Title: Chesapeake City Vacation Rentals from CA $170: Short-Term Rentals for 2026 | 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)[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)

![](https://images.trvl-media.com/place/177517/30c1fc19-3278-4d8b-9ab8-b49b3730e600.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=177517&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two 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)

In three months

[May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=177517&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 12 - Jun 14](https://www.expedia.ca/Hotel-Search?regionId=177517&startDate=2026-06-12&endDate=2026-06-14&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 vacation rentals

![Marina](https://images.trvl-media.com/lodging/102000000/101170000/101162200/101162170/0755ba72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101170000/101162200/101162170/e0b7e131.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/102000000/101170000/101162200/101162170/0828db4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/102000000/101170000/101162200/101162170/w1798h809x1y1-eff01d07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Chesapeake City Stay 

[](https://www.expedia.ca/Chesapeake-City-Hotels-Historic-Chesapeake-City-Stay.h101162170.Hotel-Information)

Chesapeake City

9.0/10

Wonderful

(20 reviews)

"Yes she was welcoming "

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

Garry B.

CA $147

CA $382 total

includes taxes & fees

Feb 20 - Feb 21

[](https://www.expedia.ca/Chesapeake-City-Hotels-Historic-Chesapeake-City-Stay.h101162170.Hotel-Information)

![Smart TV, foosball, books](https://images.trvl-media.com/lodging/108000000/107550000/107548500/107548497/17549aa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, foosball, books](https://images.trvl-media.com/lodging/108000000/107550000/107548500/107548497/c0f57747.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/108000000/107550000/107548500/107548497/9c7733fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107550000/107548500/107548497/f4f48073.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

[](https://www.expedia.ca/Chesapeake-City-Hotels-Cozy-2-Bedroom-Apartment-Close-To-Canal-Bike-Trail-In-Wonderful-Chesapeake-City.h107548497.Hotel-Information)

Chesapeake City

9.4/10

Exceptional

(3 reviews)

"House clean ac work great on hot weekends. Great bike path near by and nice restaurants by and the river was great on bike . Not to far from Dover for race I would stay again "

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

Wayne

CA $215

CA $424 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Chesapeake-City-Hotels-Cozy-2-Bedroom-Apartment-Close-To-Canal-Bike-Trail-In-Wonderful-Chesapeake-City.h107548497.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/122000000/121440000/121439000/121438942/f13c8992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/122000000/121440000/121439000/121438942/41395ce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121440000/121439000/121438942/2be59d11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/122000000/121440000/121439000/121438942/df13b022.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Amish Countryside Escape at Forest Edge Farm

[](https://www.expedia.ca/Nottingham-Hotels-Amish-Countryside-Escape-At-Forest-Edge-Farm.h121438942.Hotel-Information)

Nottingham

CA $132

CA $253 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Nottingham-Hotels-Amish-Countryside-Escape-At-Forest-Edge-Farm.h121438942.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/104000000/103800000/103796700/103796689/4dada2e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/104000000/103800000/103796700/103796689/w507h683x259y0-8197f073.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/104000000/103800000/103796700/103796689/49544c8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103800000/103796700/103796689/594c8656.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

###  Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland. 

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

Port Deposit

10/10

Exceptional

(37 reviews)

"Very cool place. "

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

Eric L.

CA $239

CA $287 total

includes taxes & fees

Feb 22 - Feb 23

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

![Exterior](https://images.trvl-media.com/lodging/84000000/83760000/83756800/83756776/w304h683x360y0-05e44098.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/84000000/83760000/83756800/83756776/w303h683x361y0-76f6826d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/84000000/83760000/83756800/83756776/0a2d3f8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/84000000/83760000/83756800/83756776/340596d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Country Get Away 1 Bedroom Apartment

[](https://www.expedia.ca/Elkton-Hotels-Country-Get-Away-1-Bedroom-Apartment.h83756776.Hotel-Information)

Elkton

9.8/10

Exceptional

(40 reviews)

"The accommodation description is good; the actual accommodations are great, better than expected, truly a quiet country getaway with many unexpected extras. Deciding to stay here was great decision. It's done right."

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

John L.

CA $95

CA $152 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/Elkton-Hotels-Country-Get-Away-1-Bedroom-Apartment.h83756776.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/112000000/111820000/111819700/111819612/05f7fb5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111820000/111819700/111819612/f65b9e5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/112000000/111820000/111819700/111819612/a673c6f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/112000000/111820000/111819700/111819612/dbf4caf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 2-bedroom house in Aberdeen with WiFi and AC

[](https://www.expedia.ca/Aberdeen-Hotels-Charming-2-Bedroom-House-In-Aberdeen-With-WiFi-And-AC.h111819612.Hotel-Information)

Aberdeen

8.0/10

Very good

(12 reviews)

"Pleasant stay"

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

Yommali G.

