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Check prices for these dates

In two weeks
3 Oct - 5 Oct
In two months
14 Nov - 16 Nov
In three months
12 Dec - 14 Dec
In four months
9 Jan - 11 Jan

Vacation Homes in Chesapeake Beach

Family Beach House: Spacious Deck, Grill & Views
Pool

Family Beach House: Spacious Deck, Grill & Views

9.0 out of 10, Wonderful, (6)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
Family Beach House: Spacious Deck, Grill & Views
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, (40)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
The price is SAR 276
SAR 960 total
includes taxes & fees
17 Sep - 18 Sep
Relax on Kent Island in 3 Bedroom Home w/Waterview
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. "
Waterfront Getaway, Dock Your Boat & Play!
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."
Edgewater/Mayo Gateaway w/ Hot Tub
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."
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."
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Londontowne Hideaway
Exterior detail

Londontowne Hideaway

4.0 out of 10, (1)
"The house was much smaller then it originally appeared to be in the listing photos and what they had available was the bare minimum. The neighborhood was rowdy and there was screaming late into the night. The shower also sprayed water all over the floor and caused a massive puddle. The house was overall nice and clean but not worth the price that it was listed for. A hotel would have much better accommodated our needs. "
Londontowne Hideaway
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)
"The property was well cleaned and communication with owner was excellent. Would stay again"
Wright's Cottage- Pet's Welcome & EV Charging
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. "
Holly Hill Haven - Sleeps 10
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."
Annapolis Retreat - 7 mins from downtown Annapolis!
Beautiful Waterfront Retreat in Cambridge!
Interior

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (47)
"Beautifully decorated home, clean and spacious. We really enjoyed the private waterfront and kayak. Would love to come back. "
The price is SAR 797
SAR 1,648 total
includes taxes & fees
24 Sep - 25 Sep
Beautiful Waterfront Retreat in Cambridge!
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 SAR 1,313
SAR 2,465 total
includes taxes & fees
17 Oct - 18 Oct
The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Terrace/patio

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

10.0 out of 10, Exceptional, (9)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is SAR 709
SAR 1,770 total
includes taxes & fees
17 Sep - 18 Sep
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
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, (30)
"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. "
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)
"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!"
Walk to Beach! King Bed & Free Beach Passes
Sunset Breezes - quiet waterfront retreat
Property grounds

Sunset Breezes - quiet waterfront retreat

10.0 out of 10, Exceptional, (40)
"Good time with my friends "
The price is SAR 1,283
SAR 1,599 total
includes taxes & fees
5 Oct - 6 Oct
Sunset Breezes - quiet waterfront retreat
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Terrace/patio

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

2BR, 1BA Boutique Brick Beauty located in historic Eastport.
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 SAR 1,493
SAR 2,584 total
includes taxes & fees
29 Sep - 30 Sep
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Welcoming 3-bedroom townhome with AC in Waldorf
3 bedrooms, iron/ironing board, WiFi, bed sheets

Welcoming 3-bedroom townhome with AC in Waldorf

The price is SAR 654
SAR 1,210 total
includes taxes & fees
2 Oct - 3 Oct
Welcoming 3-bedroom townhome with AC in Waldorf
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 SAR 2,194
SAR 3,566 total
includes taxes & fees
21 Sep - 22 Sep
Spacious waterfront home with amazing views, private pier, fishing and crabbing.
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

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG

10/10 Excellent
"Our stay here is excellent as usual. I love the kitchen, the refridgerator, and the roominess. We feed the mids and bring food in our trailer for the next day's game. It is nice to have a full size fridge in order to put perishables that cannot stay in the trailer overnight. The room is very clean, the people at the front desk are very accomodating and kind. I love all our stays here and am sad to not be able to find a room here for next home game. This will always be my first choice when going to a home game."
Josie 3-night trip
Posted 21 hours ago
Candlewood Suites Annapolis by IHG