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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Chesapeake Beach holiday homes

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 HK$589
HK$1,997 total
includes taxes & fees
28 Jan - 29 Jan
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Dining

Haven 2

Haven 2
2.5 star property
Waldorf
The price is HK$347
HK$776 total
includes taxes & fees
6 Feb - 7 Feb
Haven 2
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 HK$1,228
HK$2,905 total
includes taxes & fees
25 Jan - 26 Jan
Beautiful Waterfront Retreat in Cambridge!
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 HK$523
HK$2,402 total
includes taxes & fees
27 Jan - 28 Jan
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 HK$909
HK$3,346 total
includes taxes & fees
5 Feb - 6 Feb
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
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 HK$1,344
HK$3,781 total
includes taxes & fees
29 Jan - 30 Jan
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
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 HK$1,240
HK$4,044 total
includes taxes & fees
25 Jan - 26 Jan
Annapolis Retreat - 7 mins from downtown Annapolis!
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 HK$1,200
HK$3,448 total
includes taxes & fees
1 Feb - 2 Feb
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
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 HK$1,614
HK$3,858 total
includes taxes & fees
3 Feb - 4 Feb
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Interior

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
The price is HK$1,240
HK$3,068 total
includes taxes & fees
28 Jan - 29 Jan
Sunset Cottage - West River Access and Views!
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)
"Everything was amazing. "
United States
Lorie S.
The price is HK$1,559
HK$3,033 total
includes taxes & fees
26 Jan - 27 Jan
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
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 HK$1,193
HK$3,840 total
includes taxes & fees
9 Feb - 10 Feb
London Towne Bungalow w/Loft - Walk to the Beach!
TV, books, offices

Holly Hill Haven - Sleeps 10

Holly Hill Haven - Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (3 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is HK$1,232
HK$4,462 total
includes taxes & fees
1 Feb - 2 Feb
Holly Hill Haven - Sleeps 10
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 HK$2,046
HK$4,119 total
includes taxes & fees
29 Jan - 30 Jan
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Games room

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

2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Eastport
The price is HK$1,287
HK$2,587 total
includes taxes & fees
25 Jan - 26 Jan
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
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 HK$1,754
HK$2,782 total
includes taxes & fees
26 Jan - 27 Jan
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
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 HK$1,583
HK$5,280 total
includes taxes & fees
25 Jan - 26 Jan
Golden Anchor Retreat; Lux Living! - Sleeps 7
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 HK$1,474
HK$1,760 total
includes taxes & fees
25 Jan - 26 Jan
Cozy Winter 4BR Near DC • Fire Pit + Cocoa Bar
TV

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$2,339
HK$4,777 total
includes taxes & fees
4 Feb - 5 Feb
5 Mi to Show Place Arena: Quiet Townhome w/ Patio
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 HK$3,501
HK$5,831 total
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

Sleep Inn & Suites Near Joint Base Andrews - Washington Area

Sleep Inn & Suites Near Joint Base Andrews - Washington Area

10/10 Excellent
"Everything was great. The only problem was that the shower did not get very hot "
Crystal 4-night trip
Posted 2 days ago
Sleep Inn & Suites Near Joint Base Andrews - Washington Area

Find out more about Chesapeake Beach

Chesapeake Beach Vacation Homes information

Number of reviews
207
Accommodation
381 Vacation Homes
Lowest Price
HK$1,760
Highest Price
HK$5,831

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