CA $92

CA $127 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Aberdeen-Hotels-Charming-2-Bedroom-House-In-Aberdeen-With-WiFi-And-AC.h111819612.Hotel-Information)

![1 bedroom](https://images.trvl-media.com/lodging/101000000/100710000/100705000/100704954/w905h683x59y0-61b1dcc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/101000000/100710000/100705000/100704954/w906h683x60y0-661a042e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/101000000/100710000/100705000/100704954/w906h683x59y0-5188d62b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100710000/100705000/100704954/w906h683x59y0-68e9d507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Summer Rustic Camping with AC and King Bed

[](https://www.expedia.ca/Elkton-Hotels-Luxury-Camping-King-Bed-Sustainable-Farm.h100704954.Hotel-Information)

Elkton

9.6/10

Exceptional

(5 reviews)

"The owners were very attentive to our needs, and everything was exactly as advertised. We came up for a horse show in Maryland and the convenience to the grounds was exceptional, and everything was wonderful from the privacy to the beauty of the property."

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

Rees L.

CA $96

CA $206 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Elkton-Hotels-Luxury-Camping-King-Bed-Sustainable-Farm.h100704954.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w1024h677x0y0-664bab42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w423h683x305y0-6862acf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w584h683x220y0-d805a755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w876h683x74y0-d9537acd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Guest Suite for up to 2 in a Victorian on the Chester River

[](https://www.expedia.ca/Millington-Hotels-Guest-Suite-For-Up-To-2-In-A-Victorian-On-The-Chester-River.h101992106.Hotel-Information)

Millington

9.6/10

Exceptional

(20 reviews)

"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."

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

Cynthia C.

CA $96

CA $174 total

includes taxes & fees

Mar 22 - Mar 23

[](https://www.expedia.ca/Millington-Hotels-Guest-Suite-For-Up-To-2-In-A-Victorian-On-The-Chester-River.h101992106.Hotel-Information)

![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)

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

![Property grounds](https://images.trvl-media.com/lodging/83000000/82890000/82880900/82880842/4791e965.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)

### Quarry Landing - Center of Town & River View - 3 Bedroom

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

Port Deposit

10/10

Exceptional

(11 reviews)

"Was a great stay would definitely stay again "

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

jerel p.

CA $182

CA $292 total

includes taxes & fees

Feb 23 - Feb 24

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

![Interior](https://images.trvl-media.com/lodging/113000000/112770000/112768900/112768841/17b445ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112770000/112768900/112768841/d72c7004.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112770000/112768900/112768841/542ae8cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112770000/112768900/112768841/2d6c2e99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

[](https://www.expedia.ca/Elkton-Hotels-Charming-3-Bedroom-House-With-WiFi.h112768841.Hotel-Information)

Elkton

8.6/10

Excellent

(14 reviews)

"Nice and quiet place to stay"

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

Gary M.

CA $184

CA $387 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Elkton-Hotels-Charming-3-Bedroom-House-With-WiFi.h112768841.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/108000000/107970000/107967700/107967644/cb191506.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107970000/107967700/107967644/da5a6ac4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/108000000/107970000/107967700/107967644/1170f398.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/108000000/107970000/107967700/107967644/f8c70b01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

[](https://www.expedia.ca/Elkton-Hotels-Cozy-Studio-In-Charming-Elkton-With-AC-And-WiFi-Included-3-Miles-From-Fair-Hill.h107967644.Hotel-Information)

Elkton

9.8/10

Exceptional

(8 reviews)

"Great stay. Everything you need, quiet and clean. "

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

Melissa J.

CA $164

CA $220 total

includes taxes & fees

Feb 20 - Feb 21

[](https://www.expedia.ca/Elkton-Hotels-Cozy-Studio-In-Charming-Elkton-With-AC-And-WiFi-Included-3-Miles-From-Fair-Hill.h107967644.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/80000000/79880000/79873400/79873394/73b7467a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, computer monitors](https://images.trvl-media.com/lodging/80000000/79880000/79873400/79873394/3db48e82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/80000000/79880000/79873400/79873394/e33d8702.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/80000000/79880000/79873400/79873394/8a5b9d92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

[](https://www.expedia.ca/Newark-Hotels-Townhome-Within-Serene-Setting-Minutes-Away-From-Christiana-Mall.h79873394.Hotel-Information)

Newark

9.6/10

Exceptional

(21 reviews)

"Very nice property, just right size for our needs. Great neighborhood. Kitchen very nice, check in easy."

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

Lori W.

