Title: Chester, MD Condos for Rent | Expedia.com

[Chester Travel Guide](https://expedia.com/Chester.dx3000440455)[Hotels in Chester](https://expedia.com/Chester-Hotels.d3000440455.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.com/Chester-Vacation-Rentals.d3000440455.Travel-Guide-VacationRentals)[Flights to Chester](https://expedia.com/Cheap-Flights-To-Chester.d3000440455.Travel-Guide-Flights)[Car Rentals in Chester](https://expedia.com/Car-Rentals-In-Chester.d3000440455.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.com/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

![](https://images.trvl-media.com/place/3000440455/ea96dd54-4b86-4885-83c9-585f6f8e1fb2.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=3000440455&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=3000440455&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=3000440455&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 17 - Jul 19](https://www.expedia.com/Hotel-Search?regionId=3000440455&startDate=2026-07-17&endDate=2026-07-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chester condo rentals

![Living area](https://images.trvl-media.com/lodging/128000000/127580000/127573900/127573894/76b64c08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/128000000/127580000/127573900/127573894/097fb495.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room](https://images.trvl-media.com/lodging/128000000/127580000/127573900/127573894/e5b77c2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/128000000/127580000/127573900/127573894/54dc68b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chapel Gate 3BR Steps to City Dock & Naval Academy

[](https://www.expedia.com/Annapolis-Hotels-Chapel-Gate-3BR-Steps-To-City-Dock-Naval-Academy.h127573894.Hotel-Information)

Historic District

$438 nightly

$495 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Annapolis-Hotels-Chapel-Gate-3BR-Steps-To-City-Dock-Naval-Academy.h127573894.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/119000000/118830000/118824200/118824130/964bce68.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/119000000/118830000/118824200/118824130/38d6910b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/119000000/118830000/118824200/118824130/70b0ea71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118830000/118824200/118824130/4940f0a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Upscale Condo in Annapolis w/Private Parking

[](https://www.expedia.com/Annapolis-Hotels-Upscale-Condo-In-Annapolis.h118824130.Hotel-Information)

Historic District

10/10

Exceptional

(2 reviews)

"Great condo! Very clean and convenient to everything in Annapolis. We will definitely be back."

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

Scott P.

$453 nightly

$516 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Annapolis-Hotels-Upscale-Condo-In-Annapolis.h118824130.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/119000000/118900000/118891600/118891568/c5b533c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/119000000/118900000/118891600/118891568/4d32484b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/119000000/118900000/118891600/118891568/bbbfca07.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/119000000/118900000/118891600/118891568/7d0396b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Row Home in Downtown Annapolis

[](https://www.expedia.com/Annapolis-Hotels-Historic-Row-Home-In-Downtown-Annapolis.h118891568.Hotel-Information)

Historic District

$494 nightly

$563 total

Mar 26 - Mar 27

Total with taxes and fees

[](https://www.expedia.com/Annapolis-Hotels-Historic-Row-Home-In-Downtown-Annapolis.h118891568.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/123000000/122160000/122155400/122155356/59267fce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/123000000/122160000/122155400/122155356/fa1377ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/123000000/122160000/122155400/122155356/c212ca56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122160000/122155400/122155356/w1197h799x0y0-f89ec878.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Rowhome in Downtown Annapolis

[](https://www.expedia.com/Annapolis-Hotels-Charming-Rowhome-In-Downtown-Annapolis.h122155356.Hotel-Information)

Historic District

$452 nightly

$515 total

Mar 26 - Mar 27

Total with taxes and fees

[](https://www.expedia.com/Annapolis-Hotels-Charming-Rowhome-In-Downtown-Annapolis.h122155356.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/125000000/124420000/124410600/124410574/646644d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/125000000/124420000/124410600/124410574/35660170.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/125000000/124420000/124410600/124410574/dde9cbe4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/125000000/124420000/124410600/124410574/b37b0734.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxe Row Home Steps to USNA Gate 3!

