Title: Chesapeake City Vacation Rentals : Search Short-Term Rentals | Expedia.com

[Chesapeake City Travel Guide](https://expedia.com/Chesapeake-City.dx177517)[Hotels in Chesapeake City](https://expedia.com/Chesapeake-City-Hotels.d177517.Travel-Guide-Hotels)[Flights to Chesapeake City](https://expedia.com/Cheap-Flights-To-Chesapeake-City.d177517.Travel-Guide-Flights)[Car Rentals in Chesapeake City](https://expedia.com/Car-Rentals-In-Chesapeake-City.d177517.Car-Rental-Guide)[Chesapeake City Vacation Packages](https://expedia.com/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)

## Check prices for these dates

In two weeks

[Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=177517&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=177517&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=177517&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=177517&startDate=2026-07-03&endDate=2026-07-05&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)

![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)

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

### Historic Chesapeake City Stay 

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

Chesapeake City

9.0/10

Wonderful

(20 reviews)

"Cleaned, beautifully decorated, not like a rental but more like a home!"

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

Manjetjola P.

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

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

![Exterior](https://images.trvl-media.com/lodging/122000000/121440000/121439000/121438942/f19183c0.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.com/Nottingham-Hotels-Amish-Countryside-Escape-At-Forest-Edge-Farm.h121438942.Hotel-Information)

Nottingham

10/10

Exceptional

(1 review)

[](https://www.expedia.com/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/104000000/103800000/103796700/103796689/1ef29f78.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.com/Unique-Cottage-Built-In-The-1800s.h103796689.Hotel-Information)

Port Deposit

10/10

Exceptional

(38 reviews)

"Very cool place. "

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

Eric L.

[](https://www.expedia.com/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)

![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83760000/83756800/83756776/w303h683x361y0-8bb8126f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Country Get Away Studio Apartment

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

Elkton

9.8/10

Exceptional

(40 reviews)

"Perfect in every way… a great stay"

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

Robert B.

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

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

![1 bedroom](https://images.trvl-media.com/lodging/101000000/100710000/100705000/100704954/w905h683x59y0-ba7b72a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Summer Rustic Camping with AC and King Bed

[](https://www.expedia.com/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.

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/80000000/79880000/79873400/79873394/28a3908e.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)

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

[](https://www.expedia.com/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.

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

![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)

![Interior](https://images.trvl-media.com/lodging/112000000/111820000/111819700/111819612/7f5de9e0.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.com/Aberdeen-Hotels-Charming-2-Bedroom-House-In-Aberdeen-With-WiFi-And-AC.h111819612.Hotel-Information)

Aberdeen

7.6/10

Good

(13 reviews)

"Met our needs. Great stay."

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

Robert C.

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

![Property grounds](https://images.trvl-media.com/lodging/106000000/105620000/105613900/105613889/7a295dfb.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)

![Interior](https://images.trvl-media.com/lodging/106000000/105620000/105613900/105613889/9f222576.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Charlestown

10/10

Exceptional

(6 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.

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

![Exterior](https://images.trvl-media.com/lodging/113000000/112770000/112768900/112768841/184e980a.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)

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

[](https://www.expedia.com/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.

[](https://www.expedia.com/Elkton-Hotels-Charming-3-Bedroom-House-With-WiFi.h112768841.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.com/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.

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

![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)

![Living area](https://images.trvl-media.com/lodging/92000000/91020000/91010800/91010763/ac946998.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/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.

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

![Smart TV](https://images.trvl-media.com/lodging/108000000/107970000/107967700/107967644/f8c70b01.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)

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

[](https://www.expedia.com/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)

"Clean and comfortable. Very nice stay in the country!"

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

Daniel B.

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

![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)

![Interior](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/1afdcb86.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)

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

[](https://www.expedia.com/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.

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

![Interior](https://images.trvl-media.com/lodging/114000000/113300000/113298400/113298347/0cd3925a.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/e26e59da.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.com/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.

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

![Property grounds](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w509h683x257y0-37962ab6.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)

![Interior](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w423h683x305y0-6862acf5.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.com/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.

