Title: Chesapeake Beach Vacation Rentals from CA $411: Short-Term Rentals for 2025 | Expedia.ca

  

[Chesapeake Beach Travel Guide](https://expedia.ca/Chesapeake-Beach.dx88967)[Hotels in Chesapeake Beach](https://expedia.ca/Chesapeake-Beach-Hotels.d88967.Travel-Guide-Hotels)[Things to do in Chesapeake Beach](https://expedia.ca/Things-To-Do-In-Chesapeake-Beach.d88967.Travel-Guide-Activities)[Chesapeake Beach Car Rentals](https://expedia.ca/Car-Rentals-In-Chesapeake-Beach.d88967.Car-Rental-Guide)[Chesapeake Beach Vacation Packages](https://expedia.ca/Chesapeake-Beach.d88967.Destination-Travel-Guides)

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Photo by Ronanne Vinson

# Chesapeake Beach Vacation Rentals

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## Check prices for these dates

Tonight

[Nov 1 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=88967&startDate=2025-11-01&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Nov 2 - Nov 3](https://www.expedia.ca/Hotel-Search?regionId=88967&startDate=2025-11-02&endDate=2025-11-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=88967&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=88967&startDate=2025-11-14&endDate=2025-11-16&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Vacation Rentals in Chesapeake Beach

![Marina](https://images.trvl-media.com/lodging/106000000/105760000/105758700/105758639/9f651e90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/106000000/105760000/105758700/105758639/7cf6f375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105760000/105758700/105758639/5a48c8aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/106000000/105760000/105758700/105758639/30aed7f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Floating 2 bed 2 bath condo stunning views of the bay

Stevensville

7.0/10

Good

(6)

"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Natalia F.

[](https://www.expedia.ca/Stevensville-Hotels-Floating-2-Bed-2-Bath-Condo-Stunning-Views-Of-The-Bay.h105758639.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/116000000/115920000/115915900/115915900/w1290h1714x0y14-f0c33c6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/115920000/115915900/115915900/7a22672e_edited_eae3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, in-room safe, WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115920000/115915900/115915900/w1280h955x0y7-8f5da894.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115920000/115915900/115915900/634c5499.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

North Beach

9.8/10

Exceptional

(12)

"The place was inviting and beautiful. Will definitely stay there again."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anita P.

[](https://www.expedia.ca/Owings-Hotels-The-Cozy-Crab-Your-Charming-Haven-In-Lovely-North-Beach.h115915900.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/85000000/84360000/84356100/84356021/6651f277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/85000000/84360000/84356100/84356021/f2dfd0b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/85000000/84360000/84356100/84356021/b6ac87da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/85000000/84360000/84356100/84356021/8acee54b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Tracys Landing

9.8/10

Exceptional

(50)

"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Andrea J.

[](https://www.expedia.ca/Spacious-5-Bedroom-Waterfront-Oasis-With-Private-Dock.h84356021.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/33000000/32570000/32562400/32562385/c5bdec51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/33000000/32570000/32562400/32562385/c9d30e18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/33000000/32570000/32562400/32562385/afb23ce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/33000000/32570000/32562400/32562385/10a98dfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Saint Michaels

9.6/10

Exceptional

(122)

"The house and location was perfect for a girls weekend with my mom and 2 daughters! The 1/2 bathrooms in each bedroom were nice to have upstairs!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kimberly L.

[](https://www.expedia.ca/St-Michaels-Hotels-John-Bruff-Waterview-Cottage-On-Harbor-And-On-Park-In-Town-St-Michaels.h32562385.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/24000000/23930000/23921900/23921839/7094a412.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach, sun loungers](https://images.trvl-media.com/lodging/24000000/23930000/23921900/23921839/060f4535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/24000000/23930000/23921900/23921839/4f65749e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/24000000/23930000/23921900/23921839/c21d2141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Port Republic

10/10

Exceptional

(180)

"Cottage was just as pictured. Lots of character and charm. Host, Brett was easy to work with and very helpful!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michelle R.

[](https://www.expedia.ca/Port-Republic-Hotels-Stunning-Views-From-Waterfront-Log-Cabin-With-Fireplace-On-The-Chesapeake-Bay.h23921839.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305189/60e252be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305189/8fd48299.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305189/a4a9eedd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305189/d7bd9b55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Waterfront Getaway, Dock Your Boat & Play!

