Chesapeake Beach Vacation Rentals from $263: Search Short-Term Rentals

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

Relax on Kent Island in a 4 Bedroom Home w/Waterview! : This vacation home rental near Chesapeake Beach offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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In two weeks

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Our top choices for Chesapeake Beach vacation rentals

Family Beach House: Spacious Deck, Grill & Views

Chesapeak beach

Bryan P.

$462 nightly

May 27 - May 28

Total with taxes and fees

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Stevensville

"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."

Brian

$311 nightly

Jun 1 - Jun 2

Total with taxes and fees

1 bedroom in a basement with private Private bathroom with cool AC

Waldorf

$90 nightly

May 27 - May 28

Total with taxes and fees

Walk to Beach! King Bed & Free Beach Passes

North Beach

Kimberly F.

$383 nightly

Jun 1 - Jun 2

Total with taxes and fees

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Owings

Joan K.

$302 nightly

May 27 - May 28

Total with taxes and fees

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

Benedict

Coulter L.

$238 nightly

May 27 - May 28

Total with taxes and fees

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Annapolis

William

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

North Beach

Becky S.

$369 nightly

May 27 - May 28

Total with taxes and fees

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Top Chesapeake Beach Hotel Reviews

Sleep Inn & Suites Near Joint Base Andrews - Washington Area

10/10 Excellent

"I stayed at this hotel for 3 nights and had a great experience. Everything was very clean and well-maintained, the staff was friendly, and the breakfast had a great variety of options each morning. The overall atmosphere made our stay comfortable and enjoyable. I would definitely stay here again and would recommend it to others."

Courtyard Marriott Waldorf

4/10 Poor

"For this to be a Mariott property it left a LOT to be desired. The room was clean and the staff was nice, but that is about where the good ended. The cleaning staff held a box of tissues hostage like it was a box of gold, demanding that the empty box of tissues be provided before providing a new box. Who wants to hoard or steal a box of tissues? There were kids running and jumping in the room above me at 11:00pm. It was so bad that I finally called the front desk to complain at 11:30pm. The front desk clerk claims to have gone up to speak with the guest(s), but if that was done, it didn't work as I had to call again at midnight because the running and jumping continued. It stopped and I was able to fall asleep, but was awakened to it again at 7:00am. SMH! Finally, I went to the front desk and requested a new room. As far as the property itself is concerned, the pool is and apparently has been out of service for several weeks now. Had this been made known prior to booking I probably would have opted to stay elsewhere. The hotel seems to be a bit dated and it just did not fit the standard of other Mariott hotels that I've stayed. In all honesty the Holiday Inn Express up the street is a better stay AND they offer free buffet breakfast. In a nutshell, I won't be back to this location and definitely won't recommend to it others."

Holiday Inn Express Waldorf by IHG

2/10 Terrible

"I had requested a walk-in shower over the phone prior to arriving at hotel and again at check-in because of my knee and both times was assured the room had one. Upon entering the room I found out there was a tub so I immediately went back to registration to ask if I could get another room and was then told there were no rooms with walk-in showers. The receptionist apologized and stated all she could do was refund my money and I could go somewhere else. I wasn't about to go searching all over Waldorf to find another place to stay so I figured at least I could go swimming in the indoor pool. Wrong, the water was ice cold, the concrete around the pool was all cracked up and the handrail was very unsafe! I will say the rooms weren't too bad other than the shower but overall I was very disappointed in my stay."

SpringHill Suites by Marriott Annapolis

6/10 Okay

"Carpet was old and needed replacement and cleaning. Quite smelly Once I mentioned to the front desk, they got maintenance on it and reported it to corporate. Needs some updates. Could not use the gym or pool area Gym smelled bad not cleaned though lots of housekeeping around and the pool water was and hot tub were merky. It was also insane that they were charging for unsecured parking that used to be free."

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 $263 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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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?

Relax on Kent Island in a 4 Bedroom Home w/Waterview!: This vacation home rental near Chesapeake Beach offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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 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.

Chesapeake Beach Vacation Rentals

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Check prices for these dates

Our top choices for Chesapeake Beach vacation rentals

Family Beach House: Spacious Deck, Grill & Views

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

1 bedroom in a basement with private Private bathroom with cool AC

Walk to Beach! King Bed & Free Beach Passes

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

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

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

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

Cottage Located on the Patuxent River!

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

Charming Annapolis WaterVIEW Home

Annapolis Retreat - 7 mins from downtown Annapolis!

3-Bedroom Beach Home w/ Backyard

Waterfront Unit | Dock, Kayaks & SUPs Included

Renovated Bungalow | Walk to Beach | Dog-Friendly

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Sunset Cottage - West River Access and Views!

Bright and airy waterfront getaway

Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

Find vacation rentals that suit your style

Top Chesapeake Beach Hotel Reviews

Sleep Inn & Suites Near Joint Base Andrews - Washington Area

Find out more about Chesapeake Beach

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