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

![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)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/107000000/106020000/106012200/106012168/1e9a0fab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Newark

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

![Beach](https://images.trvl-media.com/lodging/104000000/103190000/103180100/103180013/e8d235bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/104000000/103190000/103180100/103180013/7109c6c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/104000000/103190000/103180100/103180013/2fa15be2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103190000/103180100/103180013/655332ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Waterfront Retreat with Private Dock and Beach

[](https://www.expedia.com/Worton-Hotels-Cozy-Waterfront-Retreat-With-Private-Dock-And-BeachSleeps-4-Studio-1-Bath.h103180013.Hotel-Information)

Worton

10/10

Exceptional

(25 reviews)

"The apartment, including kitchen and bathroom, was very clean. Plenty of linens available for use. Perfect spot for fishing off of their dock. Very pleased with our reservation. "

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

Debbie S.

[](https://www.expedia.com/Worton-Hotels-Cozy-Waterfront-Retreat-With-Private-Dock-And-BeachSleeps-4-Studio-1-Bath.h103180013.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)

![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)

![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)

### Cozy loft above ink shop

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

Bear

9.8/10

Exceptional

(8 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.

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

![Interior](https://images.trvl-media.com/lodging/67000000/66430000/66422600/66422541/fc3579ab_edited_81cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/67000000/66430000/66422600/66422541/74a27cb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/67000000/66430000/66422600/66422541/ab188a6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/67000000/66430000/66422600/66422541/468d1e03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private 3 room Queen Suite w/Kitchenette 

[](https://www.expedia.com/Port-Deposit-Hotels-Private-3-Room-Queen-Suite-WKitchenette.h66422541.Hotel-Information)

Port Deposit

10/10

Exceptional

(29 reviews)

"Perfect location for that town. "

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

Hisham M.

[](https://www.expedia.com/Port-Deposit-Hotels-Private-3-Room-Queen-Suite-WKitchenette.h66422541.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.com/Hotel-Search?startDate=2026-03-23&endDate=2026-03-24&regionId=177517&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

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

[Book now](https://expedia.com/deals?rfrr=VR_SPRING_PROMO_177517)

## Find vacation rentals that suit your style

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Chesapeake+City%2C+Maryland%2C+United+States+of+America&regionId=177517&latLong=39.530952%2C-75.807444&adults=2&startDate=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=COTTAGE)

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Chesapeake+City%2C+Maryland%2C+United+States+of+America&regionId=177517&latLong=39.530952%2C-75.807444&adults=2&startDate=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=CABIN)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Chesapeake+City%2C+Maryland%2C+United+States+of+America&regionId=177517&latLong=39.530952%2C-75.807444&adults=2&startDate=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=VACATION_HOME)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Chesapeake+City%2C+Maryland%2C+United+States+of+America&regionId=177517&latLong=39.530952%2C-75.807444&adults=2&startDate=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=APARTMENT)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Chesapeake+City%2C+Maryland%2C+United+States+of+America&regionId=177517&latLong=39.530952%2C-75.807444&adults=2&startDate=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=CONDO)

Houseboats

[](https://www.expedia.com/Hotel-Search?destination=Chesapeake+City%2C+Maryland%2C+United+States+of+America&regionId=177517&latLong=39.530952%2C-75.807444&adults=2&startDate=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=HOUSE_BOAT)

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## Top Chesapeake City Hotel Reviews

![Red Roof Inn & Suites Newark - University](https://images.trvl-media.com/lodging/1000000/10000/8500/8462/72a36958_y.jpg)

### Red Roof Inn & Suites Newark - University

6/10 Okay

"Average stay.... comfortable bed.... no breakfast.... apparently no washroom in the lobby area.... (After a long drive, and just before the checking in process, it is reasonable to ask to use a washroom, no?)"

