Chester Vacations

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

Choose two or more items and save on your trip:

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 ...
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
24.03 km from city center
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 ...
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
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

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
18.04 km from city center
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 ...
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
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

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 ...
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3 out of 5
2600 Housley Road Annapolis MD
23.15 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 ...
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St Annapolis MD
16.96 km from city center
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 ...
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3 out of 5
3028 KENT NARROW WAY S Grasonville MD
3.98 km from city center
Book a stay at this business-friendly hotel in Grasonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

3 out of 5
2559 Riva Rd Annapolis MD
22.83 km from city center
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

The Westin Annapolis

4 out of 5
100 Westgate Cir Annapolis MD
18.57 km from city center
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. ...
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

2.5 out of 5
2451 Riva Rd Annapolis MD
21.77 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 helpful staff in our reviews. ...
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

4 out of 5
180 Pier One Road Stevensville MD
3.18 km from city center
Book a stay at this spa hotel in Stevensville. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
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
Book a stay at this business-friendly hotel in Grasonville. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff ...
Don't see what you're looking for?
See all available properties in Chester
View all properties
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.

Frontier Airlines
Tue, Oct 20 - Sat, Oct 24
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$98 Roundtrip, found 3 days ago
$98
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Oct 20 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Oct 24, priced at $98 found 3 days ago
Southwest Airlines
Thu, Sep 24 - Mon, Sep 28
DAL
Love Field
BWI
Baltimore Washington Intl. Thurgood Marshall
$251 Roundtrip, found 5 days ago
$251
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Sep 24 from Love Field to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Sep 28, priced at $251 found 5 days ago
Delta
Tue, Aug 18 - Mon, Aug 24
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$259 Roundtrip, found 21 hours ago
$259
Roundtrip
found 21 hours ago
Select Delta flight, departing Tue, Aug 18 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Aug 24, priced at $259 found 21 hours ago
United
Wed, Oct 7 - Tue, Oct 13
LAX
Los Angeles Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$291 Roundtrip, found 5 days ago
$291
Roundtrip
found 5 days ago
Select United flight, departing Wed, Oct 7 from Los Angeles Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Oct 13, priced at $291 found 5 days ago
American Airlines
Wed, Oct 7 - Tue, Oct 13
LAX
Los Angeles Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$311 Roundtrip, found 5 days ago
$311
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Oct 7 from Los Angeles Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Oct 13, priced at $311 found 5 days ago