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Chesapeake Beach Vacation Rentals

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Vacation Rentals in Chesapeake Beach

Family Beach House: Spacious Deck, Grill & Views
Pool
Family Beach House: Spacious Deck, Grill & Views
10.0 out of 10, Exceptional, 1 review
"The house was clean and quiet. The hosts were helpful and available for communication. This is a lovely house for a vacation away from crowds and by the beach."
Family Beach House: Spacious Deck, Grill & Views
Mid-Century Modern and Marvelous on the Bay
Property grounds
Mid-Century Modern and Marvelous on the Bay
10.0 out of 10, Exceptional, 61 reviews
"The house was lovely. We had 3 days of rain but the view and the beach made it interesting at all times. The hosts make sure you have everything you need for your comfort and entertainment. This is by far the best appointed house we have rented. Thank you for a wonderful week!"
Mid-Century Modern and Marvelous on the Bay
Pool and Bay Views on wrap around deck in Kent Island
Outdoor pool
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, 21 reviews
"Everyone really loved the house and the location. The pool was great"
Pool and Bay Views on wrap around deck in Kent Island
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Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Exterior
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, 186 reviews
"The cottage is fully stocked, clean, and cozy. We thoroughly enjoyed sitting on the deck and watching all the wildlife."
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
3 bedrooms, desk, iron/ironing board, free WiFi
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
10.0 out of 10, Exceptional, 102 reviews
"Loved the house!"
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Property grounds
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
10.0 out of 10, Exceptional, 25 reviews
"I chose to stay at this property for the duration of my wedding weekend. It was really great to be able to spend that extra time with family all together! Getting ready at the house, rather than a hotel was also really nice because we had much more room to space out. The make up artist and hair stylist also complimented the ample natural light and space to work. The pool and hot tub were beautiful! The only downside was a lack of curtains in the master bedroom. The sunrise is beautiful but...
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Charming Annapolis WaterVIEW Home
Property grounds
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, 43 reviews
"Beautiful house and views. Amenities and grounds were great. Loved the playground and beach. Peace and quiet at its finest in nature."
The price is $399
$766 total
includes taxes & fees
Jun 6 - Jun 7
Charming Annapolis WaterVIEW Home
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, 105 reviews
"This is our third visit. You can’t have a better location! We love St. Michael’s and this historical cottage."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Maryland Vacation Rental w/ Private Pool & Dock
Property grounds
Maryland Vacation Rental w/ Private Pool & Dock
10.0 out of 10, Exceptional, 4 reviews
"Had a great time fishing from the dock while we got out of the city for a weekend."
Maryland Vacation Rental w/ Private Pool & Dock
Bay View Studio Apartment
Outdoor spa tub
Bay View Studio Apartment
10.0 out of 10, Exceptional, 25 reviews
"If you are looking for a very spacious well-appointed one bedroom apt. style accommodation in a residential setting with lovely waterfront bay views, I highly recommend this place!"
Bay View Studio Apartment
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Fridge, microwave, stovetop, dishwasher
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, 4 reviews
"We extremely enjoyed our stay. The house was beautiful, kitchen was well equipped and the view was spectacular, especially with the Eagles that have nested on the 32 acre property. However was disappointed in the fact that the fire places were not in working conditions and rooms should have been number. We enjoy kayaking up and down the bay and taking it all in. I would definitely stay again."
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
The Blue Crab Beach House - Free beach passes
Beach nearby, sun loungers, beach umbrellas, beach towels
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, 39 reviews
"It was clean and had everything we needed. We had a very comfortable stay. There are one or two steps between many of the rooms so keep that in mind."
The Blue Crab Beach House - Free beach passes
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
9.8 out of 10, Exceptional, 74 reviews
"The cottage provides a wonderful way to experience Deale and the surrounding area. Well equipped and clean, I had everything I needed and didn't want to leave,"
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Chesapeake Houseboat Getaway on Kent Island, Maryland
Property grounds
Chesapeake Houseboat Getaway on Kent Island, Maryland
10.0 out of 10, Exceptional, 7 reviews
"My husband and I and our dog had a lovely getaway on "Julia's Arc". This was our first time on a Houseboat and it was a wonderful experience. So much light! And the movement of the boat was just enough to be comforting. The home was very clean and beautifully adorned with great attention to detail. Julia, the host, was very responsive and very generous in doing all she could to make our trip as comfortable and pleasurable as possible. The views over the water were gorgeous and we really...
Chesapeake Houseboat Getaway on Kent Island, Maryland
Waterfront Cottage on the Eastern Shore
Fridge, microwave, oven, stovetop
Waterfront Cottage on the Eastern Shore
9.4 out of 10, Exceptional, 3 reviews
"Very much as pictured in ad. Convenient to we did venue we were attending"
The price is $599
$1,134 total
includes taxes & fees
Jun 17 - Jun 18
Waterfront Cottage on the Eastern Shore
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Property grounds
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, 108 reviews
"VRBO link hasn’t enabled me to communicate with property manger/owner as I’m unable to access account via the VRBO link. I’ve re-registered multiple times now."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard
Property grounds
Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard
9.6 out of 10, Exceptional, 12 reviews
"Our stay in Oyster Harbor was very nice. The weather didn't cooperate but the house itself was very nice and I would certainly stay there again. It's about a 10 minute drive to downtown Annapolis so that made it convenient as well!"
Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard
Indulge or be still near Naval Academy/ Annapolis
Beach
Indulge or be still near Naval Academy/ Annapolis
9.2 out of 10, Wonderful, 9 reviews
"Great place, super neighborhood!"
Indulge or be still near Naval Academy/ Annapolis
The Lazy Crab Beach House - Free beach passes
Property grounds
The Lazy Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, 25 reviews
"Everything was perfect and the host was very kind! Would definitely recommend, especially for anyone staying in the area for a wedding."
The Lazy Crab Beach House - Free beach passes
Relaxing Waterfront Cottage Near St Michaels, Maryland
Exterior
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, 197 reviews
"We had our boat with us. Split out time between being on the water and going into St Michaels"
Relaxing Waterfront Cottage Near St Michaels, Maryland
Don't see what you're looking for?
See all available properties in Chesapeake Beach
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.