[](https://expedia.com/Wilmington-Hotels-Red-Roof-Inn-Suites-Newark-University.h8462.Hotel-Information)

![Holiday Inn Express & Suites Wilmington-Newark by IHG ](https://images.trvl-media.com/lodging/1000000/20000/14200/14182/f97697a5_y.jpg)

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

10/10 Excellent

"Room was clean, check in was quick and easy, complimentary breakfast had many options"

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

![Hyatt Place Wilmington Riverfront](https://images.trvl-media.com/lodging/35000000/34930000/34927700/34927626/5d36bf4b_y.jpg)

### Hyatt Place Wilmington Riverfront

8/10 Good

"Clean"

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

![Comfort Inn & Suites Newark - Wilmington](https://images.trvl-media.com/lodging/1000000/20000/12000/11904/c9c370cc_y.jpg)

### Comfort Inn & Suites Newark - Wilmington

10/10 Excellent

"Staff was friendly and bed was comfortable after a long day. "

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

![Baymont by Wyndham Newark at University of Delaware](https://images.trvl-media.com/lodging/1000000/50000/42000/41973/b4ea9c0d_y.jpg)

### Baymont by Wyndham Newark at University of Delaware

4/10 Poor

"The male check-in agent was rude. To watch TV, you need to connect the smart TV to WiFi, as you would with a laptop. That is fine; however, you must pay $5 to access the WiFi. It's not free. The engineered floor in the room buckled and creaked, waking the other person at night. Plumbing from other rooms next door and above were extremely loud. The Candlewood down the street is a better choice at this price point. We will not be back. "

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

![Extended Stay America Suites Newark Christiana Wilmington](https://images.trvl-media.com/lodging/1000000/120000/119100/119061/02a2e620_y.jpg)

### Extended Stay America Suites Newark Christiana Wilmington

2/10 Terrible

"Absolutely disgusting, health hazard and safety concern. This was without question the most disgusting hotel room I have ever stepped foot in. Honestly, they should be paying me for the ten minutes I had to endure inside that place. The first room they gave us wouldn’t even open. After three trips up and down the elevator, the front desk employee came up and still couldn’t get the door unlocked. That should have been the warning sign to leave. The second room was worse than anything I could have imagined. The smell hit immediately — a mix of mildew, smoke, and something that honestly smelled like decay. The countertops were burned all over from what appeared to be drug use. There were holes in the walls, and black gunk was literally dripping from the bathroom ceiling. The bed looked like something out of a jail cell — just a metal frame with sheets thrown on it. No headboard, no blanket. The kitchen counters had what looked like bodily fluids, and the couch looked like someone drained motor oil across it. I couldn’t even take many photos because the smell was so overwhelming I was trying not to vomit. I lasted about two minutes before leaving. The website advertises this hotel as “newly renovated,” but the photos online look nothing like the reality. Charging normal hotel rates for rooms in this condition is completely misleading. If you value your health, money, and sanity, stay far away from this place. "

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

![Quality Inn Newark - Wilmington](https://images.trvl-media.com/lodging/1000000/30000/25100/25008/12f7b572_y.jpg)

### Quality Inn Newark - Wilmington

10/10 Excellent

"Polite staff "

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

![Red Roof Inn PLUS+ Wilmington - Newark](https://images.trvl-media.com/lodging/1000000/10000/7900/7845/5b453b31_y.jpg)

### Red Roof Inn PLUS+ Wilmington - Newark

2/10 Terrible

"They had roaches all in the bathroom, the rooms was small."

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

![Woodspring Suites Wilmington Riverfront](https://images.trvl-media.com/lodging/120000000/119450000/119444000/119443969/28f580ab_y.jpg)

### Woodspring Suites Wilmington Riverfront

4/10 Poor

"The room above me had kids jumping around from 7pm to 2 am for 3 consecutive days, made the front desk aware of the issue and it stopped for 30 minutes then back to noise"

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

## Find out more about Chesapeake City

**Everything you need to know about Chesapeake City 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 City vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 City vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

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

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

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

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

At Expedia, we put the best Chesapeake City 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 City 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 City 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 City. 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.com
- All accommodation types in Chesapeake City

### Trending destinations on Expedia.com

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- [Galveston Vacation Rentals ](https://www.expedia.com/Galveston-Vacation-Rentals.d1341.Travel-Guide-VacationRentals)
- [Clearwater Beach Vacation Rentals ](https://www.expedia.com/Clearwater-Beach-Vacation-Rentals.d10759.Travel-Guide-VacationRentals)
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- [Florida Keys Vacation Rentals ](https://www.expedia.com/Florida-Keys-Vacation-Rentals.d6023765.Travel-Guide-VacationRentals)
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- [Lake of the Ozarks Vacation Rentals ](https://www.expedia.com/Lake-Ozark-Vacation-Rentals.d177772.Travel-Guide-VacationRentals)
- [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

