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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for Chesapeake Beach holiday homes

Dining

Haven 2

Haven 2
2.5 star property
Waldorf
The price is £75
includes taxes & fees
15 Feb - 16 Feb
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 £203
includes taxes & fees
17 Feb - 18 Feb
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
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 £378
includes taxes & fees
9 Feb - 10 Feb
Annapolis Retreat - 7 mins from downtown Annapolis!
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, (18 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 £240
includes taxes & fees
9 Mar - 10 Mar
Walk to Beach! King Bed & Free Beach Passes
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, (31 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is £302
includes taxes & fees
11 Feb - 12 Feb
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Fridge, microwave, oven, stovetop

Beautiful Waterfront Retreat in Cambridge!

Beautiful Waterfront Retreat in Cambridge!
Cambridge
10.0 out of 10, Exceptional, (50 reviews)
"The house was completely spotless - the location was perfect! And the host included a s'mores kit, and baited crab traps and had them waiting with crabs in them when we arrived! This was an excellent weekend - we would recommend Hudson House to anyone!"
United States
Elizabeth G.
The price is £358
includes taxes & fees
10 Feb - 11 Feb
Beautiful Waterfront Retreat in Cambridge!
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 £355
includes taxes & fees
9 Feb - 10 Feb
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
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 £327
includes taxes & fees
9 Feb - 10 Feb
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
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 £258
includes taxes & fees
9 Mar - 10 Mar
Wright's Cottage- Pet's Welcome & EV Charging
Outdoor spa tub

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

London Towne Bungalow w/Loft - Walk to the Beach!
Edgewater
8.8 out of 10, Excellent, (3 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is £348
includes taxes & fees
9 Feb - 10 Feb
London Towne Bungalow w/Loft - Walk to the Beach!
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 £286
includes taxes & fees
9 Feb - 10 Feb
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
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 £371
includes taxes & fees
9 Feb - 10 Feb
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
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 £260
includes taxes & fees
9 Feb - 10 Feb
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
Games room

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

2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Eastport
The price is £261
includes taxes & fees
9 Feb - 10 Feb
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Interior

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
The price is £293
includes taxes & fees
16 Feb - 17 Feb
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 £485
includes taxes & fees
9 Feb - 10 Feb
Golden Anchor Retreat; Lux Living! - Sleeps 7
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)
"Amazing news out of the back.Great for kayaking.We brought our own kayaksAnd also use yoursThere were four of usWe also took a nice trip over to Saint Michael’s"
United States
Sandy S.
The price is £381
includes taxes & fees
9 Feb - 10 Feb
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Fridge, microwave, oven, stovetop

Cozy Winter 4BR Near DC • Fire Pit + Cocoa Bar

Cozy Winter 4BR Near DC • Fire Pit + Cocoa Bar
Waldorf
7.4 out of 10, Good, (3 reviews)
"At first glance I just knew this place was the vision of professional designer, but the host, Andre, said he just went with what he liked! Available day or night, Andre was the most pleasant young man, a wonderful host. We had a marvelous visit. It was so quiet here. The neighborhood was beautiful with lots of new shopping and dining closeby. They are centrally located to so many fabulous areas. MGM Grand in one direction and Colonial Beach (VA) going south. Anyone planning a trip to...
United States
Nicki P.
The price is £193
includes taxes & fees
16 Feb - 17 Feb
Cozy Winter 4BR Near DC • Fire Pit + Cocoa Bar
Dining

Welcoming 3-bedroom townhome with AC in Waldorf

Welcoming 3-bedroom townhome with AC in Waldorf
Waldorf
7.6 out of 10, Good, (5 reviews)
"Location was perfect and the pool/ping pong table made it more enjoyable."
United States
pamela h.
The price is £362
includes taxes & fees
9 Feb - 10 Feb
Welcoming 3-bedroom townhome with AC in Waldorf
Exterior

Chesapeake Paradise House-Stunning 6+br4ba Wtrfrnt

Chesapeake Paradise House-Stunning 6+br4ba Wtrfrnt
Deale
9.4 out of 10, Exceptional, (12 reviews)
"Beautiful property! Water on two sides, lots of outdoor space , we had 11 people from 2-92 years staying for almost a week and had a great time. Wonderful sitting areas and screened porch. We crabbed, kayaked, had a campfire grilled. Relaxing getaway"
United States
Jody P.
The price is £539
includes taxes & fees
18 Feb - 19 Feb
Chesapeake Paradise House-Stunning 6+br4ba Wtrfrnt
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

Wingate by Wyndham Waldorf/Washington DC Area

Wingate by Wyndham Waldorf/Washington DC Area

4/10 Poor
"WiFi extremely unstable, roaches in room "
QUEENTIA 6-night trip
Posted 3 days ago
Wingate by Wyndham Waldorf/Washington DC Area

Find out more about Chesapeake Beach

Chesapeake Beach Holiday Homes information

Number of reviews
230
Accommodation
381 Holiday Homes
Lowest Price
£193
Highest Price
£539