
Search Inns in Chester
- Bundle & SaveGet more, spend less whenever you see Bundle & Save deals
- OneKeyCashEarn OneKeyCash on all your eligible bookings
- Upfront pricingWe are not like the others - we include taxes and fees
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
No exact matches found, but these alternatives could be just right
Recommended hotels in Chester

1. Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
9.2 out of 10, Wonderful, (1,002 reviews)
$101 nightly
The price is $112
Nov 22 - Nov 23
Total with taxes and fees

2. Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island MarinaGrasonville
9.0 out of 10, Wonderful, (1,000 reviews)
$125 nightly
The price is $139
Nov 29 - Nov 30
Total with taxes and fees

3. Best Western Kent Narrows Inn
Best Western Kent Narrows InnGrasonville
8.0 out of 10, Very good, (1,004 reviews)
$90 nightly
The price is $100
Nov 9 - Nov 10
Total with taxes and fees

4. Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & MarinaGrasonville
9.4 out of 10, Exceptional, (853 reviews)
$173 nightly
The price is $192
Nov 3 - Nov 4
Total with taxes and fees

5. Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent IslandGrasonville
7.8 out of 10, Good, (1,000 reviews)
$83 nightly
The price is $93
Nov 29 - Nov 30
Total with taxes and fees

6. The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach ClubStevensville
9.4 out of 10, Exceptional, (505 reviews)
$207 nightly
The price is $230
Dec 2 - Dec 3
Total with taxes and fees

7. Kent Island Resort
Kent Island ResortStevensville
9.2 out of 10, Wonderful, (189 reviews)
$155 nightly
The price is $169
Nov 18 - Nov 19
Total with taxes and fees

8. Historic Inns of Annapolis
Historic Inns of AnnapolisHistoric District
9.0 out of 10, Wonderful, (2,065 reviews)
$122 nightly
The price is $139
Dec 3 - Dec 4
Total with taxes and fees

9. Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis DowntownAnnapolis
8.6 out of 10, Excellent, (1,002 reviews)
$99 nightly
The price is $113
Nov 22 - Nov 23
Total with taxes and fees

10. Cass-N-Reel Luxury Houseboat
Cass-N-Reel Luxury HouseboatGrasonville
10.0 out of 10, Exceptional, (54 reviews)
$232 nightly
The price is $257
Nov 12 - Nov 13
Total with taxes and fees

11. Charming Coastal/Country Home w/3 Acres & Sauna!
Charming Coastal/Country Home w/3 Acres & Sauna!Stevensville
9.8 out of 10, Exceptional, (50 reviews)
$254 nightly
The price is $273
Nov 3 - Nov 4
Total with taxes and fees

12. Holiday Inn Express & Suites Annapolis by IHG
Holiday Inn Express & Suites Annapolis by IHGAnnapolis
8.4 out of 10, Very good, (1,000 reviews)
$88 nightly
The price is $100
Nov 23 - Nov 24
Total with taxes and fees

13. Inn at Huntingfield Creek
Inn at Huntingfield CreekRock Hall
10.0 out of 10, Exceptional, (74 reviews)
$156 nightly
The price is $173
Nov 16 - Nov 17
Total with taxes and fees

14. Village Inn Annapolis MD
Village Inn Annapolis MDAnnapolis
6.2 out of 10, (532 reviews)
$80 nightly
The price is $91
Nov 3 - Nov 4
Total with taxes and fees

15. St Michaels Inn
St Michaels InnSt. Michaels
8.0 out of 10, Very good, (1,014 reviews)
$77 nightly
The price is $85
Dec 2 - Dec 3
Total with taxes and fees

16. Graduate by Hilton Annapolis
Graduate by Hilton AnnapolisAnnapolis
9.4 out of 10, Exceptional, (1,005 reviews)
$130 nightly
The price is $149
Nov 29 - Nov 30
Total with taxes and fees

17. Best Western Annapolis
Best Western AnnapolisAnnapolis
7.8 out of 10, Good, (1,002 reviews)
$68 nightly
The price is $77
Nov 23 - Nov 24
Total with taxes and fees

18. DoubleTree by Hilton Hotel Annapolis
DoubleTree by Hilton Hotel AnnapolisAnnapolis
8.8 out of 10, Excellent, (1,267 reviews)
$89 nightly
The price is $102
Nov 10 - Nov 11
Total with taxes and fees

