Chestertown Holiday Rentals: Short-Term Accommodations for Rent

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Our top choices for Chestertown holiday rentals

1. First Floor Studio Apartment in Historic Chestertown

Chestertown

S G.

HK$1,245 total

includes taxes & fees

2 Sept - 3 Sept

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

Chestertown

HK$2,269 total

includes taxes & fees

8 Sept - 9 Sept

3. Secluded Cottage in Middle of Chestertown

Chestertown

Amy D.

HK$2,215 total

includes taxes & fees

1 Sept - 2 Sept

4. Newly restored apartment in the heart of Chestertown

Chestertown

Anonymous traveller

HK$2,761 total

includes taxes & fees

31 Aug - 1 Sept

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

Chestertown

Mandy D.

HK$3,923 total

includes taxes & fees

1 Sept - 2 Sept

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

Millington

Riley B.

HK$981 total

includes taxes & fees

10 Sept - 11 Sept

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

Rock Hall

lisa p.

HK$2,257 total

includes taxes & fees

31 Aug - 1 Sept

8. Waterfront Retreat with Private Dock and Beach

Worton

Max G.

HK$2,952 total

includes taxes & fees

31 Aug - 1 Sept

9. Turtle Cove Room

Kent County

HK$1,366 total

includes taxes & fees

31 Aug - 1 Sept

10. 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.

HK$1,554 total

includes taxes & fees

31 Aug - 1 Sept

11. BAYSIDE BUNGALOW

Rock Hall

Diane V.

HK$2,475 total

includes taxes & fees

31 Aug - 1 Sept

12. Studio Apartment 5 Miles from Dover in quiet town of Hartly w/Dollar Store

Hartly

HK$1,197 total

includes taxes & fees

31 Aug - 1 Sept

13. Bayside Cottage steps from Rock Hall Harbor

Rock Hall

Adam S.

HK$2,851 total

includes taxes & fees

29 Sept - 30 Sept

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

Stevensville

HK$2,108 total

includes taxes & fees

31 Aug - 1 Sept

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

Aberdeen

HK$1,479 total

includes taxes & fees

31 Aug - 1 Sept

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

Aberdeen

christine

HK$877 total

includes taxes & fees

6 Sept - 7 Sept

17. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Stevensville

Dawn G.

HK$2,152 total

includes taxes & fees

31 Aug - 1 Sept

18. Cass-Away Luxury Houseboat

Grasonville

Jamie L.

HK$2,467 total

includes taxes & fees

25 Sept - 26 Sept

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

Fells Point

Tammy

HK$1,730 total

includes taxes & fees

31 Aug - 1 Sept

20. Hidden Fells Point Gem / Private Courtyard Patio

Fells Point

Mark M.

HK$1,838 total

includes taxes & fees

2 Sept - 3 Sept

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Top Chestertown Hotel Reviews

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

8/10 Good

"The room was large, clean and comfortable. The breakfast was OK. We ate scrambled eggs and sausages. The issues were that the hotel was old and not updated to today's standards. For example, there were sufficient wall outlets, but no charging ports for devices such as cell phones. This is expected in hotel rooms today. The TV set was inoperative, the refrigerator wasn't cold enough, and the lavatory sink was cracked. The decor was too dark for our tastes. Coffee was provided at breakfast, but there were no lids for the cups for taking in the car after checkout."

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good

"Lovely room, clean, comfortable, well appointed & quiet. We’d be happy to stay longer in such a nice room! We asked for early check-in, & were told we’d be contacted when the room was ready, but there was no follow-up contact. Our morning shower had no hot water so we washed quickly! We knew there was ongoing work with the water supply but didn’t expect cold showers. When we reported the issue at the front desk, we were graciously offered breakfast at the on-site restaurant. So glad we accepted! Food (& service & view) were excellent. We didn’t consider the restaurant previously because there was no evidence of it aside from a sign on the door. A posted menu could help. It’s a long walk down a cold hallway and we totally would have not considered it as a breakfast option. Definitely recommend eating at the restaurant!"

Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

10/10 Excellent

"The staff is always very welcoming. The staff who cleans are the same. I do know that when I look out the window to the back parking lot...people leave their trash all over the place same with over filling the trash cans on the 2nd floor. The staff tends to these areas all of the time."

Find out more about Chestertown

Search for holiday rentals in Chestertown on Expedia! You can easily find your home rentals, villas, holiday apartments in Chestertown using one of the methods below:

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Frequently asked questions

Are there holiday rentals in Chestertown?

Yes, there are holiday rentals in Chestertown close to Garfield Center for the Arts at the Prince Theater, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Chestertown has to offer?

Cute, Cozy 2-bedroom house near Annapolis with water access: This holiday home rental outside of Chestertown offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of books in this rental home to help you unwind.

How many holiday rentals are there in Chestertown?

Expedia has 28 holiday 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 holiday rentals like in Chestertown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chestertown. Holiday rentals offer extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.

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Check prices for these dates

Our top choices for Chestertown holiday rentals

1. First Floor Studio Apartment in Historic Chestertown

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

3. Secluded Cottage in Middle of Chestertown

4. Newly restored apartment in the heart of Chestertown

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

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

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

8. Waterfront Retreat with Private Dock and Beach

9. Turtle Cove Room

10. Beachcomber Suite

11. BAYSIDE BUNGALOW

12. Studio Apartment 5 Miles from Dover in quiet town of Hartly w/Dollar Store

13. Bayside Cottage steps from Rock Hall Harbor

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

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

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

17. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

18. Cass-Away Luxury Houseboat

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

20. Hidden Fells Point Gem / Private Courtyard Patio

Find holiday rentals that suit your style

Top Chestertown Hotel Reviews

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

Hampton Inn Baltimore/White Marsh

Pendry Baltimore

Best Western Kent Narrows Inn

Annapolis Waterfront Hotel, Autograph Collection

Holiday Inn Express Annapolis East-Kent Island by IHG

Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

Find out more about Chestertown

Frequently asked questions

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