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

Find 3 Star Hotels in Chestertown, MD from $69

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Check availability on Chestertown 3 Star Hotels

Tonight
Sep 13 - Sep 14
Tomorrow
Sep 14 - Sep 15
Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27

Our top choices for Chestertown 3-star hotels

A modern kitchen with a built-in coffee station, a toaster, and a variety of food items on display.
A reception area with two reception desks, a cityscape mural, and a clock on the wall.
A hotel room with two beds, a desk, a TV, a lamp, and a window with curtains.
A gym with exercise equipment, weight racks, and a large mirror.

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

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Rossville
United States
Brandi
$73 nightly
$84 total
Sep 27 - Sep 28
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.
A historic brick building with a red roof, multiple windows, and a central staircase.
A marina with multiple boats docked during sunset.
A spacious indoor area with brick walls, multiple tables and chairs, and string lights.

2. Historic Inns of Annapolis

Historic Inns of Annapolis
Historic District
United States
Amy
$141 nightly
$160 total
Oct 12 - Oct 13
Total with taxes and fees
Historic Inns of Annapolis
A hotel room with a bed, a desk with a chair, a sofa, and a coffee table. There is a TV on the desk and a window with curtains.
A wedding ceremony in front of a large, classical building with steps leading up to the entrance.
A hotel with a prominent sign, multiple parking spaces, and a covered entrance.
A spacious lobby with a television, multiple seating options, a coffee station, and a large pillar.

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

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Edgewood
United States
Jenri
$78 nightly
$88 total
Sep 24 - Sep 25
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
A modern building with a patio area featuring outdoor seating and a fire pit.
A modern restaurant with a long counter, multiple seating areas, and pendant lighting.
A modern living room with a stone fireplace, wooden ceiling, and a large TV mounted above it.
A modern living room with a stone accent wall, a flat-screen TV, a dining area with a table and chairs, and a sofa with cushions.

4. Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
Middletown
United States
Sharon
$119 nightly
$132 total
Sep 20 - Sep 21
Total with taxes and fees
Fairfield Inn & Suites by Marriott Middletown
A lobby with a reception desk, seating area, and a fireplace.
A kitchenette with a microwave, refrigerator, and shelves stocked with snacks and beverages.
A hotel dining area with tables and chairs, a television mounted on the wall, and a patterned carpet.
A hotel room with a large bed, a wooden headboard, a desk with a chair, and a patterned carpet.

5. Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh
Nottingham
United States
Michele
$101 nightly
$117 total
Sep 20 - Sep 21
Total with taxes and fees
Fairfield Inn & Suites by Marriott White Marsh
An indoor swimming pool with clear water, a changing room, and exercise equipment.
A spacious lobby with a fireplace, comfortable seating, and large windows.
An outdoor patio area with wicker furniture and a small table, surrounded by brick buildings and a well-maintained garden.
A living room with a fireplace, a television mounted above it, and a coffee table with decorative items.

6. Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh
Nottingham
United States
Zack
$98 nightly
$113 total
Sep 27 - Sep 28
Total with taxes and fees
Hilton Garden Inn Baltimore/White Marsh
A hotel room with two beds, a desk with a television, a chair, and a microwave.
A Hampton Inn hotel with a modern facade, a welcoming entrance, and an American flag.
Two EV charging stations labeled 'EV INSTITUTE' with a sign indicating 'ELECTRIC VEHICLE CHARGING' nearby.
A conference room with rows of chairs, a whiteboard, a coffee station, and a painting on the wall.

7. Hampton Inn Baltimore Bayview Campus

Hampton Inn Baltimore Bayview Campus
Pulaski Industrial Area
United States
Amy
$128 nightly
$151 total
Sep 27 - Sep 28
Total with taxes and fees
Hampton Inn Baltimore Bayview Campus
An indoor swimming pool with clear glass walls, a tiled floor, and a bench near the pool.
A modern living room with a flat-screen TV, a desk with drawers, a sofa, and a coffee table.
A hotel room with a desk, chair, and a bed. There is a window with curtains, a lamp, and a mirror on the wall.
A hotel room with a living area, a desk with a computer, a bed, and a wardrobe.

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

Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
Edgewood
United States
Linda
$62 nightly
$69 total
Sep 20 - Sep 21
Total with taxes and fees
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
A hotel entrance with a clear sign reading "LA QUINTA".
A hotel lobby with multiple dining tables and chairs, a reception area with a counter and a television, and large windows with red curtains.
A modern hotel lobby with a reception desk, two computer workstations, a seating area, and a decorative vase on a table.
A vending area with two beverage dispensers, a wall-mounted display of personal care items, and shelves stocked with snacks and beverages.

9. La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG
Aberdeen
United States
Niall
$119 nightly
$133 total
Sep 14 - Sep 15
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Aberdeen-APG
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.
An outdoor event area with round tables and a view of the water.
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.

10. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
United States
Karen
$152 nightly
$169 total
Oct 4 - Oct 5
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
A hotel lobby with a reception desk, seating area, and a television screen displaying an advertisement.
A hotel reception area with a counter displaying a coffee machine, a glass with a beverage, and a signboard advertising hotel amenities.
A banquet hall with rows of tables, white chairs, and red drapery.
A hotel room with two beds, a desk, a TV, a lamp, and a window with curtains.

11. Garner Hotel Glen Burnie BWI Airport Area by IHG

Garner Hotel Glen Burnie BWI Airport Area by IHG
Glen Burnie
United States
gendell
$71 nightly
$81 total
Oct 11 - Oct 12
Total with taxes and fees
Garner Hotel Glen Burnie BWI Airport Area by IHG
A Country Inn & Suites hotel with a covered entrance, multiple floors, and a brick facade.
A breakfast bar with waffle makers, coffee machines, a microwave, and various food containers.
A living room with a fireplace, a sofa, a coffee table, and bookshelves.
An indoor swimming pool with clear glass walls, white lounge chairs, and a clock on the wall.

12. Country Inn & Suites by Radisson, Baltimore North, MD

Country Inn & Suites by Radisson, Baltimore North, MD
Rossville
United States
Lenny
$91 nightly
$105 total
Oct 5 - Oct 6
Total with taxes and fees
Country Inn & Suites by Radisson, Baltimore North, MD
A Courtyard by Marriott hotel with a modern facade, large windows, and a well-lit entrance area.
An outdoor patio with a fire feature, seating, and a view of the sky.
A modern hotel lobby with grey upholstered chairs, a round wooden table, and a flat-screen TV mounted on a wooden panel wall.
A modern bar area with a long counter, multiple stools, and a well-lit space with a wooden accent wall and a large window.

13. Courtyard by Marriott Baltimore Downtown/McHenry Row

Courtyard by Marriott Baltimore Downtown/McHenry Row
Locust Point
United States
Karen
$134 nightly
$158 total
Oct 11 - Oct 12
Total with taxes and fees
Courtyard by Marriott Baltimore Downtown/McHenry Row
An outdoor patio area with seating, a fire pit, and string lights.
A swimming pool with a tiled deck, red chairs, and a view of the outdoors.
A multi-story hotel with a modern design, featuring a covered entrance and a parking area.
A modern lounge area with a green sofa, red ottomans, a wooden bench, and a wooden table.

14. Home2 Suites by Hilton Baltimore/White Marsh

Home2 Suites by Hilton Baltimore/White Marsh
Nottingham
United States
Rhande
$114 nightly
$132 total
Sep 27 - Sep 28
Total with taxes and fees
Home2 Suites by Hilton Baltimore/White Marsh
A spacious living area with a staircase, a fireplace, a sofa, and a dining area.
A dual-monitor workstation with two chairs, a desktop computer, and framed artwork on the wall.
A hotel room with two beds, a desk with a television, a chair, and a window with curtains.
A gym with treadmills, elliptical machines, and a weight machine.

15. Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Bel Air
United States
Tatsiana
$89 nightly
$100 total
Sep 20 - Sep 21
Total with taxes and fees
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
A patio with outdoor seating, overlooking a marina with boats.
A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.
A waterfront hotel with multiple balconies, a marina with yachts, and a well-lit exterior.
An indoor swimming pool with clear views of boats and water.

16. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
United States
roney
$127 nightly
$141 total
Oct 13 - Oct 14
Total with taxes and fees
Hilton Garden Inn Kent Island Marina
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
A large brick building with a symmetrical facade, multiple chimneys, and a central entrance.
A marina with docked boats, a wooden walkway with railings, and a sign indicating 'D DOCK'.
A campfire in a stone fire pit by a lakeside at sunset.

17. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
United States
Irma
$124 nightly
$137 total
Sep 16 - Sep 17
Total with taxes and fees
The Lodge at Great Oak Landing
An outdoor patio area with wicker furniture, a fire pit, and umbrellas.
A restaurant interior with multiple tables and booths, wooden flooring, and artwork on the walls.
A modern living room with a stone accent wall, a flat-screen TV, and a dining area with wooden furniture.
A modern hotel with a flat roof, multiple floors, and a prominent entrance.

18. Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
Aberdeen
United States
Courtney
$115 nightly
$129 total
Sep 28 - Sep 29
Total with taxes and fees
Fairfield Inn & Suites by Marriott Aberdeen
A large brick building with a waterfront view, a flag, and a dock with boats.
A spacious living area with leather sofas, a coffee table, and a TV mounted on the wall.
A large brick building with a courtyard and marina.
A dining area with round tables set for a meal, featuring white tablecloths, chairs, and floral centerpieces.

