Vacation Rentals in Chestertown, MD

· House in Chestertown
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
6 Beds · 7 baths · Sleeps 16 ·
Ceiling Fan · Hardwood Floor · Balcony ·
From
$1,048/night
Check availability
Amenities
Ceiling Fan
Hardwood Floor
Waterfront
Dishwasher
Oven
Air Conditioning
In Unit Laundry
Wifi
Other spaces
Balcony, Kitchen
· Hotel in Chestertown
Comfort Inn & Suites Chestertown
1 Bed · Sleeps 6 ·
Carpet · Free Parking · On Site Laundry ·
From
$129/night
Check availability
Amenities
Carpet
Free Parking
On Site Laundry
Air Conditioning
Wifi
Furnished
Business Center
Elevator
Other spaces
Workspace
· Apartment in Chestertown
Carriage House Hideaway in Middle of Chestertown
Studio · 1 bath · Sleeps 2 ·
Assigned Parking · Fireplace · Workspace ·
From
$132/night
Check availability
Amenities
Assigned Parking
Fireplace
Oven
Air Conditioning
In Unit Laundry
Wifi
Furnished
Other spaces
Workspace, Kitchen
· House in Chestertown
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
2 Beds · 2 baths · Sleeps 6 ·
Deck · Ceiling Fan · Hardwood Floor ·
From
$329/night
Check availability
Amenities
Ceiling Fan
Hardwood Floor
Beach
On Site Laundry
Fireplace
Waterfront
Fitness Center
Dishwasher
Other spaces
Deck, Kitchen
· House in Chestertown
Hidden gem with water and golf course views! Bike ride to downtown!
3 Beds · 3 baths · Sleeps 7 ·
Balcony · Waterfront · Fitness Center ·
From
$360/night
Check availability
Amenities
Waterfront
Fitness Center
Dishwasher
Oven
Air Conditioning
In Unit Laundry
Wifi
Furnished
Other spaces
Balcony, Kitchen
· House in Chestertown
790 Acre Estate: Waterfront | HOT TUB | 1600 sq foot Deck
4 Beds · 3 baths · Sleeps 8 ·
Lake · Hot Tub · On Site Laundry ·
From
$647/night
Check availability
Amenities
Lake
Hot Tub
On Site Laundry
Waterfront
Fitness Center
Dishwasher
Oven
Air Conditioning
Other spaces
Kitchen
· House in Chestertown
Charming Chestertown Waterfront Cottage
3 Beds · 2 baths · Sleeps 6 ·
Fireplace · Waterfront · Dishwasher ·
From
$279/night
Check availability
Amenities
Fireplace
Waterfront
Dishwasher
Oven
Air Conditioning
In Unit Laundry
Wifi
Furnished
Other spaces
Kitchen
· House in Chestertown
Victorian Hideaway: Beautiful Exterior, Modern interior
4 Beds · 3 baths · Sleeps 8 ·
High Ceilings · Dishwasher · Oven ·
From
$643/night
Check availability
Amenities
High Ceilings
Dishwasher
Oven
Air Conditioning
In Unit Laundry
Furnished
Garage Parking
Other spaces
Kitchen

