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
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

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)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
$480 nightly
The price is $504
Sep 2 - Sep 3
Total with taxes and fees
Family Beach House: Spacious Deck, Grill & Views
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)
"Lovely ! "
United States
Ellen B.
$417 nightly
The price is $460
Aug 25 - Aug 26
Total with taxes and fees
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)
"Such a great house! "
United States
Stephanie V.
$662 nightly
The price is $731
Aug 30 - Aug 31
Total with taxes and fees
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Coffee/tea maker, fridge, microwave, oven

4. Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
Rose Haven
$631 nightly
The price is $719
Aug 4 - Aug 5
Total with taxes and fees
Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
Dining

5. Chic retreat steps to Water, Piers & Waterfront Park

Chic retreat steps to Water, Piers & Waterfront Park
Deale
10.0 out of 10, Exceptional, (1 review)
"This place is beautiful, and big. The back yard is nice. We played games out back and had a cookout. Walking distance to the pier and a playground. The"
United States
Jamie C.
$528 nightly
The price is $602
Aug 5 - Aug 6
Total with taxes and fees
Chic retreat steps to Water, Piers & Waterfront Park
Interior

6. 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.
$608 nightly
The price is $619
Aug 10 - Aug 11
Total with taxes and fees
Sunset Cottage - West River Access and Views!
Exterior

7. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
$415 nightly
The price is $458
Aug 12 - Aug 13
Total with taxes and fees
Plum Point Cottage #17
Property grounds

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
9.4 out of 10, Exceptional, (14 reviews)
"The owner was very nice "
United States
karen
$241 nightly
The price is $266
Aug 3 - Aug 4
Total with taxes and fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Exterior detail

9. 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.
$279 nightly
The price is $319
Aug 11 - Aug 12
Total with taxes and fees
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
TV, offices

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

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (4 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
$608 nightly
The price is $693
Aug 3 - Aug 4
Total with taxes and fees
Family Home on Mayo Peninsula | Deck | Sleeps 10
Beach nearby, sun loungers, beach towels

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, (16 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
$570 nightly
The price is $650
Aug 25 - Aug 26
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Smart TV

12. 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.
$704 nightly
The price is $746
Aug 31 - Sep 1
Total with taxes and fees
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Property grounds

13. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (21 reviews)
"Sophia was an amazing host and the place was exactly as advertised. I couldn't recommend the place enough!"
United States
William N.
$335 nightly
The price is $355
Aug 3 - Aug 4
Total with taxes and fees
Bright and airy waterfront getaway
House (3 Bedrooms) | Interior

14. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
3.0 star property
Lusby
$994 nightly
The price is $1,104
Aug 3 - Aug 4
Total with taxes and fees
Lakefront Cabin Near Solomons Island w/ Hot Tub
Exterior

15. 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, (49 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
$292 nightly
The price is $316
Aug 11 - Aug 12
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Outdoor dining

16. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (73 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.
$672 nightly
The price is $766
Aug 5 - Aug 6
Total with taxes and fees
Charming Annapolis WaterVIEW Home
Terrace/patio

17. 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
$320 nightly
The price is $365
Aug 10 - Aug 11
Total with taxes and fees
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
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.
$648 nightly
The price is $739
Aug 3 - Aug 4
Total with taxes and fees
Londontowne Home | Beach | 3BR
Outdoor dining

19. Waterfront Escape with Pool Nature Lover Paradise

Waterfront Escape with Pool Nature Lover Paradise
Stevensville
10.0 out of 10, Exceptional, (2 reviews)
"Very spacious property for a family of 14. Sleeping arrangements required a bit of creativity but everything worked out! Everyone had a great time by the pool and the property was very clean. Host was responsive and helpful during the stay!"
United States
Hoi C.
$1,158 nightly
The price is $1,228
Aug 30 - Aug 31
Total with taxes and fees
Waterfront Escape with Pool Nature Lover Paradise
Coffee/tea maker, fridge, microwave, oven

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

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (10 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.
$486 nightly
The price is $554
Aug 3 - Aug 4
Total with taxes and fees
Renovated Bungalow | Walk to Beach | Dog-Friendly
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

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

10/10 Excellent
"Everything was wonderful"
Melissa 4-night trip
Posted 1 hour ago
SpringHill Suites by Marriott Annapolis

Find out more about Chesapeake Beach

Everything you need to know about Chesapeake Beach vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake Beach vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesapeake Beach vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chesapeake Beach vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesapeake Beach. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chesapeake Beach in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $266 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chesapeake Beach rentals

At Expedia, we put the best Chesapeake Beach vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chesapeake Beach rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesapeake Beach vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesapeake Beach. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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 9 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 Bruce Gabrielson's Surf Art Gallery and Museum.

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.