Edgewater

10/10

Exceptional

(3)

"Great place to stay. It is clean, comfortable, and not lacking convenience.Quick communication with the host. We would definitely recommend!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Daniel K.

CA $139

CA $435 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Edgewater-Hotels-Waterfront-Getaway.h96305189.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/34000000/33510000/33506200/33506110/1dc9ddc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33510000/33506200/33506110/438bfc90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/34000000/33510000/33506200/33506110/c5d1df22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor banquet area](https://images.trvl-media.com/lodging/34000000/33510000/33506200/33506110/d6f3062d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Family and Pet-Friendly, Waterfront with Pier

Cambridge

10/10

Exceptional

(262)

"Our stay was great and Rob and Clarissa were very welcoming!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Allison L.

[](https://www.expedia.ca/Cambridge-Hotels-Family-And-Pet-Friendly.h33506110.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34330000/34323900/34323855/179041b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34330000/34323900/34323855/691f4295.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34330000/34323900/34323855/w1919h1439x0y0-289d79c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/35000000/34330000/34323900/34323855/3245ad2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

St Michaels

9.6/10

Exceptional

(145)

"Perfect place to stay for a cousins reunion, Central location to all the shops and restaurants."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Amh S.

[](https://www.expedia.ca/St-Michaels-Hotels-Premier-St-Michaels-Cottage-T-Blades-House-Walk-To-Everything-In-Town.h34323855.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/34000000/33550000/33549200/33549150/w1624h1084x0y2-ec718b23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33550000/33549200/33549150/f9c952d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33550000/33549200/33549150/28ff1584.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33550000/33549200/33549150/afb6f363.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

Woolford

9.8/10

Exceptional

(74)

"We had a wonderful stay including boating, kayaking, swimming, fishing, campfires and crabs! The house was perfect for our group and the owner was very accommodating."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Susan G.

[](https://www.expedia.ca/Woolford-Hotels-Newer-Luxury-Waterfront-Beach.h33549150.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/93000000/92010000/92008700/92008639/0809820d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92010000/92008700/92008639/8a60f7ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/93000000/92010000/92008700/92008639/1a21e043.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/93000000/92010000/92008700/92008639/0310a691.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cambridge

10/10

Exceptional

(13)

"Really nice property. Relaxing weekend. Stayed here with my daughter for two nights. We had a great time. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dara M.

[](https://www.expedia.ca/Cambridge-Hotels-Cozy-Cottage-With-Private-Dock-Chesapeake-Bay-Cambridge.h92008639.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/58000000/57120000/57118800/57118800/9810d5db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/58000000/57120000/57118800/57118800/1470bd05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/58000000/57120000/57118800/57118800/7c9c2c90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/58000000/57120000/57118800/57118800/7ce59dfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis

Cape St. John

10/10

Exceptional

(111)

"Made a short family trip out of needing to attend a wedding in Baltimore but did not expect how wonderful the trip would be just being in this home. Incredibly family friendly and accommodating for our 11, 10 and not even 1 year old. Very clean, close to amenities and attractions. The hosts were so kind, friendly and accommodating with our needs. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Hana K.

[](https://www.expedia.ca/Annapolis-Hotels-La-Maison-Stunning-Waterfront-Views-With-Pool.h57118800.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/c77382da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/99582f9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/12356e9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/b482bb5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Relax on Kent Island in 3 Bedroom Home w/Waterview

Stevensville

9.8/10

Exceptional

(41)

"Place was clean and welcoming."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sophie B.

CA $145

CA $411 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Stevensville-Hotels-Relax-On-Kent-Island-In-3-Bedroom-Home-WWaterview.h84063656.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34350000/34340300/34340251/f36704f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/35000000/34350000/34340300/34340251/6e046b2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/35000000/34350000/34340300/34340251/81a65b36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/35000000/34350000/34340300/34340251/39c9a1b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Cambridge

10/10

Exceptional

(78)

"Good stay overall"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Bill C.