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· House in Chestertown
Country Estate in Historic District
5 Beds · 4 baths · Sleeps 10 ·
Balcony · Fireplace · Workspace ·
From
$200/night
Check availability
Amenities
Fireplace
Dishwasher
Oven
Air Conditioning
In Unit Laundry
Wifi
Furnished
Residents Lounge
Other spaces
Balcony, Workspace, Kitchen
· House in Chestertown
Beautiful Waterfront Estate
11 Beds · 9 baths · Sleeps 27 ·
Private Pool · Pool · On Site Laundry ·
From
$2,263/night
Check availability
Amenities
Private Pool
Pool
On Site Laundry
Waterfront
Fitness Center
Dishwasher
Oven
Air Conditioning
Other spaces
Kitchen
· House in Chestertown
Historic Stepne Manor on Maryland's Eastern Shore
5 Beds · 4 baths · Sleeps 15 ·
Fitness Center · Outdoor Space · Dishwasher ·
From
$627/night
Check availability
Amenities
Fitness Center
Dishwasher
Oven
Air Conditioning
In Unit Laundry
Wifi
Furnished
Business Center
Other spaces
Kitchen
· Apartment in Chestertown
First Floor Studio Apartment in Historic Chestertown
1 Bed · 1 bath · Sleeps 4 ·
Private Pool · Pool · Fitness Center ·
From
$95/night
Check availability
Amenities
Private Pool
Pool
Fitness Center
Air Conditioning
In Unit Laundry
Wifi
Furnished
Swimming Pool
· House in Chestertown
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
4 Beds · 3 baths · Sleeps 8 ·
Hot Tub · Fireplace · Waterfront ·
From
$431/night
Check availability
Amenities
Hot Tub
Fireplace
Waterfront
Dishwasher
Oven
Air Conditioning
In Unit Laundry
Wifi
Other spaces
Kitchen
· House in Chestertown
Private pier and pool at this waterfront Chestertown home
5 Beds · 5 baths · Sleeps 12 ·
Pool · On Site Laundry · Workspace ·
From
$619/night
Check availability
Amenities
Pool
On Site Laundry
Fitness Center
Dishwasher
Oven
Air Conditioning
In Unit Laundry
Wifi
Other spaces
Workspace, Kitchen
· House in Chestertown
Breathtaking waterfront home on the Chester River
4 Beds · 5 baths ·
Pool · Balcony · Fireplace ·
From
$591/night
Check availability
Amenities
Pool
Fireplace
Fitness Center
Dishwasher
Oven
Air Conditioning
In Unit Laundry
Wifi
Other spaces
Balcony, Workspace, Kitchen
· House in Chestertown
Circa 1900 Home in the Heart of Historic Downtown Chestertown
4 Beds · 2 baths · Sleeps 6 ·
Workspace · Fitness Center · Outdoor Space ·
From
$302/night
Check availability
Amenities
Fitness Center
Dishwasher
Oven
Air Conditioning
In Unit Laundry
Wifi
Furnished
Other spaces
Workspace, Kitchen
· House in Chestertown
Historic downtown Chestertown Home. #1 Location.
2 Beds · 3 baths · Sleeps 5 ·
Dishwasher · Oven · Kitchen ·
From
$280/night
Check availability
Amenities
Dishwasher
Oven
Air Conditioning
In Unit Laundry
Wifi
Furnished
Other spaces
Kitchen
· House in Chestertown
Chestertown's Pet-Friendly Little Red Cottage
2 Beds · 1 bath · Sleeps 4 ·
Workspace · Outdoor Space · Dishwasher ·
From
$235/night
Check availability
Amenities
Dishwasher
Oven
Air Conditioning
In Unit Laundry
Wifi
Furnished
Other spaces
Workspace, Kitchen
· House in Chestertown
The Lazy River House
3 Beds · 4 baths · Sleeps 12 ·
In Unit Laundry · Wifi · Furnished ·
From
$450/night
Check availability
Amenities
In Unit Laundry
Wifi
Furnished
· House in Chestertown
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
3 Beds · 2 baths ·
Beach · Fireplace · Waterfront ·
From
$450/night
Check availability
Amenities
Beach
Fireplace
Waterfront
Fitness Center
Dishwasher
Air Conditioning
In Unit Laundry
Wifi
Other spaces
Kitchen
Showing 1 - 20 of 20 results
Home > Maryland Vacation Rentals > Chestertown Vacation Rentals
Updated: March 9, 2023

Learn about vacation rentals in

Chestertown

Explore 20 vacation rentals near Chestertown, Maryland. Whether you’re a tourist or on a staycation, there’s plenty of things to do and restaurants to try around the city. If you’re looking to take a trip to Chestertown, you can see photos of Chestertown vacation rentals, view amenities and features, browse by specific property types, and more. Use our interactive map to find Chestertown vacation rentals in specific areas. Whether you’re looking for a Chestertown staycation, weekend getaway, or a long vacation, we’ve got you covered. Use the date filters at the top to select your travel dates and view availability. The lowest vacation rental price in Chestertown is $95 per night and the highest price is $2,263 per night.
2 of the vacation rentals near Chestertown are apartments or condos. The average bathroom count for this property type is 1. The median price for these vacation units is $113 per night. There are currently 1 vacation units under this price. 17 of the vacation rentals near Chestertown are houses. The average bathroom count for a vacation house near Chestertown is 4. The average price for vacation houses near Chestertown is $574 per night. There are 10 vacation homes under this price. The most common amenities for vacation rentals near Chestertown are: furnished, in-unit laundry, and air conditioning. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.

1 bed rentals

2 available

2 bed rentals

3 available

3 bed rentals

4 available

4+ bed rentals

10 available

Getting around Chestertown

Pedestrian friendly

4/10
Fewer daily needs are within walking distance (unless you’re up for a challenge).

Car friendly

10/10
Commuting is easy with multiple accessible routes and plenty of parking.

Transit friendly

1/10
FYI, there are little to no public transit options within walking distance.

Points of interest in Chestertown

Groceries

4/10
At least one grocery store within a 30-minute walk

Shopping

2/10
Few or no shops within walking distance

Cafes

3/10
Few or no cafés within walking distance

Restaurants

4/10
Some restaurants within walking distance

Nightlife

3/10
Few or no bars within walking distance

Vacation Rentals in Chestertown, MD FAQ

How many vacation rentals in Chestertown are available?

There are currently 20 vacation rentals in Chestertown available. Our vacation rentals in Chestertown include nightly rentals, weekend rentals, weekly rentals, and monthly rentals.

Are there any pet friendly vacation rentals in Chestertown?

Yes, right now there are 9 pet friendly vacation rentals in Chestertown. A pet friendly vacation rental in Chestertown means a rental home that is dog friendly or cat friendly. Some pet friendly homes may accommodate other types of pets, as well. Contact the listing agent for any pet related inquiries.

Are there any vacation rentals in Chestertown with a pool?

Yes there are vacation rentals with a pool available in Chestertown, MD. View more detailed vacation spots on Vacations by Zumper.

Are there any vacation rentals in Chestertown with internet access?

As of March 9, 2023, there are vacation rentals with internet access available in Chestertown, Maryland. Check out more enjoyable destinations on Vacations by Zumper.

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