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Search Vacation Homes in Chesapeake Beach

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Dec 5 - Dec 7
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Dec 12 - Dec 14
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Dec 26 - Dec 28
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Jan 23 - Jan 25

Vacation Homes in Chesapeake Beach

Pool
Family Beach House: Spacious Deck, Grill & Views

Vacation Home in Chesapeake Beach

9.0 out of 10, Wonderful, (6)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
$417 nightly
The price is $439
Nov 25 - Nov 26
Total with taxes and fees
Family Beach House: Spacious Deck, Grill & Views
Beach nearby
Walk to Beach! King Bed & Free Beach Passes

Vacation Home in North Beach

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!"
United States
Jennifer B.
$297 nightly
The price is $328
Dec 1 - Dec 2
Total with taxes and fees
Walk to Beach! King Bed & Free Beach Passes
Marina
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Vacation Home in Stevensville

9.8 out of 10, Exceptional, (42)
"Wonderful home and host. Very easy to check-in and communication was excellent. "
United States
Ann T.
$246 nightly
The price is $261
Nov 25 - Nov 26
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Beach nearby, sun loungers, beach towels
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Vacation Home in North Beach

10.0 out of 10, Exceptional, (31)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
$419 nightly
The price is $462
Dec 1 - Dec 2
Total with taxes and fees
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Interior
Beautiful Waterfront Retreat in Cambridge!

Vacation Home in Cambridge

10.0 out of 10, Exceptional, (49)
"Wonderful stay. The Crab Shack and dock were the highlights. We spent most of our time there. It was awesome. Highly recommend. "
United States
Christopher D.
$357 nightly
The price is $378
Nov 30 - Dec 1
Total with taxes and fees
Beautiful Waterfront Retreat in Cambridge!
TV, books, offices
Holly Hill Haven - Sleeps 10

Vacation Home in Edgewater

10.0 out of 10, Exceptional, (3)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
$474 nightly
The price is $504
Dec 9 - Dec 10
Total with taxes and fees
Holly Hill Haven - Sleeps 10
Fridge, microwave, oven, stovetop
Edgewater/Mayo Gateaway w/ Hot Tub

Vacation Home in Edgewater

9.8 out of 10, Exceptional, (24)
"Very clean, had everything we needed for our stay!"
United States
Jackie R.
$570 nightly
The price is $613
Dec 9 - Dec 10
Total with taxes and fees
Edgewater/Mayo Gateaway w/ Hot Tub
3 bedrooms, iron/ironing board, travel crib, free WiFi
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Vacation Home in Prince Frederick

9.4 out of 10, Exceptional, (3)
"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "
United States
Carrie K.
$327 nightly
The price is $347
Nov 25 - Nov 26
Total with taxes and fees
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Beach
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Vacation Home in Prince Frederick

10.0 out of 10, Exceptional, (8)
"Clean and easy "
United States
Robert R.
$322 nightly
The price is $341
Nov 25 - Nov 26
Total with taxes and fees
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Property grounds
Cozy Private Suite in Eastport, Near USNA

Vacation Home in Eastport

Cozy Private Suite in Eastport, Near USNA
TV, offices
Wright's Cottage- Pet's Welcome & EV Charging

Vacation Home in Annapolis

9.2 out of 10, Wonderful, (15)
"The property was well cleaned and communication with owner was excellent. Would stay again"
United States
Kristen
$327 nightly
The price is $372
Dec 10 - Dec 11
Total with taxes and fees
Wright's Cottage- Pet's Welcome & EV Charging
Exterior
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Vacation Home in Shady Side

10.0 out of 10, Exceptional, (4)
"Would stay here again "
United States
Thomas D.
$376 nightly
The price is $429
Nov 25 - Nov 26
Total with taxes and fees
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Terrace/patio
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Vacation Home in Arundel on the Bay

9.8 out of 10, Exceptional, (11)
"Very clean - well equipped - perfect for our relaxing weekend."
United States
Chris J.
$432 nightly
The price is $492
Dec 2 - Dec 3
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
TV
Golden Anchor Retreat; Lux Living! - Sleeps 7

Vacation Home in Edgewater

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!"
United States
Sam A.
$605 nightly
The price is $649
Dec 9 - Dec 10
Total with taxes and fees
Golden Anchor Retreat; Lux Living! - Sleeps 7
Beach
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

Vacation Home in Edgewater

10.0 out of 10, Exceptional, (2)
"Very comfortable home. We only stayed one night but the property was quiet and safe. Nice neighborhood to walk around, including a marina and small beach down the street."
United States
Jay B.
$315 nightly
The price is $359
Dec 3 - Dec 4
Total with taxes and fees
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
Terrace/patio
2BR, 1BA Boutique Brick Beauty located in historic Eastport.

Vacation Home in Eastport

$332 nightly
The price is $378
Dec 8 - Dec 9
Total with taxes and fees
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Fridge, microwave, oven, stovetop
Cozy Winter 4BR Near DC • Fire Pit + Cocoa Bar

Vacation Home in Waldorf

7.4 out of 10, Good, (3)
"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.
$339 nightly
The price is $359
Dec 1 - Dec 2
Total with taxes and fees
Cozy Winter 4BR Near DC • Fire Pit + Cocoa Bar
Outdoor dining
The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.

Vacation Home in Prince Frederick

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."
United States
Timothy H.
$550 nightly
The price is $583
Nov 29 - Nov 30
Total with taxes and fees
The Hidaway on the Patuxent River<br>Children allowed and welcomed to stay.
3 bedrooms, iron/ironing board, WiFi, bed sheets
Welcoming 3-bedroom townhome with AC in Waldorf

Vacation Home in Waldorf

10.0 out of 10, Exceptional, (2)
"Location was perfect and the pool/ping pong table made it more enjoyable."
United States
pamela h.
$295 nightly
The price is $313
Dec 6 - Dec 7
Total with taxes and fees
Welcoming 3-bedroom townhome with AC in Waldorf
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

Residence Inn by Marriott Waldorf

Residence Inn by Marriott Waldorf

10/10 Excellent
"I had a wonderful experience but then one of the guests dog got loose and i am not a pet person. This was the only trun off"
Desiray 2-night trip
Posted 16 hours ago
Residence Inn by Marriott Waldorf

Find out more about Chesapeake Beach

Chesapeake Beach Vacation Homes information

Number of reviews
212
Accommodation
402 Vacation Homes
Lowest Price
$261
Highest Price
$649

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