Holiday Homes in Chesapeake Beach

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Our top choices for Chesapeake Beach holiday homes

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 €374
includes taxes & fees
15 Mar - 16 Mar
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

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 €230
includes taxes & fees
16 Mar - 17 Mar
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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 €413
includes taxes & fees
12 Mar - 13 Mar
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

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)
"Delightful one-night stay! Place was clean, quiet, convenient and very comfortable. Especially grateful that our beloved dog was welcomed"
United States
Elaine D.
The price is €322
includes taxes & fees
18 Mar - 19 Mar
Walk to Beach! King Bed & Free Beach Passes

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 €451
includes taxes & fees
17 Mar - 18 Mar
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

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 €316
includes taxes & fees
30 Mar - 31 Mar
Wright's Cottage- Pet's Welcome & EV Charging

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 €449
includes taxes & fees
15 Mar - 16 Mar
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

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 €364
includes taxes & fees
15 Mar - 16 Mar
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

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.
The price is €301
includes taxes & fees
30 Mar - 31 Mar
Sunset Breezes - quiet waterfront retreat

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 €381
includes taxes & fees
16 Mar - 17 Mar
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

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)
"Our family had a great stay. Thank you!"
United States
Colleen G.
The price is €344
includes taxes & fees
30 Mar - 31 Mar
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

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 €364
includes taxes & fees
12 Mar - 13 Mar
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

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 €395
includes taxes & fees
17 Mar - 18 Mar
London Towne Bungalow w/Loft - Walk to the Beach!

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is €437
includes taxes & fees
16 Mar - 17 Mar
Annapolis Retreat - 7 mins from downtown Annapolis!

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
The price is €359
includes taxes & fees
17 Mar - 18 Mar
Sunset Cottage - West River Access and Views!

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 €849
includes taxes & fees
11 Apr - 12 Apr
Golden Anchor Retreat; Lux Living! - Sleeps 7

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 €301
includes taxes & fees
12 Mar - 13 Mar
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

Cozy 3BR Annapolis sleeps 10 Private Deck, Parking

Cozy 3BR Annapolis sleeps 10 Private Deck, Parking
Annapolis
The price is €494
includes taxes & fees
12 Mar - 13 Mar
Cozy 3BR Annapolis sleeps 10 Private Deck, Parking

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 €432
includes taxes & fees
12 Mar - 13 Mar
5 Mi to Show Place Arena: Quiet Townhome w/ Patio

2BR, 1BA Boutique Brick Beauty located in historic Eastport.

2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Eastport
The price is €376
includes taxes & fees
1 Apr - 2 Apr
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

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Chesapeake Beach Holiday Homes information

Number of reviews
209
Accommodation
381 Holiday Homes
Lowest Price
€230
Highest Price
€849