Chestertown Vacation Rentals from ￥28,495: Search Short-Term Rentals

Q: 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.

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Our top choices for Chestertown vacation rentals

1. First Floor Studio Apartment in Historic Chestertown

Chestertown

John R.

￥24,399 total

includes taxes & fees

Sep 14 - Sep 15

2. Newly restored apartment in the heart of Chestertown

Chestertown

Anonymous traveler

￥54,255 total

includes taxes & fees

Sep 13 - Sep 14

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

Chestertown

Mandy D.

￥73,927 total

includes taxes & fees

Sep 30 - Oct 1

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

Chestertown

￥42,497 total

includes taxes & fees

Oct 5 - Oct 6

5. Secluded Cottage in Middle of Chestertown

Chestertown

Amy D.

￥42,086 total

includes taxes & fees

Sep 21 - Sep 22

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

Millington

Riley B.

￥19,213 total

includes taxes & fees

Sep 14 - Sep 15

7. Hidden Fells Point Gem / Private Courtyard Patio

Fells Point

Mark M.

￥32,469 total

includes taxes & fees

Sep 13 - Sep 14

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

Rock Hall

lisa p.

￥44,052 total

includes taxes & fees

Sep 13 - Sep 14

9. Cozy Fells Point Gem / In The Heart of Fells Point

Fells Point

Tammy

￥33,533 total

includes taxes & fees

Sep 21 - Sep 22

10. Turtle Cove Room

Kent County

￥26,764 total

includes taxes & fees

Sep 28 - Sep 29

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

Aberdeen

christine

￥16,592 total

includes taxes & fees

Sep 22 - Sep 23

12. BAYSIDE BUNGALOW

Rock Hall

Diane V.

￥48,489 total

includes taxes & fees

Sep 14 - Sep 15

13. Waterfront Retreat with Private Dock and Beach

Worton

Max G.

￥46,372 total

includes taxes & fees

Oct 5 - Oct 6

14. Beachcomber Suite

Kent County

"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...

Lisa E.

￥30,126 total

includes taxes & fees

Sep 14 - Sep 15

Luxury House, Multiple Bedrooms, Lake View | Laptop workspace, WiFi (free)

15. Bohemia Manor Farm

Chesapeake City

￥57,443 total

includes taxes & fees

Oct 13 - Oct 14

16. Cass-Away Luxury Houseboat

Grasonville

Jamie L.

￥47,837 total

includes taxes & fees

Sep 28 - Sep 29

17. Cass-N-Reel Luxury Houseboat

Grasonville

Danny B.

￥43,412 total

includes taxes & fees

Oct 8 - Oct 9

Coffee/tea maker, fridge, microwave, oven

18. Cute, Cozy 2-bedroom house near Annapolis with water access

Herald Harbor

Taylor C.

￥35,723 total

includes taxes & fees

Oct 6 - Oct 7

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

Stevensville

Michelle P.

￥50,013 total

includes taxes & fees

Sep 17 - Sep 18

1 bedroom, in-room safe, desk, iron/ironing board

20. Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals

Nottingham City

"At the end of a multi-city trip filled with mixed hotel experiences, this stay was a true breath of fresh air. Everything was spotlessly clean, beautifully organized, and exactly as pictured. What truly set it apart were the thoughtful touches throughout the space—it was clear our host anticipated our every need, which even saved us an extra trip to the store! Parking was effortless, and the location made getting into the city by car or public transit super easy. Communication with our host was...

Jennifer R.

￥23,738 total

includes taxes & fees

Sep 17 - Sep 18

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Top Chestertown Hotel Reviews

Best Western Plus Hotel & Conference Center

10/10 Excellent

"They have 2 DC fast charger level 3 EV chargers on site! This is an absolute must for any hotel. 5 stars!"

Historic Inns of Annapolis

10/10 Excellent

"Lovely historic hotel. Our room was comfortable and spacious. We used valet parking. The cars are locked and parked below the inn and the gate is pulled down at night. We liked that since we had golf clubs in the car. Valet guys were very friendly Very convenient location. We parked and walked everywhere for two days."

Quality Inn & Suites Bel Air I-95 Exit 77A

8/10 Good

"Everything else was great except, i was placed in a room with an in-between door i didn't appreciate or felt safe. On opening the door, the room smells like construction work was just completed, very dissatisfied. Had 2 stains in the tub. Morning was great, except for the individual cleaning up at breakfast, she did not respect others as the were making their waffles, counter top was clean but she continues to disturb others buy wiping counter & other had to wait on her while their food was getting cold"

Hyatt Place Kent Narrows & Marina

10/10 Excellent

"Would gladly book again. Upgrading to a room with a balcony overlooking the Bay was too expensive but it was a special occasion, so I paid it. The upgrade would be a lot cheaper, most likely, it I had done in it advance. The desk clerk allowed us to check in early because the room was clean and ready. This was very kind and not usually offer in any case at hotels and motels. It made it easier when we came back later in the afternoon and went directly to the room. Thanks!"

Find out more about Chestertown

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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.

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Check prices for these dates

Our top choices for Chestertown vacation rentals

1. First Floor Studio Apartment in Historic Chestertown

2. Newly restored apartment in the heart of Chestertown

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

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

5. Secluded Cottage in Middle of Chestertown

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

7. Hidden Fells Point Gem / Private Courtyard Patio

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

9. Cozy Fells Point Gem / In The Heart of Fells Point

10. Turtle Cove Room

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

12. BAYSIDE BUNGALOW

13. Waterfront Retreat with Private Dock and Beach

14. Beachcomber Suite

15. Bohemia Manor Farm

16. Cass-Away Luxury Houseboat

17. Cass-N-Reel Luxury Houseboat

18. Cute, Cozy 2-bedroom house near Annapolis with water access

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

20. Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals

Find vacation rentals that suit your style

Top Chestertown Hotel Reviews

Best Western Plus Hotel & Conference Center

Pendry Baltimore

Historic Inns of Annapolis

Quality Inn & Suites Bel Air I-95 Exit 77A

Comfort Inn & Suites Chestertown

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

Annapolis Waterfront Hotel, Autograph Collection

Hampton Inn Baltimore/Glen Burnie

Hyatt Place Kent Narrows & Marina

Find out more about Chestertown

Frequently asked questions

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