[](https://www.expedia.ca/Cambridge-Hotels-Year-Round-Waterfront-Estate-Family-Reunions-Retreats-Sleeps-28.h34340251.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/31000000/30530000/30524700/30524635/w799h599x1y1-51c4d4f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/31000000/30530000/30524700/30524635/accde279.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/31000000/30530000/30524700/30524635/c5088270.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/31000000/30530000/30524700/30524635/5c7b7caa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Million Dollar View of the Chesapeake Bay

Deale

9.8/10

Exceptional

(129)

"Property was just what I was after for a short break to relax and take in the stunning view. Nice quiet neighborhood to take walks around and a community pier to appreciate the water views for sunrise and sunset."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

JP H.

[](https://www.expedia.ca/Deale-Hotels-Million-Dollar-View-Of-The-Chesapeake-Bay.h30524635.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33700000/33691100/33691023/bb559863.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33700000/33691100/33691023/6beced05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33700000/33691100/33691023/996d9ced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33700000/33691100/33691023/cfc6a700.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

Stevensville

9.8/10

Exceptional

(43)

"Great location. Beautiful home on the water with plenty of room for everyone. Would highly recommend!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joseph C.

[](https://www.expedia.ca/Stevensville-Hotels-Waterfront-Home-On-The-Chesapeake-Bay-With-Pier-Only-30-Min-From-Naval-Academy.h33691023.Hotel-Information)

![Smart TV, fireplace, books, printers](https://images.trvl-media.com/lodging/109000000/108010000/108008600/108008595/d04c7b73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/109000000/108010000/108008600/108008595/d98176c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/109000000/108010000/108008600/108008595/37ea1a39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, printers](https://images.trvl-media.com/lodging/109000000/108010000/108008600/108008595/dcb17a56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Stevensville

10/10

Exceptional

(6)

"This VRBO was very clean. Since it is a fairly new addition to VRBO, we thought it could use a little more info, like a portfolio with the combination to the bike locks, where to go to eat and visit, etc. Also, the only coffeemaker was a Keurig and we didn’t bring any K-cups. The 4 of us had a nice 50th Anniversary long weekend."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sharon M.

CA $586

CA $1,273 total

includes taxes & fees

Nov 6 - Nov 7

[](https://www.expedia.ca/Stevensville-Hotels-Charming-2-Bedroom-Waterfront-Cottage-In-Peaceful-Stevensville-With-AC.h108008595.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/33000000/32600000/32590200/32590170/7dc8015a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/33000000/32600000/32590200/32590170/831e4185.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/33000000/32600000/32590200/32590170/w1919h1440x0y0-69f18a52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/33000000/32600000/32590200/32590170/22b0e30e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

St Michaels

9.6/10

Exceptional

(124)

"Beautiful house Great location. We really enjoyed our first visit to St. Michaels!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

JIM S.

[](https://www.expedia.ca/St-Michaels-Hotels-Location.h32590170.Hotel-Information)

![Private beach](https://images.trvl-media.com/lodging/93000000/92610000/92607300/92607228/caba515d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92610000/92607300/92607228/b49e7cfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/93000000/92610000/92607300/92607228/275e7818.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/93000000/92610000/92607300/92607228/f992df15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

Sherwood

10/10

Exceptional

(18)

"Gorgeous views and location. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ryan D.

[](https://www.expedia.ca/Sherwood-Hotels-Time-Stands-Still.h92607228.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34590000/34583000/34582947/954f8aa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/35000000/34590000/34583000/34582947/2aaf171c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/35000000/34590000/34583000/34582947/0ffdd0ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/35000000/34590000/34583000/34582947/c6df8085.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Saint Michaels

9.8/10

Exceptional

(191)

"This house has the perfect location to explore the town. We stayed in this house for the St. Michael’s Running Festival and it couldn’t have been better. The location was so close to the start/finish lines and there were so many restaurants within a few minutes walk. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jen R.

[](https://www.expedia.ca/St-Michaels-Hotels-Carpenter-St-Cottage-In-The-Heart-Of-St-Michaels-Village-Large-Screened-Porch.h34582947.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/49000000/48380000/48378600/48378570/b94b1ba5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/49000000/48380000/48378600/48378570/7c8f8b76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/49000000/48380000/48378600/48378570/7c62e911.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/49000000/48380000/48378600/48378570/fb9a7f0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

St. Michaels

9.8/10

Exceptional

(44)

"This cottage is adorable. Great amenities and great location. We thoroughly enjoyed our time in St Michael’s."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Audra B.