CA $264

CA $452 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/Newark-Hotels-Townhome-Within-Serene-Setting-Minutes-Away-From-Christiana-Mall.h79873394.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/114000000/113300000/113298400/113298347/01162ab4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/114000000/113300000/113298400/113298347/3d8089a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113300000/113298400/113298347/0cd3925a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/114000000/113300000/113298400/113298347/5b6a5afe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

[](https://www.expedia.ca/Havre-De-Grace-Hotels-Cozy-2-Bedroom-Apartment-With-WiFi.h113298347.Hotel-Information)

Havre de Grace

10/10

Exceptional

(5 reviews)

"It is a warm and welcoming little home away from home. We will be back!"

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

Brittany C.

CA $184

CA $262 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Havre-De-Grace-Hotels-Cozy-2-Bedroom-Apartment-With-WiFi.h113298347.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/92000000/91020000/91010800/91010763/6971f3ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/92000000/91020000/91010800/91010763/ac946998.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)

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

### Thunder Hill Retreat - Spacious/Deck/Hot tub

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

Lincoln University

10/10

Exceptional

(19 reviews)

"Had a nice stay."

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

Todd H.

CA $236

CA $613 total

includes taxes & fees

Feb 23 - Feb 24

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

![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/86c67d62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/76b495fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/cf034cb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/02f199f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Amazing Modern house with a full kitchen and parking 

[](https://www.expedia.ca/Smyrna-Hotels-Amazing-Modern-House-With-A-Full-Kitchen-And-Parking.h101539294.Hotel-Information)

Smyrna

9.2/10

Wonderful

(9 reviews)

"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "

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

Laurie S.

CA $245

CA $484 total

includes taxes & fees

Feb 21 - Feb 22

[](https://www.expedia.ca/Smyrna-Hotels-Amazing-Modern-House-With-A-Full-Kitchen-And-Parking.h101539294.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106020000/106012200/106012168/05bd8bc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/107000000/106020000/106012200/106012168/77168f78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/107000000/106020000/106012200/106012168/55b4ac56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106020000/106012200/106012168/9c347239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!

[](https://www.expedia.ca/Newark-Hotels-Free-Breakfast-Outdoor-Pool-10-Min-From-University-Of-Delaware.h106012168.Hotel-Information)

Newark

CA $180

CA $228 total

includes taxes & fees

Feb 26 - Feb 27

[](https://www.expedia.ca/Newark-Hotels-Free-Breakfast-Outdoor-Pool-10-Min-From-University-Of-Delaware.h106012168.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/120000000/119260000/119254200/119254176/w1127h1518x4y11-28b78c36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119260000/119254200/119254176/00b6ccfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119260000/119254200/119254176/a2dbbaad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer, towels, soap, shampoo](https://images.trvl-media.com/lodging/120000000/119260000/119254200/119254176/1816e77d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy loft above ink shop

[](https://www.expedia.ca/Bear-Hotels-Peaceful-Stay-Above-Ink-Shop.h119254176.Hotel-Information)

Bear

9.8/10

Exceptional

(7 reviews)

"Second time staying in as many weeks. Place is spot on for what we needed for our quick trips. Close to food and shopping as well as easy access to highways if needed."

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

Jeffrey R.

CA $133

CA $166 total

includes taxes & fees

Feb 21 - Feb 22

[](https://www.expedia.ca/Bear-Hotels-Peaceful-Stay-Above-Ink-Shop.h119254176.Hotel-Information)

![TV, fireplace](https://images.trvl-media.com/lodging/106000000/105620000/105613900/105613889/d1664408.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, coffee/tea maker](https://images.trvl-media.com/lodging/106000000/105620000/105613900/105613889/b5af4d14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, coffee/tea maker](https://images.trvl-media.com/lodging/106000000/105620000/105613900/105613889/094fc880.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/106000000/105620000/105613900/105613889/7a295dfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Long Beach Cottage, (romantic couple’s getaway)

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

Charlestown

10/10

Exceptional

(5 reviews)

"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 $388

CA $624 total

includes taxes & fees

Feb 23 - Feb 24

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

![Interior](https://images.trvl-media.com/lodging/113000000/112920000/112913500/112913470/ded66cc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112920000/112913500/112913470/ea0930dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/113000000/112920000/112913500/112913470/e227d316.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi

[](https://www.expedia.ca/Pennsville-Hotels-Charming-3-Bedroom-House-In-Wonderful-Pennsville-Township-With-AC.h112913470.Hotel-Information)

Pennsville Township

CA $273

CA $428 total

includes taxes & fees

Feb 21 - Feb 22

[](https://www.expedia.ca/Pennsville-Hotels-Charming-3-Bedroom-House-In-Wonderful-Pennsville-Township-With-AC.h112913470.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=2026-03-05&endDate=2026-03-06&regionId=177517&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## 

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Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

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## Find vacation rentals that suit your style

Aparthotels

[](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=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=APART_HOTEL)

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=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=COTTAGE)

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=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&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=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=VACATION_HOME)

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=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&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=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=CABIN)

Villas

[](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=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=VILLA)

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=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&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

"Breakfast was great quality."