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

## Frequently asked questions

### Can I find vacation rentals in Chesapeake City?

### What are some of the best vacation rentals in Chesapeake City?

### How many vacation rentals are there in Chesapeake City?

### What can I see and do in Chesapeake City?

### What are vacation rentals like in Chesapeake City?

### Expedia's Latest Trends

Hotels

- [Hotels in Waldorf](https://expedia.com/Waldorf-Hotels.d6057464.Travel-Guide-Hotels)
- [Ocean City Pet-friendly Hotels](https://expedia.com/Ocean-City-Hotels-Pet-Friendly-Hotel.0-0-d9151-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [Hotels in Hagerstown](https://expedia.com/Hagerstown-Hotels.d6057475.Travel-Guide-Hotels)
- [Hotels in Silver Spring](https://expedia.com/Silver-Spring-Hotels.d6891.Travel-Guide-Hotels)
- [Hotels in Ocean City](https://expedia.com/Ocean-City-Hotels.d9151.Travel-Guide-Hotels)
- [Ocean City Oceanfront Hotels](https://expedia.com/Ocean-City-Hotels-Oceanfront-Hotels.0-0-d9151-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Ocean City Cheap Hotels](https://expedia.com/Ocean-City-Hotels-Cheap-Hotels.0-0-d9151-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Hotels in Bowie](https://expedia.com/Bowie-Hotels.d6278.Travel-Guide-Hotels)
- [Hotels in Upper Marlboro](https://expedia.com/Upper-Marlboro-Hotels.d168650.Travel-Guide-Hotels)
- [Hotels in Rockville](https://expedia.com/Rockville-Hotels.d6353.Travel-Guide-Hotels)
- [Hotels in Salisbury](https://expedia.com/Salisbury-Hotels.d6057491.Travel-Guide-Hotels)
- [Hotels in Aberdeen](https://expedia.com/Aberdeen-Hotels.d6044.Travel-Guide-Hotels)
- [Hotels in Annapolis](https://expedia.com/Annapolis-Hotels.d6034082.Travel-Guide-Hotels)
- [Hotels in St. Michaels](https://expedia.com/St-Michaels-Hotels.d5940.Travel-Guide-Hotels)
- [Hotels in Cumberland](https://expedia.com/Cumberland-Hotels.d6057474.Travel-Guide-Hotels)
- [Hotels in College Park](https://expedia.com/College-Park-Hotels.d6057494.Travel-Guide-Hotels)
- [Hotels in Frederick](https://expedia.com/Frederick-Hotels.d6057476.Travel-Guide-Hotels)
- [Annapolis Oceanfront Hotels](https://expedia.com/Annapolis-Hotels-Oceanfront-Hotels.0-0-d6034082-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Hotels in Bel Air](https://expedia.com/Bel-Air-Hotels.d6023736.Travel-Guide-Hotels)
- [Ocean City Luxury Hotels](https://expedia.com/Ocean-City-Hotels-Luxury-Hotel.0-0-d9151-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Hotels in Gaithersburg](https://expedia.com/Gaithersburg-Hotels.d7427.Travel-Guide-Hotels)

Flights

- [Flights to Ocean City](https://expedia.com/Cheap-Flights-To-Ocean-City.d9151.Travel-Guide-Flights)

Cars

- [Car rentals in Rockville](https://expedia.com/Car-Rentals-In-Rockville.d6353.Car-Rental-Guide)
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- [Car rentals in Frederick](https://expedia.com/Car-Rentals-In-Frederick.d6057476.Car-Rental-Guide)

Activities

- [Things to do in Annapolis](https://expedia.com/Things-To-Do-In-Annapolis.d6034082.Travel-Guide-Activities)
- [Things to do in Ocean City](https://expedia.com/Things-To-Do-In-Ocean-City.d9151.Travel-Guide-Activities)

Packages

- [Ocean City Vacation](https://expedia.com/Ocean-City.d9151.Destination-Travel-Guides)

Vacation Rentals

- [Rentals in Ocean City](https://expedia.com/Ocean-City-Vacation-Rentals.d9151.Travel-Guide-VacationRentals)

General

- [Visit Ocean City](https://expedia.com/Ocean-City.dx9151)