Photo by Ronanne Vinson

Search Vacation Homes in Chesapeake Beach

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

Vacation Homes in Chesapeake Beach

The Blue Crab Beach House - Free beach passes
Miscellaneous

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (57)
"The property was well- maintained and the kitchen was well-equipped for our needs. Short walk to North Beach for dining and Boardwalk strolls. Nice and toasty for our winter stay - really enjoyed the trip."
The Blue Crab Beach House - Free beach passes
Dollhouse in Central Historic St Michaels
Exterior

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (49)
"This is a lovely historic home that is close to town. It's nicely decorated, has a screened deck out back, and makes for a comfortable stay."
Dollhouse in Central Historic St Michaels
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis
Miscellaneous

Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis

10.0 out of 10, Exceptional, (102)
"Had a wonderful, peaceful stay."
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis
Adorable waterside cottage with pool Beach community
Outdoor pool

Adorable waterside cottage with pool Beach community

9.4 out of 10, Exceptional, (39)
"This was a wonderful place to stay! My husband, dog, and I enjoyed our time, the pool and location near the beach were wonderful."
Adorable waterside cottage with pool Beach community
Beach Home with King Bed and Beach Passes in a Cute Town
Miscellaneous

Beach Home with King Bed and Beach Passes in a Cute Town

10.0 out of 10, Exceptional, (11)
"We had everything we needed in this townhome in North Beach. Nicely decorated, clean and the beds were comfortable! Perfect spot for our girl's weekend."
The price is AED 657
AED 1,618 total
includes taxes & fees
22 Jun - 23 Jun
Beach Home with King Bed and Beach Passes in a Cute Town
Rising Sun Bay View Cottage
Terrace/patio

Rising Sun Bay View Cottage

Rising Sun Bay View Cottage
Private Cottage on gated estate
Beach

Private Cottage on gated estate

10.0 out of 10, Exceptional, (24)
"Excellent location, Excellent property, Excellent owners!"
Private Cottage on gated estate
Wright's Cottage- Pet's Welcome & EV Charging
Interior

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

9.8 out of 10, Exceptional, (11)
"This was a wonderful peaceful stay and the host was great. Loved it!!! "
The price is AED 514
AED 1,474 total
includes taxes & fees
18 Jun - 19 Jun
Wright's Cottage- Pet's Welcome & EV Charging
Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants
Beach nearby

Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants

10.0 out of 10, Exceptional, (26)
"Everything about our stay was wonderful..the hosts were so quick to respond to any questions amd were very patient with me with all of my questions..I would DEFINITELY stay here again!!"
The price is AED 516
AED 1,673 total
includes taxes & fees
18 Jun - 19 Jun
Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants
Bright and airy waterfront getaway
On the beach, sun loungers

Bright and airy waterfront getaway

9.8 out of 10, Exceptional, (11)
"This property was everything we wanted. We hope to return next year."
Bright and airy waterfront getaway
Searenity Stays, a Cozy Home
Marina

Searenity Stays, a Cozy Home

10.0 out of 10, Exceptional, (29)
"Our stay was very comfortable here. The kitchen was well stocked for cooking, the beds were comfortable, plenty of towels, and very clean. We would definitely stay here again."
Searenity Stays, a Cozy Home
Saint Leonard Long Beach Beach House
Beach nearby, sun loungers, beach towels

Saint Leonard Long Beach Beach House

10.0 out of 10, Exceptional, (38)
"The house was amazing and the short walk to the private beach was even better! Everyone we met was so kind and helpful! We found a few sharks teeth while there too! We can wait to come back!"
Saint Leonard Long Beach Beach House
Family & Friends Paradise – Pool, BBQ, & More!
Pool

Family & Friends Paradise – Pool, BBQ, & More!

Family & Friends Paradise – Pool, BBQ, & More!
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, (36)
"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
18 Jun - 19 Jun
Relax on Kent Island in 3 Bedroom Home w/Waterview
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, (38)
"Very clean, great location"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Kick back and enjoy the Chesapeake & this 3-bedroom, calm, stylish space.
3 bedrooms, iron/ironing board, WiFi, bed sheets

Kick back and enjoy the Chesapeake & this 3-bedroom, calm, stylish space.

10.0 out of 10, Exceptional, (1)
"We stayed here for 2 nights with 3 other couples. Bedrooms are very spacious. There are 2 rollaway beds and it looks like a pack n play as well for families with kids. Both couches pull out into beds. Everything was perfect for our needs. You can fit 3 cars in the front driveway but there’s also 2 spots available behind the house. You can also see the Bay from the front windows. Close to stores and gas as well. Would definitely recommend! "
The price is AED 731
AED 1,312 total
includes taxes & fees
19 Jun - 20 Jun
Kick back and enjoy the Chesapeake & this 3-bedroom, calm, stylish space.
Beautiful Waterfront Retreat in Cambridge!
Fridge, microwave, oven, stovetop

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (36)
"The house was so cute and the fact that we were able to do early check in was amazing!"
The price is AED 992
AED 1,833 total
includes taxes & fees
22 Jun - 23 Jun
Beautiful Waterfront Retreat in Cambridge!
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, (115)
"Clean and spacious. Great views! Loved the beach! Found a bunch of fossils. Enjoyed kayaking. Overall outstanding!"
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
The Cottage
Exterior

The Cottage

10.0 out of 10, Exceptional, (6)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is AED 808
AED 1,746 total
includes taxes & fees
7 Jul - 8 Jul
The Cottage
Charming Cottage with Hot Tub 1 Block from the Bay
Miscellaneous

Charming Cottage with Hot Tub 1 Block from the Bay

10.0 out of 10, Exceptional, (9)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is AED 1,579
AED 2,893 total
includes taxes & fees
2 Jul - 3 Jul
Charming Cottage with Hot Tub 1 Block from 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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free