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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Chestertown apartments

Property grounds

1. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (120 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is HK$777
HK$1,246 total
includes taxes & fees
20 Aug - 21 Aug
First Floor Studio Apartment in Historic Chestertown
Smart TV, books

2. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (32 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveller
The price is HK$1,765
HK$2,771 total
includes taxes & fees
19 Aug - 20 Aug
Newly restored apartment in the heart of Chestertown
TV, fireplace

3. 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.
The price is HK$1,440
HK$2,216 total
includes taxes & fees
19 Aug - 20 Aug
Secluded Cottage in Middle of Chestertown
Exterior

4. 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, (26 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.
The price is HK$533
HK$981 total
includes taxes & fees
10 Sept - 11 Sept
Guest Suite for up to 2 in a Victorian on the Chester River
Beach

5. 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, (28 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is HK$924
HK$2,258 total
includes taxes & fees
19 Aug - 20 Aug
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
1 bedroom, WiFi, bed sheets

6. Turtle Cove Room

Turtle Cove Room
Kent County
The price is HK$1,101
HK$1,367 total
includes taxes & fees
24 Aug - 25 Aug
Turtle Cove Room
Beach nearby

7. Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (26 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is HK$1,765
HK$2,970 total
includes taxes & fees
30 Aug - 31 Aug
Waterfront Retreat with Private Dock and Beach
Property grounds

8. 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.
The price is HK$1,251
HK$1,547 total
includes taxes & fees
24 Aug - 25 Aug
Beachcomber Suite
Terrace/patio

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

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Aberdeen
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful location, nicely decorated. The host thought of everything you may need including a free snack basket, washer/dryer with detergent and dryer sheets, BBQ grill with utensils, board games and cards, kayaks and life vests, hot tub, firetable etc."
United States
Andy W.
The price is HK$1,601
HK$1,938 total
includes taxes & fees
31 Aug - 1 Sept
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Marina

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

Cozy Fells Point Gem / In The Heart of Fells Point
Fells Point
9.8 out of 10, Exceptional, (210 reviews)
"We enjoyed our stay. It was a cute little place and perfect for 3 of us. The area is pretty quiet for the most part. We would definitely stay here again."
United States
Tammy
The price is HK$408
HK$1,722 total
includes taxes & fees
24 Aug - 25 Aug
Cozy Fells Point Gem / In The Heart of Fells Point
Smart TV

11. Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Havre de Grace
10.0 out of 10, Exceptional, (12 reviews)
"Very cool place, walking distance to everything."
United States
Brett S.
The price is HK$1,137
HK$1,612 total
includes taxes & fees
30 Aug - 31 Aug
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Outdoor pool, a heated pool

12. Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (87 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is HK$1,518
HK$3,108 total
includes taxes & fees
19 Aug - 20 Aug
Waterfront Oasis of Annapolis Star
Coffee/tea maker, fridge, microwave, oven

13. 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.
The price is HK$1,511
HK$3,833 total
includes taxes & fees
19 Aug - 20 Aug
Pool Loft Suite | Bay Access & Beach Passes
1 bedroom, in-room safe, desk, iron/ironing board

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

Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
Nottingham City
The price is HK$565
HK$1,196 total
includes taxes & fees
24 Aug - 25 Aug
Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
Living area

15. Home away from home with WiFi and AC in delightful Parkville

Home away from home with WiFi and AC in delightful Parkville
Carney
The price is HK$1,255
HK$1,767 total
includes taxes & fees
23 Aug - 24 Aug
Home away from home with WiFi and AC in delightful Parkville
Coffee/tea maker, fridge, microwave, oven

16. 18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.0 out of 10, Wonderful, (14 reviews)
"Jen was an amazing host. The property was meticulously maintained. She made sure we had everything we needed! Shen created an environment where we could socialize with other guests or keep to ourselves. She made plenty of recommendations for local eateries and entertainment. We would definitely stay again!"
United States
Maureens B.
The price is HK$1,829
HK$3,354 total
includes taxes & fees
19 Aug - 20 Aug
18th Cent. Charm in Historic Downtown Annapolis
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

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"Super old building and elevators"
Dariia 3-night trip
Posted 11 hours ago
Best Western Plus Hotel & Conference Center

Find out more about Chestertown

Chestertown Apartments information

Number of reviews
567
Accommodation
80 Apartments
Lowest Price
HK$981
Highest Price
HK$3,833

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, free WiFi and a patio . A fitness centre and on-site laundry facilities are on site . Waterfront Oasis of Annapolis Star: Located 25.8 mi/41.5 km away in Annapolis . A private pool, free WiFi and a fireplace are included . Access to an outdoor pool is available on site . Annapolis Spa Retreat, Sauna, Jacuzzi, King Bed Couples Quiet Loft Apt. Getaway: Located 24.5 mi/39.4 km away in Annapolis . Free WiFi, a sofa bed and in-room jetted baths are included . On-site laundry facilities and 1 hot tub are on site . WORLD'S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD: It's located in Earleville , 16.1 mi/25.9 km from Chestertown. Includes free WiFi and a Smart TV .
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 Northern Chesapeake Bay and Chesapeake Bay are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Chestertown Historic District and Rolphs Wharf Marina.
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.

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