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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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 £337
includes taxes & fees
4 Oct - 5 Oct
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

2. 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 £383
includes taxes & fees
14 Oct - 15 Oct
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

3. 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, (24 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is £244
includes taxes & fees
5 Oct - 6 Oct
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A market with a covered seating area and a sign indicating parking for curbside pickup.

4. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
10.0 out of 10, Exceptional, (1 review)
"Great place to stay! Location was nice and close to water views. House was charming and CLEAN. Owners went above and beyond to make the stay welcoming and convenient. Price was reasonable until additional Vrbo fees were added."
United States
Sharon t.
The price is £330
includes taxes & fees
4 Oct - 5 Oct
Rose Haven Coastal Cottage
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

5. 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 £218
includes taxes & fees
5 Oct - 6 Oct
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A single-story house with a gabled roof, a front porch, and a small front yard with a flag.

6. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is £354
includes taxes & fees
2 Oct - 3 Oct
Plum Point Cottage #17
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 £371
includes taxes & fees
27 Oct - 28 Oct
3-bedroom house in Deale located on Bay many amenities and great views
A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

8. 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, (8 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is £204
includes taxes & fees
6 Oct - 7 Oct
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A lakeside view with chairs and a table, a rainbow, and trees.

9. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (24 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 £287
includes taxes & fees
4 Oct - 5 Oct
Bright and airy waterfront getaway
A deck with outdoor furniture, a red door, and a house with windows.

10. 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
9.0 out of 10, Wonderful, (2 reviews)
"The location was spectacular, the host was communicative, and we had a great time! A beautiful and clean home with everything needed to make a trip a success. One small issue with some needed essentials meant a quick run to the store (TP!) but otherwise a great location, great stay, and would stay again!"
United States
David S.
The price is £285
includes taxes & fees
27 Oct - 28 Oct
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A beach with chairs and a pier in the background.

11. 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 £412
includes taxes & fees
20 Oct - 21 Oct
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

12. 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 £438
includes taxes & fees
7 Oct - 8 Oct
Sunset Cottage - West River Access and Views!
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

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

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (13 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 £458
includes taxes & fees
4 Oct - 5 Oct
Renovated Bungalow | Walk to Beach | Dog-Friendly
A covered outdoor area with a view of the water, a wicker chair, a table with a plant, and a sofa with pillows.

14. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (78 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.
Charming Annapolis WaterVIEW Home
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

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 £443
includes taxes & fees
1 Nov - 2 Nov
Annapolis Retreat - 7 mins from downtown Annapolis!
A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

16. 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 £551
includes taxes & fees
4 Oct - 5 Oct
Family Home on Mayo Peninsula | Deck | Sleeps 10
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

17. 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, (16 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is £427
includes taxes & fees
7 Oct - 8 Oct
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A spacious living room with a fireplace, a television, and a dining area with a table and chairs.

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

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

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 £573
includes taxes & fees
7 Oct - 8 Oct
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

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"The staff was welcoming and very pleasant at check in. I was able to park my car next to my room so i did not have to walk a lot together to my room. The room and amenities at this hotel is amazing! Full kitchen! Easy accred walking path to the breakfast buffet. The breakfast was excellent with healthy choices . I enjoyed my stay!!"
Esther 1-night trip
Posted 19 hours ago
Sonesta ES Suites Annapolis

Find out more about Chesapeake Beach

Chesapeake Beach Holiday Homes information

Number of reviews
205
Accommodation
408 Holiday Homes
Lowest Price
£204
Highest Price
£573