[](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

"Amenities and cleanliness"

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

"Just need more towels in rooms and better water pressure "

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

![Red Roof Inn & Suites Wilmington - New Castle](https://images.trvl-media.com/lodging/1000000/30000/25100/25051/3560c2da_y.jpg)

### Red Roof Inn & Suites Wilmington - New Castle

10/10 Excellent

"The staff was very courteous. The room was nice and quiet. "

[](https://expedia.ca/Wilmington-Hotels-Red-Roof-Inn-Suites-Wilmington-New-Castle.h25051.Hotel-Information)

![Sonesta ES Suites Wilmington - Newark](https://images.trvl-media.com/lodging/1000000/20000/19100/19062/98de1f1c_y.jpg)

### Sonesta ES Suites Wilmington - Newark

10/10 Excellent

"Amenities, and staff "

[](https://expedia.ca/Wilmington-Hotels-Sonesta-ES-Suites-Wilmington-Newark.h19062.Hotel-Information)

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

### Quality Inn Newark - Wilmington

8/10 Good

"Nice staff, room quiet"

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

![Hilton Wilmington/Christiana](https://images.trvl-media.com/lodging/1000000/10000/7100/7053/7640fa86_y.jpg)

### Hilton Wilmington/Christiana

10/10 Excellent

"Nice accessible room, pleasant staff. Nice nightcap and dessert at the bar too. "

[](https://expedia.ca/Wilmington-Hotels-Hilton-WilmingtonChristiana.h7053.Hotel-Information)

![Red Roof Inn PLUS+ Wilmington - Newark](https://images.trvl-media.com/lodging/1000000/10000/7900/7845/aa58fe8d_y.jpg)

### Red Roof Inn PLUS+ Wilmington - Newark

10/10 Excellent

"Perfect place with amazing staff"

[](https://expedia.ca/Wilmington-Hotels-Red-Roof-Inn-PLUS-Wilmington-Newark.h7845.Hotel-Information)

![Hyatt Place Wilmington Riverfront](https://images.trvl-media.com/lodging/35000000/34930000/34927700/34927626/a064dc72_y.jpg)

### Hyatt Place Wilmington Riverfront

10/10 Excellent

"Room was clean staff throughout the hotel was hands down amazing. Helpful kind over the top helpful multiple times. Just amazing staff. Thank you,"

[](https://expedia.ca/Wilmington-Hotels-Hyatt-Place-Wilmington-Riverfront.h34927626.Hotel-Information)

## Find out more about Chesapeake City

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chesapeake City. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Prince Edward Island Vacation Rentals ](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations)
- [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

- [Vacation Homes in Chesapeake City ](https://expedia.ca/Chesapeake-City-Private-Vacation-Homes.d177517-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Chesapeake City ](https://expedia.ca/Chesapeake-City-Apartments.d177517-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Chesapeake City ](https://expedia.ca/Chesapeake-City-Cottages.d177517-aaCottages.Travel-Guide-Accommodation)
- [Guest Houses in Chesapeake City ](https://expedia.ca/Chesapeake-City-Guest-Houses.d177517-aaGuestHouses.Travel-Guide-Accommodation)
- [Motels in Chesapeake City ](https://expedia.ca/Chesapeake-City-Motels.d177517-aaMotels.Travel-Guide-Accommodation)
- [Condo Rentals in Chesapeake City ](https://expedia.ca/Chesapeake-City-Condos.d177517-aaCondos.Travel-Guide-Accommodation)
- [Cabin Rentals in Chesapeake City ](https://expedia.ca/Chesapeake-City-Cabins.d177517-aaCabins.Travel-Guide-Accommodation)
- [B&B in Chesapeake City ](https://expedia.ca/Chesapeake-City-Bed-And-Breakfast.d177517-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Farmstay in Chesapeake City ](https://expedia.ca/Chesapeake-City-Agritourism.d177517-aaAgritourism.Travel-Guide-Accommodation)
- [Villas in Chesapeake City ](https://expedia.ca/Chesapeake-City-Villas.d177517-aaVillas.Travel-Guide-Accommodation)
- [Houseboats in Chesapeake City ](https://expedia.ca/Chesapeake-City-Houseboats.d177517-aaHouseboats.Travel-Guide-Accommodation)
- [Aparthotels in Chesapeake City ](https://expedia.ca/Chesapeake-City-Apart-Hotels.d177517-aaApartHotels.Travel-Guide-Accommodation)
- [Inns in Chesapeake City ](https://expedia.ca/Chesapeake-City-Inns.d177517-aaInns.Travel-Guide-Accommodation)

## Frequently asked questions

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