Photo by Ronanne Vinson

Chesapeake Beach Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Chesapeake Beach holiday rentals

Pool
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Holiday Home in Chesapeake Beach

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
9.0 out of 10, Wonderful, (6)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Beach nearby
Walk to Beach! King Bed & Free Beach Passes

Holiday Home in North Beach

Walk to Beach! King Bed & Free Beach Passes
10.0 out of 10, Exceptional, (17)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
The price is HK$630
HK$2,534 total
includes taxes & fees
12 Jan - 13 Jan 2026
Walk to Beach! King Bed & Free Beach Passes
Outdoor pool
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Cottage in Owings

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
10.0 out of 10, Exceptional, (48)
"We love this place!"
United States
Joan K.
The price is HK$1,120
HK$2,268 total
includes taxes & fees
28 Dec - 29 Dec
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Exterior
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Holiday Home in Stevensville

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
9.8 out of 10, Exceptional, (42)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is HK$714
HK$2,143 total
includes taxes & fees
5 Jan - 6 Jan 2026
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Outdoor dining
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Holiday Home in North Beach

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
10.0 out of 10, Exceptional, (31)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is HK$748
HK$3,171 total
includes taxes & fees
4 Jan - 5 Jan 2026
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Exterior detail
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Cottage in North Beach

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
2.0 star property
9.6 out of 10, Exceptional, (4)
"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"
United States
Jana S.
The price is HK$996
HK$2,144 total
includes taxes & fees
1 Jan - 2 Jan 2026
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Outdoor dining
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD

Apartment in Port Republic

Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD
9.4 out of 10, Exceptional, (6)
"Very friendly and convenient!"
United States
Robin B.
The price is HK$591
HK$1,339 total
includes taxes & fees
6 Jan - 7 Jan 2026
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD
Fridge, microwave, oven, stovetop
Beautiful Waterfront Retreat in Cambridge!

Holiday 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 HK$1,226
HK$2,899 total
includes taxes & fees
4 Jan - 5 Jan 2026
Beautiful Waterfront Retreat in Cambridge!
Property grounds
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Cottage in Benedict

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
9.0 out of 10, Wonderful, (8)
"The owner was very nice "
United States
karen
The price is HK$1,401
HK$2,329 total
includes taxes & fees
24 Dec - 25 Dec
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Interior
Commute to Alexandria & DC: Home w/ Shared Yard

Cottage in Waldorf

Commute to Alexandria & DC: Home w/ Shared Yard
3.0 star property
The price is HK$1,097
HK$4,073 total
includes taxes & fees
21 Jan - 22 Jan 2026
Commute to Alexandria & DC: Home w/ Shared Yard
Terrace/patio
Commuter-Friendly Studio Near DC & Alexandria!

Apartment in Waldorf

Commuter-Friendly Studio Near DC & Alexandria!
2.0 star property
The price is HK$591
HK$3,582 total
includes taxes & fees
24 Dec - 25 Dec
Commuter-Friendly Studio Near DC & Alexandria!
Sun-loungers
Cottage Located on the Patuxent River!

Cottage in Prince Frederick

Cottage Located on the Patuxent River!
10.0 out of 10, Exceptional, (42)
"This place was very lovely. Beautiful atmosphere and very spacious cottage. Didn’t get to see the owners but really enjoyed their property. Loved having the coffee maker, comfy bed and awesome tub! I will definitely be back. "
United States
RACHEL S.
The price is HK$2,066
HK$2,470 total
includes taxes & fees
24 Dec - 25 Dec
Cottage Located on the Patuxent River!
Smart TV, books
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Holiday Home in Prince Frederick

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
9.6 out of 10, Exceptional, (5)
"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "
United States
Carrie K.
The price is HK$1,556
HK$3,052 total
includes taxes & fees
5 Jan - 6 Jan 2026
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Fridge, microwave, oven, stovetop
Edgewater/Mayo Gateaway w/ Hot Tub

Holiday 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.
Edgewater/Mayo Gateaway w/ Hot Tub
Beach
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Holiday Home in Prince Frederick

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
10.0 out of 10, Exceptional, (8)
"Everything was amazing. "
United States
Lorie S.
The price is HK$1,684
HK$3,055 total
includes taxes & fees
14 Jan - 15 Jan 2026
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Smart TV
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Holiday Home in Cambridge

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
10.0 out of 10, Exceptional, (14)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
The price is HK$2,041
HK$4,135 total
includes taxes & fees
2 Jan - 3 Jan 2026
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Interior
Annapolis Retreat - 7 mins from downtown Annapolis!

Holiday Home in Hillsmere

Annapolis Retreat - 7 mins from downtown Annapolis!
10.0 out of 10, Exceptional, (4)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is HK$1,315
HK$4,116 total
includes taxes & fees
12 Jan - 13 Jan 2026
Annapolis Retreat - 7 mins from downtown Annapolis!
TV, offices
Wright's Cottage- Pet's Welcome & EV Charging

Holiday Home in Annapolis

Wright's Cottage- Pet's Welcome & EV Charging
9.2 out of 10, Wonderful, (16)
"Nice little spot, very quiet "
United States
Susan S.
The price is HK$1,602
HK$3,183 total
includes taxes & fees
28 Dec - 29 Dec
Wright's Cottage- Pet's Welcome & EV Charging
Smart TV
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Holiday Home in Shady Side

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
10.0 out of 10, Exceptional, (4)
"Would stay here again "
United States
Thomas D.
The price is HK$1,354
HK$3,637 total
includes taxes & fees
4 Jan - 5 Jan 2026
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Interior
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Cottage in Lusby

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
The price is HK$3,322
HK$7,042 total
includes taxes & fees
30 Dec - 31 Dec
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
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

The Wildset

The Wildset

10/10 Excellent
"Everything was outstanding, however the lot and handicap ramp were VERY ICY. We almost fell multiple times. Just a caution"
nichole 1-night trip
Posted 2 days ago
The Wildset

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 holiday rental in Chesapeake Beach?

Yes, there are holiday rentals in Chesapeake Beach close to Chesapeake Beach Water Park, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Chesapeake Beach has to offer?

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28: This holiday home rental outside of Chesapeake Beach is located on a river, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Chesapeake Beach?

With 7 Expedia holiday rentals, you're guaranteed 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 holiday rental in Chesapeake Beach like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chesapeake Beach. Holiday rentals provide amenities like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for small groups.