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.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
Save 100% on your flight
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) 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 Capital One Arena and Smithsonian Institution are located nearby.

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Washington (WAS)
Stay at this 3-star business-friendly hotel in Washington. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Union Station Shopping Center and Smithsonian Institution are located nearby.

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Washington (DCA)
Stay at this hotel in Washington. Enjoy free WiFi, valet parking (surcharge), and a 24-hour front desk. Popular attractions White House and Capital One Arena are located nearby.

Club Quarters Hotel in Washington DC

Club Quarters Hotel in Washington DC

3 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Washington (DCA)
Stay at this 3-star business-friendly hotel in Washington. Enjoy free WiFi, a 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.

Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Northwest
Save 100% on your flight
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Washington (DCA)
Stay at this 4.5-star luxury hotel in Washington. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the bar in our reviews. Popular attractions White House and Capital One Arena are located nearby.

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Washington (DCA)
Stay at this 5-star 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 National Museum of African American History and Culture 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 ...
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
Stay at this 4-star business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
Best Western Annapolis

Best Western Annapolis

2.5 out of 5
2520 Riva Rd, Annapolis, MD
22.31 km from city center
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 ...
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. ...
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 ...
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

3 out of 5
3206 Main St, Grasonville, MD
4.31 km from city center
Stay at this 3-star business-friendly hotel in Grasonville. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff ...
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 ...
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 ...
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See all available properties in Chester
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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, Oct 7 - Sat, Oct 11
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$86 Roundtrip, found 1 day ago
$86
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Oct 7 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Oct 11, priced at $86 found 1 day ago
Frontier Airlines
Tue, Oct 7 - Sat, Oct 11
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$93 Roundtrip, found 1 day ago
$93
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Oct 7 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Oct 11, priced at $93 found 1 day ago
Delta
Tue, Oct 7 - Wed, Oct 15
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$160 Roundtrip, found 3 days ago
$160
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Oct 7 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Oct 15, priced at $160 found 3 days ago
United
Wed, Aug 27 - Sun, Aug 31
LAX
Los Angeles Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$239 Roundtrip, just found
$239
Roundtrip
just found
Select United flight, departing Wed, Aug 27 from Los Angeles Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Aug 31, priced at $239 just found
Alaska Airlines
Tue, Oct 7 - Wed, Oct 15
SFO
San Francisco Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$336 Roundtrip, found 1 day ago
$336
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Tue, Oct 7 from San Francisco Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Oct 15, priced at $336 found 1 day ago