Chester Vacations

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

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Chester Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Sheraton Pentagon City Hotel

Sheraton Pentagon City Hotel

3.5 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 10
found 5 hours ago
Roundtrip flight included
Charleston (CHS) to Washington (DCA)
Stay at this 3.5-star business-friendly hotel in Arlington. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Arlington National Cemetery and White House are located nearby.

Hamilton Hotel Washington DC

Hamilton Hotel Washington DC

4 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Jun 6 - Jun 10
found 5 hours ago
Roundtrip flight included
Charleston (CHS) to Washington (DCA)
Book a stay at this business-friendly hotel in Washington. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the restaurant and the bar in our reviews. Popular attractions White House and Capital One Arena are located nearby.

The Watergate Hotel

The Watergate Hotel

5 out of 5
Northwest
Save 100% on your flight
per person
Jun 6 - Jun 10
found 5 hours ago
Roundtrip flight included
Charleston (CHS) to Washington (DCA)
Book a stay at this spa hotel in Washington. Enjoy free WiFi, a full-service spa, and 3 bars/lounges. Our guests praise the bar and the helpful staff in our reviews. Popular attractions White House and Arlington National Cemetery are located nearby.

YOTEL Washington DC

YOTEL Washington DC

4 out of 5
Northwest
Save 100% on your flight
per person
Jun 6 - Jun 10
found 5 hours ago
Roundtrip flight included
Charleston (CHS) to Washington (DCA)
Stay at this 4-star boutique hotel in Washington. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular attractions Union Station Shopping Center and Capital One Arena are located nearby.

The Baron Hotel

The Baron Hotel

3 out of 5
Northwest
Save 100% on your flight
per person
Jun 6 - Jun 10
found 5 hours ago
Roundtrip flight included
Charleston (CHS) to Washington (DCA)
Stay at this 3-star hotel in Washington. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions White House and Capital One Arena are located nearby.

Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
Save 100% on your flight
per person
Jun 6 - Jun 10
found 5 hours ago
Roundtrip flight included
Charleston (CHS) to Washington (DCA)
Book a stay at this business-friendly hotel in Washington. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Union Station Shopping Center and Capital One Arena are located nearby.

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Top Hotel Deals

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
17.34 km from city center
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 ...
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St, Annapolis, MD
18.04 km from city center
Stay at this 4-star business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and ...
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3 out of 5
2600 Housley Road, Annapolis, MD
23.1 km from city center
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
The Westin Annapolis

The Westin Annapolis

4 out of 5
100 Westgate Cir, Annapolis, MD
18.57 km from city center
Stay at this 4-star spa hotel in Annapolis. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. ...
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3 out of 5
174 West Street, Annapolis, MD
18.24 km from city center
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3 out of 5
3028 KENT NARROW WAY S, Grasonville, MD
3.99 km from city center
Stay at this 3-star business-friendly hotel in Grasonville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

3 out of 5
189 Admiral Cochrane Drive, Annapolis, MD
22.47 km from city center
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and ...
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3 out of 5
170 Admiral Cochrane Dr, Edgewater, MD
22.62 km from city center
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

Courtyard by Marriott Annapolis

3 out of 5
2559 Riva Rd, Annapolis, MD
22.83 km from city center
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St, Annapolis, MD
17.01 km from city center
Stay at this 4-star eco-certified hotel in Annapolis. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and ...
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court, Annapolis, MD
22.18 km from city center
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 ...
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd, Annapolis, MD
22.02 km from city center
Stay at this 3.5-star business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis

3 out of 5
305 Harry S Truman Pkwy, Annapolis, MD
22.9 km from city center
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
21.28 km from city center
Book a stay at this luxury hotel in St. Michaels. Enjoy free WiFi, free valet parking, and a full-service spa. Our guests praise the helpful staff in our reviews. ...
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

2.5 out of 5
124 Womack Dr, Annapolis, MD
22.39 km from city center
Book a stay at this family-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful ...
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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.

Spirit Airlines
Tue, May 13 - Tue, May 13
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$51 Roundtrip, found 3 days ago
$51
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, May 13 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, May 13, priced at $51 found 3 days ago
Frontier Airlines
Sat, Jun 7 - Sat, Jun 7
CLT
Charlotte-Douglas Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$88 Roundtrip, found 3 days ago
$88
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Jun 7 from Charlotte-Douglas Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Jun 7, priced at $88 found 3 days ago
Frontier Airlines
Mon, Jun 9 - Sun, Jun 15
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$108 Roundtrip, found 6 hours ago
$108
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Mon, Jun 9 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Jun 15, priced at $108 found 6 hours ago
Spirit Airlines
Sat, May 10 - Sat, May 10
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$122 Roundtrip, found 4 days ago
$122
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Sat, May 10 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, May 10, priced at $122 found 4 days ago