A coastal town with a marina, a bridge, and a highway.

Find 3 Star Hotels in Chester, MD from $104

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Check availability on Chester 3 Star Hotels

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

Our top choices for Chester 3-star hotels

A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.
A spacious indoor area with brick walls, multiple tables and chairs, and string lights.
A historic brick building with a red roof, multiple windows, and a central staircase.
A marina with multiple boats docked during sunset.

1. Historic Inns of Annapolis

Historic Inns of Annapolis
Historic District
United States
Ashley
$119 nightly
$136 total
Nov 11 - Nov 12
Total with taxes and fees
Historic Inns of Annapolis
An indoor swimming pool with clear glass ceilings, large windows, and lounge chairs.
A bar area with multiple seating options, including bar stools and round tables, and a well-stocked bar counter.
A modern lounge area with two grey armchairs, a round coffee table, a fireplace, and decorative shelves.
A multi-story hotel with a brick facade, large windows, and an American flag.

2. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
Annapolis
United States
Jose
$110 nightly
$125 total
Oct 25 - Oct 26
Total with taxes and fees
Crowne Plaza Annapolis by IHG
Lobby
Bar (on property)
A hotel room with two beds, a flat-screen TV, a painting, and a desk with a lamp.
Breakfast area

3. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
Annapolis
United Kingdom
petra
$106 nightly
$121 total
Oct 25 - Oct 26
Total with taxes and fees
Hilton Garden Inn Annapolis Downtown
A modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.
A patio area with a stone fire pit, outdoor furniture, and a covered seating area.
A gym with treadmills, weight machines, and dumbbells.
A hotel room with a sofa, a desk, a television, a chair, a bed, and a fireplace.

4. Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
Edgewater
United States
Dennis
$94 nightly
$107 total
Nov 9 - Nov 10
Total with taxes and fees
Sonesta ES Suites Annapolis
A courtyard with a stone fire pit surrounded by wicker furniture and a grassy lawn.
Bar (on property)
A modern Courtyard by Marriott hotel with a well-lit entrance, landscaped garden, and a clear sky.
A section of a hotel with a wall labeled "the market" and two refrigerated display cases filled with beverages and snacks.

5. Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
Annapolis
United States
Jim
$100 nightly
$114 total
Nov 1 - Nov 2
Total with taxes and fees
Courtyard by Marriott Annapolis
A modern kitchen with grey cabinets, a white countertop, and various kitchen appliances.
A hotel reception area with a reception desk, a television, and seating area.
A modern hotel with a flat roof and a sign reading "SPRINGHILL SUITES BY MARRIOTT".
A hotel room with a bed, a desk, a chair, a coffee machine, and a tray table.

6. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
Annapolis
United States
Lisa
$119 nightly
$136 total
Nov 1 - Nov 2
Total with taxes and fees
SpringHill Suites by Marriott Annapolis
A spacious living room with a large wooden coffee table, a leather sofa, and a chandelier.
A swimming pool with a tiled edge, wooden chairs, and tables around it.
A hotel room with a large bed, a bedside table with a lamp, a phone, a mirror, and a bathroom with a bathtub and toilet.
A spacious dining area with multiple tables and chairs, a central bar area, and large windows providing natural light.

7. Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
Annapolis
United States
Catherine
$91 nightly
$104 total
Nov 9 - Nov 10
Total with taxes and fees
Country Inn & Suites by Radisson, Annapolis, MD
A large, stately house with a grand entrance, multiple windows, and a symmetrical facade.
An indoor corridor with brick walls, a brick floor, and a sign reading "DECANTER WINE ROOM".
A spacious dining area with multiple tables and chairs, wooden ceiling beams, and large windows with blinds.
A bedroom with a large bed, a nightstand, a lamp, and a window with blinds.

