Chestertown, MD Vacation Rentals

Our Favorite Vacation Rentals in Chestertown

  • 104 Chesapeake House Condo
     Home/Apartment
    Booking.com
    From
    $334
  • Cozy & Spacious Chestertown Home
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $358
  • Belle Rose Cottage at Victory Farm (Pet Friendly!)
    ExcellentHome/Apartment
    HolidayLettings
    From
    $209
  • Retreat at a quiet, water front cottage
    Good3br Home/Apartment
    HolidayLettings
    From
    $427
  • Sailors Crossing
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $458
  • Cottage On Kent
    ExcellentCottage
    HolidayLettings
    From
    $245
  • Summer House in Rock Hall
     3br Home/Apartment
    HolidayLettings
    From
    $338
  • Cozy Airstream on a beautiful horse farm
    ExcellentHome/Apartment
    Airbnb
    From
    $112

Check prices for these upcoming dates

Chestertown Vacation Rentals with a Pool

  • Piney Grove Farm
    Excellent5br Farm Stay
    Airbnb
    From
    $537
  • Pet Friendly Guest Cottage with pool and dock
    Excellent3br Home/Apartment
    Airbnb
    From
    $452
  • Creek Cottage
    Excellent4br Home/Apartment
    Airbnb
    From
    $1,015
  • Water View Condo with pool use in Rock Hall Harbor
    Excellent2br Home/Apartment
    Airbnb
    From
    $387

Chestertown Vacation Rentals with Wi-Fi

  • Historic Chestertown
    Excellent3br Home/Apartment
    Airbnb
    From
    $367
  • RIVER WATCH
    Excellent3br Home/Apartment
    Airbnb
    From
    $237
  • Rivershore Retreat
    Excellent2br Home/Apartment
    Airbnb
    From
    $333
  • River Lodge
    Excellent4br Home/Apartment
    Airbnb
    From
    $757

Chestertown Pet-Friendly Vacation Rentals

  • Running Fox
    Excellent4br Home/Apartment
    Airbnb
    From
    $754
  • Entire River Front Home - 4 Bedrooms 4.5 Baths
    Excellent4br Home/Apartment
    Airbnb
    From
    $636
  • Enjoy 8 acres of woods of your AirBnB
    Okay3br Home/Apartment
    Airbnb
    From
    $212
  • Egret's Nest, A Waterfront Oasis near Rock Hall
     Home/Apartment
    Airbnb
    From
    $367

Chestertown Travel Guide

Chestertown is located in Maryland, east of Baltimore. It is an excellent vacation spot for family fun, a couples’ getaway or even a long weekend away with friends. Chestertown is mainly known for being a quaint mid-Atlantic town.

Things to Do in Chestertown

To learn more about the city, you are definitely going to want to check out the self-guided downtown tour, it’s a must see and a great opportunity for everyone in your group. The Chestertown River cruise is also a great option if you want to see more of the city.

Another top activity is to roam the aisles of the Chestertown Farmer's Market and Artisan's Market and buy some vacation gifts for loved ones, and of course, some treats for yourself!

Best Time to Visit Chestertown

The best time of year to visit Chestertown is during the summer.

Food in Chestertown

There are some mouthwatering spots for foodies to sample when visiting Chestertown. The two that stand out are Luisa's Cucina Italiana, which is known for having some of the best Italian food in the area, or if you like seafood, check out Fish Whistle.

Price and Availability in Chestertown

Most expensive
Most availability
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0
Powered by:
The cheapest day to stay at a vacation rental in Chestertown tends to be Tuesday, while the most expensive day tends to be Sunday. Vacation homes in Chestertown tend to be busiest on Saturdays, while it tends to be much quieter on Mondays.
The most expensive month to stay in a vacation rental in Chestertown is in July, while the cheapest month is in January. The most popular time to book a vacation rental in Chestertown is in the high season in July. Chestertown has its low season in December, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Chestertown

Rainy days
92 º56
5
86 º35
3
74 º20
4
64 º22
4
66 º2
3
74 º18
5
73 º27
3
82 º32
3
89 º44
8
94 º54
3
97 º55
4
95 º60
2
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Rainy days

This climate histogram shows you the weather patterns in Chestertown. The warmest months in Chestertown are June and May, when temperatures reach 97 ˚F. The coolest month is December, when temperatures drop to 2 ˚F. The wettest month in Chestertown is August with 8.2 inches of rain, while the driest month is May with 2.36 inches of rain.

What Expert Travelers Think

  • — Packed full of information, from the best time of year to visit (I love NYC in Spring) to top tips from locals, All The Rooms provides the best accommodation, whether you are looking to enjoy your first time visit to New York or want to experience a new location

    Jaz
    JazThe Life of a Social Butterfly
  • — My favorite thing about AllTheRooms is that it combines both rentals and hotels available so you can see an entire view of what is available in a certain area. I was able to see listings on AllTheRooms that I never even saw on other travel sites!

    Daniella Flores
    Daniella FloresILIKETODABBLE
  • — AllTheRooms.com makes travel easier, enjoyable and inexpensive through its provision of ample information, data and every possible accommodation available to choose from

    ArtMatters.Info
    ArtMatters.InfoArtMatters.Info

Vacation Rentals in Chestertown

Choose the perfect rental for your vacation at AllTheRooms.com. We aggregate Airbnb, Bed and Breakfast, Priceline and more. We have 166 vacation rentals, hotels and other accommodation types in Chestertown ranging from inexpensive options to extravagant places to stay. For those traveling on a budget, the most economical place to stay in Chestertown is available at $55 per night. The average price of a vacation rental is around $323 per night.

If you need an internet connection during your time in Chestertown, then you can choose from over 80 accommodations that provide WiFi internet. 21 of our accommodations come with breakfast in the price. You can maintain your workout regime by staying at one of 4 accommodations that provide gym facilities. Driving to Chestertown? Then choose one of the 75 places to stay that comes with a parking spot included. 9 vacation rentals have a a pool or jacuzzi

If you're traveling with a furry friend, then be sure to choose one of the 23 pet-friendly accommodations available.

108 accommodations in Chestertown have been reviewed; 72% are rated excellent or good. 32 accommodations allow instant booking.

Destinations near Chestertown

  • Ocean City7,414 Properties
  • Oakland2,201 Properties
  • McHenry1,742 Properties
  • Swanton1,406 Properties
  • Baltimore1,232 Properties
  • Annapolis1,224 Properties
  • Bethesda597 Properties
  • Ocean Pines509 Properties
  • Silver Spring477 Properties
  • Frederick441 Properties
  • Cambridge387 Properties
  • Rockville372 Properties
  • Berlin367 Properties
  • Gaithersburg356 Properties
  • Columbia303 Properties
  • Laurel293 Properties
  • Oxon Hill287 Properties
  • Salisbury283 Properties
  • Hanover282 Properties
  • Aberdeen254 Properties
  • Easton222 Properties
  • Fort Washington207 Properties
  • Takoma Park200 Properties
  • Stevensville177 Properties
  • Hyattsville149 Properties
  • College Park97 Properties
  • St. Michaels78 Properties
  • North Beach63 Properties
  • Mount Rainier53 Properties
  • Accokeek52 Properties
  • Lusby47 Properties
  • Chesapeake Beach43 Properties
  • West Ocean City22 Properties
  • Emmitsburg13 Properties