Title: Chestertown Vacation Rentals from $265: Search Short-Term Rentals | Expedia.com

[Chestertown Travel Guide](https://expedia.com/Chestertown.dx7215)[Hotels in Chestertown](https://expedia.com/Chestertown-Hotels.d7215.Travel-Guide-Hotels)[Flights to Chestertown](https://expedia.com/Cheap-Flights-To-Chestertown.d7215.Travel-Guide-Flights)[Car Rentals in Chestertown](https://expedia.com/Car-Rentals-In-Chestertown.d7215.Car-Rental-Guide)[Chestertown Vacation Packages](https://expedia.com/Chestertown.d7215.Destination-Travel-Guides)

![Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA](https://images.trvl-media.com/place/7215/2127ed08-151b-4865-9870-3d0463a3d88b.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/7215/2127ed08-151b-4865-9870-3d0463a3d88b.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

## Check prices for these dates

In two weeks

[Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=7215&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=7215&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=7215&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 four months

[Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=7215&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)

![](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)

## 

The Annual Vacation Sale

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## Find vacation rentals that suit your style

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=COTTAGE)

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=CABIN)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=CONDO)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=APARTMENT)

Houseboats

[](https://www.expedia.com/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=HOUSE_BOAT)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=VILLA)

Residences

[](https://www.expedia.com/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America&regionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=RESIDENCE)

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## Top Chestertown Hotel Reviews

![Hampton Inn Baltimore/Glen Burnie](https://images.trvl-media.com/lodging/1000000/10000/2800/2759/2b57d3ba_y.jpg)

### Hampton Inn Baltimore/Glen Burnie

10/10 Excellent

" Cl"

[](https://expedia.com/Baltimore-Hotels-Hampton-Inn-BaltimoreGlen-Burnie.h2759.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

"Was at Governor Calvert House. Beautiful historic building that is well maintained. Room was clean and comfortable. Parking is minimal, and valet parking is quite expensive, with "dynamic pricing". Hotel is walking distance to many shops and restaurants. Staff was pleasant and accommodating. "

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

![Holiday Inn Express White Marsh by IHG](https://images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/9b37b4b6_y.jpg)

### Holiday Inn Express White Marsh by IHG

8/10 Good

"Upon arrival, we were greeted with friendly staff with a quick check in. The hotel is very clean, the linens were so comfortable and the beds were too. The room was spacious and the bathroom was very nice. I love that there are Dove products in the bathroom so you don’t have to worry about bringing those things. "

[](https://expedia.com/Baltimore-Hotels-Holiday-Inn-Express-White-Marsh.h71532135.Hotel-Information)

![La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/40d24dc0_y.jpg)

### La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

2/10 Terrible

"I had a one night stay at this property, and I came home with bedbugs and bedbug bites all over my body… I actually had to seek medical attention. The condition of the hotel is very poor and disgusting. I believe it serves as a hotel and a homeless shelter in One. Please be aware of this property."

[](https://expedia.com/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.Hotel-Information)

![Hampton Inn Baltimore Bayview Campus](https://images.trvl-media.com/lodging/24000000/23840000/23830900/23830804/e92cee9e_y.jpg)

### Hampton Inn Baltimore Bayview Campus

2/10 Terrible

"The bed was extremely uncomfortable and the maid came busting in my room no knock or anything."

[](https://expedia.com/Baltimore-Hotels-Hampton-Inn-Baltimore-Bayview-Campus.h23830804.Hotel-Information)

![Country Inn & Suites by Radisson, Baltimore North, MD](https://images.trvl-media.com/lodging/3000000/2410000/2410000/2410000/7de3cb16_y.jpg)

### Country Inn & Suites by Radisson, Baltimore North, MD

8/10 Good

"The room was nice and clean and the staff was nice and very helpful "

[](https://expedia.com/Baltimore-Hotels-Country-Inn-Suites-By-Radisson.h2410000.Hotel-Information)

![Best Western Plus Hotel & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/314defe9_y.jpg)

### Best Western Plus Hotel & Conference Center

6/10 Okay

"great price for my CIAA weekend stay"

[](https://expedia.com/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information)

![Americas Best Value Inn Edgewood](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/ee9bd670_y.jpg)

