Holiday Homes in Chesapeake Beach

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 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 AU$358
includes taxes & fees
19 Jan - 20 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 AU$152
includes taxes & fees
19 Jan - 20 Jan
Haven 2
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, (17 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 AU$488
includes taxes & fees
19 Jan - 20 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 AU$602
includes taxes & fees
21 Jan - 22 Jan
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)
"Beautiful place! Loved all the activities, will return in the future! Our family and friends had a blast! Thank you so much!!"
United States
Karen L.
The price is AU$542
includes taxes & fees
20 Jan - 21 Jan
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 AU$711
includes taxes & fees
19 Jan - 20 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 AU$798
includes taxes & fees
19 Jan - 20 Jan
Annapolis Retreat - 7 mins from downtown Annapolis!
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 AU$815
includes taxes & fees
9 Feb - 10 Feb
Holly Hill Haven - Sleeps 10
Interior

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
2.0 star property
Shady Side
The price is AU$609
includes taxes & fees
20 Jan - 21 Jan
Sunset Cottage - West River Access and Views!
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 AU$724
includes taxes & fees
9 Feb - 10 Feb
London Towne Bungalow w/Loft - Walk to the Beach!
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 AU$794
includes taxes & fees
19 Jan - 20 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 AU$500
includes taxes & fees
19 Jan - 20 Jan
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
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 AU$658
includes taxes & fees
25 Jan - 26 Jan
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 AU$756
includes taxes & fees
1 Feb - 2 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 AU$538
includes taxes & fees
21 Jan - 22 Jan
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
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 AU$602
includes taxes & fees
25 Jan - 26 Jan
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
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 AU$1,003
includes taxes & fees
19 Jan - 20 Jan
Golden Anchor Retreat; Lux Living! - Sleeps 7
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)
"When we walked in, the host had the dining room table set nicely. We thought, "Wow, this place is fancy." We enjoyed the ping pong table and plenty of rooms for our family gathering. "
United States
Keith A.
The price is AU$752
includes taxes & fees
19 Jan - 20 Jan
Welcoming 3-bedroom townhome with AC in Waldorf
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 AU$417
includes taxes & fees
15 Feb - 16 Feb
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
2.0 star property
Upper Marlboro
The price is AU$907
includes taxes & fees
19 Jan - 20 Jan
5 Mi to Show Place Arena: Quiet Townhome w/ Patio
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

Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"Extremely nice remodel, everyone was nice to talk to and friendly "
Tyler 2-night trip
Posted 2 days ago
Rod 'N' Reel Resort

Find out more about Chesapeake Beach

Chesapeake Beach Holiday Homes information

Number of reviews
197
Accommodation
381 Holiday Homes
Lowest Price
AU$358
Highest Price
AU$1,003