[](https://www.expedia.com/Annapolis-Hotels-Luxe-Row-Home-Steps-To-USNA-Gate-3.h124410574.Hotel-Information)

Historic District

10/10

Exceptional

(1 review)

$540 nightly

$616 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Annapolis-Hotels-Luxe-Row-Home-Steps-To-USNA-Gate-3.h124410574.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/125000000/124430000/124429400/124429321/5e9a1735.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/125000000/124430000/124429400/124429321/95f7bc1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/125000000/124430000/124429400/124429321/32b40208.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/125000000/124430000/124429400/124429321/4fc14796.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.

[](https://www.expedia.com/Annapolis-Hotels-Luxury-Annapolis-Condo.h124429321.Hotel-Information)

Eastport

$555 nightly

$606 total

Mar 26 - Mar 27

Total with taxes and fees

[](https://www.expedia.com/Annapolis-Hotels-Luxury-Annapolis-Condo.h124429321.Hotel-Information)

![4 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/125000000/124420000/124410700/124410604/c45d9462.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124420000/124410700/124410604/5db5573a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/125000000/124420000/124410700/124410604/1fe478cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/125000000/124420000/124410700/124410604/b3a3d588.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Two Historic Rowhomes in Downtown Annapolis

[](https://www.expedia.com/Annapolis-Hotels-Two-Historic-Rowhomes-In-Downtown-Annapolis.h124410604.Hotel-Information)

Historic District

$786 nightly

$896 total

Mar 26 - Mar 27

Total with taxes and fees

[](https://www.expedia.com/Annapolis-Hotels-Two-Historic-Rowhomes-In-Downtown-Annapolis.h124410604.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=2026-04-08&endDate=2026-04-09&regionId=3000440455&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Houseboats

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Private vacation homes

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Cottages

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Condos

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Apartments

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Villas

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## Top Chester Hotel Reviews

![Hyatt Place Kent Narrows & Marina](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/d7f9ddda_y.jpg)

### Hyatt Place Kent Narrows & Marina

10/10 Excellent

"."

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

![Sonesta ES Suites Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/eac8c079_y.jpg)

### Sonesta ES Suites Annapolis

10/10 Excellent

"Clean room, gym "

[](https://expedia.com/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information)

![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1_y.jpg)

### Historic Inns of Annapolis

10/10 Excellent

"Clean room, friendly staff, and the PERFECT location for walking downtown Annapolis. "

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

![Best Western Kent Narrows Inn](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/3217cd56_y.jpg)

### Best Western Kent Narrows Inn

2/10 Terrible

"Meh"

[](https://expedia.com/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information)

![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/be920909_y.jpg)

### DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"Not sure but it’s a great location "

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

![Crowne Plaza Annapolis by IHG](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/0f404f98_y.jpg)

### Crowne Plaza Annapolis by IHG

10/10 Excellent

"Very close to several restaurants and the mall is close as well. Golf course is within 15 mins "

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

![Graduate by Hilton Annapolis](https://images.trvl-media.com/lodging/1000000/10000/900/846/ca081b22_y.jpg)

### Graduate by Hilton Annapolis

8/10 Good

"The toilet ran every few minutes. Some of the carpet as we entered the room was worn away."

[](https://expedia.com/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information)

![Hilton Garden Inn Annapolis Downtown](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/8ee1610f_y.jpg)

### Hilton Garden Inn Annapolis Downtown

10/10 Excellent

"I’m not a fan of pets in hotels, so it was particularly disturbing to step into the elevator and find pet feces. Guests next to us were questionable. Slamming against furniture and yelling and screaming meant a disturbed sleep. Not the property’s fault, but the response to my phone call to the front desk was appalling, I was advised to call the police if I thought safety was an issue. The male front desk associate communicated with irritation and a pompous attitude. I’m not looking to get anybody fired, but it would seem to me that a guest services refresher course would be a good idea."

