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Holiday Homes in Chesapeake Beach

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Check prices for these dates

Next weekend
12 Sept - 14 Sept
In two weeks
19 Sept - 21 Sept
In one month
3 Oct - 5 Oct
In two months
31 Oct - 2 Nov

Featured Holiday Homes in Chesapeake Beach

Our top choices for Chesapeake Beach holiday homes

Waterfront Getaway, Dock Your Boat & Play!
Outdoor dining

Waterfront Getaway, Dock Your Boat & Play!

10.0 out of 10, Exceptional, (2)
"Lovely stay, don't let the RV aspect.of it scare you. Nicer than most other bnbs ice stayed in. Quiet, clean and beautiful view of the water. "
The price is AU$470
includes taxes & fees
14 Sept - 15 Sept
Waterfront Getaway, Dock Your Boat & Play!
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Pool

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

9.0 out of 10, Wonderful, (6)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
The price is AU$628
includes taxes & fees
15 Sept - 16 Sept
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Relax on Kent Island in 3 Bedroom Home w/Waterview
Marina

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (39)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is AU$407
includes taxes & fees
3 Sept - 4 Sept
Relax on Kent Island in 3 Bedroom Home w/Waterview
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Beach nearby, sun-loungers, beach towels

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

10.0 out of 10, Exceptional, (29)
"Absolutely beautiful and spacious home perfectly located in North Beach. Very peaceful area and close to the beach, restaurants and shopping. We really enjoyed our stay and hope to visit again in the future. "
The price is AU$658
includes taxes & fees
3 Sept - 4 Sept
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Walk to Beach! King Bed & Free Beach Passes
Beach nearby

Walk to Beach! King Bed & Free Beach Passes

10.0 out of 10, Exceptional, (16)
"Excellent"
The price is AU$507
includes taxes & fees
3 Sept - 4 Sept
Walk to Beach! King Bed & Free Beach Passes
Holly Hill Haven - Sleeps 10
TV, books, offices

Holly Hill Haven - Sleeps 10

10.0 out of 10, Exceptional, (3)
"House was clean and comfortable. Great layout. "
The price is AU$721
includes taxes & fees
15 Sept - 16 Sept
Holly Hill Haven - Sleeps 10
The Cottage
Exterior

The Cottage

10.0 out of 10, Exceptional, (7)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is AU$735
includes taxes & fees
15 Sept - 16 Sept
The Cottage
Beautiful Waterfront Retreat in Cambridge!
Interior

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (44)
"Beautifully decorated home, clean and spacious. We really enjoyed the private waterfront and kayak. Would love to come back. "
The price is AU$678
includes taxes & fees
8 Sept - 9 Sept
Beautiful Waterfront Retreat in Cambridge!
London Towne Bungalow w/Loft - Walk to the Beach!
Marina

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

8.0 out of 10, Very good, (2)
"The water that comes out of the house tastes bad."
The price is AU$724
includes taxes & fees
15 Sept - 16 Sept
London Towne Bungalow w/Loft - Walk to the Beach!
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Exterior

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

10.0 out of 10, Exceptional, (2)
"The property is newly renovated and very comfortable. Property owner is responsive to any questions, and we enjoyed our stay here. Would recommend it for anyone staying in Shady Side."
The price is AU$766
includes taxes & fees
3 Sept - 4 Sept
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Wright's Cottage- Pet's Welcome & EV Charging
TV, offices

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

9.0 out of 10, Wonderful, (12)
"This was a wonderful peaceful stay and the host was great. Loved it!!! "
The price is AU$566
includes taxes & fees
3 Sept - 4 Sept
Wright's Cottage- Pet's Welcome & EV Charging
New! Golden Anchor Retreat; Lux Living! - Sleeps 7
Interior

New! Golden Anchor Retreat; Lux Living! - Sleeps 7

10.0 out of 10, Exceptional, (2)
"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!"
The price is AU$933
includes taxes & fees
15 Sept - 16 Sept
New! Golden Anchor Retreat; Lux Living! - Sleeps 7
Londontowne Hideaway
Exterior detail

Londontowne Hideaway

The price is AU$731
includes taxes & fees
15 Sept - 16 Sept
Londontowne Hideaway
The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.
Outdoor dining

The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.

9.2 out of 10, Wonderful, (9)
"Got to go fishing, kayaking, and swimming in the pool. Had a great time, views are wonderful and it’s a peaceful environment. 10/10 would stay again."
The price is AU$745
includes taxes & fees
15 Sept - 16 Sept
The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Smart TV

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

10.0 out of 10, Exceptional, (13)
"very serene, peaceful home on the bay! Amazing getaway! "
The price is AU$997
includes taxes & fees
1 Oct - 2 Oct
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Edgewater/Mayo Gateaway w/ Hot Tub
Fridge, microwave, oven, stovetop

Edgewater/Mayo Gateaway w/ Hot Tub

9.8 out of 10, Exceptional, (21)
"We had a very good time. Fenced backyard for the pet was a great added value. We could relax and visit the beach and the towns around. We really enjoyed our stay."
The price is AU$804
includes taxes & fees
8 Sept - 9 Sept
Edgewater/Mayo Gateaway w/ Hot Tub
Annapolis Retreat - 7 mins from downtown Annapolis!
Microwave, oven, stovetop, dishwasher

Annapolis Retreat - 7 mins from downtown Annapolis!

10.0 out of 10, Exceptional, (2)
"The house was roomy, perfect for a large group and it was very clean and cozy. They also provided everything that was needed to have a comfortable stay."
The price is AU$881
includes taxes & fees
9 Sept - 10 Sept
Annapolis Retreat - 7 mins from downtown Annapolis!
Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier
Terrace/patio

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

10.0 out of 10, Exceptional, (9)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is AU$774
includes taxes & fees
9 Sept - 10 Sept
Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier
Spacious waterfront home with amazing views, private pier, fishing and crabbing.
Property grounds

Spacious waterfront home with amazing views, private pier, fishing and crabbing.

9.4 out of 10, Exceptional, (25)
"A nice, quiet location on the water. Exactly as advertised. We would definitely stay again if we were in the area."
The price is AU$1,592
includes taxes & fees
21 Sept - 22 Sept
Spacious waterfront home with amazing views, private pier, fishing and crabbing.
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Terrace/patio

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

The price is AU$507
includes taxes & fees
15 Sept - 16 Sept
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

Find out more about Chesapeake Beach

Find out more about Chesapeake Beach

Chesapeake Beach Holiday Homes information

Number of reviews
Accommodation
411 Holiday Homes
Lowest Price
AU$678
Highest Price
AU$678

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