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
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Chesapeake Beach holiday homes

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 NZ$816
includes taxes & fees
8 Sept - 9 Sept
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

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 NZ$540
includes taxes & fees
26 Aug - 27 Aug
Beachside Oasis with Beach Passes & King Suite by A Haven Away
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

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)
"Such a great house! "
United States
Stephanie V.
The price is NZ$801
includes taxes & fees
8 Sept - 9 Sept
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A single-story house with a gabled roof, a front porch, and a small front yard with a flag.

4. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is NZ$768
includes taxes & fees
25 Aug - 26 Aug
Plum Point Cottage #17
A deck with outdoor furniture, a red door, and a house with siding.

5. 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 NZ$588
includes taxes & fees
30 Aug - 31 Aug
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

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 NZ$560
includes taxes & fees
31 Aug - 1 Sept
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

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 NZ$923
includes taxes & fees
8 Sept - 9 Sept
3-bedroom house in Deale located on Bay many amenities and great views
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

8. 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 NZ$861
includes taxes & fees
9 Sept - 10 Sept
Sunset Cottage - West River Access and Views!
A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

9. 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, (6 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is NZ$441
includes taxes & fees
21 Sept - 22 Sept
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A lakeside view with chairs and a table, a rainbow, and trees.

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 NZ$583
includes taxes & fees
24 Aug - 25 Aug
Bright and airy waterfront getaway
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

11. 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 NZ$967
includes taxes & fees
27 Aug - 28 Aug
Renovated Bungalow | Walk to Beach | Dog-Friendly
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

12. 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 NZ$936
includes taxes & fees
15 Sept - 16 Sept
Annapolis Retreat - 7 mins from downtown Annapolis!
A waterfront town with historic buildings, a dock with boats, and a prominent white dome structure in the background.

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 NZ$834
includes taxes & fees
26 Aug - 27 Aug
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

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 NZ$1,160
includes taxes & fees
24 Aug - 25 Aug
Family Home on Mayo Peninsula | Deck | Sleeps 10
A beach with chairs and a pier in the background.

15. 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 NZ$1,076
includes taxes & fees
25 Aug - 26 Aug
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

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, (15 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is NZ$1,047
includes taxes & fees
2 Sept - 3 Sept
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A covered outdoor area with a view of the water, a wicker chair, a table with a plant, and a sofa with pillows.

17. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (74 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 NZ$1,089
includes taxes & fees
14 Sept - 15 Sept
Charming Annapolis WaterVIEW Home
A calm lake with a sandy shore, surrounded by trees and houses.

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 NZ$1,221
includes taxes & fees
24 Aug - 25 Aug
Londontowne Home | Beach | 3BR
A spacious living room with a fireplace, a television, and a dining area with a table and chairs.

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

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
The price is NZ$1,069
includes taxes & fees
23 Aug - 24 Aug
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
A spacious living room with a sofa set, a coffee table, and a chair. There is a painting on the wall and a window providing natural light.

20. 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 NZ$1,166
includes taxes & fees
23 Aug - 24 Aug
Londontowne Rancher | 3BR | Near Waterfront
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

8/10 Good
"Nice but expensive"
Gregory 2-night trip
Posted less than an hour ago
Rod 'N' Reel Resort

Find out more about Chesapeake Beach

Chesapeake Beach Holiday Homes information

Number of reviews
182
Accommodation
409 Holiday Homes
Lowest Price
NZ$441
Highest Price
NZ$1,221