Photo by Ronanne Vinson

Chesapeake Beach Vacation Rentals

Vacation Rentals in Chesapeake Beach

Mid-Century Modern and Marvelous on the Bay
Property grounds
Mid-Century Modern and Marvelous on the Bay
10.0 out of 10, Exceptional, (68)
"The ratings were Exceptional, so I was skeptical. However, it was beyond exceptional. The most well equipped rental we have seen. Great location. Well stocked. Excellent communication with the host. Couldn’t have asked for anything more. Definitely recommend, and will stay here again when in the area. We had a great time."
Mid-Century Modern and Marvelous on the Bay
Family Beach House: Spacious Deck, Grill & Views
Pool
Family Beach House: Spacious Deck, Grill & Views
9.6 out of 10, Exceptional, (4)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
The price is $486
includes taxes & fees
$467 per night
Nov 6 - Nov 7
Family Beach House: Spacious Deck, Grill & Views
Charming Annapolis WaterVIEW Home
Outdoor dining
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (48)
"This house was perfect for our group of friends especially with infants. Easy check in, comfortable beds and room for pack and plays. Water view is amazing. Definitely worth the rent and would be interested in coming back!"
Charming Annapolis WaterVIEW Home
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, (202)
"This was a lovely home. I especially appreciated how clean and well-stocked it was. Liz and Tom were very responsive and accommodating! This truly added to a wonderful reunion weekend with friends and family. Thank you!"
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
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, (111)
"Perfect stay in a historic home in the heart of town."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Relaxing Waterfront Cottage Near St Michaels, Maryland
Exterior
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (214)
"Manager alway accessible, helpful and friendly. Neighborhood very quiet. The view can’t be beat. Hope to be able to enjoy it for years to come. "
Relaxing Waterfront Cottage Near St Michaels, Maryland
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Outdoor dining
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
9.8 out of 10, Exceptional, (34)
"Family stayed for my 50th birthday over a long weekend. Amazing property. Beautiful view and amazing amenities with hosts who are flexible. We had a small issue with the alarm system that we finally resolved. Will definitely book again."
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Maryland Vacation Rental w/ Private Pool & Dock
Outdoor dining
Maryland Vacation Rental w/ Private Pool & Dock
10.0 out of 10, Exceptional, (6)
"We needed a house for a quick stay in Lusby. The hosts have thought of everything to make the stay easy. They communicated ahead of our trip and were easy to work with. "
Maryland Vacation Rental w/ Private Pool & Dock
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, (17)
" October 11-14, 2024, we rented the “Willoughby” for a family reunion. Let me start out by saying this home is amazing. It looks exactly as pictured based on the website photos. It was even better than I expected. If you are considering this property, I highly recommend booking it! Believe me when I say the Willoughby is a rare gem. The location of the home is perfect and extremely private. The grounds are pristine and the view of the water is breathtaking. The home sits on the Hudson...
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Chesapeake Houseboat Getaway on Kent Island, Maryland
Marina
Chesapeake Houseboat Getaway on Kent Island, Maryland
9.6 out of 10, Exceptional, (19)
"We loved our stay. It was particularly nice to get away from all the "hustle and bustle" of the Sailboat Show. The unit was well-equipped and comfortable. We loved the upper deck! In fact, we had morning coffee, on day, and watched 2 eagles in a nearby tree. "
Chesapeake Houseboat Getaway on Kent Island, Maryland
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, (24)
"We loved everything about the Kent Island House! Would book again in a hot minute"
Pool and Bay Views on wrap around deck in Kent Island
The Blue Crab Beach House - Free beach passes
Miscellaneous
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (47)
"Everything close by!"
The Blue Crab Beach House - Free beach passes
Walk to Everything House
Fridge, microwave, oven, stovetop
Walk to Everything House
10.0 out of 10, Exceptional, (72)
"We thoroughly enjoyed the convenience of walking to shops, restaurants, and waterfront! Residence was charming and clean! Only minor issue was we couldn’t locate the iron- just the ironing board! We still had fun but we’re just a bit wrinkled!😁"
Walk to Everything House
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Sun loungers, beach towels
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
10.0 out of 10, Exceptional, (31)
"House was spacious, clean, and exactly as described in the listings. We had a great time!"
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Relax on Kent Island in 3 Bedroom Home w/Waterview
Marina
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (28)
"A most comfortable rental! Clean, roomy, and a well equipped kitchen. TV…all the channels you could ever want.. a great rental!!"
The price is $263
includes taxes & fees
$248 per night
Nov 3 - Nov 4
Relax on Kent Island in 3 Bedroom Home w/Waterview
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
Fridge, microwave, oven, stovetop
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
9.6 out of 10, Exceptional, (11)
"We appreciate the hospitality and responsiveness of our gracious host. We would stay again and look forward to our next visit. Recommend staying to all looking for a tranquil getaway in the Annapolis area."
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
View from property
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
9.8 out of 10, Exceptional, (87)
"This lovely home sets in a beautful location. The hosts are available and accommodating. They are definitely available if needed. The house itself is very comfy. All amenities you need are there. "
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Your Annapolis Adventure Starts Here!!
Fridge, microwave, oven, stovetop
Your Annapolis Adventure Starts Here!!
10.0 out of 10, Exceptional, (134)
"Beautifully decorated home in a safe neighborhood. Centrally located to Annapolis for shopping , dining and sight seeing. Loved the cozy seating in living space and the inviting patio. Perfect place for a girl’s get-away. Highly recommend. Five stars all the way. "
Your Annapolis Adventure Starts Here!!
The Lazy Crab Beach House - Free beach passes
Property grounds
The Lazy Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (37)
"Had a great long weekend seeing the sights around North Beach and surrounding area. Cozy spot, easy and convenient check in. Boardwalk, pier and restaurants within walking distance. Took about an hr to get to Navy game; enjoyed it all! Home is pleasantly decorated, clean and comfortable!!! Even able to bring our 12 yr old lab!! 5 stars"
The Lazy Crab Beach House - Free beach passes
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (31)
"Other than arriving with no sheets on beds, no towels, and no basic toiletries or kitchen cleaning set, place is very good. Cleaning service, owner, or property management firm mismanaged the prep for our arrival. Absence of sheets, towels, etc. was rectified in a bit more than 1 hour. Nice place and superb location for seeing the village. Quiet, but right in the middle of all shops, farmers market, restaurants, etc. There was a bit of a pet odor in the 1st floor bedroom. Only other comment is...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
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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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, (1005)
"Front desk are very pleasant always!!"
The price is $154
includes taxes & fees
$140 per night
Nov 5 - Nov 6
Rod 'N' Reel Resort
Family Beach House: Spacious Deck, Grill & Views
Pool
Family Beach House: Spacious Deck, Grill & Views
9.6 out of 10, Exceptional, (4)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
The price is $486
includes taxes & fees
$467 per night
Nov 6 - Nov 7
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, (68)
"The ratings were Exceptional, so I was skeptical. However, it was beyond exceptional. The most well equipped rental we have seen. Great location. Well stocked. Excellent communication with the host. Couldn’t have asked for anything more. Definitely recommend, and will stay here again when in the area. We had a great time."
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.

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?

Family Beach House: Spacious Deck, Grill & Views: 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 11 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.