Title: Chester Apartment Rentals from CA $217 | Expedia.ca

[Hotels in Chester](https://expedia.ca/Chester-Hotels.d3000440455.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d3000440455.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d3000440455.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d3000440455.Destination-Travel-Guides)

![Kent Narrows Maryland, USA, the narrows are just north of the Chesapeake bay and about an hour from Washington DC. Here the crabs are abundant and we had a great pick and peel crab dinner and Harrah's Crab house. Boats along this area go out each morning and pick the crabs out of the crab cages and get the catch of the day out in the Chesapeake bay . The Route 50 bridge is directly straight ahead, it the route into the Chesapeake bay bridge which is  at least 3 miles long.](https://images.trvl-media.com/place/3000440455/ea96dd54-4b86-4885-83c9-585f6f8e1fb2.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Patricia Knorr

# Search Apartment Rentals in Chester

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## Check prices for these dates

In two weeks

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=3000440455&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 four months

[Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chester apartments

![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/04bd524d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/a4be0d3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/c04c0cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/92366292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Chestertown

[](https://www.expedia.ca/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information)

9.6/10

Exceptional

(108)

"Amazing and neat and very private "

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

Alexander M.

CA $135

CA $217 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/f520f52a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, in-room safe, free WiFi, bed sheets](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/d5668d89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/0fab08c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/0e2deec0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Annapolis

[](https://www.expedia.ca/Annapolis-Hotels-Waterfront-Oasis-Sleep-4-Close-To-Downtown.h68986275.Hotel-Information)

10/10

Exceptional

(81)

"Owners were great hosts. Loved this property!"

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

Thomas

CA $283

CA $563 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Annapolis-Hotels-Waterfront-Oasis-Sleep-4-Close-To-Downtown.h68986275.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76590000/76586000/76585906/7d32385a.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/77000000/76590000/76586000/76585906/a8b6b33a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/77000000/76590000/76586000/76585906/1af81f7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76590000/76586000/76585906/b07ecc79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Historic District

[](https://www.expedia.ca/Annapolis-Hotels-Spacious-Downtown-Getaway-Across-From-US-Naval-Academy.h76585906.Hotel-Information)

9.6/10

Exceptional

(27)

"Loved this place - well appointed, convenient and great hosts ! Definitely will rent again!"

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

betsy b.

CA $226

CA $426 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Annapolis-Hotels-Spacious-Downtown-Getaway-Across-From-US-Naval-Academy.h76585906.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630208/14451366.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630208/99788b82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630208/w1199h800x1y0-94cb1016.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630208/w1200h798x0y13-06d6d7c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Historic District

[](https://www.expedia.ca/Annapolis-Hotels-Dean-Streets-Lower-Deck-House.h117630208.Hotel-Information)

10/10

Exceptional

(4)

"We had a great time—the location is fantastic and our dog loved the backyard! A great base to rest and recover between adventures in Annapolis. "

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

Nathaniel R.

CA $289

CA $622 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/Annapolis-Hotels-Dean-Streets-Lower-Deck-House.h117630208.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630212/27a8090f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630212/697fbff5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630212/2d43a6e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630212/w1200h799x0y1-55bb08bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Eastport

[](https://www.expedia.ca/Annapolis-Hotels-Annapolis-Gem-Stylish-And-Cozy.h117630212.Hotel-Information)

10/10

Exceptional

(3)

"Great spot"

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

Brian F.

CA $338

CA $660 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Annapolis-Hotels-Annapolis-Gem-Stylish-And-Cozy.h117630212.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/88000000/87580000/87576400/87576375/w1201h914x0y1-e8fa6c0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87580000/87576400/87576375/dee76b7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, books](https://images.trvl-media.com/lodging/88000000/87580000/87576400/87576375/4478d3ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/88000000/87580000/87576400/87576375/a1631ad7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Admiral Heights

[](https://www.expedia.ca/Annapolis-Hotels-Gorgeous-Carriage-House-Close-To-USNA.h87576375.Hotel-Information)

10/10

Exceptional

(48)

"Convenient location, very clean, beautiful yard for a pet friendly visit. We had a great time! Would go back again. "

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

Jackie C.

