Title: Chesapeake City Vacation Rentals from CA $129: 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

[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 two months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=177517&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 26 - Jun 28](https://www.expedia.ca/Hotel-Search?regionId=177517&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 24 - Jul 26](https://www.expedia.ca/Hotel-Search?regionId=177517&startDate=2026-07-24&endDate=2026-07-26&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)

![Exterior](https://images.trvl-media.com/lodging/102000000/101170000/101162200/101162170/442dd688.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)

"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.

CA $151

CA $392 total

includes taxes & fees

Apr 6 - Apr 7

[](https://www.expedia.ca/Chesapeake-City-Hotels-Historic-Chesapeake-City-Stay.h101162170.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/dbf4caf7.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)

![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)

### 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

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.

CA $94

CA $129 total

includes taxes & fees

Apr 6 - Apr 7

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

![Interior](https://images.trvl-media.com/lodging/104000000/103800000/103796700/103796689/1ef29f78.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)

![Property grounds](https://images.trvl-media.com/lodging/104000000/103800000/103796700/103796689/49544c8c.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

(40 reviews)

"Very unique and cozy property close to everything we needed. "

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

John H.

CA $245

CA $293 total

includes taxes & fees

Apr 6 - Apr 7

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

![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)

### 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 $95

CA $174 total

includes taxes & fees

Apr 8 - Apr 9

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

![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)

![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)

### Country Get Away Studio Apartment

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

Elkton

9.8/10

Exceptional

(40 reviews)

"This place is out in the country, but a short distance to lots of places we wanted to see, shop at, visit."

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

Richard

CA $98

CA $155 total

includes taxes & fees

Apr 20 - Apr 21

[](https://www.expedia.ca/Elkton-Hotels-Country-Get-Away-1-Bedroom-Apartment.h83756776.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/80000000/79880000/79873400/79873394/8a5b9d92.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 $270

CA $462 total

includes taxes & fees

Apr 8 - Apr 9

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

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

CA $386

CA $628 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Perryville-Hotels-Long-Beach-Cottage.h105613889.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 $167

CA $225 total

includes taxes & fees

Apr 6 - Apr 7

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

![Dining](https://images.trvl-media.com/lodging/101000000/100710000/100705000/100704954/w906h683x59y0-5188d62b.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)

![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

9.8/10

Exceptional

(6 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 $107

CA $221 total

includes taxes & fees

Apr 8 - Apr 9

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

![3 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/83000000/82890000/82880900/82880842/8f79d270.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 $220

CA $339 total

includes taxes & fees

Apr 6 - Apr 7

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

![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)

![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.ca/Smyrna-Hotels-Amazing-Modern-House-With-A-Full-Kitchen-And-Parking.h101539294.Hotel-Information)

Smyrna

9.2/10

Wonderful

(10 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 $167

CA $396 total

includes taxes & fees

Apr 6 - Apr 7

[](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/122000000/121440000/121439000/121438942/f13c8992.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)

![Dining](https://images.trvl-media.com/lodging/122000000/121440000/121439000/121438942/41395ce9.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

10/10

Exceptional

(1 review)

CA $170

CA $298 total

includes taxes & fees

Apr 20 - Apr 21

[](https://www.expedia.ca/Nottingham-Hotels-Amish-Countryside-Escape-At-Forest-Edge-Farm.h121438942.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/e26e59da.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)

![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 $212

CA $297 total

includes taxes & fees

Apr 6 - Apr 7

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

![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)

![Fitness facility](https://images.trvl-media.com/lodging/107000000/106020000/106012200/106012168/77168f78.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 $194

CA $243 total

includes taxes & fees

Apr 6 - Apr 7

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

![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104490000/104487400/104487369/721a9af0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sport court](https://images.trvl-media.com/lodging/105000000/104490000/104487400/104487369/7755e20e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104490000/104487400/104487369/be73aa7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/105000000/104490000/104487400/104487369/db92da17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tiny Home Tranquil Oasis

[](https://www.expedia.ca/Bear-Hotels-Tiny-Home-Tranquil-Oasis.h104487369.Hotel-Information)

Bear

CA $264

CA $335 total

includes taxes & fees

Apr 16 - Apr 17

[](https://www.expedia.ca/Bear-Hotels-Tiny-Home-Tranquil-Oasis.h104487369.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/105000000/104910000/104908000/104907991/3967e546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/105000000/104910000/104908000/104907991/w1077h750x1y0-1131a203.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/105000000/104910000/104908000/104907991/d4fc6149.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/105000000/104910000/104908000/104907991/845c9d4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### New Construction townhome close to everything downtown w/transparent pricing 

[](https://www.expedia.ca/Wilmington-Hotels-2-Master-Bedrooms-Each-Wprivate-Full-Baths-Quick-Drive-Or-Walk-To-Everything.h104907991.Hotel-Information)

Hilltop

9.6/10

Exceptional

(24 reviews)

"Property was spacious with open kitchen/living room area and 2 bedrooms with their own baths."

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

Mark F.

CA $195

CA $392 total

includes taxes & fees

Apr 9 - Apr 10

[](https://www.expedia.ca/Wilmington-Hotels-2-Master-Bedrooms-Each-Wprivate-Full-Baths-Quick-Drive-Or-Walk-To-Everything.h104907991.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)

![Interior](https://images.trvl-media.com/lodging/120000000/119260000/119254200/119254176/f497b7a6.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.ca/Bear-Hotels-Peaceful-Stay-Above-Ink-Shop.h119254176.Hotel-Information)

Bear

9.6/10

Exceptional

(10 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 $138

CA $172 total

includes taxes & fees

Apr 7 - Apr 8

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

![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104430000/104421300/104421286/be71615d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/105000000/104430000/104421300/104421286/5b5015e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/105000000/104430000/104421300/104421286/acab3a2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/105000000/104430000/104421300/104421286/20d5f241.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Nature's Haven Tiny Home

[](https://www.expedia.ca/Bear-Hotels-Natures-Haven-Tiny-Home.h104421286.Hotel-Information)

Bear

10/10

Exceptional

(4 reviews)

"Nature’s Haven Tiny Home worked great for us. Karin was a great communicator and we really enjoyed ourselves. "

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

James S.

