A boat docked at a pier during twilight with a city skyline in the background.

Find hotels in Chester, MD from ā‚©137,316

  • 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

This weekend
Jul 31 - Aug 2
Next weekend
Aug 7 - Aug 9

Filter by

Star rating

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Our top choices for Chester hotels

Pet friendly
Terrace/patio

1. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (797 reviews)
"Great location"
United States
jeanette
The price is ā‚©276,979
ā‚©307,446 total
includes taxes & fees
Aug 11 - Aug 12
Hyatt Place Kent Narrows & Marina
Exterior

2. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (1,001 reviews)
"I have stayed several times over the last few years and the place continues to be very good."
United States
Thomas R.
The price is ā‚©170,991
ā‚©189,803 total
includes taxes & fees
Aug 30 - Aug 31
Holiday Inn Express Annapolis East-Kent Island by IHG
Indoor pool

3. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,004 reviews)
"good for a short stay"
United States
chanel
The price is ā‚©157,950
ā‚©175,319 total
includes taxes & fees
Aug 2 - Aug 3
Best Western Kent Narrows Inn
Reception

4. Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (170 reviews)
"Wonderful room, bar and food!"
United States
Leigh
The price is ā‚©232,250
ā‚©306,882 total
includes taxes & fees
Aug 12 - Aug 13
Kent Island Resort
Lobby

5. Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
2.5 star property
Easton
9.2 out of 10, Wonderful, (1,011 reviews)
"Was very comfortable room very clean with easy parking and a fabulous hot breakfast!"
United States
Margaret
The price is ā‚©200,521
ā‚©220,574 total
includes taxes & fees
Aug 2 - Aug 3
Best Western Plus Easton Inn & Suites
Front of property - evening/night

6. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (472 reviews)
"helpful staff, nice rooms"
United Kingdom
Jamie
The price is ā‚©339,833
ā‚©413,911 total
includes taxes & fees
Aug 3 - Aug 4
The Inn at Chesapeake Bay Beach Club
Terrace/patio

7. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,000 reviews)
"Me and my husband went for a one year anniversary. Staying at the hilton was wonderful relaxing, everyone was so pleasant and helpful.The restaurants nearby were great. I love the view we'll be coming back again."
United States
Tammy
The price is ā‚©236,353
ā‚©262,352 total
includes taxes & fees
Aug 20 - Aug 21
Hilton Garden Inn Kent Island Marina
Front of property

8. St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1,005 reviews)
"Room was pleasant and clean and breakfast was great!"
United States
Karen
The price is ā‚©128,535
ā‚©141,388 total
includes taxes & fees
Aug 24 - Aug 25
St Michaels Inn
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, WiFi (free), bed sheets

9. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (946 reviews)
"Great staff and breakfast crew. Extremely reasonable price, for convenient location."
United States
Jonathan
The price is ā‚©156,429
ā‚©173,636 total
includes taxes & fees
Aug 11 - Aug 12
Quality Inn Grasonville near Kent Island
Exterior

10. Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (909 reviews)
"It was pleasant having a room that overlooked the courtyard."
United States
Karen
The price is ā‚©145,919
ā‚©160,511 total
includes taxes & fees
Aug 24 - Aug 25
Quality Inn
Lobby

11. Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
3.0 star property
Easton
9.6 out of 10, Exceptional, (383 reviews)
"Clean, friendly and easily accessible from rt 50."
United States
Stephanie
The price is ā‚©194,967
ā‚©214,464 total
includes taxes & fees
Aug 23 - Aug 24
Fairfield Inn & Suites by Marriott Easton
Reception

12. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,061 reviews)
"Beautiful hotel. Very clean and amazing staff."
United States
Lena
The price is ā‚©157,936
ā‚©180,051 total
includes taxes & fees
Aug 30 - Aug 31
DoubleTree by Hilton Hotel Annapolis
Dining

13. Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,001 reviews)
"EXCELLENTE STAFF AND GREAT BREAKFAST..."
United States
Julian
The price is ā‚©120,453
ā‚©137,316 total
includes taxes & fees
Aug 4 - Aug 5
Best Western Annapolis
Free daily buffet breakfast

14. Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG
3.0 star property
Easton
9.0 out of 10, Wonderful, (622 reviews)
"A clean hotel and a great breakfast."
United States
Maura
The price is ā‚©223,603
ā‚©245,963 total
includes taxes & fees
Aug 2 - Aug 3
Holiday Inn Express Easton by IHG
Meeting facility

15. Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,899 reviews)
"Great location!!! Very comfortable stay."
United States
Monica
The price is ā‚©180,801
ā‚©255,456 total
includes taxes & fees
Aug 5 - Aug 6
Historic Inns of Annapolis
Indoor pool

16. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1,013 reviews)
"It was a nice place. Located very close to good restaurants"
United States
Douglas and Lori
The price is ā‚©170,227
ā‚©194,059 total
includes taxes & fees
Aug 9 - Aug 10
Crowne Plaza Annapolis by IHG
Lobby

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

Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,061 reviews)
"Clean room, good breakfast, and nice staff."
United States
Jing
The price is ā‚©156,219
ā‚©178,089 total
includes taxes & fees
Aug 2 - Aug 3
Country Inn & Suites by Radisson, Annapolis, MD
Free daily self-serve breakfast

18. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,000 reviews)
"Clean, good breakfast, very helpful and friendly staff"
United States
Thomas
The price is ā‚©171,669
ā‚©195,703 total
includes taxes & fees
Aug 23 - Aug 24
SpringHill Suites by Marriott Annapolis
Lobby

19. Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very Good, (1,001 reviews)
"Nice place to stay friendly service"
United States
Glenn
The price is ā‚©140,769
ā‚©160,477 total
includes taxes & fees
Aug 26 - Aug 27
Hilton Garden Inn Annapolis
Free daily buffet breakfast

20. Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
Edgewater
8.8 out of 10, Excellent, (1,001 reviews)
"Always a pleasant stay at this hotel."
United States
Daniela
The price is ā‚©154,204
ā‚©175,793 total
includes taxes & fees
Aug 18 - Aug 19
Sonesta ES Suites 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Stay near popular Chester attractions

Chesapeake Exploration Center

Learn about the events happening at Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.
See properties

Learn more about Chester

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

See all hotels in Chester
A boat docked at a pier during twilight with a city skyline in the background.
Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chester Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Shuttle to Downtown was amazing and very appreciated šŸ‘"
Loren 2-night trip
Posted 1 hour ago
DoubleTree by Hilton Hotel Annapolis

More cheap stays in Chester

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd Annapolis MD
The price is ā‚©120,453 per night from Aug 4 to Aug 5
ā‚©120,453
ā‚©137,316 total
Aug 4 - Aug 5
includes taxes & fees

Frequently asked questions

What's the best place to stay in Chester?
Located 10.8 mi (17.3 km) from the heart of Chester, Historic Inns of Annapolis is a top choice for your stay based on our traveler data. Other good choices for your visit to the area are DoubleTree by Hilton Hotel Annapolis and Crowne Plaza Annapolis by IHG. See all available top hotels, or vacation rentals in Chester.
If I need to cancel my hotel reservation in Chester, will I receive a refund?
Yes! You'll find that most hotel room reservations are fully refundable if you cancel before the accommodation'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 booking. Filter your search by fully refundable to find flexible hotel deals in Chester.
Where can I learn more about changing or cancelling my trip to Chester?
To find more details about rescheduling or cancelling your trip to Chester, head over to our customer service page.
What are some accommodations with pools in Chester?
Crowne Plaza Annapolis by IHG: Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool, and complimentary wireless internet access. St Michaels Inn and Country Inn & Suites by Radisson, Annapolis, MD are a couple of other choices with an onsite pool. View all hotels with pools in Chester.
What is staying in Chester like?
Visitors can enjoy all that Chester has to offer including the waterfront, seafood restaurants, and golf courses. In Chester, there are 9 hotels and other accommodations to choose from. Find out more about Chester.
What is there to see in Chester?
Places to visit in the wider area include Paul Reed Smith Guitars, Northern Chesapeake Bay, and Matapeake State Park. You'll also find Chesapeake Bay Environmental Center and Love Point State Park in the area. Check out what more to see and do in Expedia's Chester guide.
What's the weather like in Chester?
The hottest months are usually July and August with an average temp of 74Ā°F, while the coldest months are January and February with an average of 39Ā°F. Average annual precipitation for Chester is 56 inches.