8. The Tidewater Inn

The Tidewater Inn
Easton
United States
Miriam
$163 nightly
$179 total
Nov 2 - Nov 3
Total with taxes and fees
The Tidewater Inn
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
An outdoor event area with round tables and a view of the water.
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.
Marina

9. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
United States
Joseph
$152 nightly
$169 total
Oct 25 - Oct 26
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
A hotel room with two beds, a wooden headboard, a nightstand with a lamp, and a framed picture on the wall.
A reception area with two reception desks, a wall-mounted sign reading "Holiday Inn Express," and a telephone on the right side.
A modern hotel lobby with multiple seating areas, including tables and chairs, and a reception desk.
A Holiday Inn Express sign with a green and blue logo, surrounded by landscaped garden beds and trimmed hedges.

10. Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG
Easton
United States
Emily
$149 nightly
$164 total
Oct 18 - Oct 19
Total with taxes and fees
Holiday Inn Express Easton by IHG
A conference room with a large table, chairs, water bottles, and a flat-screen TV on the wall.
A gym with exercise equipment, including a treadmill, stationary bike, and weights.
Restaurant
An outdoor patio with tables and chairs, a brick floor, and a building with a green roof in the background.

11. Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
Annapolis
United States
Glenn
$93 nightly
$106 total
Nov 9 - Nov 10
Total with taxes and fees
Hilton Garden Inn Annapolis
A patio with outdoor seating, overlooking a marina with boats.
An indoor swimming pool with clear views of boats and water.
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.

12. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
United States
Charles
$147 nightly
$163 total
Oct 25 - Oct 26
Total with taxes and fees
Hilton Garden Inn Kent Island Marina
An outdoor patio with tables, chairs, and a fire feature.
A modern dining area with multiple tables and chairs, large windows with a view of greenery, and decorative wall mirrors.
A modern lounge area with a sofa, round tables, and chairs, featuring geometric wall decor and large windows.
A bar area with a long counter, multiple stools, and a television above.

13. Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
Annapolis
United States
Imola
$135 nightly
$154 total
Oct 27 - Oct 28
Total with taxes and fees
Fairfield Inn & Suites By Marriott Annapolis
A circular fire pit surrounded by outdoor seating with a brick wall and a multi-story building in the background.
A hotel with a modern design, featuring a mix of brick and siding exteriors, a covered entrance, and a parking area.
A compact hotel room with a kitchenette, a desk with two chairs, a sofa, and a bed.
A reception desk with a 'HELLO' sign and 'Annapolis' text, wooden paneling, and hanging pendant lights.

14. TownePlace Suites by Marriott Annapolis

TownePlace Suites by Marriott Annapolis
Annapolis
United States
Nkusu Lauren
$118 nightly
$135 total
Nov 1 - Nov 2
Total with taxes and fees
TownePlace Suites by Marriott Annapolis
A modern lobby with a stone fireplace, a blue patterned rug, a blue sofa with colorful cushions, a brown leather chair, and a round coffee table.
A hotel with a covered entrance, multiple floors, and a parking lot.
A hotel lobby with a large wooden reception desk, multiple seating areas, a television, and a patterned carpet.
An outdoor patio with tables and chairs, a large umbrella, and a brick building in the background.

15. Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
Easton
United States
Amanda
$135 nightly
$149 total
Oct 25 - Oct 26
Total with taxes and fees
Fairfield Inn & Suites by Marriott Easton
An outdoor patio with tables, chairs, and a fire feature.
A modern lounge area with a sofa, round tables, and chairs, featuring geometric wall decor and large windows.
A bar area with a long counter, multiple stools, and a television screen above.
A modern dining area with wooden tables and leather chairs, large windows with a view of greenery, and decorative wall mirrors.

16. Residence Inn By Marriott Annapolis

Residence Inn By Marriott Annapolis
Annapolis
United States
Francis
$152 nightly
$173 total
Oct 27 - Oct 28
Total with taxes and fees
Residence Inn By Marriott Annapolis
A lakeside view with sailboats, grassy areas, and white Adirondack chairs.
A beach with clear water, sandy shore, and some vegetation.
A bottle of Merlot wine and two glasses on a wooden tray by a window overlooking a lake.
A large, two-story house with a balcony, situated on a grassy lawn with autumn leaves, near a body of water.