CA $486

CA $630 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Annapolis-Hotels-Gorgeous-Carriage-House-Close-To-USNA.h87576375.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/77000000/76580000/76579700/76579660/05703878.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76580000/76579700/76579660/bec6a7fa.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/77000000/76580000/76579700/76579660/985e9e07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/77000000/76580000/76579700/76579660/42aee333.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Historic District

[](https://www.expedia.ca/Annapolis-Hotels-Charming-Downtown-3rd-Floor-1-Bedroom-Apt.h76579660.Hotel-Information)

9.8/10

Exceptional

(20)

"We had a great time staying that this home. It was a perfect stay for my wife and I."

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

Eric S.

CA $219

CA $399 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Annapolis-Hotels-Charming-Downtown-3rd-Floor-1-Bedroom-Apt.h76579660.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-12&endDate=2026-01-13&regionId=3000440455&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-03-29&d1=2026-03-29&endDate=2026-04-01&d2=2026-04-01&lodging=VACATION_HOME)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-03-29&d1=2026-03-29&endDate=2026-04-01&d2=2026-04-01&lodging=APARTMENT)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-03-29&d1=2026-03-29&endDate=2026-04-01&d2=2026-04-01&lodging=COTTAGE)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-03-29&d1=2026-03-29&endDate=2026-04-01&d2=2026-04-01&lodging=HOUSE_BOAT)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-03-29&d1=2026-03-29&endDate=2026-04-01&d2=2026-04-01&lodging=VILLA)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-03-29&d1=2026-03-29&endDate=2026-04-01&d2=2026-04-01&lodging=CONDO)

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## Top Chester Hotel Reviews

![Crowne Plaza Annapolis by IHG](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/6084a9f0_y.jpg)

### Crowne Plaza Annapolis by IHG

10/10 Excellent

"Yes!"

[](https://expedia.ca/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information)

![Country Inn & Suites by Radisson, Annapolis, MD](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/d2b7f950_y.jpg)

### Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent

"Room was perfect"

[](https://expedia.ca/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information)

![Hyatt Place Kent Narrows & Marina](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/35e0cb86_y.jpg)

### Hyatt Place Kent Narrows & Marina

10/10 Excellent

"The staff are the absolute best. Our room was perfect."

[](https://expedia.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information)

![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg)

### DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"Overall great experience "

[](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information)

![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg)

### Historic Inns of Annapolis

10/10 Excellent

"Best place to stay is the main building"

[](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information)

![The Westin Annapolis](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/w3998h2667x0y0-54f847ff_y.jpg)

### The Westin Annapolis

10/10 Excellent

"Beautiful and perfect location"

[](https://expedia.ca/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information)

![Annapolis Waterfront Hotel, Autograph Collection](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d_y.jpg)

### Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"Lovely hotel, my favorite place to stay in Annapolis!"

[](https://expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information)

![Fairfield Inn & Suites By Marriott Annapolis](https://images.trvl-media.com/lodging/101000000/100980000/100975900/100975886/ba30667e_y.jpg)

### Fairfield Inn & Suites By Marriott Annapolis

10/10 Excellent

"Beautiful hotel, clean, very comfortable bed, delicious breakfast. The only negative thing is the $30 parking- not even valet- it’s kind of ridiculous when they have their own dedicated lot. It’s kind of a racket. Everything else was top notch, though!"

[](https://expedia.ca/Annapolis-Hotels-Fairfield-Inn-Suites-By-Marriott-Annapolis.h100975886.Hotel-Information)

![Best Western Annapolis](https://images.trvl-media.com/lodging/1000000/10000/2900/2882/ff227afc_y.jpg)

### Best Western Annapolis

10/10 Excellent

"We've stayed at this hotel at least 20 times, despite being in the corner, in the back near the highway, we've found that the rooms are consistently clean and cozy. In the summer, the pool is awesome. And the breakfast is great. We'll be back"

[](https://expedia.ca/Annapolis-Hotels-Best-Western-Annapolis.h2882.Hotel-Information)

## Find out more about Chester

## Chester Apartments information

| Number of reviews | 286           |
| ----------------- | ------------- |
| Accommodation     | 78 Apartments |
| Lowest Price      | CA $217       |
| Highest Price     | CA $660       |

## Frequently asked questions

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