Photo by Patricia Knorr

Find hotels in Chester, MD from 2.379.540 ₫

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Top 10 Chester hotels and places to stay

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
9.2 out of 10, Wonderful, (906)
"Nice Holiday Inn Express with great water views."
The price is 3.241.665 ₫
3.598.248 ₫ total
includes taxes & fees
30 Oct - 31 Oct
Holiday Inn Express Annapolis East-Kent Island by IHG
The Westin Annapolis
4.0 star property
8.6 out of 10, Excellent, (1005)
"Would stay there again very soon "
The price is 5.244.645 ₫
5.978.896 ₫ total
includes taxes & fees
26 Oct - 27 Oct
The Westin Annapolis
Hyatt Place Kent Narrows & Marina
3.0 star property
9.4 out of 10, Exceptional, (639)
"Great location and rooms. Great place!"
The price is 3.793.536 ₫
4.210.825 ₫ total
includes taxes & fees
23 Oct - 24 Oct
Hyatt Place Kent Narrows & Marina
Hilton Garden Inn Kent Island Marina
3.0 star property
9.0 out of 10, Wonderful, (1003)
"Hotel was great, beautiful location near the water"
The price is 3.866.772 ₫
4.292.117 ₫ total
includes taxes & fees
28 Oct - 29 Oct
Hilton Garden Inn Kent Island Marina
Kent Island Resort
3.5 star property
9.2 out of 10, Wonderful, (114)
"Great INN super nice staff"
The price is 4.979.016 ₫
6.516.189 ₫ total
includes taxes & fees
28 Oct - 29 Oct
Kent Island Resort
Courtyard by Marriott Annapolis
3.0 star property
8.6 out of 10, Excellent, (1000)
"The room was great, and the staff was great. "
The price is 2.767.275 ₫
3.154.693 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Courtyard by Marriott Annapolis
Hampton Inn & Suites Annapolis
2.5 star property
8.2 out of 10, Very good, (1008)
"We had a nice stay. "
The price is 2.506.888 ₫
2.857.852 ₫ total
includes taxes & fees
29 Oct - 30 Oct
Hampton Inn & Suites Annapolis
Crowne Plaza Annapolis by IHG
3.5 star property
8.8 out of 10, Excellent, (1003)
"Good location"
The price is 2.635.500 ₫
3.004.471 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Crowne Plaza Annapolis by IHG
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1854)
"The hotel was absolutely clean and close to the shops and restaurants. "
Historic Inns of Annapolis
DoubleTree by Hilton Hotel Annapolis
4.0 star property
8.6 out of 10, Excellent, (1016)
"Comfortable place to stay, nice shopping area close by. "
The price is 2.787.832 ₫
3.178.128 ₫ total
includes taxes & fees
19 Oct - 20 Oct
DoubleTree by Hilton Hotel Annapolis
Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
9.0 out of 10, Wonderful, (1015)
"Great place to stay Friendly staff secure rooms Thank you "
The price is 2.553.800 ₫
2.911.332 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Country Inn & Suites by Radisson, Annapolis, MD
Hilton Garden Inn Annapolis
3.0 star property
8.2 out of 10, Very good, (1010)
"I had a lovely stay."
The price is 2.313.442 ₫
2.637.324 ₫ total
includes taxes & fees
29 Oct - 30 Oct
Hilton Garden Inn Annapolis
Sonesta ES Suites Annapolis
3.0 star property
8.8 out of 10, Excellent, (917)
"Had a great stay."
The price is 2.292.885 ₫
2.613.889 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Sonesta ES Suites Annapolis
Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
8.8 out of 10, Excellent, (871)
"Clean room. Friendly staff awesome location. "
The price is 5.354.018 ₫
6.103.581 ₫ total
includes taxes & fees
9 Nov - 10 Nov
Annapolis Waterfront Hotel, Autograph Collection
Village Inn Annapolis MD
2.0 star property
6.2 out of 10, (504)
"The room was very nice, clean and quiet. Great location"
The price is 2.187.465 ₫
2.493.710 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Village Inn Annapolis MD
SpringHill Suites by Marriott Annapolis
3.0 star property
9.0 out of 10, Wonderful, (1008)
"Clean room, Good breakfast and friendly staff."
The price is 2.777.817 ₫
3.166.711 ₫ total
includes taxes & fees
2 Nov - 3 Nov
SpringHill Suites by Marriott Annapolis
The Tilghman Island Inn
3.5 star property
9.6 out of 10, Exceptional, (114)
"Great staff and food!"
The price is 5.271.000 ₫
5.798.100 ₫ total
includes taxes & fees
2 Nov - 3 Nov
The Tilghman Island Inn
Holiday Inn Express & Suites Annapolis by IHG
2.5 star property
8.2 out of 10, Very good, (1001)
"Great location. "
The price is 2.825.256 ₫
3.220.845 ₫ total
includes taxes & fees
26 Oct - 27 Oct
Holiday Inn Express & Suites Annapolis by IHG
Best Western Annapolis
2.5 star property
7.8 out of 10, Good, (1014)
"Clean room, nice staff and plenty of parking "
The price is 2.087.316 ₫
2.379.540 ₫ total
includes taxes & fees
9 Nov - 10 Nov
Best Western Annapolis
Hilton Garden Inn Annapolis Downtown
3.0 star property
8.6 out of 10, Excellent, (1007)
"Good central location "
The price is 2.586.216 ₫
2.948.286 ₫ total
includes taxes & fees
3 Nov - 4 Nov
Hilton Garden Inn Annapolis Downtown
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.
Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Chester attractions

Learn more about Chester

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

Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chester Hotel Reviews

More cheap stays in Chester

Hotels in Chester with star rating

Frequently asked questions

What's the weather like in Chester?
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 Chester is 1414 mm.

Explore a world of travel with Expedia