Chesapeake Beach Vacation Rentals from $264: Search Short-Term Rentals

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Our top choices for Chesapeake Beach vacation rentals

1. Family Beach House: Spacious Deck, Grill & Views

Chesapeak beach

Ben W.

$354 nightly

Dec 2 - Dec 3

Total with taxes and fees

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

North Beach

Johanna S.

$287 nightly

Nov 15 - Nov 16

Total with taxes and fees

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!

North Beach

James L.

$292 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

North Beach

Sarah

$366 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

Deale

Maude H.

$276 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

Deale

"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...

Amelia

$383 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

Stevensville

Anthony P.

$263 nightly

Nov 15 - Nov 16

Total with taxes and fees

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.

Benedict

ed r.

$239 nightly

Nov 15 - Nov 16

Total with taxes and fees

A modern kitchen with a large window, a dishwasher, and a ceiling fan.

9. Sunset Cottage - West River Access and Views!

Shady Side

Michelle H.

$431 nightly

Dec 1 - Dec 2

Total with taxes and fees

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

Shady Side

"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"

Jenny A.

$314 nightly

Nov 15 - Nov 16

Total with taxes and fees

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.

Prince Frederick

Sean B.

$374 nightly

Nov 20 - Nov 21

Total with taxes and fees

12. Plum Point Cottage #17

Huntingtown

Three Adirondack chairs facing a beach with a clear view of the ocean.

13. Plum Point Cottage #14

Huntingtown

Yonnick H.

$484 nightly

Nov 15 - Nov 16

Total with taxes and fees

14. Plum Point Cottage #15

Maryland

$509 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

Edgewater

Diane D.

$466 nightly

Nov 15 - Nov 16

Total with taxes and fees

A lakeside view with chairs and a table, a rainbow, and trees.

16. Bright and airy waterfront getaway

Benedict

George

$345 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

Saint Leonard

Nancy P.

$257 nightly

Dec 7 - Dec 8

Total with taxes and fees

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

Edgewater

Kristin G.

$590 nightly

Nov 15 - Nov 16

Total with taxes and fees

A beach with chairs and a pier in the background.

19. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Arundel on the Bay

Ryan C.

$414 nightly

Nov 16 - Nov 17

Total with taxes and fees

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.

Cambridge

$245 nightly

Nov 15 - Nov 16

Total with taxes and fees

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Top Chesapeake Beach Hotel Reviews

Sonesta ES Suites Annapolis

10/10 Excellent

"Good location, very clean, very good breakfast, great staff"

SpringHill Suites by Marriott Annapolis

8/10 Good

"The staff was very helpful & accommodating when we expressed our concerns. We had booked this stay as an in between stop on our long vacation & mainly booked it because it had an indoor pool the kids could use for the few days in the middle. We also were unaware there is a parking fee of 8 dollars every night you stay. We did leave a night early simply because the pool was closed for the weekend. When we arrived it was closed & we were told it would be closed all weekend but was open around 9 at night & filled with people. It was open again when we walked by around 2pm the next day with people in it once again. So we got dressed & went down to get in & it was once again closed & we were told again it was closed all weekend for maintenance. After the disappointment from the kiddos & the extra money I paid for a pool specifically ( not to mention the nightly parking fee ) we decided to leave early & just continue our driving travels. The front desk was very understanding & kind. They also offered to refund me a night even though we hadn’t decided to leave until 2pm the day before checking out. So that was very nice & I know the inconveniences were not the responsibility of the staff! Over all it was a great hotel room, comfy beds, & very nice stuff. Only issues were the pool, the lack of information regarding it & the parking fee."

Springhill Suites by Marriott Prince Frederick

10/10 Excellent

"The only think I would change is the coffee to one of the more modern automatic types and maybe add flavored creamer. The room coffee maker is older and they only provide a powder packet. I brought my own but the hotel was nice and I would sty again."

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 $264 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.

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Things to do in Chesapeake Beach

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.

Room 1

Check prices for these dates

Our top choices for Chesapeake Beach vacation rentals

1. Family Beach House: Spacious Deck, Grill & Views

2. Beachside Oasis with Beach Passes & King Suite by A Haven Away

3. The Cozy Crab- Your Charming Haven in Lovely North Beach!

4. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

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

6. 3-bedroom house in Deale located on Bay many amenities and great views

7. Relax on Kent Island in 4 Bedroom Home w/Waterview

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

9. Sunset Cottage - West River Access and Views!

10. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

11. Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

12. Plum Point Cottage #17

13. Plum Point Cottage #14

14. Plum Point Cottage #15

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

16. Bright and airy waterfront getaway

17. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

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

19. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

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

Find vacation rentals that suit your style

Top Chesapeake Beach Hotel Reviews

Sonesta ES Suites Annapolis

Sleep Inn & Suites Near Joint Base Andrews - Washington Area

Hilton Garden Inn Solomons

The Wildset

Candlewood Suites Annapolis by IHG

Towneplace Suites by Marriott Clinton at Joint Base Andrews

Courtyard Marriott Waldorf

SpringHill Suites by Marriott Annapolis

Springhill Suites by Marriott Prince Frederick

Find out more about Chesapeake Beach

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