A harbor with boats docked, a pier, and a row of houses along the water.

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Chesapeake Beach vacation homes

A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

1. The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!
North Beach
9.6 out of 10, Exceptional, (30 reviews)
"Wonderful place to visit "
United States
James L.
The price is ￥20,393
￥48,055 total
includes taxes & fees
Oct 29 - Oct 30
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Living area

2. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (25 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is ￥16,606
￥54,158 total
includes taxes & fees
Nov 1 - Nov 2
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A cozy outdoor seating area with a fire pit, a wooden table, and chairs.

3. 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, (40 reviews)
"This property and host were excellent. Property was as advertised. Lovely, clean, quiet and comfortable. Owner was super responsive and check in and check out was easy. 100% recommend."
United States
Sarah
The price is ￥23,650
￥72,494 total
includes taxes & fees
Oct 30 - Oct 31
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A dining area with a wooden spiral staircase, a round table with chairs, a chandelier, and a clock on the wall.

4. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
10.0 out of 10, Exceptional, (4 reviews)
"Warm and cozy- amazing home, beautiful area"
United States
Sodbileg
Rose Haven Coastal Cottage
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

5. 3-bedroom house in Deale located on Bay many amenities and great views

3-bedroom house in Deale located on Bay many amenities and great views
Deale
10.0 out of 10, Exceptional, (1 review)
"Everything at this location was as shown on the listing and it was very clean. We were very satisfied with all elements of this stay. We were there for a weekend and did not use the place heavily, but it suited our needs. It's a quiet location. They had all the major points covered. The only negative comment I have is that the water out of the tap was smelly. I suggest bringing a couple of bottles of water and not drinking the water out of the taps. This is obviously a well maintained home...
United States
Amelia
The price is ￥28,348
￥68,943 total
includes taxes & fees
Oct 29 - Oct 30
3-bedroom house in Deale located on Bay many amenities and great views
A spacious living room with a grey sectional sofa, a round wooden coffee table, and a patterned rug.

6. Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Prince Frederick
9.2 out of 10, Wonderful, (12 reviews)
"A great place to crash and explore the area."
United States
Sean B.
The price is ￥24,411
￥57,427 total
includes taxes & fees
Nov 2 - Nov 3
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
A deck with outdoor furniture, a red door, and a house with windows.

7. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Shady Side
9.0 out of 10, Wonderful, (2 reviews)
"The location was spectacular, the host was communicative, and we had a great time! A beautiful and clean home with everything needed to make a trip a success. One small issue with some needed essentials meant a quick run to the store (TP!) but otherwise a great location, great stay, and would stay again!"
United States
David S.
The price is ￥26,931
￥59,787 total
includes taxes & fees
Nov 18 - Nov 19
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

8. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
The price is ￥31,498
￥70,937 total
includes taxes & fees
Nov 4 - Nov 5
Sunset Cottage - West River Access and Views!
A spacious living room with a ceiling fan, a staircase, and a view of the outdoors.

9. 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, (56 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
The price is ￥14,287
￥45,908 total
includes taxes & fees
Nov 1 - Nov 2
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

10. Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (13 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
United States
Diane D.
The price is ￥30,213
￥87,020 total
includes taxes & fees
Oct 29 - Oct 30
Renovated Bungalow | Walk to Beach | Dog-Friendly
A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

11. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Saint Leonard
10.0 out of 10, Exceptional, (8 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is ￥21,970
￥44,823 total
includes taxes & fees
Nov 2 - Nov 3
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

12. Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (6 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is ￥37,978
￥111,073 total
includes taxes & fees
Oct 29 - Oct 30
Family Home on Mayo Peninsula | Deck | Sleeps 10
A hot tub with a white deck and railing, surrounded by trees and a house in the background.

13. 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
9.6 out of 10, Exceptional, (19 reviews)
"Super clean, well furnished and in a nice quiet neighborhood close to downtown Annapolis. Great place to stay!"
United States
Ryan C.
The price is ￥30,474
￥75,675 total
includes taxes & fees
Nov 3 - Nov 4
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A lakeside view with chairs and a table, a rainbow, and trees.

14. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (26 reviews)
"Amazing host and home, great view with the water right there, and short drive to any shopping needs. It was the serene getaway I needed to recharge from city life and corporate burnout."
United States
George
The price is ￥36,080
￥60,028 total
includes taxes & fees
Nov 15 - Nov 16
Bright and airy waterfront getaway
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

15. Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is ￥31,217
￥89,058 total
includes taxes & fees
Nov 10 - Nov 11
Annapolis Retreat - 7 mins from downtown Annapolis!
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

16. 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, (17 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is ￥38,823
￥73,372 total
includes taxes & fees
Oct 29 - Oct 30
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

17. Londontowne Home | Beach | 3BR

Londontowne Home | Beach | 3BR
Edgewater
9.4 out of 10, Exceptional, (3 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 ￥38,128
￥117,437 total
includes taxes & fees
Oct 29 - Oct 30
Londontowne Home | Beach | 3BR
A spacious living room with a sofa set, a coffee table, and a chair. There is a painting on the wall and a window providing natural light.

18. Londontowne Rancher | 3BR | Near Waterfront

Londontowne Rancher | 3BR | Near Waterfront
Edgewater
7.0 out of 10, Good, (2 reviews)
"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. "
United States
rebekah h.
The price is ￥41,577
￥115,982 total
includes taxes & fees
Nov 2 - Nov 3
Londontowne Rancher | 3BR | Near Waterfront
Three birds perched on a wooden structure by the water.

19. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (75 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is ￥125,835
￥218,330 total
includes taxes & fees
Nov 1 - Nov 2
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A modern living room with a grey sofa, a dining table with chairs, and large windows with autumn foliage views.

20. Tranquil Modern Farmhouse

Tranquil Modern Farmhouse
Waldorf
9.2 out of 10, Wonderful, (10 reviews)
"Overall I had a wonderful stay... however I wish it was booked for a summertime day... the brand new pool looked very appealing & I wish I couldve enjoyed using it. Will have to try & stay again during the summer for a nice pool day!"
United States
Jay W.
The price is ￥77,958
￥136,354 total
includes taxes & fees
Nov 3 - Nov 4
Tranquil Modern Farmhouse
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

8/10 Good
"Didn't like the one hour wait to get the room...it was well after 5 to be assigned a room....the television in the common area of the room didn't work and staff was notified but no one came to fix it. The fire alarm went off early am and had to get up and the rowdy guess...well the police was there for them several times throughout the night."
Walker 1-night trip
Posted 17 hours ago
Residence Inn by Marriott Waldorf

Find out more about Chesapeake Beach

Chesapeake Beach Vacation Homes information

Number of reviews
285
Accommodation
405 Vacation Homes
Lowest Price
￥44,823
Highest Price
￥218,330