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Chesapeake Beach Holiday Rentals

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Check prices for these dates

Tonight
6 Nov - 7 Nov
Tomorrow
7 Nov - 8 Nov
This weekend
7 Nov - 9 Nov
Next weekend
14 Nov - 16 Nov

Holiday Rentals in Chesapeake Beach

Pool
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
9.0 out of 10, Wonderful, (6)
"This house could not have a better location. There’s a gorgeous beach right across the street. My family and I spent many hours walking the beach looking for beach glass and shark teeth, which were surprisingly plentiful. There was even a nice dock to fish on. The house is very well kept. The upstairs table on the patio was a favorite of mine. The owner was in constant contact. We had a blast."
United States
Jeff B.
The price is HK$1,322
HK$3,409 total
includes taxes & fees
23 Nov - 24 Nov
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Outdoor dining
Waterfront Getaway, Dock Your Boat & Play!
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.
The price is HK$770
HK$2,416 total
includes taxes & fees
11 Nov - 12 Nov
Waterfront Getaway, Dock Your Boat & Play!
Marina
Relax on Kent Island in 3 Bedroom Home w/Waterview
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (41)
"This is a great place for a small family and friends' weekend reunion."
United States
Paul G.
The price is HK$727
HK$2,179 total
includes taxes & fees
17 Nov - 18 Nov
Relax on Kent Island in 3 Bedroom Home w/Waterview
Fridge, microwave, stovetop, coffee/tea maker
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD
9.4 out of 10, Exceptional, (6)
"Great place to stay"
United States
Sherry R.
The price is HK$622
HK$1,373 total
includes taxes & fees
14 Nov - 15 Nov
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD
Beach nearby
Walk to Beach! King Bed & Free Beach Passes
Walk to Beach! King Bed & Free Beach Passes
10.0 out of 10, Exceptional, (16)
"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$823
HK$2,771 total
includes taxes & fees
2 Dec - 3 Dec
Walk to Beach! King Bed & Free Beach Passes
Outdoor pool
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
10.0 out of 10, Exceptional, (48)
"Lovely property."
United States
Melissa W.
The price is HK$879
HK$1,986 total
includes taxes & fees
13 Nov - 14 Nov
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Microwave, oven, stovetop, dishwasher
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
2.0 star property
10.0 out of 10, Exceptional, (1)
"Great location! Everything was on hand and it was an easy sweet little cottage to be in.It was clean and very functional with the added bonus of being so close to all the activity in North Beach.Heather was responsive and obviously cares about her guests and their stay.Highly recommend! "
United States
Georgina P.
The price is HK$995
HK$2,085 total
includes taxes & fees
2 Dec - 3 Dec
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Interior
Beautiful Waterfront Retreat in Cambridge!
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (49)
"Beautifully decorated home, clean and spacious. We really enjoyed the private waterfront and kayak. Would love to come back. "
United States
Woobum H.
The price is HK$1,399
HK$3,107 total
includes taxes & fees
10 Nov - 11 Nov
Beautiful Waterfront Retreat in Cambridge!
Beach nearby, sun-loungers, beach towels
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
10.0 out of 10, Exceptional, (30)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is HK$1,318
HK$3,876 total
includes taxes & fees
2 Dec - 3 Dec
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Exterior
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
10.0 out of 10, Exceptional, (4)
"Very comfortable bedrooms and sitting area. Perfect location for the event we were attending. Very clean. Friendly host. "
United States
Mark E.
The price is HK$1,120
HK$3,315 total
includes taxes & fees
7 Nov - 8 Nov
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
On the beach
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
9.6 out of 10, Exceptional, (5)
"Sophia the host is super attentive and responsive"
United States
Mayela
The price is HK$1,399
HK$2,327 total
includes taxes & fees
17 Nov - 18 Nov
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Marina
#2 Egret Cottage Harris Cove
#2 Egret Cottage Harris Cove
10.0 out of 10, Exceptional, (1)
The price is HK$2,021
HK$2,983 total
includes taxes & fees
16 Nov - 17 Nov
#2 Egret Cottage Harris Cove
Sun-loungers
Cottage Located on the Patuxent River!
Cottage Located on the Patuxent River!
10.0 out of 10, Exceptional, (42)
"Nice and quiet beautiful cottage. A+ communication and a gem. 10/10 will stay again."
United States
chris W.
The price is HK$2,064
HK$2,468 total
includes taxes & fees
12 Nov - 13 Nov
Cottage Located on the Patuxent River!
Terrace/patio
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
9.8 out of 10, Exceptional, (11)
"Very clean - well equipped - perfect for our relaxing weekend."
United States
Chris J.
The price is HK$1,644
HK$3,895 total
includes taxes & fees
18 Nov - 19 Nov
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Fridge, microwave, oven, stovetop
Annapolis Gem: Stylish and Cozy
Annapolis Gem: Stylish and Cozy
10.0 out of 10, Exceptional, (2)
"Clean and nicely decorated. Did not realize it was a basement unit."
United States
Amy B.
The price is HK$1,925
HK$3,754 total
includes taxes & fees
19 Nov - 20 Nov
Annapolis Gem: Stylish and Cozy
Microwave, oven, stovetop, dishwasher
Annapolis Retreat - 7 mins from downtown Annapolis!
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$1,516
HK$4,378 total
includes taxes & fees
7 Dec - 8 Dec
Annapolis Retreat - 7 mins from downtown Annapolis!
3 bedrooms, iron/ironing board, WiFi, bed sheets
Welcoming 3-bedroom townhome with AC in Waldorf
Welcoming 3-bedroom townhome with AC in Waldorf
10.0 out of 10, Exceptional, (1)
"When we walked in, the host had the dining room table set nicely. We thought, "Wow, this place is fancy." We enjoyed the ping pong table and plenty of rooms for our family gathering. "
United States
Keith A.
The price is HK$1,392
HK$2,596 total
includes taxes & fees
2 Dec - 3 Dec
Welcoming 3-bedroom townhome with AC in Waldorf
Smart TV, fireplace, books, printers
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
2.0 star property
10.0 out of 10, Exceptional, (6)
"This VRBO was very clean. Since it is a fairly new addition to VRBO, we thought it could use a little more info, like a portfolio with the combination to the bike locks, where to go to eat and visit, etc. Also, the only coffeemaker was a Keurig and we didn’t bring any K-cups. The 4 of us had a nice 50th Anniversary long weekend."
United States
Sharon M.
The price is HK$3,102
HK$6,881 total
includes taxes & fees
1 Dec - 2 Dec
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Smart TV
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
10.0 out of 10, Exceptional, (14)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is HK$2,147
HK$4,229 total
includes taxes & fees
16 Nov - 17 Nov
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
TV, books, offices
Holly Hill Haven - Sleeps 10
Holly Hill Haven - Sleeps 10
10.0 out of 10, Exceptional, (3)
"Only thing is I would better stock the kitchen. Other than that NO COMPLAINTS! Great location, great clean and comfortable home to host thanksgiving "
United States
Brittany B.
The price is HK$1,221
HK$3,958 total
includes taxes & fees
17 Nov - 18 Nov
Holly Hill Haven - Sleeps 10
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

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG

10/10 Excellent
"Was able to park in handicap spots right in front of hotel. Only there overnight, so many other questions were not applicable."
Joan 1-night trip
Posted 4 days ago
Candlewood Suites Annapolis by IHG

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?

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub: This holiday home rental outside of Chesapeake Beach is located on the waterfront, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 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 garden 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 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.