Default HTG hotel image

Chestertown Hotel Guide - Chase Island hotels in Chestertown, United States of America.

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
15 Oct - 16 Oct
Tomorrow
16 Oct - 17 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Filter by

Star rating

Guest rating

Our top choices for Chase Island hotels

A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.
A spacious dining area with multiple tables and chairs, a central island, and a kitchen in the background.
A hotel room with two beds, a desk, a flat-screen TV, and a window with curtains.
A Comfort Inn & Suites hotel with a brick facade, arched entryway, and a well-maintained lawn.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
11.1 km from Chase Island
United States
Amy
€97
includes taxes & fees
8 Nov - 9 Nov
Comfort Inn & Suites Chestertown
A hotel room with a sofa, two beds, a painting, and a lamp.
A hotel sign with a red background and white lettering, a parking lot, and a building with a brick facade.
A living room with a fireplace, a television, and a stone accent wall.
A hotel room with a bed, two bedside lamps, a sofa, a small table, and a painting on the wall.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
11.1 km from Chase Island
United States
Kate
€71
includes taxes & fees
3 Nov - 4 Nov
Red Roof Inn & Suites Chestertown
A row of motel rooms with stone walls and red doors.
A two-story building with a brick facade, large windows, and a sloped roof.
A hotel room with a bed, a small refrigerator, a lamp, a picture on the wall, and a curtain.
A living room with a wooden cabinet, a television, a sofa, and a dining table.

3. Driftwood Inn

Driftwood Inn
11.1 km from Chase Island
United States
Kathy
€63
includes taxes & fees
16 Oct - 17 Oct
Driftwood Inn
View all properties

Top Chase Island Hotel Reviews

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

8/10 Good
"Hotel was great. Really nice. loved having doormen considering area is not great. Just wished"
Lisa 1-night trip
Posted 23 hours ago
Fairfield Inn & Suites by Marriott Middletown
Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG

8/10 Good
"Friendly staff. Breakfast was adequate. Parking was close."
Charles 1-night trip
Posted 1 day ago
Holiday Inn Express & Suites Middletown by IHG
Red Roof Inn & Suites Dover Downtown

Red Roof Inn & Suites Dover Downtown

10/10 Excellent
"Great. Just an overnight stay"
Ronald 1-night trip
Posted 2 days ago
Red Roof Inn & Suites Dover Downtown
Sleep Inn & Suites Dover University Area

Sleep Inn & Suites Dover University Area

8/10 Good
"Room card did not work, we had to go to the front desk every time that we need to get into the room, because the card did not work at the room door."
Daryl 2-night trip
Posted 2 days ago
Sleep Inn & Suites Dover University Area
Hampton Inn Middletown

Hampton Inn Middletown

10/10 Excellent
"The male employee working night shift hours on 10/03/2026 was more than accommodating and polite."
Heather 1-night trip
Posted 11 days ago
Hampton Inn Middletown
Hampton Inn Dover

Hampton Inn Dover

10/10 Excellent
"nice"
Dawn 4-night trip
Posted 2 weeks ago
Hampton Inn Dover
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

10/10 Excellent
"We had a wonderful long weekend at the cottage. It is beautifully decorated and very clean. It was perfect for our needs. We spent our days boating on the upper bay (gorgeous weather) and evenings relaxing on the deck with a perfect view of the sunset and turkey point lighthouse. Thank you Chris and we would love to come back next season."
JoAnn W. 4-night trip
Posted 2 months ago
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Other attractions near Chase Island

Crumpton Park

After visiting Crumpton Park, make a plan to see the other sights and activities in Crumpton.
See properties

Crumpton Auction

8.8/10 (3 reviews)
Take the family on an outing to Crumpton Auction during your trip to Chestertown. Take in the festivals while you're in the area.
See properties

Pinkney Park

Explore the great outdoors at Pinkney Park, a lovely green space in Millington.
See properties

Roundtop Park

Roundtop Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Experience the area's festivals and art scene.
See properties

Rolling Road Park

Rolling Road Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Experience the area's festivals and art scene.
See properties

Kings Town Park

Kings Town Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Experience the area's festivals and art scene.
See properties

Frequently asked questions

What's the area like around Chase Island?
Chase Island is located in Chestertown. Travellers like the surrounding area for its university setting. You'll find 16 hotels and other accommodations within a few miles for a convenient home base.
Where is the best place to stay near Chase Island?
Red Roof Inn & Suites Chestertown is one of the top choices for your stay based on our traveller data, and this hotel offers free parking and free WiFi. You'll find it 6.9 mi (11.1 km) from Chase Island. Other good options in the area include Comfort Inn & Suites Chestertown and The Lodge at Great Oak Landing.
How many hotels are there near Chase Island?
Expedia has 16 hotels and other accommodation options a few miles from Chase Island.
If I need to cancel the hotel reservation for my stay near Chase Island, will I receive a refund?
Yes, you'll find most hotel room reservations are fully refundable if you cancel before the hotel's cancellation deadline, which is usually within 24-48 hours of your check-in date. If your reservation is non-refundable, you might be able to still cancel and receive a refund within a 24-hour period of your booking. Add your dates and click on "Search", then filter by "fully refundable" to view the best deals available near Chase Island.