Title: Chesapeake City Cottages from CA $288 | Expedia.ca

[Chesapeake City Travel Guide](https://expedia.ca/Chesapeake-City.dx177517)[Hotels in Chesapeake City](https://expedia.ca/Chesapeake-City-Hotels.d177517.Travel-Guide-Hotels)[Vacation Rentals in Chesapeake City](https://expedia.ca/Chesapeake-City-Vacation-Rentals.d177517.Travel-Guide-VacationRentals)[Chesapeake City Car Rentals](https://expedia.ca/Car-Rentals-In-Chesapeake-City.d177517.Car-Rental-Guide)[Chesapeake City Vacation Packages](https://expedia.ca/Chesapeake-City.d177517.Destination-Travel-Guides)

![An aerial view of historic Annapolis, situated on the Chesapeake Bay, during an early November morning.](https://images.trvl-media.com/place/177517/30c1fc19-3278-4d8b-9ab8-b49b3730e600.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Search Chesapeake City Cottage Rentals from CA $288

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## Check prices for these dates

In two weeks

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=177517&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=177517&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=177517&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=177517&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chesapeake City cottages

![Property grounds](https://images.trvl-media.com/lodging/83000000/82890000/82880900/82880842/4791e965.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/83000000/82890000/82880900/82880842/a5883b4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82890000/82880900/82880842/c1ae5468.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/83000000/82890000/82880900/82880842/3618b010.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Port Deposit

[](https://www.expedia.ca/Port-Deposit-Hotels-Cheerful-3-Bedroom-Cottage-In-The-Center-Of-Town-Located-On-High-Street.h82880842.Hotel-Information)

10/10

Exceptional

(11)

"Was a great stay would definitely stay again "

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

jerel p.

CA $208

CA $324 total

includes taxes & fees

Jan 13 - Jan 14, 2026

[](https://www.expedia.ca/Port-Deposit-Hotels-Cheerful-3-Bedroom-Cottage-In-The-Center-Of-Town-Located-On-High-Street.h82880842.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/92000000/91020000/91010800/91010763/0195b285.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/92000000/91020000/91010800/91010763/37adc979.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91020000/91010800/91010763/8184389c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91020000/91010800/91010763/e088966c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Lincoln University

[](https://www.expedia.ca/Thunder-Hill-Retreat-Peaceful-Sleeps-12.h91010763.Hotel-Information)

10/10

Exceptional

(16)

"Our stay was perfect! We had a wonderful time with family celebrating our daughter's UD graduation."

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

Heidi Z.

CA $237

CA $611 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Thunder-Hill-Retreat-Peaceful-Sleeps-12.h91010763.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/104000000/103800000/103796700/103796689/0a987fcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103800000/103796700/103796689/0c3a95fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/104000000/103800000/103796700/103796689/1747fc02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/104000000/103800000/103796700/103796689/w907h683x58y0-01d62268.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Port Deposit

[](https://www.expedia.ca/Unique-Cottage-Built-In-The-1800s.h103796689.Hotel-Information)

10/10

Exceptional

(31)

"The River Cottage is very charming, cozy, and well-stocked with all the essentials. The host is quick to respond to inquiries. We had a wonderful and relaxing stay!"

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

Xiaodong F.

CA $240

CA $288 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/Unique-Cottage-Built-In-The-1800s.h103796689.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/114000000/113590000/113586700/113586648/w1536h2048x598y0-350049dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/114000000/113590000/113586700/113586648/w1536h2048x598y0-a7dcc44d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113590000/113586700/113586648/w1536h2048x598y0-de4eba85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113590000/113586700/113586648/w1536h2048x598y0-f666fabb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Betterton

[](https://www.expedia.ca/Betterton-Hotels-Grandmas-Cottage-Will-Wrap-Around-You-Like-A-Warm-Hug.h113586648.Hotel-Information)

CA $308

CA $570 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Betterton-Hotels-Grandmas-Cottage-Will-Wrap-Around-You-Like-A-Warm-Hug.h113586648.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/106000000/105620000/105613900/105613889/0d4a4309.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/106000000/105620000/105613900/105613889/ba6c2c65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/106000000/105620000/105613900/105613889/2a80bf3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/106000000/105620000/105613900/105613889/w1278h851x2y2-2ebae160.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Charlestown

[](https://www.expedia.ca/Perryville-Hotels-Long-Beach-Cottage.h105613889.Hotel-Information)

10/10

Exceptional

(4)

"Loved the property and the decor. Very well done and luxurious!"

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

Elisheva K.

CA $445

CA $675 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Perryville-Hotels-Long-Beach-Cottage.h105613889.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=2026-01-07&endDate=2026-01-08&regionId=177517&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Chesapeake+City%2C+Maryland%2C+United+States+of+America&regionId=177517&latLong=39.530952%2C-75.807444&adults=2&startDate=2026-03-24&d1=2026-03-24&endDate=2026-03-27&d2=2026-03-27&lodging=APARTMENT)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Chesapeake+City%2C+Maryland%2C+United+States+of+America&regionId=177517&latLong=39.530952%2C-75.807444&adults=2&startDate=2026-03-24&d1=2026-03-24&endDate=2026-03-27&d2=2026-03-27&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Chesapeake+City%2C+Maryland%2C+United+States+of+America&regionId=177517&latLong=39.530952%2C-75.807444&adults=2&startDate=2026-03-24&d1=2026-03-24&endDate=2026-03-27&d2=2026-03-27&lodging=COTTAGE)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Chesapeake+City%2C+Maryland%2C+United+States+of+America&regionId=177517&latLong=39.530952%2C-75.807444&adults=2&startDate=2026-03-24&d1=2026-03-24&endDate=2026-03-27&d2=2026-03-27&lodging=CONDO)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Chesapeake+City%2C+Maryland%2C+United+States+of+America&regionId=177517&latLong=39.530952%2C-75.807444&adults=2&startDate=2026-03-24&d1=2026-03-24&endDate=2026-03-27&d2=2026-03-27&lodging=CABIN)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Chesapeake+City%2C+Maryland%2C+United+States+of+America&regionId=177517&latLong=39.530952%2C-75.807444&adults=2&startDate=2026-03-24&d1=2026-03-24&endDate=2026-03-27&d2=2026-03-27&lodging=HOUSE_BOAT)

