neighborhood close to downtown Annapolis. Great place to stay!"
United States
Ryan C.
The price is AED 760
AED 1,734 total
includes taxes & fees
16 Nov - 17 Nov
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

14. 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, (9 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is AED 522
AED 1,033 total
includes taxes & fees
16 Nov - 17 Nov
3-bedroom house in soothing Saint Leonard with AC for relaxing stays

15. 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 AED 771
AED 1,951 total
includes taxes & fees
30 Nov - 1 Dec
Annapolis Retreat - 7 mins from downtown Annapolis!

16. 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, (17 reviews)
"We had a lovely weekend at this waterfront home. We did lots of kayaking and also crabbed and biked. The house was very nicely decorated and had everything we needed. The place was peaceful and restful- highly recommend for a getaway"
United States
Virginia V.
The price is AED 935
AED 1,708 total
includes taxes & fees
19 Nov - 20 Nov
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

17. 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 AED 889
AED 2,601 total
includes taxes & fees
16 Nov - 17 Nov
Londontowne Home | Beach | 3BR

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

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (75 reviews)
"Great stay, exactly as advertised, Donna was great!"
United States
Sam C.
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

19. 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 AED 970
AED 2,450 total
includes taxes & fees
30 Nov - 1 Dec
Londontowne Rancher | 3BR | Near Waterfront

20. Tranquil Modern Farmhouse

Tranquil Modern Farmhouse
Waldorf
9.2 out of 10, Wonderful, (10 reviews)
"Overall I had a wonderful stay... however I wish it was booked for a summertime day... the brand new pool looked very appealing & I wish I couldve enjoyed using it. Will have to try & stay again during the summer for a nice pool day!"
United States
Jay W.
The price is AED 1,500
AED 2,683 total
includes taxes & fees
16 Nov - 17 Nov
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