19. The Westin Annapolis
The Westin AnnapolisAnnapolis
8.8 out of 10, Excellent, (1,001 reviews)
$169 nightly
The price is $193
Nov 22 - Nov 23
Total with taxes and fees

20. Country Inn & Suites by Radisson, Annapolis, MD
Country Inn & Suites by Radisson, Annapolis, MDAnnapolis
9.0 out of 10, Wonderful, (1,055 reviews)
$83 nightly
The price is $95
Nov 23 - Nov 24
Total with taxes and fees
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.
Top Chester Hotel Reviews

Crowne Plaza Annapolis by IHG
10/10 Excellent
Find out more about Chester
Chester Inns information
Number of reviews | 7,456 |
|---|---|
Accommodation | 4 Inns |
Lowest Price | $77 |
Highest Price | $273 |
Explore a world of travel with Expedia
- Houseboats in Stevensville
- Vacation Homes in Annapolis
- Guest Houses in Annapolis
- Apartments in Annapolis
- All-Inclusive Resorts in Maryland
- B&B in Grasonville
- Ryokans in Annapolis
- Motels in Kent Narrows
- St. Michaels Hotels
- Cabin Rentals in Anne Arundel County
- Villas in Stevensville
- Aparthotels in Anne Arundel County
- Stevensville Hotels
- Lodges in Kent Island
- Ryokans in Maryland
- Motels in Kent Island
- Condo Rentals in Kent Narrows
- Cruise Ships in Annapolis
- Rv Parks in Maryland
- B&B in Maryland
- Cottages in Anne Arundel County
- Cheap Hotels in Maryland
- Houseboats in Maryland
- Motels in Annapolis
- Houseboats in Kent Island
- Cabin Rentals in Maryland
- Vacation Homes in Kent Island
- Inns in Romancoke
- National Harbor Hotels
- Motels in Maryland
- Houseboats in Chester
- B&B in Annapolis
- Condo Rentals in Kent Island
- Inner Harbor Hotels
- Treehouses in Annapolis
- Cottages in Kent Narrows
- Vacation Homes in Stevensville
- Hostels in Annapolis
- Maryland Hotels
- Beach Hotels in Maryland
- Motels in Grasonville
- Hotels near Baltimore Washington Intl. Thurgood Marshall
- B&B in Chester
- Apartments in Kent Narrows
- Baltimore Hotels
- Cheap Hotels in Washington
- Motels in Stevensville
- Washington Hotels
- Cheap Hotels in Baltimore
- Annapolis Hotels
- Castles in Annapolis
- Guest Houses in Kent Island
- Hotels with Free Airport Shuttle in Baltimore
- Houseboats in Kent Narrows
- Treehouses in Maryland
- Oceanfront Hotels in Annapolis
- Villas in Kent Island
- Cabin Rentals in Chester
- Flights from Orlando (MCO) to Baltimore (BWI)
- Flights from Atlanta (ATL) to Baltimore (BWI)
- Flights from Charlotte (CLT) to Baltimore (BWI)
- Flights from Miami (MIA) to Baltimore (BWI)
- Flights from Boston (BOS) to Baltimore (BWI)
- Flights from Honolulu (HNL) to Baltimore (BWI)
- Flights from Austin (AUS) to Baltimore (BWI)
- Flights from Minneapolis (MSP) to Baltimore (BWI)
- Flights to Annapolis
- Flights from Houston (IAH) to Baltimore (BWI)
- Flights to Maryland
- Flights to Washington
- Flights from Raleigh (RDU) to Baltimore (BWI)
- Flights from Portland (PDX) to Baltimore (BWI)
- Flights from Dallas (DFW) to Baltimore (BWI)
- Flights to Baltimore
- Flights from Seattle (SEA) to Baltimore (BWI)
- Flights from Baltimore Washington Intl. Thurgood Marshall
- Flights from Los Angeles (LAX) to Baltimore (BWI)
- Flights from New York (JFK) to Baltimore (BWI)
- Flights from Detroit (DTW) to Baltimore (BWI)
- Flights from Fort Lauderdale (FLL) to Baltimore (BWI)
- Flights from Chicago (ORD) to Baltimore (BWI)
- Flights from San Francisco (SFO) to Baltimore (BWI)
- Flights from Phoenix (PHX) to Baltimore (BWI)
- Flights from Denver (DEN) to Baltimore (BWI)
- Flights from Tampa (TPA) to Baltimore (BWI)
- Flights from Las Vegas (LAS) to Baltimore (BWI)
- Flights from San Diego (SAN) to Baltimore (BWI)






























