### Americas Best Value Inn Edgewood

10/10 Excellent

"Super comfortable and quiet "

[](https://expedia.com/Edgewood-Hotels-Hilltop-Motel.h20063.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

"We liked it"

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

## Find out more about Chestertown

**Everything you need to know about Chestertown 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 Chestertown 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 Chestertown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Chestertown vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Chestertown. 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 Chestertown 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 $265 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 Chestertown rentals**

At Expedia, we put the best Chestertown 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 Chestertown 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 Chestertown 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 Chestertown. 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

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- All accommodation types in Chestertown

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- [Vacation Homes in Chestertown ](https://expedia.com/Chestertown-Private-Vacation-Homes.d7215-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Chestertown ](https://expedia.com/Chestertown-Apartments.d7215-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Chestertown ](https://expedia.com/Chestertown-Cottages.d7215-aaCottages.Travel-Guide-Accommodation)
- [Guest Houses in Chestertown ](https://expedia.com/Chestertown-Guest-Houses.d7215-aaGuestHouses.Travel-Guide-Accommodation)
- [Houseboats in Chestertown ](https://expedia.com/Chestertown-Houseboats.d7215-aaHouseboats.Travel-Guide-Accommodation)
- [Motels in Chestertown ](https://expedia.com/Chestertown-Motels.d7215-aaMotels.Travel-Guide-Accommodation)
- [RV Parks in Chestertown ](https://expedia.com/Chestertown-RV-Parks.d7215-aaRVParks.Travel-Guide-Accommodation)
- [B&B in Chestertown ](https://expedia.com/Chestertown-Bed-And-Breakfast.d7215-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Farmstay in Chestertown ](https://expedia.com/Chestertown-Agritourism.d7215-aaAgritourism.Travel-Guide-Accommodation)
- [Villas in Chestertown ](https://expedia.com/Chestertown-Villas.d7215-aaVillas.Travel-Guide-Accommodation)
- [Condo Rentals in Chestertown ](https://expedia.com/Chestertown-Condos.d7215-aaCondos.Travel-Guide-Accommodation)
- [Cabin Rentals in Chestertown ](https://expedia.com/Chestertown-Cabins.d7215-aaCabins.Travel-Guide-Accommodation)
- [Lodges in Chestertown ](https://expedia.com/Chestertown-Lodges.d7215-aaLodges.Travel-Guide-Accommodation)

## Frequently asked questions

### Are there vacation rentals in Chestertown?

### What are some of the best vacation home rentals that Chestertown has to offer?

### How many vacation rentals are there in Chestertown?

### What can I see and do in Chestertown?

### What are vacation rentals like in Chestertown?

### Expedia's Latest Trends

Hotels

- [Hotel Rooms 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)
- [Hotel Rooms in Hagerstown](https://expedia.com/Hagerstown-Hotels.d6057475.Travel-Guide-Hotels)
- [Hotel Rooms in Silver Spring](https://expedia.com/Silver-Spring-Hotels.d6891.Travel-Guide-Hotels)
- [Hotel Rooms 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)
- [Hotel Rooms in Bowie](https://expedia.com/Bowie-Hotels.d6278.Travel-Guide-Hotels)
- [Hotel Rooms in Rockville](https://expedia.com/Rockville-Hotels.d6353.Travel-Guide-Hotels)
- [Hotel Rooms in Salisbury](https://expedia.com/Salisbury-Hotels.d6057491.Travel-Guide-Hotels)
- [Hotel Rooms in Aberdeen](https://expedia.com/Aberdeen-Hotels.d6044.Travel-Guide-Hotels)
- [Hotel Rooms in Annapolis](https://expedia.com/Annapolis-Hotels.d6034082.Travel-Guide-Hotels)
- [Hotel Rooms in St. Michaels](https://expedia.com/St-Michaels-Hotels.d5940.Travel-Guide-Hotels)
- [Hotel Rooms in Cumberland](https://expedia.com/Cumberland-Hotels.d6057474.Travel-Guide-Hotels)
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Flights

- [Flights to SBY](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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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

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

Vacation Rentals

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

General

- [Visit Ocean City](https://expedia.com/Ocean-City.dx9151)
- [Visit Chesapeake City](https://expedia.com/Chesapeake-City.dx177517)