Photo by Ronanne Vinson

Chesapeake Beach Holiday Rentals

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Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

Our top choices for Chesapeake Beach holiday rentals

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, (43 reviews)
"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$547
HK$1,952 total
includes taxes & fees
13 Jan - 14 Jan
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
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 reviews)
"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$634
HK$2,542 total
includes taxes & fees
12 Jan - 13 Jan
Walk to Beach! King Bed & Free Beach Passes
Dining
Haven 2

Holiday Home in Waldorf

Haven 2
2.5 star property
The price is HK$360
HK$790 total
includes taxes & fees
16 Jan - 17 Jan
Haven 2
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 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is HK$909
HK$3,370 total
includes taxes & fees
12 Jan - 13 Jan
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
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 reviews)
"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$926
HK$2,543 total
includes taxes & fees
13 Jan - 14 Jan
Beautiful Waterfront Retreat in Cambridge!
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 reviews)
"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"
United States
Jana S.
The price is HK$1,122
HK$2,305 total
includes taxes & fees
13 Jan - 14 Jan
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
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 reviews)
"We love this place!"
United States
Joan K.
The price is HK$1,294
HK$2,479 total
includes taxes & fees
15 Jan - 16 Jan
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
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 reviews)
"The owner was very nice "
United States
karen
The price is HK$1,403
HK$2,333 total
includes taxes & fees
12 Jan - 13 Jan
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
TV, books, offices
Holly Hill Haven - Sleeps 10

Holiday Home in Edgewater

Holly Hill Haven - Sleeps 10
10.0 out of 10, Exceptional, (3 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is HK$1,122
HK$4,176 total
includes taxes & fees
3 Feb - 4 Feb
Holly Hill Haven - Sleeps 10
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 reviews)
"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$2,069
HK$2,499 total
includes taxes & fees
13 Jan - 14 Jan
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 reviews)
"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.
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
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, (5 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is HK$1,317
HK$4,132 total
includes taxes & fees
12 Jan - 13 Jan
Annapolis Retreat - 7 mins from downtown Annapolis!
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 reviews)
"Amazing news out of the back.Great for kayaking.We brought our own kayaksAnd also use yoursThere were four of usWe also took a nice trip over to Saint Michael’s"
United States
Sandy S.
The price is HK$2,045
HK$4,117 total
includes taxes & fees
13 Jan - 14 Jan
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Outdoor spa tub
London Towne Bungalow w/Loft - Walk to the Beach!

Holiday Home in Edgewater

London Towne Bungalow w/Loft - Walk to the Beach!
8.8 out of 10, Excellent, (3 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is HK$1,309
HK$3,910 total
includes taxes & fees
5 Feb - 6 Feb
London Towne Bungalow w/Loft - Walk to the Beach!
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$2,853
HK$6,527 total
includes taxes & fees
12 Jan - 13 Jan
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
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 reviews)
"Would stay here again "
United States
Thomas D.
The price is HK$1,249
HK$3,512 total
includes taxes & fees
12 Jan - 13 Jan
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
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 reviews)
"Everything was amazing. "
United States
Lorie S.
The price is HK$1,686
HK$3,184 total
includes taxes & fees
14 Jan - 15 Jan
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Fridge, microwave, oven, stovetop
Golden Anchor Retreat; Lux Living! - Sleeps 7

Holiday Home in Edgewater

Golden Anchor Retreat; Lux Living! - Sleeps 7
10.0 out of 10, Exceptional, (2 reviews)
"The property was beautiful with plenty of space to have a getaway with friends. The host was super communicative when we had issues with check in. Would highly recommend staying here!"
United States
Sam A.
The price is HK$1,551
HK$5,021 total
includes taxes & fees
12 Jan - 13 Jan
Golden Anchor Retreat; Lux Living! - Sleeps 7
Beach nearby, sun-loungers, beach towels
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Holiday Home in Arundel on the Bay

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
9.8 out of 10, Exceptional, (11 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is HK$1,793
HK$4,087 total
includes taxes & fees
3 Feb - 4 Feb
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Games room
2BR, 1BA Boutique Brick Beauty located in historic Eastport.

Holiday Home in Eastport

2BR, 1BA Boutique Brick Beauty located in historic Eastport.
The price is HK$1,286
HK$2,577 total
includes taxes & fees
12 Jan - 13 Jan
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
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

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

10/10 Excellent
"We use this property for business travel .Good clean property, nice location. Good breakfast and coffee. Reasonably priced (except parking fee)"
Michael 2-night trip
Posted 3 days ago
SpringHill Suites by Marriott Annapolis

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?

Edgewater/Mayo Gateaway w/ Hot Tub: This holiday home rental outside of Chesapeake Beach offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind.

How many holiday rentals will I find in Chesapeake Beach?

With 6 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.