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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 405 Vacation Homes in Chesapeake Beach with updated reviews, rates, and availability.

The Blue Crab Beach House - Free beach passes
Miscellaneous

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (54)
"We really enjoyed our stay at The Blue Crab Beach House. The home was very clean and well accessorized. The host was very responsive and I would definitely come stay again !"
The Blue Crab Beach House - Free beach passes
Modern Waterfront House with amazing views of the ChesapeakeBay!
Fridge, microwave, oven, stovetop

Modern Waterfront House with amazing views of the ChesapeakeBay!

Modern Waterfront House with amazing views of the ChesapeakeBay!
Sweet Bamboo Beach Cottage
Fridge, microwave, oven, stovetop

Sweet Bamboo Beach Cottage

10.0 out of 10, Exceptional, (74)
"This house was the perfect place to visit old friends. Beds were comfortable, house had everything I needed for a long weekend, and the neighborhood was quiet and friendly. It is walking distance (a few blocks) to the boardwalk and restaurants. "
Sweet Bamboo Beach Cottage
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, (89)
"Great house, great location and great host!"
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
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, (36)
"Very clean, great location"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
On the beach

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

10.0 out of 10, Exceptional, (114)
"Location was perfect for what we needed (quiet, on the beach, great views). Family & pup will definitely be back! We wished we could have stayed longer. Owner communication was wonderful, we never needed anything but knew we could reach out if we did. Very comfortable experience throughout. "
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Book for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
Interior

Book for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

2.0 star property
10.0 out of 10, Exceptional, (1)
"We had a great Springtime vacation with kids and a grandparent - our kids enjoyed kayaking and paddle boarding from the doc and gramps was very comfortable watching from the yard. It’s a very convenient location for a family. House was small but had everything we needed and well maintained. We recommend it!!"
Book for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
The Lazy Crab Beach House - Free beach passes
Property grounds

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (48)
"Would stay again."
The Lazy Crab Beach House - Free beach passes
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, (35)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is AED 251
AED 955 total
includes taxes & fees
11 May - 12 May
Relax on Kent Island in 3 Bedroom Home w/Waterview
The Cottage
Exterior

The Cottage

10.0 out of 10, Exceptional, (5)
"Our stay at the house was great. The host had amazing customer service and the location is beautiful."
The Cottage
7 mins away from Downtown Annapolis
Outdoor dining

7 mins away from Downtown Annapolis

9.8 out of 10, Exceptional, (15)
"A warm and cozy property that can hold that big holiday gathering you want. Well stocked, comfortable, and full of what you need."
7 mins away from Downtown Annapolis
Walk to Everything House
Fridge, microwave, oven, stovetop

Walk to Everything House

10.0 out of 10, Exceptional, (78)
"Clean and nice place to stay"
Walk to Everything House
Private Waterview Estate with 4 bedroom Suites, game room and Hot Tub
Fridge, microwave, oven, stovetop

Private Waterview Estate with 4 bedroom Suites, game room and Hot Tub

9.6 out of 10, Exceptional, (24)
"Great location and house! We all had a great time!"
Private Waterview Estate with 4 bedroom Suites, game room and Hot Tub
25-50% Off~Private Beach~Hot Tub~Fire Table~
On the beach, beach towels

25-50% Off~Private Beach~Hot Tub~Fire Table~

10.0 out of 10, Exceptional, (24)
"It was the perfect romantic getaway! "
25-50% Off~Private Beach~Hot Tub~Fire Table~
Wright's Cottage- Pet's Welcome & EV Charging
Interior

Wright's Cottage- Pet's Welcome & EV Charging

9.8 out of 10, Exceptional, (8)
"Great location. Small but perfect for myself, my daughter & our big goofy dog. Old house but well maintained and cozy, fenced back yard. Really enjoyed our stay!"
The price is AED 386
AED 1,306 total
includes taxes & fees
11 May - 12 May
Wright's Cottage- Pet's Welcome & EV Charging
Newly Renovated River Retreat w/Dock and Pool
Terrace/patio

Newly Renovated River Retreat w/Dock and Pool

Newly Renovated River Retreat w/Dock and Pool
Time Stands Still At the Dock.
Outdoor dining

Time Stands Still At the Dock.

10.0 out of 10, Exceptional, (3)
"What a wonderful experience! A relaxing time with an amazing view! Thank you Jennifer"
Time Stands Still At the Dock.
Cozy Cottage 3 beds 2 baths
Outdoor dining

Cozy Cottage 3 beds 2 baths

9.8 out of 10, Exceptional, (78)
"Absolutely perfect, will stay here again and again when visting family in Maryland. "
Cozy Cottage 3 beds 2 baths
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, (39)
"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Beautiful Waterfront Retreat in Cambridge!
Fridge, microwave, oven, stovetop

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (34)
"The house was so cute and the fact that we were able to do early check in was amazing!"
The price is AED 1,010
AED 1,853 total
includes taxes & fees
12 May - 13 May
Beautiful Waterfront Retreat in Cambridge!
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 property types in Chesapeake Beach

Family Beach House: Spacious Deck, Grill & Views
Pool

Family Beach House: Spacious Deck, Grill & Views

9.2 out of 10, Wonderful, (5)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
Family Beach House: Spacious Deck, Grill & Views
Mid-Century Modern on Private Beach, Designed by Award Winning Architect!
Property grounds

Mid-Century Modern on Private Beach, Designed by Award Winning Architect!

10.0 out of 10, Exceptional, (77)
"Absolutely amazing place to get away and relax. 3rd time staying here."
Mid-Century Modern on Private Beach, Designed by Award Winning Architect!
The Blue Crab Beach House - Free beach passes
Miscellaneous

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (54)
"We really enjoyed our stay at The Blue Crab Beach House. The home was very clean and well accessorized. The host was very responsive and I would definitely come stay again !"
The Blue Crab Beach House - Free beach passes
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.