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

Chesapeake Beach Vacation Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Chesapeake Beach vacation rentals

Pool

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.
The price is AED 522
AED 1,404 total
includes taxes & fees
2 Dec - 3 Dec
Family Beach House: Spacious Deck, Grill & Views
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, (25 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is AED 323
AED 1,091 total
includes taxes & fees
22 Nov - 23 Nov
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

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 1,137 total
includes taxes & fees
15 Nov - 16 Nov
The Cozy Crab- Your Charming Haven in Lovely North Beach!
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

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
A house with a yellow door and a window with a lamp outside.

5. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
The price is AED 479
AED 1,154 total
includes taxes & fees
15 Nov - 16 Nov
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

6. 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
14 Nov - 15 Nov
3-bedroom house in Deale located on Bay many amenities and great views
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

7. 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 309
AED 1,039 total
includes taxes & fees
15 Nov - 16 Nov
Relax on Kent Island in 4 Bedroom Home w/Waterview
A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

8. Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.0 out of 10, Wonderful, (16 reviews)
"Beautiful view from the house. Extremely clean. Had everything we needed. Can't wait to come back"
United States
ed r.
The price is AED 593
AED 969 total
includes taxes & fees
14 Nov - 15 Nov
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

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 760
AED 1,601 total
includes taxes & fees
1 Dec - 2 Dec
Sunset Cottage - West River Access and Views!
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
9.4 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 1,315 total
includes taxes & fees
14 Nov - 15 Nov
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A spacious living room with a grey sectional sofa, a round wooden coffee table, and a patterned rug.

11. 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.
Fire pit (2)

12. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
Plum Point Cottage #17
Three Adirondack chairs facing a beach with a clear view of the ocean.

13. Plum Point Cottage #14

Plum Point Cottage #14
Huntingtown
9.8 out of 10, Exceptional, (10 reviews)
"we had a great stay at this property for an impromptu weekend getaway. "
United States
Yonnick H.
The price is AED 1,256
AED 1,967 total
includes taxes & fees
14 Nov - 15 Nov
Plum Point Cottage #14
Fire pit (2)

14. Plum Point Cottage #15

Plum Point Cottage #15
Maryland
The price is AED 1,252
AED 2,068 total
includes taxes & fees
14 Nov - 15 Nov
Plum Point Cottage #15
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

15. 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 1,950 total
includes taxes & fees
14 Nov - 15 Nov
Renovated Bungalow | Walk to Beach | Dog-Friendly
A lakeside view with chairs and a table, a rainbow, and trees.

16. 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
15 Nov - 16 Nov
Bright and airy waterfront getaway
A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

17. 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 572
AED 1,093 total
includes taxes & fees
16 Nov - 17 Nov
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

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

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (6 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is AED 889
AED 2,471 total
includes taxes & fees
14 Nov - 15 Nov
Family Home on Mayo Peninsula | Deck | Sleeps 10
A beach with chairs and a pier in the background.

19. 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
A lakeside view from a deck with a wooden railing, a sandy area with a boat, and a dock extending into the water.

20. 2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.

2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.
Cambridge
The price is AED 826
AED 954 total
includes taxes & fees
14 Dec - 15 Dec
2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.
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
"Check-in was easy and the room was very clean, the waterfront view was awesome. We had dinner at the restaurant and the food was good, maybe a bit overpriced but very tasty. I would recommend staying at this resort and we will be back. Also the staff was very friendly and responsive to all our questions and needs."
Reginald 1-night trip
Posted 1 hour ago
Rod 'N' Reel Resort

Frequently asked questions

Can I find a vacation rental in Chesapeake Beach?

Yes, you can find vacation rentals in Chesapeake Beach near Chesapeake Beach Water Park, or you can select a more remote option if you're looking for extra privacy while you relax. Discover why Chesapeake Beach is known for its spas and beaches. While you're here, grab a bite or have a drink at the restaurants.

What are some of the best vacation home rentals that Chesapeake Beach has to offer?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: This vacation home rental near Chesapeake Beach is located near the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Chesapeake Beach?

With 8 Expedia vacation rentals, you're sure to find just the right place for your Chesapeake Beach stay.

What’s there to see and do in Chesapeake Beach?

Family-friendly attractions include Chesapeake Beach Water Park and Chesapeake Beach Railway Museum, whereas Breezy Point Beach and Northern Chesapeake Bay are a couple of great spots to enjoy the outdoors. Other places in town to visit include Rod n Reel Charter Fishing and Chesapeake Bay.

What’s a vacation rental in Chesapeake Beach like?

Vacation rentals are privately owned properties you can book for several days or longer in Chesapeake Beach. Vacation rentals feature amenities like laundry facilities and kitchens so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.