[](https://www.expedia.ca/St-Michaels-Hotels-Carpenter-Alley-Newly-Renovated-Cottage-In-Center-Of-Historic-St-Michaels.h48378570.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-15&endDate=2025-11-16&regionId=88967&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Top Chesapeake Beach Hotel Reviews

![Towneplace Suites by Marriott Clinton at Joint Base Andrews](//images.trvl-media.com/lodging/3000000/2310000/2308600/2308579/eb7a3f7b_y.jpg)

### Towneplace Suites by Marriott Clinton at Joint Base Andrews

10/10 Excellent

"staff are very good. I prefer room with sofa not just one chair"

[](https://expedia.ca/Waldorf-Hotels-Towneplace-Suites-By-Marriott-Clinton-At-Joint-Base-Andrews.h2308579.Hotel-Information)

![Sonesta ES Suites Annapolis](//images.trvl-media.com/lodging/1000000/10000/3000/2982/e773fcbe_y.jpg)

### Sonesta ES Suites Annapolis

10/10 Excellent

"Room was very clean."

[](https://expedia.ca/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information)

![Inn at Perry Cabin](//images.trvl-media.com/lodging/1000000/20000/14600/14576/38b8c334_y.jpg)

### Inn at Perry Cabin

10/10 Excellent

"Friendly and attentive staff, good cleaning services"

[](https://expedia.ca/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information)

![Candlewood Suites Annapolis by IHG](//images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/9088c5e1_y.jpg)

### Candlewood Suites Annapolis by IHG

10/10 Excellent

"Tight front parking, lots of spaces.behind bld, excellent people, good decor very good room"

[](https://expedia.ca/Annapolis-Hotels-Homestyle-Suites.h1160798.Hotel-Information)

![Rod 'N' Reel Resort](//images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/4803b1f5_y.jpg)

### Rod 'N' Reel Resort

10/10 Excellent

"we did not have the breakfast, the beds are amazingly comfortable rooms spotless. The water pressure was poor. The staff was over the top helpful and friendly. We would definitely stay again."

[](https://expedia.ca/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.Hotel-Information)

![SpringHill Suites by Marriott Annapolis](//images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/80b99d82_y.jpg)

### SpringHill Suites by Marriott Annapolis

10/10 Excellent

"We received excellent service and our needs were cared for. The hotel's WiFi went on tne fritz on Thursday but was fully restored by Thursday night. The staff was friendly and helpful. When were surprised with parking charges, the manager agreed to waive them. A good experience throughout our stay of more than a week."

[](https://expedia.ca/Annapolis-Hotels-SpringHill-Suites-By-Marriott-Annapolis.h1364028.Hotel-Information)

![Spark by Hilton Waldorf](//images.trvl-media.com/lodging/1000000/30000/26400/26379/abeb45bb_y.jpg)

### Spark by Hilton Waldorf

10/10 Excellent

"I wish they would have provided bacon and eggs. "

[](https://expedia.ca/Waldorf-Hotels-Spark-By-Hilton-Waldorf.h26379.Hotel-Information)

![The Wildset](//images.trvl-media.com/lodging/65000000/64420000/64410600/64410566/38a42051_y.jpg)

### The Wildset

10/10 Excellent

"Good breakfast "

[](https://expedia.ca/St-Michaels-Hotels-The-Wildset.h64410566.Hotel-Information)

![Holiday Inn Express Waldorf by IHG](//images.trvl-media.com/lodging/1000000/30000/25500/25493/9a1d7d08_y.jpg)

### Holiday Inn Express Waldorf by IHG

10/10 Excellent

"It was amazing!! "

[](https://expedia.ca/Waldorf-Hotels-Holiday-Inn-Express-Waldorf.h25493.Hotel-Information)

## Find out more about Chesapeake Beach

**Everything you need to know about** **Chesapeake Beach** **vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake Beach vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesapeake Beach vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**Chesapeake Beach vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Chesapeake Beach. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesapeake Beach vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesapeake Beach vacation rentals we have selected for you start as low as CA $411 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on Chesapeake Beach rentals**

At Expedia, we put the best Chesapeake Beach vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chesapeake Beach rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesapeake Beach vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesapeake Beach. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