19. The Inn at Henderson's Wharf, an Ascend Collection Hotel

The Inn at Henderson's Wharf, an Ascend Collection Hotel
Fells Point
United States
Kristen
$214 nightly
$251 total
Oct 12 - Oct 13
Total with taxes and fees
The Inn at Henderson's Wharf, an Ascend Collection Hotel
A hotel room with a large bed, a sofa, a TV, and a wall-mounted artwork.
A pool area with chairs and a changing room.
A modern lounge area with sofas, armchairs, and tables.
A modern hotel with a blue and white facade, a covered entrance, and a parking lot.

20. SpringHill Suites by Marriott Edgewood/Aberdeen

SpringHill Suites by Marriott Edgewood/Aberdeen
Bel Air
United States
Bierca
$110 nightly
$123 total
Sep 27 - Sep 28
Total with taxes and fees
SpringHill Suites by Marriott Edgewood/Aberdeen
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 3-star hotels. See all 4-star hotels in Chestertown.
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

80 Compromise St Annapolis MD
$223 nightly
$254 total
Sep 20 - Sep 21
Total with taxes and fees
Annapolis Waterfront Hotel, Autograph Collection
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

180 Pier One Road Stevensville MD
$214 nightly
$238 total
Sep 28 - Sep 29
Total with taxes and fees
The Inn at Chesapeake Bay Beach Club
Hudson house

Hudson house

3037 Hudson St Baltimore MD
Get rates
7.6/10 Good! (5 reviews)
Hudson house
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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.

Learn more about Chestertown

Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbor.

See all hotels in Chestertown
A lakeside town with a marina, a bridge, and a mix of residential and commercial buildings.

Top Chestertown Hotel Reviews

Country Inn & Suites by Radisson, Baltimore North, MD

Country Inn & Suites by Radisson, Baltimore North, MD

8/10 Good
"The place was very quiet and not a lot going on. So if you like a more relaxed hotel, this is the place for you"
Christopher 3-night trip
Posted 1 hour ago
Country Inn & Suites by Radisson, Baltimore North, MD
Home2 Suites by Hilton Baltimore/White Marsh

Home2 Suites by Hilton Baltimore/White Marsh

10/10 Excellent
"Will stay here over and over again. Great staff, welcoming, clean and convenient."
Rhande 1-night trip
Posted 2 days ago
Home2 Suites by Hilton Baltimore/White Marsh
Hyatt Place Kent Narrows & Marina

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!"
Doug 1-night trip
Posted 5 days ago
Hyatt Place Kent Narrows & Marina
Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent
"The staff was very helpful and friendly! The facilities are well maintained and clean. The room was clean and spacious. Overall my ten days stay was great!"
Dannette 2-night trip
Posted 6 days ago
Hilton Garden Inn Baltimore/White Marsh

Find out more about Chestertown

Three Star Hotel Guide for Chestertown

There’s a reason the top 3 star hotels in Chestertown, Maryland are so incredibly popular: They combine comforting amenities and just-for-you service with some of the best rates and discounts the area has to offer. When you book a stay at a three star hotel in Chestertown, you’ll get access to perfect little perks like on-site restaurants and cocktail bars, well-appointed fitness centers, and spacious rooms.

Search for a cheap deal on a 3 star upscale hotel in Chestertown for the most elegant experience, or grab a low rate on one of the cheap 3 star hotels in Chestertown near the local attractions, if you want something a touch more unassuming. Whatever your traveling style, make sure to use the search tools at Expedia to track down prices, read more about amenities, and score a few local discounts.

From business trips to family getaways, the Chestertown 3 star hotels offer a fantastic home base for any type of vacation.

Frequently asked questions

How much does it cost to stay in a 3-star hotel in Chestertown?
Make use of Expedia's sort and search filters to find a good-value 3-star hotel for your upcoming Chestertown getaway. Just set your maximum rate with our handy pricing tool. You can also choose the amenities you'd like, desired neighborhood and a lot more.
  • Search for the lowest price per night right now from $238
What is the difference between a 4-star and 3-star hotel in Chestertown?
Book a stay at a 3-star hotel and you can expect comfortable and well-kept rooms and amenities such as free WiFi, gym equipment and coffee and tea facilities. These stays may also feature a restaurant and bar on-site. Elevate your Chestertown getaway by picking a 4-star hotel. With things like a day spa, round-the-clock room service and luxury toiletries, you'll experience a heightened sense of comfort.
What is the difference between a 3-star hotel and a motel in Chestertown?
One of the benefits of choosing a motel in or close to Chestertown is affordable rates. This means extra bucks in your pocket for activities and tours. Often set near highways and airport terminals, and with ample parking, this property type is popular among road trippers. When you check in to a 3-star hotel, you'll get more than just a cozy room to chill out in. You'll also usually have access to conveniences like business services and free WiFi.

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