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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 HK$1,331
HK$3,450 total
includes taxes & fees
18 Mar - 19 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 wonderful stay! The host was incredibly kind, responsive, and helpful throughout, making everything smooth and stress-free. The house itself was a great place to stay. It is clean, comfortable, and exactly as described. We really appreciated the thoughtful touches and would happily stay here again. Highly recommended!"
United States
Supriya V.
The price is HK$845
HK$2,314 total
includes taxes & fees
19 Mar - 20 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 HK$1,349
HK$3,787 total
includes taxes & fees
18 Mar - 19 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 HK$734
HK$2,660 total
includes taxes & fees
18 Mar - 19 Mar
Walk to Beach! King Bed & Free Beach Passes

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 HK$1,941
HK$3,477 total
includes taxes & fees
18 Mar - 19 Mar
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

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 HK$777
HK$3,192 total
includes taxes & fees
18 Mar - 19 Mar
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

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 HK$1,902
HK$4,266 total
includes taxes & fees
24 Mar - 25 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 HK$1,375
HK$2,915 total
includes taxes & fees
23 Mar - 24 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 HK$2,054
HK$4,127 total
includes taxes & fees
18 Mar - 19 Mar
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

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 HK$1,240
HK$3,493 total
includes taxes & fees
18 Mar - 19 Mar
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

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 HK$1,660
HK$3,153 total
includes taxes & fees
30 Mar - 31 Mar
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

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 HK$2,012
HK$2,424 total
includes taxes & fees
12 Apr - 13 Apr
Sunset Breezes - quiet waterfront retreat

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 HK$1,034
HK$3,651 total
includes taxes & fees
18 Mar - 19 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 HK$1,401
HK$4,275 total
includes taxes & fees
18 Mar - 19 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 HK$1,417
HK$3,377 total
includes taxes & fees
18 Mar - 19 Mar
Sunset Cottage - West River Access and Views!

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 HK$1,761
HK$2,811 total
includes taxes & fees
18 Mar - 19 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 HK$1,578
HK$4,610 total
includes taxes & fees
18 Mar - 19 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 HK$1,667
HK$4,044 total
includes taxes & fees
5 Apr - 6 Apr
5 Mi to Show Place Arena: Quiet Townhome w/ Patio

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 HK$1,558
HK$5,265 total
includes taxes & fees
18 Mar - 19 Mar
Golden Anchor Retreat; Lux Living! - Sleeps 7

Tranquil Modern Farmhouse

Tranquil Modern Farmhouse
Waldorf
9.2 out of 10, Wonderful, (7 reviews)
"This property was super gorgeous and spacious so we were able to relax. Guests had more than enough space and didn’t feel like they were on top of each other sleeping wise! We were able to just have dinner and feel safe! The owner answered any questions we had within 15 minutes, which was super helpful! "
United States
khaddija j.
The price is HK$2,290
HK$4,736 total
includes taxes & fees
30 Mar - 31 Mar
Tranquil Modern Farmhouse
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

Find out more about Chesapeake Beach

Chesapeake Beach Vacation Homes information

Number of reviews
205
Accommodation
381 Vacation Homes
Lowest Price
HK$2,314
Highest Price
HK$5,265

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