## Explore a world of travel with Expedia

-   Trending destinations on Expedia.ca
-   All accommodation types in Chesapeake Beach

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-   [Québec Vacation Rentals](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

-   [Vacation Homes in Chesapeake Beach](https://expedia.ca/Chesapeake-Beach-Private-Vacation-Homes.d88967-aaPrivateVacationHomes.Travel-Guide-Accommodation)
-   [Cottages in Chesapeake Beach](https://expedia.ca/Chesapeake-Beach-Cottages.d88967-aaCottages.Travel-Guide-Accommodation)
-   [Apartments in Chesapeake Beach](https://expedia.ca/Chesapeake-Beach-Apartments.d88967-aaApartments.Travel-Guide-Accommodation)
-   [B&B in Chesapeake Beach](https://expedia.ca/Chesapeake-Beach-Bed-And-Breakfast.d88967-aaBedAndBreakfast.Travel-Guide-Accommodation)
-   [Houseboats in Chesapeake Beach](https://expedia.ca/Chesapeake-Beach-Houseboats.d88967-aaHouseboats.Travel-Guide-Accommodation)
-   [Farmstay in Chesapeake Beach](https://expedia.ca/Chesapeake-Beach-Agritourism.d88967-aaAgritourism.Travel-Guide-Accommodation)
-   [Cabin Rentals in Chesapeake Beach](https://expedia.ca/Chesapeake-Beach-Cabins.d88967-aaCabins.Travel-Guide-Accommodation)
-   [Guest Houses in Chesapeake Beach](https://expedia.ca/Chesapeake-Beach-Guest-Houses.d88967-aaGuestHouses.Travel-Guide-Accommodation)
-   [Inns in Chesapeake Beach](https://expedia.ca/Chesapeake-Beach-Inns.d88967-aaInns.Travel-Guide-Accommodation)
-   [Motels in Chesapeake Beach](https://expedia.ca/Chesapeake-Beach-Motels.d88967-aaMotels.Travel-Guide-Accommodation)
-   [Aparthotels in Chesapeake Beach](https://expedia.ca/Chesapeake-Beach-Apart-Hotels.d88967-aaApartHotels.Travel-Guide-Accommodation)
-   [Condo Rentals in Chesapeake Beach](https://expedia.ca/Chesapeake-Beach-Condos.d88967-aaCondos.Travel-Guide-Accommodation)
-   [Villas in Chesapeake Beach](https://expedia.ca/Chesapeake-Beach-Villas.d88967-aaVillas.Travel-Guide-Accommodation)
-   [RV Parks in Chesapeake Beach](https://expedia.ca/Chesapeake-Beach-RV-Parks.d88967-aaRVParks.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find a vacation rental in Chesapeake Beach?

> Yes, you can find vacation rentals in Chesapeake Beach near Chesapeake Beach Water Park, or you can select a more remote option if you're looking for extra privacy while you relax. Discover why Chesapeake Beach is known for its spas and beaches. While you're here, grab a bite or have a drink at the restaurants.

### What are some of the best vacation home rentals that Chesapeake Beach has to offer?

> [Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub](https://www.expedia.ca/Spacious-5-Bedroom-Waterfront-Oasis-With-Private-Dock.h84356021.Hotel-Information): This vacation home rental near Chesapeake Beach is located on the waterfront and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a hot tub so you can immerse yourself in your vacation.

### How many vacation rentals will I find in Chesapeake Beach?

> With 7 Expedia vacation rentals, you're sure to find just the right place for your Chesapeake Beach stay.

### What’s there to see and do in Chesapeake Beach?

> Family-friendly attractions include Chesapeake Beach Water Park and Chesapeake Beach Railway Museum, whereas Breezy Point Beach and Chesapeake Bay are a couple of great spots to enjoy the outdoors. Other places in town to visit include Rod n Reel Charter Fishing and Bruce Gabrielson's Surf Art Gallery and Museum.

### What’s a vacation rental in Chesapeake Beach like?

> Vacation rentals are privately owned properties you can book for several days or longer in Chesapeake Beach. Vacation rentals feature amenities like laundry facilities and kitchens so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.

![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg)

## Go further with the Expedia app

Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app

![QR code to download the app](data:image/png;base64,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)