Chester Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Chester Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Eaton DC
Downtown Washington D.C.
$671
per person
Oct 27 - Oct 31
found 5 hours ago
Roundtrip flight included
Raleigh (RDU) to Baltimore (BWI)
Book a stay at this luxury hotel in Washington. Enjoy free WiFi, a full-service spa, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Capital One Arena and White House are located nearby.
Sofitel Washington DC Lafayette Square
Downtown Washington D.C.
$898
per person
Oct 27 - Oct 31
found 5 hours ago
Roundtrip flight included
Raleigh (RDU) to Baltimore (BWI)
Book a stay at this luxury hotel in Washington. Enjoy free WiFi, breakfast (surcharge), and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions White House and Capital One Arena are located nearby.
Clean room and professional staff
Reviewed on Sep 14, 2026
Club Quarters Hotel White House, Washington DC
Downtown Washington D.C.
$756
per person
Oct 27 - Oct 31
found 5 hours ago
Roundtrip flight included
Raleigh (RDU) to Baltimore (BWI)
Book a stay at this business-friendly hotel in Washington. Enjoy free WiFi, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions White House and Capital One Arena are located nearby.
Perfect location. Room was very reasonably priced. Free coffee (decaf, too). I'll be back 100%
Reviewed on Sep 14, 2026
Arlo Washington DC
Northwest
$856
per person
Oct 27 - Oct 31
found 5 hours ago
Roundtrip flight included
Raleigh (RDU) to Baltimore (BWI)
Stay at this hotel in Washington. Enjoy free WiFi, an outdoor pool, and 2 bars/lounges. Popular attractions Capital One Arena and Union Station Shopping Center are located nearby.
.
Reviewed on Sep 15, 2026
Hotel Washington
Downtown Washington D.C.
$859
per person
Oct 27 - Oct 31
found 5 hours ago
Roundtrip flight included
Raleigh (RDU) to Baltimore (BWI)
Book a stay at this luxury hotel in Washington. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions White House and National Mall are located nearby.
Great place!
Reviewed on Sep 15, 2026
Kimpton Banneker Hotel by IHG
Downtown Washington D.C.
$756
per person
Oct 27 - Oct 31
found 5 hours ago
Roundtrip flight included
Raleigh (RDU) to Baltimore (BWI)
Book a stay at this luxury hotel in Washington. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions White House and Capital One Arena are located nearby.
Although still doing renovations, the hotel was clean and quite quiet. The staff was excellent, especially our wonderful bartender, Mek. Our room was very spacious and beautiful. I would definitely recommend this hotel which was in a very good location.
Reviewed on Sep 15, 2026
Top Hotel Deals
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
Historic Inns of Annapolis
58 State Circle Annapolis MD
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Graduate by Hilton Annapolis
126 West St Annapolis MD
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and ...
St Michaels Inn
1228 S Talbot Street St. Michaels MD
Book a stay at this business-friendly hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Hilton Garden Inn Annapolis Downtown
174 West Street Annapolis MD
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
Sonesta ES Suites Annapolis
170 Admiral Cochrane Dr Edgewater MD
Book a stay at this business-friendly hotel in Edgewater. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the clean ...
Courtyard by Marriott Annapolis
2559 Riva Rd Annapolis MD
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
The Westin Annapolis
100 Westgate Cir Annapolis MD
Book a stay at this spa hotel in Annapolis. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Annapolis Waterfront Hotel, Autograph Collection
80 Compromise St Annapolis MD
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff ...
The Tidewater Inn
101 E Dover St Easton MD
Book a stay at this spa hotel in Easton. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions ...
Best Western Annapolis
2520 Riva Rd Annapolis MD
Book a stay at this business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hilton Garden Inn Kent Island Marina
3206 Main St Grasonville MD
Book a stay at this business-friendly hotel in Grasonville. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff ...
Holiday Inn Express & Suites Annapolis by IHG
2451 Riva Rd Annapolis MD
Book a stay at this business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Country Inn & Suites by Radisson, Annapolis, MD
2600 Housley Road Annapolis MD
Book a stay at this business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
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 Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Wed, Sep 30 - Wed, Oct 7
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$58
Roundtrip
found 6 days ago
Thu, Oct 29 - Mon, Nov 9
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$197
Roundtrip
found 3 days ago
Mon, Oct 19 - Sat, Oct 24
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$202
Roundtrip
found 4 days ago
Mon, Oct 19 - Sat, Oct 24
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$207
Roundtrip
found 4 days ago
Wed, Nov 4 - Sat, Nov 7
DEN
Denver Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$273
Roundtrip
found 1 day ago
Best points of interest in Chester
- Chesapeake Exploration Center Vacations
- U.S. Naval Academy Vacations
- Annapolis City Dock Vacations
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- Sandy Point State Park Vacations
- Chesapeake Bay Bridge Vacations
- Anne Arundel Medical Center Vacations
- Navy-Marine Corps Memorial Stadium Vacations
- Westfield Annapolis Mall Vacations
- Maryland State House Vacations
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