Chesapeake Beach Vacation Rental Travel Info

Number of vacation rentals
3
Popular accommodation
Chesapeake Beach private vacation homes
Known landmarks
Chesapeake Beach Water Park, Breezy Point Beach and Bayside History Museum
International airports
Washington, DC (IAD-Washington Dulles Intl.) and Washington, DC (DCA-Ronald Reagan Washington National)

Other types of properties in Chesapeake Beach you may be interested in

Rod 'N' Reel Resort
Superior Studio Suite | Balcony
Rod 'N' Reel Resort
3.0 star property
8.2 out of 10, Very Good, 1,010 reviews
"Rooms need to be updated. All renovations are outdoors. The guest rooms needs attention as well. bathtub handle was extremely lose when turning on water nearly fell off."
The price is $179
$219 total
includes taxes & fees
Jun 9 - Jun 10
Rod 'N' Reel Resort
Family Beach House: Spacious Deck, Grill & Views
Pool
Family Beach House: Spacious Deck, Grill & Views
10.0 out of 10, Exceptional, 1 review
"The house was clean and quiet. The hosts were helpful and available for communication. This is a lovely house for a vacation away from crowds and by the beach."
Family Beach House: Spacious Deck, Grill & Views
Mid-Century Modern and Marvelous on the Bay
Property grounds
Mid-Century Modern and Marvelous on the Bay
10.0 out of 10, Exceptional, 61 reviews
"The house was lovely. We had 3 days of rain but the view and the beach made it interesting at all times. The hosts make sure you have everything you need for your comfort and entertainment. This is by far the best appointed house we have rented. Thank you for a wonderful week!"
Mid-Century Modern and Marvelous on the Bay
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.

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 $399 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.

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?

Bay Views |Breezy point Beach: 4BD 2BA King bed: Visitors give good reviews to this Chesapeake Beach vacation home rental, which is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease 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. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals will I find in Chesapeake Beach?

With 10 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 is a spot 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.

Recent reviews of Chesapeake Beach properties
Expedia verified reviews

Wingate by Wyndham Waldorf/Washington DC Area

Wingate by Wyndham Waldorf/Washington DC Area

5/5 Excellent
"Recommend it alot. Good breakfast."
A verified traveler stayed at Wingate by Wyndham Waldorf/Washington DC Area
Posted 19 hours ago
Wingate by Wyndham Waldorf/Washington DC Area