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Chesapeake Beach Vacation Rentals

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Check prices for these dates

Tonight
Dec 19 - Dec 20
Tomorrow
Dec 20 - Dec 21
This weekend
Dec 19 - Dec 21
Next weekend
Dec 26 - Dec 28

Our top choices for Chesapeake Beach vacation rentals

Marina
Floating 2 bed 2 bath condo stunning views of the bay

Houseboat in Stevensville

Floating 2 bed 2 bath condo stunning views of the bay
2.0 star property
6.4 out of 10, (7)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
United States
Natalia F.
Floating 2 bed 2 bath condo stunning views of the bay
Terrace/patio
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Vacation Home in Cambridge

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
10.0 out of 10, Exceptional, (81)
"Great for 10 adults and 4 grandchildren!"
United States
Phil S.
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Cottage in Downtown St. Michaels

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (125)
"Always a great stay at the John Bruff house! Location is perfect, great view of the harbor and even saw a free concert in the park!!"
United States
Meghan K.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Interior
Beautiful Waterfront Retreat in Cambridge!

Vacation Home in Cambridge

Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (50)
"Beautiful place! Loved all the activities, will return in the future! Our family and friends had a blast! Thank you so much!!"
United States
Karen L.
The price is ￥27,214
￥61,320 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Beautiful Waterfront Retreat in Cambridge!
Exterior detail
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cottage in Cambridge

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
10.0 out of 10, Exceptional, (16)
"Well equipped and super clean; great place!"
United States
Steve S.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Dining
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Cabin in Port Republic

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
10.0 out of 10, Exceptional, (181)
"We thoroughly enjoyed our stay in this kitschy, cool, rustic cabin with a million-dollar view. Communing with the ospreys, hummingbirds and the bald eagle who perched numerous times on a nearby tree was an added bonus. And, the owner may be the most friendly/helpful we’ve ever rented from. We hope to be back some day. Thanks!"
United States
Brennan H.
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Outdoor dining
Waterfront Getaway, Dock Your Boat & Play!

Mobile Home in Edgewater

Waterfront Getaway, Dock Your Boat & Play!
10.0 out of 10, Exceptional, (3)
"Great place to stay. It is clean, comfortable, and not lacking convenience.Quick communication with the host. We would definitely recommend!"
United States
Daniel K.
Waterfront Getaway, Dock Your Boat & Play!
Terrace/patio
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Vacation Home in Cambridge

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
9.8 out of 10, Exceptional, (133)
"This was our second time staying here. Love the location and size of the property. Plenty of space for the kids to play catch, ride bikes, and lots of crabbing and fishing. "
United States
Joe B.
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Fridge, microwave, oven, stovetop
Edgewater/Mayo Gateaway w/ Hot Tub

Vacation Home in Edgewater

Edgewater/Mayo Gateaway w/ Hot Tub
9.8 out of 10, Exceptional, (25)
"Very clean, had everything we needed for our stay!"
United States
Jackie R.
The price is ￥34,854
￥101,499 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Edgewater/Mayo Gateaway w/ Hot Tub
Dining
Million Dollar View of the Chesapeake Bay

Vacation Home in Deale

Million Dollar View of the Chesapeake Bay
9.8 out of 10, Exceptional, (131)
"Absolutely beautiful and peaceful location. Everything was appreciated- the games for lazy evenings, the crab pots, the comfortable beds and living spaces. Stunning view!"
United States
Michelle D.
Million Dollar View of the Chesapeake Bay
Interior
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly

Cottage in Stevensville

Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly
10.0 out of 10, Exceptional, (57)
"It’s a fantastic property!! Perfect for a getaway weekend. Everything was as described. A great place to stay home and enjoy all the amenities."
United States
Kurt H.
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly
Beach
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

Vacation Home in Edgewater

Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
10.0 out of 10, Exceptional, (4)
"Great location, easy check in/out. Everything we needed was available! Very comfortable bed, super cute property. "
United States
MJ S.
The price is ￥34,990
￥55,312 total
includes taxes & fees
Dec 20 - Dec 21
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Vacation Home in Downtown St. Michaels

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (46)
"Perfect location, everything as advertised. Highly recommend "
United States
Glen H.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Exterior
Modern Flat in the Heart of St. Michaels – Walk Everywhere

Apartment in Downtown St. Michaels

Modern Flat in the Heart of St. Michaels – Walk Everywhere
9.8 out of 10, Exceptional, (58)
"Such a beautiful space in a perfect location! We were able to walk to everything — shops, restaurants, farmers market, waterfront, etc! Highly recommend!"
United States
Paige R.
Modern Flat in the Heart of St. Michaels – Walk Everywhere
Dining
Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou

Vacation Home in Cambridge

Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou
9.2 out of 10, Wonderful, (5)
"Great stay"
United States
Jovan J.
Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou
Dining
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis

Vacation Home in Cape St. John

Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis
10.0 out of 10, Exceptional, (114)
"We had a wonderful stay. The house was beautiful, clean, fully equipped and the views out back are magnificent. We all loved the pool. The host was very helpful with any issues & requests. All in all we truly enjoyed our time there. Highly recommend."
United States
Zev K.
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis
Exterior
Family and Pet-Friendly, Waterfront with Pier

Cottage in Cambridge

Family and Pet-Friendly, Waterfront with Pier
10.0 out of 10, Exceptional, (265)
"The property, house and amenities were exactly as described. Absolutely gorgeous views second only to the hospitality extended by Rob and Clarissa!"
United States
Tom K.
Family and Pet-Friendly, Waterfront with Pier
Property grounds
Mid-Century Modern Lake House – Gorgeous Fall Views, Fire pit, Sauna, 4BR

Vacation Home in Lusby

Mid-Century Modern Lake House – Gorgeous Fall Views, Fire pit, Sauna, 4BR
9.6 out of 10, Exceptional, (7)
"Nice lake front view. Spacious living room. "
United States
Kijung S.
Mid-Century Modern Lake House – Gorgeous Fall Views, Fire pit, Sauna, 4BR
Marina
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Cottage in Downtown St. Michaels

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (126)
"Prime location! "
United States
Cindy V.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Property grounds
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Cottage in Downtown St. Michaels

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (147)
"This is such a great house - perfect location. Very roomy and comfortable. The owner is super responsive as well. Highly recommend!"
United States
maggie k.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
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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Top Chesapeake Beach Hotel Reviews

Residence Inn by Marriott Waldorf

Residence Inn by Marriott Waldorf

10/10 Excellent
"Great experience. Friendly staff. Loved it"
David 1-night trip
Posted 2 days ago
Residence Inn by Marriott Waldorf

Find out more about Chesapeake Beach

Search for holiday rentals in Chesapeake Beach on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesapeake Beach using one of the methods below:

  • View our selection of featured holiday rentals in Chesapeake Beach
  • Use the map to find apartments and other holiday homes in the Chesapeake Beach neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chesapeake Beach while they last

Look no further and take a look at our great range of rental properties 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?

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28: You might like this vacation home rental near Chesapeake Beach. It is located on a river and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 7 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 balcony, 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 7 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.