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Chesapeake Beach Vacation Rentals

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Find properties with these dates

Tonight
May 13 - May 14
Tomorrow
May 14 - May 15
This weekend
May 17 - May 19
Next weekend
May 24 - May 26

Vacation Rentals in Chesapeake Beach

Property grounds
Mid-Century Modern and Marvelous on the Bay
10.0 out of 10, Exceptional, (60)
"Beautiful view!!! Lovely home!! We so thoroughly enjoyed our stay and hope that this is just one of many visits. Thank you!"
Mid-Century Modern and Marvelous on the Bay
Pool
Bay Views |Breezy point Beach: 4BD 2BA King bed
10.0 out of 10, Exceptional, (1)
"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."
The price is ￥26,483
per night
May 22 - May 23
Bay Views |Breezy point Beach: 4BD 2BA King bed
Exterior
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (186)
"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
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Outdoor spa tub
Bay View Studio Apartment
10.0 out of 10, Exceptional, (25)
"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
Beach nearby, sun loungers, beach umbrellas, beach towels
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (37)
"This property is in a great location! The house is adorable and the owner was very responsive and accommodating when I needed to add an extra day. I would definitely recommend!"
The Blue Crab Beach House - Free beach passes
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
10.0 out of 10, Exceptional, (73)
"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
Property grounds
The Lazy Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (23)
"Nice neighborhood! Easy walkable area to restaurants and the beach."
The Lazy Crab Beach House - Free beach passes
Property grounds
Charming Cottage with Hot Tub 1 Block from the Bay
10.0 out of 10, Exceptional, (6)
"Was a super comfortable spot my 5 friends and I. Super comfy couches and beds, nice TV, well appointed kitchen. Took a nice walk down to the water in the am. Would stay again!"
The price is ￥41,282
per night
May 15 - May 16
Charming Cottage with Hot Tub 1 Block from the Bay
Fridge, microwave, oven, stovetop
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (15)
"The Hudson House was perfect for our stay. My boys were in awe of the house. The owners have made it so cozy and have paid such close attention to details. There were snacks, amazing notes to help you navigate the house, and games to keep the kids busy. I highly recommend this to anyone looking to have a relaxing weekend right on the water. -Nicole M."
The price is ￥41,126
per night
May 21 - May 22
Beautiful Waterfront Retreat in Cambridge!
Property grounds
Maryland Vacation Rental w/ Private Pool & Dock
10.0 out of 10, Exceptional, (3)
"Loved the house and kids loved the pool. We also managed to catch a half dozen crabs (August trip). House is on the smaller side, but with four bedrooms everyone had privacy and just what they needed. We'll be back!"
Maryland Vacation Rental w/ Private Pool & Dock
Property grounds
7 mins away from Downtown Annapolis
10.0 out of 10, Exceptional, (5)
"The home was very clean and beautifully set up. The property managers were very helpful and communicative. they even had complimentary snack, beverages, and even a hand written note with a wine bottle. Bathrooms were clean and stocked with everything incase you forgot something at home. Everyone enjoyed the home, we were planning our next visit before we even left!"
7 mins away from Downtown Annapolis
Property grounds
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
10.0 out of 10, Exceptional, (22)
"My family and I had an amazing stay!! Jacob’s correspondence was timely and very friendly from beginning to end. We had some problems with cleanliness (sheets not being washed, cobwebs, dead beetles in windowsills), and Jacob refunded our cleaning fee. Despite that, the house was beautiful and had plenty of space for our big family to move around. Be warned that there are A LOT of stairs! But nothing my older parents couldn’t handle. The views are absolutely breathtaking and every single room...
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Fridge, microwave, oven, stovetop
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
10.0 out of 10, Exceptional, (30)
"Great place to recharge for a few days as a family! Beautiful and peaceful in the fall — though my kids are ready to come back and use the pool in warmer weather!!!"
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
Exterior
Quaint cottage with serene water view!
10.0 out of 10, Exceptional, (24)
"Studio with plenty of space for one. Nicely decorated, ample supplies. Petite front porch to watch the river from. Pam was friendly and welcoming, and I will certainly happily stay here again!"
Quaint cottage with serene water view!
Property grounds
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
10.0 out of 10, Exceptional, (151)
"Quaint yet period correct. Plenty of room with decent kitchen. Especially love location and screaned back porch. Have stayed in house several times and does not disappoint!! Will go again for sure!"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (25)
"My family and I enjoyed our stay at the Carpenter Alley Cottage in Saint Michaels! The location was perfect -- walking distance from everything! Appreciated that there was a ground floor bedroom for my parents so they didn't have to climb the stairs and my daughter loved having her own bunk bed room! I did have a few questions about the cottage and the check-in process and my inquiries were all met with a prompt response. Would love to stay here again! (One note though is that it is a smaller,...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Exterior
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (19)
"We have nothing but great things to say about Adam and his beautiful home! He was so accommodating and the home was comfortable and spacious for our family of 5! Couldn’t have had a better experience :)"
The price is ￥8,015
per night
May 16 - May 17
Relax on Kent Island in 3 Bedroom Home w/Waterview
3 bedrooms, desk, iron/ironing board, free WiFi
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
9.8 out of 10, Exceptional, (100)
"Really enjoyed our time there. Very relaxing. Comfortable home. All amenities there. Especially loved the windows..."
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
Property grounds
Charming Annapolis WaterVIEW Home
9.8 out of 10, Exceptional, (41)
"We were friends gathering for a visit to relax and catch up and the house was perfect for that! It was very comfortable, in a quiet neighborhood, but close to enjoy going to local restaurants and shopping. We loved the large windows that looked out over the Bay! The decor was unique interesting touches."
The price is ￥51,407
per night
May 15 - May 16
Charming Annapolis WaterVIEW Home
Pool
Dee's Lounge, Your Relaxation Oasis
9.8 out of 10, Exceptional, (7)
"This home was beautiful and very accommodating for my guest and I. It was nice, cozy and clean and I didn’t need anything because she had it there. I will definitely book this again when I’m in the area. Thank you for your hospitality."
Dee's Lounge, Your Relaxation Oasis
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.

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

Pool
Bay Views |Breezy point Beach: 4BD 2BA King bed
10.0 out of 10, Exceptional, (1)
"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."
The price is ￥26,483
per night
May 22 - May 23
Bay Views |Breezy point Beach: 4BD 2BA King bed
Property grounds
Mid-Century Modern and Marvelous on the Bay
10.0 out of 10, Exceptional, (60)
"Beautiful view!!! Lovely home!! We so thoroughly enjoyed our stay and hope that this is just one of many visits. Thank you!"
Mid-Century Modern and Marvelous on the Bay
Egyptian cotton sheets, premium bedding, pillowtop beds, desk
Sonesta ES Suites Annapolis
3.0 star property
8.8 out of 10, Excellent, (616)
"We had a great stay bad weather and all. The room was very comfortable and inviting. Enjoyed good eats from the local restaurant and had some drinks at the bar."
The price is ￥19,091
per night
May 28 - May 29
Sonesta ES Suites Annapolis
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?

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.