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## Top Chesapeake City Hotel Reviews

![Holiday Inn Express & Suites Wilmington-Newark by IHG ](https://images.trvl-media.com/lodging/1000000/20000/14200/14182/0462a60c_y.jpg)

### Holiday Inn Express & Suites Wilmington-Newark by IHG 

10/10 Excellent

"Everything was just right. Great breakfast Friendly, helpful staff"

[](https://expedia.ca/Wilmington-Hotels-Holiday-Inn-Express-Hotel-Suites-Wilmington-Newark.h14182.Hotel-Information)

![Embassy Suites by Hilton Newark Wilmington South](https://images.trvl-media.com/lodging/1000000/330000/327600/327586/b7951f6a_y.jpg)

### Embassy Suites by Hilton Newark Wilmington South

10/10 Excellent

"Breakfast"

[](https://expedia.ca/Wilmington-Hotels-Embassy-Suites-Newark-WilmingtonSouth.h327586.Hotel-Information)

![Quality Inn Newark - Wilmington](https://images.trvl-media.com/lodging/1000000/30000/25100/25008/e605848f_y.jpg)

### Quality Inn Newark - Wilmington

10/10 Excellent

"Everything was great "

[](https://expedia.ca/Wilmington-Hotels-Quality-Inn.h25008.Hotel-Information)

![Baymont by Wyndham Newark at University of Delaware](https://images.trvl-media.com/lodging/1000000/50000/42000/41973/b371460e_y.jpg)

### Baymont by Wyndham Newark at University of Delaware

10/10 Excellent

"This hotel is reasonably priced for families that need to go to UD. Conveniently located across from the stadium!"

[](https://expedia.ca/Wilmington-Hotels-Baymont-By-Wyndham-Newark-At-University-Of-Delaware.h41973.Hotel-Information)

![Homewood Suites by Hilton Newark-Wilmington South Area](https://images.trvl-media.com/lodging/2000000/1060000/1052400/1052325/2d7e7964_y.jpg)

### Homewood Suites by Hilton Newark-Wilmington South Area

10/10 Excellent

"The staff was great....the room was OK....a bit dated but clean and had everything that was needed. I would stay again."

[](https://expedia.ca/Wilmington-Hotels-Homewood-Suites-By-Hilton-Newark-Wilmington-South.h1052325.Hotel-Information)

![Woodspring Suites Wilmington Riverfront](https://images.trvl-media.com/lodging/120000000/119450000/119444000/119443969/44b1f889_y.jpg)

### Woodspring Suites Wilmington Riverfront

10/10 Excellent

"Clean room and cannot beat the price. One bad thing was when someone above me was taking a shower you could really hear it. I thought mt bathroom was flooding - that’s how loud it was. Still, I give 5 stars because you get a nice room with a kitchen for a very good price. "

[](https://expedia.ca/Wilmington-Hotels-Woodspring-Suites-Wilmington-Riverfront.h119443969.Hotel-Information)

![Sonesta Select Newark Christiana Mall](https://images.trvl-media.com/lodging/1000000/10000/2100/2091/5b01ae08_y.jpg)

### Sonesta Select Newark Christiana Mall

10/10 Excellent

"The staff was fantastic very helpful, rooms was very nice and clean. "

[](https://expedia.ca/Wilmington-Hotels-Sonesta-Select-Newark.h2091.Hotel-Information)

![Comfort Inn & Suites Newark - Wilmington](https://images.trvl-media.com/lodging/1000000/20000/12000/11904/ea219a4a_y.jpg)

### Comfort Inn & Suites Newark - Wilmington

10/10 Excellent

"Very Clean , convenient location, very good breakfast buffet "

[](https://expedia.ca/Wilmington-Hotels-Comfort-Inn-Suites-Newark-Wilmington.h11904.Hotel-Information)

![Extended Stay America Suites Newark Christiana Wilmington](https://images.trvl-media.com/lodging/1000000/120000/119100/119061/87ad8503_y.jpg)

### Extended Stay America Suites Newark Christiana Wilmington

10/10 Excellent

"Front desk staff were friendly and accommodating"

[](https://expedia.ca/Wilmington-Hotels-Extended-Stay-America-Suites-Newark-Christiana-Wilmington.h119061.Hotel-Information)

## Find out more about Chesapeake City

## Chesapeake City Cottages information

| Number of reviews | 62          |
| ----------------- | ----------- |
| Accommodation     | 30 Cottages |
| Lowest Price      | CA $288     |
| Highest Price     | CA $675     |

## Frequently asked questions

### Why book your cottage in Chesapeake City with Expedia?

### How can I find cheap cottages in Chesapeake City?

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