CA $264

CA $326 total

includes taxes & fees

Apr 15 - Apr 16

[](https://www.expedia.ca/Bear-Hotels-Natures-Haven-Tiny-Home.h104421286.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)

![Exterior](https://images.trvl-media.com/lodging/92000000/91020000/91010800/91010763/37adc979.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)

![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.ca/Thunder-Hill-Retreat-Peaceful-Sleeps-12.h91010763.Hotel-Information)

Lincoln University

10/10

Exceptional

(19 reviews)

"The house is very spacious with comfortable beds and numerous activities and games for the family. The hot tub was a feature we all truly enjoyed, especially while watching the snow come down.The location is very tranquil and the views are beautiful!The owner is very responsive to messages and was understanding when one of us had an issue requiring a later checkout. We would definitely book a future stay at Thunderhill!"

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

Heather W.

CA $330

CA $738 total

includes taxes & fees

Apr 16 - Apr 17

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

![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120250000/120248200/120248155/7d6d0051.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120250000/120248200/120248155/296e82bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120250000/120248200/120248155/4c5f6f69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120250000/120248200/120248155/7a413e7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### High Tide Haven Suite

[](https://www.expedia.ca/Still-Pond-Hotels-High-Tide-Haven-Suite.h120248155.Hotel-Information)

Kent County

CA $242

CA $283 total

includes taxes & fees

Apr 6 - Apr 7

[](https://www.expedia.ca/Still-Pond-Hotels-High-Tide-Haven-Suite.h120248155.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=2026-04-19&endDate=2026-04-20&regionId=177517&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## 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=2026-07-04&d1=2026-07-04&endDate=2026-07-07&d2=2026-07-07&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=2026-07-04&d1=2026-07-04&endDate=2026-07-07&d2=2026-07-07&lodging=COTTAGE)

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=2026-07-04&d1=2026-07-04&endDate=2026-07-07&d2=2026-07-07&lodging=VACATION_HOME)

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=2026-07-04&d1=2026-07-04&endDate=2026-07-07&d2=2026-07-07&lodging=APARTMENT)

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=2026-07-04&d1=2026-07-04&endDate=2026-07-07&d2=2026-07-07&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=2026-07-04&d1=2026-07-04&endDate=2026-07-07&d2=2026-07-07&lodging=CABIN)

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## Top Chesapeake City Hotel Reviews

![Homewood Suites by Hilton Wilmington Downtown](https://images.trvl-media.com/lodging/38000000/37810000/37805100/37805037/4b4deb09_y.jpg)

### Homewood Suites by Hilton Wilmington Downtown

8/10 Good

"I had a fine stay. It was great."

[](https://expedia.ca/Wilmington-Hotels-Homewood-Suites-By-Hilton-Wilmington-Downtown.h37805037.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

6/10 Okay

"The sofa bed was nasty and I couldn’t use it. The pool water is very cloudy and the pool filter was not running. The hot tub is broken and had caution tape around it. The breakfast is the only good thing on this stay."

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

![Great Wolf Lodge Perryville](https://images.trvl-media.com/lodging/104000000/103100000/103097900/103097849/31e21486_y.jpg)

### Great Wolf Lodge Perryville

8/10 Good

"Everything was very clean"

[](https://expedia.ca/Perryville-Hotels-Great-Wolf-Lodge-Perryville.h103097849.Hotel-Information)

![Candlewood Suites Newark South - University Area by IHG](https://images.trvl-media.com/lodging/18000000/17800000/17793500/17793483/7f9ef0f6_y.jpg)

### Candlewood Suites Newark South - University Area by IHG

8/10 Good

"Staff immediately told me there weren’t any rooms available to check in early before checking their system . No room keys , staff let people in rooms without verifying anything . Huge safety issue there "

[](https://expedia.ca/Wilmington-Hotels-Candlewood-Suites-Newark-South-University-Area.h17793483.Hotel-Information)

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

### Hyatt Place Wilmington Riverfront

10/10 Excellent

"Everything was fine can't wait to visit again"

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

8/10 Good

"We had a good stay. Cant complain about anything. Small pool but its no big deal"

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

![Sonesta ES Suites Wilmington - Newark](https://images.trvl-media.com/lodging/1000000/20000/19100/19062/2517bae2_y.jpg)

### Sonesta ES Suites Wilmington - Newark

10/10 Excellent

"Yes"

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

10/10 Excellent

"Nice area close to places to.eat shop . "

[](https://expedia.ca/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

"Nothing close by to walk and not a great neighborhood. No dishes pots or pans or coffee maker nor any in lobby. Byo it no rental u will have to buy.. No thanks wasnt worth the cost of the room to not get the efficiency part.."

[](https://expedia.ca/Wilmington-Hotels-Woodspring-Suites-Wilmington-Riverfront.h119443969.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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- [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)
- [B&B in Chesapeake City ](https://expedia.ca/Chesapeake-City-Bed-And-Breakfast.d177517-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Cabin Rentals in Chesapeake City ](https://expedia.ca/Chesapeake-City-Cabins.d177517-aaCabins.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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