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Featured Apartments in Chestertown and around

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Fridge, microwave, oven, stovetop
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
9.8 out of 10, Exceptional, (23)
"Beautiful unit on the water with amazing views. It was a great place to gather for wedding preparation (hair/make-up) and fellowship right down the road from the venue (Celebration at the Bay)."
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Fridge, microwave, oven, stovetop
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
10.0 out of 10, Exceptional, (20)
"Thoroughly enjoyed our stay! Betty is such a great host. Beautiful area...GREAT sunsets and close to the beach! Very comfortable weekend stay! Also close to some great wineries and Alpaca farms!"
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Bay View Studio Apartment
Outdoor spa tub
Bay View Studio Apartment
10.0 out of 10, Exceptional, (28)
"Overall, we had a great stay, the kitchen was well stocked, and the unit was very clean. Only issue was the chain that you have to unlock and lock every time you enter. I would definitely recommend the property though if you want the great location, beautiful sunrises and easy access to downtown Annapolis."
Bay View Studio Apartment
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Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Pool
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
10.0 out of 10, Exceptional, (35)
"Super clean and easy to find. I encourage anyone to rent this space"
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
'At Fells Point' CitySide - 'Tons better than a hotel!'
'At Fells Point' CitySide - 'Tons better than a hotel!'
9.8 out of 10, Exceptional, (165)
"The property was very clean. Very impressed with the cleanliness. It did have an old scent upon entry, but it is an older area. Not being from this area, have not experienced a road house before along with no parking available. We did pay for the first 2 hour limit on the road two blocks over and then found a parking garage within a 12 min. walk that was affordable for the 3 nights we would be in town. All in all, excellent air b and b. The parking is what made it a bad first air b and b...
The price is €204
per night
19 Jun - 20 Jun
'At Fells Point' CitySide - 'Tons better than a hotel!'
Anchor's Away in the Heart of Eastport!
Fridge, microwave, oven, stovetop
Anchor's Away in the Heart of Eastport!
9.8 out of 10, Exceptional, (31)
"Property is very convenient to the USNA and DTA. You can walk, but they're a good 25-30 minutes and parking was available even during Commissioning week and at the local restaurants. Plus, we could park about 25 feet from the door of the VRBO all the time. It is a first floor, easy to access door. There is a full kitchen and fridge, a comfy couch, and a nice bathroom. It's really like a nice hotel suite. A couple idiocycracies however. The bed pulls down from the wall, which gives you more play...
Anchor's Away in the Heart of Eastport!
Cozy 1st Floor King George one bedroom apartment right across from USNA
Fridge, microwave, oven, stovetop
Cozy 1st Floor King George one bedroom apartment right across from USNA
10.0 out of 10, Exceptional, (19)
"My friend and I were there for Paint Annapolis run by MFA. We were close to all the locations we wanted to paint."
Cozy 1st Floor King George one bedroom apartment right across from USNA
First Floor Studio Apartment in Historic Chestertown
Property grounds
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, (60)
"It was a nice room in a nice neighborhood. Only complaint would be the coffee maker was awful."
The price is €157
per night
20 Jun - 21 Jun
First Floor Studio Apartment in Historic Chestertown
'At Fells Point' Topside - Exceeding your expectations!
'At Fells Point' Topside - Exceeding your expectations!
9.6 out of 10, Exceptional, (81)
"Great location. Very clean. Super comfortable bed. Wonderful location to get to everything downtown. Really enjoyed my stay"
The price is €235
per night
2 Jul - 3 Jul
'At Fells Point' Topside - Exceeding your expectations!
Coastal Kent Narrows Home on Bay
Fridge, microwave, oven, stovetop
Coastal Kent Narrows Home on Bay
9.2 out of 10, Wonderful, (5)
"Very nice place to stay, right on the bay"
The price is €458
per night
23 Jun - 24 Jun
Coastal Kent Narrows Home on Bay
Charming Downtown 3rd Floor 1 Bedroom Apt
Property grounds
Charming Downtown 3rd Floor 1 Bedroom Apt
10.0 out of 10, Exceptional, (12)
"Nice place, nice owners, great location."
The price is €293
per night
7 Jul - 8 Jul
Charming Downtown 3rd Floor 1 Bedroom Apt
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Sauna
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
9.6 out of 10, Exceptional, (16)
"First experience with Vrbo. It was great. Thanks again, Tim!"
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Cozy Country Setting to relax! 15 min to Dover, DE
Living area
Cozy Country Setting to relax! 15 min to Dover, DE
Cozy Country Setting to relax! 15 min to Dover, DE
Serenity on the Water
Property grounds
Serenity on the Water
10.0 out of 10, Exceptional, (2)
"My partner and I rented the beautiful "serenity on the water" to celebrate our anniversary over the Memorial Day holiday. We found the rental in immaculate condition. It is very large, and well appointed, even including a ping pong table. The place is beautifully decorated and located very close to all the amenities you could ask for. It was an awesome stay, and we were so happy with the recommendations for activities. You can even WALK to the near by vineyard."
Serenity on the Water
Modern Home 3BD/3BA Free On-Street Parking & Wifi
Exterior
Modern Home 3BD/3BA Free On-Street Parking & Wifi
8.0 out of 10, Very good, (2)
"The unit was very clean and comfortable. However, the description said that it sleeps six, but it only slept 5. There are three twin beds and one queen. The bathrooms were not adequately supplied. There was one roll of toilet paper in two of the bathrooms and none in the third. Also, there was no body wash in two of the bathrooms. Parking is limited. Uber is required to get to the Inner Harbor. All this said, I recommend the property."
Modern Home 3BD/3BA Free On-Street Parking & Wifi
Historic Downtown Garden Oasis with Private Patio
Property grounds
Historic Downtown Garden Oasis with Private Patio
10.0 out of 10, Exceptional, (15)
"A perfect stay in lovely, comfortable private guest quarters. Perfect for a couple. Well designed layout. Kitchen includes a toaster oven, microwave and coffee machine (capsules provided). Extremely well located, close to the superb Watershed Alley and Modern Stone Age Kitchen as well as the brand new Lawrence Wetlands Preserve (ideal if you are a birder!). Will definitely return to enjoy Stephen's and Marianna's guest suite. "
Historic Downtown Garden Oasis with Private Patio
Waterfront Retreat with Private Dock and Beach
Property grounds
Waterfront Retreat with Private Dock and Beach
10.0 out of 10, Exceptional, (2)
"Nice quiet place right on the water. Very scenic. Quiet, small apartment with all needed amenities. Great for a couple. Access to dock and kayak a real plus."
The price is €330
per night
19 Jun - 20 Jun
Waterfront Retreat with Private Dock and Beach
Royalty Homes - 2 bedroom apartment
Exterior
Royalty Homes - 2 bedroom apartment
Royalty Homes - 2 bedroom apartment
Bel Air Apartment w/ Pool ~ 2 Mi to Main St
Property grounds
Bel Air Apartment w/ Pool ~ 2 Mi to Main St
Bel Air Apartment w/ Pool ~ 2 Mi to Main St
Charming Eastport
Beach
Charming Eastport
9.4 out of 10, Exceptional, (3)
"This was a charming apartment nestled in the quiet side of annapolis. Everything was within walking distance. The apartment had everything you needed if you wanted to cook. Just bring your food!"
Charming Eastport
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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.

