Hotels in Chester
Free cancellation options if plans change
Earn rewards on every night you stay
Save more with Member Prices
Check prices for these dates
Tonight
Sep 6 - Sep 7Tomorrow
Sep 7 - Sep 8Next weekend
Sep 11 - Sep 13In two weeks
Sep 18 - Sep 20Where to stay in Chester?
1. Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
$119
$132 total
includes taxes & fees
Oct 5 - Oct 6
2. Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & MarinaGrasonville
$152
$169 total
includes taxes & fees
Oct 4 - Oct 5
3. Best Western Kent Narrows Inn
Best Western Kent Narrows InnGrasonville
$116
$129 total
includes taxes & fees
Sep 28 - Sep 29
4. Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island MarinaGrasonville
$147
$163 total
includes taxes & fees
Oct 4 - Oct 5
5. Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent IslandGrasonville
$100
$111 total
includes taxes & fees
Sep 28 - Sep 29
6. The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach ClubStevensville
$191
$238 total
includes taxes & fees
Sep 8 - Sep 9
7. Kent Island Resort
Kent Island ResortStevensville
$161
$213 total
includes taxes & fees
Sep 22 - Sep 23
8. DoubleTree by Hilton Hotel Annapolis
DoubleTree by Hilton Hotel AnnapolisAnnapolis
$83
$95 total
includes taxes & fees
Sep 27 - Sep 28
9. Fairfield Inn & Suites By Marriott Annapolis
Fairfield Inn & Suites By Marriott AnnapolisAnnapolis
$127
$145 total
includes taxes & fees
Sep 13 - Sep 14
10. Crowne Plaza Annapolis by IHG
Crowne Plaza Annapolis by IHGAnnapolis
$107
$122 total
includes taxes & fees
Oct 4 - Oct 5
11. St Michaels Inn
St Michaels InnSt. Michaels
$105
$116 total
includes taxes & fees
Sep 7 - Sep 8
12. Village Inn Annapolis MD
Village Inn Annapolis MDAnnapolis
$83
$95 total
includes taxes & fees
Sep 7 - Sep 8
13. Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis DowntownAnnapolis
$119
$136 total
includes taxes & fees
Sep 7 - Sep 8
14. Hilton Garden Inn Annapolis
Hilton Garden Inn AnnapolisAnnapolis
$90
$103 total
includes taxes & fees
Sep 16 - Sep 17
15. Holiday Inn Express & Suites Annapolis by IHG
Holiday Inn Express & Suites Annapolis by IHGAnnapolis
$99
$113 total
includes taxes & fees
Oct 4 - Oct 5
16. SpringHill Suites by Marriott Annapolis
SpringHill Suites by Marriott AnnapolisAnnapolis
$126
$144 total
includes taxes & fees
Sep 8 - Sep 9
17. Historic Inns of Annapolis
Historic Inns of AnnapolisHistoric District
$117
$168 total
includes taxes & fees
Sep 28 - Sep 29
18. Best Western Annapolis
Best Western AnnapolisAnnapolis
$76
$86 total
includes taxes & fees
Sep 27 - Sep 28
19. Sonesta ES Suites Annapolis
Sonesta ES Suites AnnapolisEdgewater
$91
$104 total
includes taxes & fees
Sep 27 - Sep 28
20. Hampton Inn & Suites Annapolis
Hampton Inn & Suites AnnapolisAnnapolis
$98
$111 total
includes taxes & fees
Sep 27 - Sep 28
Go beyond your typical stay in Chester
Pet friendly
Family friendly
Cottage
Top landmarks in Chester
Chesapeake Exploration Center
Chesapeake Exploration Center is worth a visit, located 0.8 mi (1.4 km) from central Kent Narrows.
Learn more about Chester
The region around Chester is home to attractions such as Chesapeake Exploration Center and Northern Chesapeake Bay.
See all hotels in Chester
Photo by Patricia Knorr
Check out reviews of Chester hotels guests love
Historic Inns of Annapolis
8/10 Good
"Fantastic location. Clean room with comfortable beds and powerful AC. Liked the history of the building. We were able to consistently get parking on the street near the hotel, which was great. The only real con was that we discovered upon reaching our room that we didn't have an exterior window--our two "windows" looked over the covered event area, which had pretty lights but was nonetheless an interior hallway, so no outside view. There were also a couple hiccups with the bathroom, one being that the glass shelf was falling down, and the other being that we were consistently given two towels even though we had four people on the reservation. But overall we were happy with our stay and appreciated being in a historic building in such a great location."
Sonesta ES Suites Annapolis
8/10 Good
"Ver nice older hotel but well maintained. Spacious rooms and good breakfast. My only complaint is that you can tell they also keep long term tenants as there were cats roaming around (which didn’t bother me but might others) and bikes/trash outside some of the rooms and plants in windows. A normal nightly rental hotel would not allow this id think so it made the atmosphere seem a lil run down even if the room was decent."
The Tidewater Inn
10/10 Excellent
"We had a wonderful stay and thoroughly enjoyed our time in Easton!"
Hyatt Place Kent Narrows & Marina
10/10 Excellent
"Great location, very clean and staff were welcoming and helpful!"
Holiday Inn Express & Suites Annapolis by IHG
10/10 Excellent
"..........................."
DoubleTree by Hilton Hotel Annapolis
10/10 Excellent
"Rooms kept very clean and comfortable. Staff excellent, extremely friendly and helpful. Food very good and good portions."
The Wildset
10/10 Excellent
"Clean and comfortable. All staff were friendly and helpful. Location made virtually the whole town walkable. Dinner at the restaurant was top notch."
Best Western Annapolis
10/10 Excellent
"Clean room."