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
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

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 HK$1,129
HK$3,584 total
includes taxes & fees
7 Sept - 8 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)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is HK$518
HK$2,407 total
includes taxes & fees
7 Sept - 8 Sept
Beachside Oasis with Beach Passes & King Suite by A Haven Away
Outdoor dining

3. 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)
"We enjoyed our stay in North Beach at this lovely residence. It was spacious, clean, nicely furnished and only a few minutes walk to the bay. The beds were so comfortable too!!"
United States
Penny N.
The price is HK$1,105
HK$3,602 total
includes taxes & fees
22 Sept - 23 Sept
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Interior

4. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
The price is HK$1,962
HK$3,738 total
includes taxes & fees
21 Sept - 22 Sept
Rose Haven Coastal Cottage
Exterior

5. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is HK$2,136
HK$3,589 total
includes taxes & fees
17 Sept - 18 Sept
Plum Point Cottage #17
Exterior

6. 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, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is HK$966
HK$2,527 total
includes taxes & fees
16 Sept - 17 Sept
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Smart TV

7. 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
The price is HK$1,757
HK$4,023 total
includes taxes & fees
29 Sept - 30 Sept
3-bedroom house in Deale located on Bay many amenities and great views
Outdoor dining

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
10.0 out of 10, Exceptional, (1 review)
"Jut as described. Easy in easy out. Great for a few days with the family."
United States
Joshua T.
The price is HK$579
HK$1,947 total
includes taxes & fees
21 Sept - 22 Sept
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Interior

9. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Lovely place and neighborhood! "
United States
Marci M.
The price is HK$2,360
HK$4,413 total
includes taxes & fees
9 Sept - 10 Sept
Sunset Cottage - West River Access and Views!
Property grounds

10. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (22 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$1,803
HK$3,000 total
includes taxes & fees
8 Sept - 9 Sept
Bright and airy waterfront getaway
TV, fireplace

11. 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, (7 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is HK$967
HK$2,047 total
includes taxes & fees
16 Sept - 17 Sept
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Beach nearby, sun-loungers, beach towels

12. 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)
"The perfect off-season get-away! "
United States
Pamela B.
The price is HK$1,482
HK$3,665 total
includes taxes & fees
9 Sept - 10 Sept
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Marina

13. 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 HK$1,501
HK$3,990 total
includes taxes & fees
9 Sept - 10 Sept
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
TV, offices

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

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (5 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is HK$2,067
HK$5,771 total
includes taxes & fees
7 Sept - 8 Sept
Family Home on Mayo Peninsula | Deck | Sleeps 10
Interior

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 HK$1,976
HK$4,960 total
includes taxes & fees
13 Sept - 14 Sept
Annapolis Retreat - 7 mins from downtown Annapolis!
Outdoor dining

16. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (76 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 HK$3,183
HK$6,077 total
includes taxes & fees
8 Sept - 9 Sept
Charming Annapolis WaterVIEW Home
Coffee/tea maker, fridge, microwave, oven

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

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (12 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 HK$2,799
HK$6,086 total
includes taxes & fees
4 Oct - 5 Oct
Renovated Bungalow | Walk to Beach | Dog-Friendly
Beach

18. 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 HK$2,258
HK$6,310 total
includes taxes & fees
8 Sept - 9 Sept
Londontowne Home | Beach | 3BR
TV

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 HK$2,258
HK$6,015 total
includes taxes & fees
16 Sept - 17 Sept
Londontowne Rancher | 3BR | Near Waterfront
Living area

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

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
The price is HK$1,932
HK$4,982 total
includes taxes & fees
9 Sept - 10 Sept
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
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

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Outstanding and affordable place to stay in Annapolis Maryland we go to visit our son at the naval academy it is the only place we consider stayong"
Michael 1-night trip
Posted 16 hours ago
Sonesta ES Suites Annapolis

Find out more about Chesapeake Beach

Chesapeake Beach Vacation Homes information

Number of reviews
166
Accommodation
416 Vacation Homes
Lowest Price
HK$1,947
Highest Price
HK$6,310

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