Other property types in Chestertown

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (53)
"Good location. House well stocked. Great pool. Short hike to river. Lots of kayaks ,a canoe and paddle boards"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
9.8 out of 10, Exceptional, (6)
"Overall the home is beautiful. There is a gorgeous mostly well stocked kitchen and 3 bedrooms with beds for couples. One of the king beds listed is a pull out couch in the pool house. The biggest con of this place is that there are no blackout curtains or anything to block the sun in the bedroom so for our June visit the rooms were very bright at 5:45AM. We also had to go out and buy some of our own things that you'd think would be included (garbage bags). Other than that its a beautiful home...
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Beach nearby, sun-loungers
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (36)
"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
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.

Chestertown Apartments information

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Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You can search through 5 apartments in Chestertown for your stay.
Why would you choose an apartment over a traditional hotel room?
Offering a kitchen for convenient meals, an apartment often has more space than a traditional hotel room. Apartments are a good option for couples who want a more local feel, and also for families wanting the conveniences of home.
What's the best apartment I should consider for a stay in Chestertown?
Below are some of the favourite apartments in the area to choose from: First Floor Studio Apartment in Historic Chestertown: Includes a private pool, a washer/dryer and free WiFi . A fitness centre and an outdoor pool are on site . Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!: Located 23 mi/36.9 km away in Annapolis . Free WiFi, a patio and a Smart TV are included . A fitness centre and a games room are on site . Milton Manor: W/D, WiFi, Free Street Parking: It’s located in Baltimore , 28 mi/45 km away. Bay View Studio Apartment: Located in Annapolis , 28 mi/45 km from Chestertown. Includes free WiFi, a patio and a fireplace . A water park and 1 hot tub are on site .
How many apartments can I expect to find in Chestertown?
Expedia has 5 apartments to book in Chestertown.
What can I expect from the weather in Chestertown?
Weather is only one factor, but it can really affect your travel plans, especially when you’re planning an extended stay in Chestertown. The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
What should I see and do in Chestertown?
Cultural attractions include Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater, whereas Wilmer Park is one spot to enjoy nature. Other places in town to visit include Rolphs Wharf Marina and Crumpton Auction.
What's the best way to get to and around Chestertown?
Knowing a bit about the transportation options can you save you a headache when you get to your destination. Fly into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) away from the heart of the city. Otherwise, you can search for flights to Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away. If you’d like to explore around the area, you may want to rent a car for your trip.

Recent Reviews in Chestertown
Expedia verified reviews

Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

5/5 Excellent
Wonderful Experience!
"Wonderful Father's Day experience at a poolside cabana during Fleet Week kick off no less! Beautiful room, great restaurant/food and service. We will be back!"
A verified traveller stayed at Sagamore Pendry Baltimore
Posted 22 hours ago
Sagamore Pendry Baltimore