An aerial view of a town with a river, buildings, and surrounding greenery.

Chestertown Vacation Rentals

Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Chestertown vacation rentals

Smart TV, books

1. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (33 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
$304 nightly
The price is $336
Sep 20 - Sep 21
Total with taxes and fees
Newly restored apartment in the heart of Chestertown
Property grounds

2. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (125 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
$144 nightly
The price is $159
Sep 29 - Sep 30
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Property grounds

3. Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
$463 nightly
The price is $481
Sep 23 - Sep 24
Total with taxes and fees
Wren Retweet- Country Estate in Center of C’Town
TV, fireplace

4. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
$264 nightly
The price is $274
Sep 21 - Sep 22
Total with taxes and fees
Secluded Cottage in Middle of Chestertown
Smart TV

5. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
$270 nightly
The price is $286
Oct 5 - Oct 6
Total with taxes and fees
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Exterior detail

6. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (65 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
$260 nightly
The price is $287
Sep 19 - Sep 20
Total with taxes and fees
BAYSIDE BUNGALOW
Exterior

7. Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.8 out of 10, Exceptional, (28 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
$118 nightly
The price is $125
Sep 21 - Sep 22
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
Beach nearby

8. Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (26 reviews)
"Everything was lovely! The dock was beautiful and the accommodations were comfortable.Thanks!"
United States
Max G.
$271 nightly
The price is $300
Oct 4 - Oct 5
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach
Beach

9. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (30 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
$260 nightly
The price is $287
Sep 20 - Sep 21
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Luxury House, Multiple Bedrooms, Lake View | Laptop workspace, WiFi (free)

10. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
$392 nightly
The price is $416
Oct 19 - Oct 20
Total with taxes and fees
Bohemia Manor Farm
Property grounds

11. Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...
United States
Lisa E.
$181 nightly
The price is $196
Sep 28 - Sep 29
Total with taxes and fees
Beachcomber Suite
Smart TV

12. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (5 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
$410 nightly
The price is $435
Sep 21 - Sep 22
Total with taxes and fees
Bayside Cottage steps from Rock Hall Harbor
1 bedroom, WiFi, bed sheets

13. Turtle Cove Room

Turtle Cove Room
Kent County
$183 nightly
The price is $199
Sep 28 - Sep 29
Total with taxes and fees
Turtle Cove Room
Dining

14. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (16 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
$460 nightly
The price is $488
Sep 21 - Sep 22
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Dining

15. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (12 reviews)
"We had an amazing stay for a wedding weekend! Beautiful grounds, beautiful house, lots of room for kids and dogs. Would definitely stay again! "
United States
Emily C.
$427 nightly
The price is $472
Sep 23 - Sep 24
Total with taxes and fees
Family Retreat at Lansdowne Manor
Terrace/patio

16. WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Aberdeen
9.8 out of 10, Exceptional, (7 reviews)
"Booked this property as a last minute, overnight getaway for myself and it was fantastic! The apartment, grounds and hot tub was squeaky clean. Kitchen was clean and stocked with utensils and even had a coffee bar, different tea packets and a snack basket. Bathroom was fully stocked with towels, basic toiletries and everything I needed. Bed was comfortable and closets had extra blankets if needed. Inside and outside patio furniture was comfy. I loved watching the sunset from the hot tub! Also...
United States
Kayla K.
$177 nightly
The price is $188
Sep 20 - Sep 21
Total with taxes and fees
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Exterior

17. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (47 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
$257 nightly
The price is $277
Sep 21 - Sep 22
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
House (3 Bedrooms) | Interior

18. Lakefront Home Firepit BWI Marleycreek River

Lakefront Home Firepit BWI Marleycreek River
3.0 star property
Marley
$270 nightly
The price is $308
Sep 21 - Sep 22
Total with taxes and fees
Lakefront Home Firepit BWI Marleycreek River
Coffee/tea maker, fridge, microwave, oven

19. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (6 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
$441 nightly
The price is $503
Sep 28 - Sep 29
Total with taxes and fees
Pool Loft Suite | Bay Access & Beach Passes
TV

20. Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.6 out of 10, Good, (19 reviews)
"Nice place"
United States
christine
$102 nightly
The price is $108
Sep 28 - Sep 29
Total with taxes and fees
Charming 2-bedroom house in Aberdeen with WiFi and AC
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.
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Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Everyone was polite and the room was extremely quiet. It was relaxing. My daughter and I enjoyed staying at the Historic Inns of Annapolis."
Isabel 3-night trip
Posted 9 hours ago
Historic Inns of Annapolis

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 $188 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

Frequently asked questions

Are there vacation rentals in Chestertown?

Yes, we offer vacation rentals in Chestertown close to Larrabee Arts Center, or you can go with a more secluded option if you're looking for extra privacy while you relax. Chestertown is known for its sporting events and university setting. Make sure you have time to check out the festivals and art during your trip.

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

Sailor's Sunrise Cottage - Chesapeake Bay: This vacation home rental outside of Chestertown is located on a lake and has a fireplace, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and a hot tub.

How many vacation rentals are there in Chestertown?

Expedia has 29 vacation rentals for your stay in Chestertown.

What can I see and do in Chestertown?

Enjoy the outdoors at Northern Chesapeake Bay and Chesapeake Bay, or simply take in cultural attractions like Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater. Chestertown Historic District and Rolphs Wharf Marina are other places to visit while you're in town.

What are vacation rentals like in Chestertown?

Vacation rentals are private properties you can stay in for a couple days or more in Chestertown. Vacation rentals feature extras such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for a family getaway.