[](https://expedia.com/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information)

![Courtyard by Marriott Annapolis](https://images.trvl-media.com/lodging/1000000/20000/11100/11049/f531cd56_y.jpg)

### Courtyard by Marriott Annapolis

10/10 Excellent

"Great place to stay 👍"

[](https://expedia.com/Annapolis-Hotels-Courtyard-By-Marriott-Annapolis.h11049.Hotel-Information)

## Find out more about Chester

## Chester Condo Rentals information

| Number of reviews | 2               |
| ----------------- | --------------- |
| Accommodation     | 9 Condo Rentals |
| Lowest Price      | $516            |
| Highest Price     | $896            |

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- [Hostels in Northern Chesapeake Bay ](https://www.expedia.com/Northern-Chesapeake-Bay-Hostels.d6051456-aaHostels.Travel-Guide-Accommodation)
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- [5 stars ](https://www.expedia.com/5Star-Northern-Chesapeake-Bay-Hotels.s50-0-d6051456.Travel-Guide-Filter-Hotels)
- [B&B in Grasonville ](https://www.expedia.com/Grasonville-Bed-And-Breakfast.d7382-aaBedAndBreakfast.Travel-Guide-Accommodation)
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- [Hotels near Chesapeake Bay Bridge ](https://www.expedia.com/Chesapeake-Bay-Bridge-Hotels.0-l6077400-0.Travel-Guide-Filter-Hotels)

- [Flights to Stevensville ](https://www.expedia.com/Cheap-Flights-To-Stevensville.d162393.Travel-Guide-Flights)
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- [Flights from Kent Island ](https://www.expedia.com/lp/flights/553248635077608788/flights-from-kent-island)
- [Flights to Northern Chesapeake Bay ](https://www.expedia.com/Cheap-Flights-To-Northern-Chesapeake-Bay.d6051456.Travel-Guide-Flights)
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- [Visit Stevensville ](https://www.expedia.com/Stevensville.dx162393)
- [Visit Kent Island ](https://www.expedia.com/Kent-Island.dx553248635077608788)
- [Kent Island Vacations ](https://www.expedia.com/Kent-Island.d553248635077608788.Destination-Travel-Guides)
- [Chesapeake Bay Environmental Center ](https://www.expedia.com/Chesapeake-Bay-Environmental-Center-Grasonville.d553248621561196328.Vacation-Attraction)
- [Northern Chesapeake Bay Vacations ](https://www.expedia.com/Northern-Chesapeake-Bay.d6051456.Destination-Travel-Guides)
- [Visit Grasonville ](https://www.expedia.com/Grasonville.dx7382)
- [Grasonville Vacations ](https://www.expedia.com/Grasonville.d7382.Destination-Travel-Guides)
- [Chesapeake Bay Bridge ](https://www.expedia.com/Chesapeake-Bay-Bridge-Annapolis.d6077400.Vacation-Attraction)

- [Car rentals near Stevensville ](https://www.expedia.com/Car-Rentals-In-Stevensville.d162393.Car-Rental-Guide)
- [Enterprise Rental Cars in Stevensville ](https://www.expedia.com/Enterprise-Car-Rentals-In-Stevensville.d162393-c15.Car-Rental-Guide-Suppliers)
- [Avis Rental Cars in Stevensville ](https://www.expedia.com/Avis-Car-Rentals-In-Stevensville.d162393-c41.Car-Rental-Guide-Suppliers)
- [Car rentals near Kent Narrows ](https://www.expedia.com/Car-Rentals-In-Kent-Narrows.d553248635077720315.Car-Rental-Guide)
- [Hertz Rental Cars in Kent Island ](https://www.expedia.com/Hertz-Car-Rentals-In-Kent-Island.d553248635077608788-c40.Car-Rental-Guide-Suppliers)
- [Car rentals near Northern Chesapeake Bay ](https://www.expedia.com/Car-Rentals-In-Northern-Chesapeake-Bay.d6051456.Car-Rental-Guide)
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- [Stevensville Vacation Rentals ](https://www.expedia.com/Stevensville-Vacation-Rentals.d162393.Travel-Guide-VacationRentals)
- [Kent Island Vacation Rentals ](https://www.expedia.com/Kent-Island-Vacation-Rentals.d553248635077608788.Travel-Guide-VacationRentals)
- [Grasonville Vacation Rentals ](https://www.expedia.com/Grasonville-Vacation-Rentals.d7382.Travel-Guide-VacationRentals)

- [Things to do in Northern Chesapeake Bay ](https://www.expedia.com/Things-To-Do-In-Northern-Chesapeake-Bay.d6051456.Travel-Guide-Activities)