17. Sandaway Suites & Beach

Sandaway Suites & Beach
Oxford
United States
Gary
$333 nightly
$367 total
Nov 11 - Nov 12
Total with taxes and fees
Sandaway Suites & Beach
An outdoor seating area with tables and chairs, overlooking a body of water and greenery.
A modern lounge area with a fireplace, seating, and a view of the outdoors.
A large building with a swimming pool, dock, and green surroundings.
A spacious indoor dining area with large windows, tables, and chairs.

18. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
United States
William
$185 nightly
$204 total
Oct 19 - Oct 20
Total with taxes and fees
The Tilghman Island Inn
A large, two-story barn-style building with a covered front porch and a garage.
A bedroom with a large bed, a bench, a dresser, and two windows with curtains.
A dining room with a round table set for six, surrounded by wooden chairs. A fireplace with ornate details is visible, and a large mirror hangs above it.
A large, two-story white house with a porch and multiple windows.

19. Kent Island Resort

Kent Island Resort
Stevensville
United States
Bethany
$155 nightly
$169 total
Oct 29 - Oct 30
Total with taxes and fees
Kent Island Resort
A room with a dark blue wall, a fireplace with lit candles, a leather armchair, and a bookshelf with decorative items.
A dining room with a fireplace, wooden chairs, a chandelier, and framed artwork on the walls.
A dark blue bookshelf with decorative items and books.
A sailboat docked at a waterfront with buildings in the background.

20. Flag House Inn

Flag House Inn
Historic District
United States
Nathan
$227 nightly
$259 total
Oct 18 - Oct 19
Total with taxes and fees
Flag House Inn
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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 Chester.
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD
$106 nightly
$121 total
Oct 18 - Oct 19
Total with taxes and fees
DoubleTree by Hilton Hotel Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

126 West St Annapolis MD
$147 nightly
$167 total
Oct 26 - Oct 27
Total with taxes and fees
9.4/10 Exceptional! (1,001 reviews)
Graduate by Hilton Annapolis
The Westin Annapolis

The Westin Annapolis

100 Westgate Cir Annapolis MD
$199 nightly
$227 total
Oct 25 - Oct 26
Total with taxes and fees
The Westin Annapolis
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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 Chester

Chester awaits: its island views, sunny weather, golf, and more!

See all hotels in Chester
A coastal town with a marina, a bridge, and a highway.

Top Chester Hotel Reviews

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

8/10 Good
"Room was awesome, very clean housekeeping staff extremely nice. Would suggest more help in the restaurant, food was excellent, poor waitress was running around trying to serve everyone!"
Andrea 3-night trip
Posted 2 days ago
Hilton Garden Inn Annapolis Downtown
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

10/10 Excellent
"We stay here frequently. The best hotel in a great location."
Bryan 1-night trip
Posted 2 days ago
Hyatt Place Kent Narrows & Marina
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Shalinda was the most welcoming front desk staff i have ever encountered."
Dennis 5-night trip
Posted 4 days ago
Sonesta ES Suites Annapolis

Find out more about Chester

Three Star Hotel Guide for Chester

There’s a reason the top 3 star hotels in Chester, 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 Chester, 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 Chester for the most elegant experience, or grab a low rate on one of the cheap 3 star hotels in Chester 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 Chester 3 star hotels offer a fantastic home base for any type of vacation.

Frequently asked questions

What are the best 3-star hotels in Chester?
Recharge your batteries in comfortable surroundings at Kent Island Resort. Situated roughly 3 mi west of downtown Chester, this 3-star hotel comes highly recommended by travelers.
How much does it cost to stay in a 3-star hotel in Chester?
Try Expedia's filters to find an affordable 3-star hotel for your upcoming Chester getaway. Simply set your ideal budget with our handy pricing tool. You can also choose your amenities, preferred neighborhood and lots more.
  • Search for the lowest price per night right now from $121
What is the difference between a 4-star and 3-star hotel in Chester?
Relaxation is easy in 3-star hotels in Chester. On top of comfortable surroundings, these more cost-effective lodgings come with an array of welcome amenities like complimentary WiFi, coffee and tea maker and on-site gym. A 4-star hotel offers a more sophisticated experience with upmarket features such as an on-site spa, outdoor or indoor pool and spacious rooms. Regardless of your desired hotel category or how much you want to spend, we have the right option for you.

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