Holiday Homes in Chesapeake Beach

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Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 June - 28 June

Our top choices for Chesapeake Beach holiday homes

Pool

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

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.0 out of 10, Wonderful, (6 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is AU$613
includes taxes & fees
17 Mar - 18 Mar
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Dining

Haven 2

Haven 2
2.5 star property
Waldorf
The price is AU$143
includes taxes & fees
13 Mar - 14 Mar
Haven 2
Exterior

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
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 AU$393
includes taxes & fees
17 Mar - 18 Mar
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Beach nearby

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (19 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 AU$464
includes taxes & fees
9 Mar - 10 Mar
Walk to Beach! King Bed & Free Beach Passes
Marina

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is AU$667
includes taxes & fees
8 Mar - 9 Mar
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
TV, offices

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

Wright's Cottage- Pet's Welcome & EV Charging
Annapolis
9.2 out of 10, Wonderful, (16 reviews)
"Nice little spot, very quiet "
United States
Susan S.
The price is AU$518
includes taxes & fees
9 Mar - 10 Mar
Wright's Cottage- Pet's Welcome & EV Charging
Beach nearby, sun-loungers, beach towels

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
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 AU$740
includes taxes & fees
17 Mar - 18 Mar
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Smart TV

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (14 reviews)
"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 AU$739
includes taxes & fees
18 Mar - 19 Mar
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Beach

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Prince Frederick
10.0 out of 10, Exceptional, (8 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
The price is AU$630
includes taxes & fees
16 Mar - 17 Mar
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Outdoor dining

Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (43 reviews)
"Clean, quiet, comfy"
United Kingdom
Deborah V.
Sunset Breezes - quiet waterfront retreat
Smart TV, books

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

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Prince Frederick
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.
The price is AU$567
includes taxes & fees
30 Mar - 31 Mar
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Beach

Cozy Beach Retreat - 3 bedrooms with 3 queen size beds. Sleeps 6

Cozy Beach Retreat - 3 bedrooms with 3 queen size beds. Sleeps 6
Saint Leonard
The price is AU$553
includes taxes & fees
6 Mar - 7 Mar
Cozy Beach Retreat - 3 bedrooms with 3 queen size beds. Sleeps 6
Smart TV

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
Shady Side
10.0 out of 10, Exceptional, (4 reviews)
"Would stay here again "
United States
Thomas D.
The price is AU$614
includes taxes & fees
8 Mar - 9 Mar
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Outdoor dining

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (32 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is AU$599
includes taxes & fees
15 Mar - 16 Mar
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Interior

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
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 AU$713
includes taxes & fees
11 Mar - 12 Mar
Annapolis Retreat - 7 mins from downtown Annapolis!
Interior

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
The price is AU$574
includes taxes & fees
11 Mar - 12 Mar
Sunset Cottage - West River Access and Views!
Fridge, microwave, oven, stovetop

Golden Anchor Retreat; Lux Living! - Sleeps 7

Golden Anchor Retreat; Lux Living! - Sleeps 7
Edgewater
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 AU$943
includes taxes & fees
10 Mar - 11 Mar
Golden Anchor Retreat; Lux Living! - Sleeps 7
Beach

Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
Edgewater
10.0 out of 10, Exceptional, (4 reviews)
"Great location, easy check in/out. Everything we needed was available! Very comfortable bed, super cute property. "
United States
MJ S.
The price is AU$492
includes taxes & fees
17 Mar - 18 Mar
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
Outdoor spa tub

London Towne Bungalow w/Loft - Walk to the Beach!

London Towne Bungalow w/Loft - Walk to the Beach!
Edgewater
9.0 out of 10, Wonderful, (4 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is AU$643
includes taxes & fees
25 Mar - 26 Mar
London Towne Bungalow w/Loft - Walk to the Beach!
TV

5 Mi to Show Place Arena: Quiet Townhome w/ Patio

5 Mi to Show Place Arena: Quiet Townhome w/ Patio
Upper Marlboro
The price is AU$709
includes taxes & fees
19 Mar - 20 Mar
5 Mi to Show Place Arena: Quiet Townhome w/ Patio
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

Towneplace Suites by Marriott Clinton at Joint Base Andrews

Towneplace Suites by Marriott Clinton at Joint Base Andrews

8/10 Good
"Hot tub out of order. Room was clean. Air conditioner was great. Kitchen area was spotless "
Coretta 2-night trip
Posted 1 hour ago
Towneplace Suites by Marriott Clinton at Joint Base Andrews

Find out more about Chesapeake Beach

Chesapeake Beach Holiday Homes information

Number of reviews
208
Accommodation
381 Holiday Homes
Lowest Price
AU$143
Highest Price
AU$943