Chester Vacations

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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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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. ...
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 ...
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
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
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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.

Frontier Airlines
Thu, Nov 19 - Sun, Dec 6
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$69 Roundtrip, found 4 days ago
$69
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Nov 19 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Dec 6, priced at $69 found 4 days ago
Delta
Thu, Dec 10 - Wed, Dec 16
CLT
Charlotte-Douglas Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$157 Roundtrip, found 5 days ago
$157
Roundtrip
found 5 days ago
Select Delta flight, departing Thu, Dec 10 from Charlotte-Douglas Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Dec 16, priced at $157 found 5 days ago
American Airlines
Thu, Dec 10 - Tue, Dec 15
CLT
Charlotte-Douglas Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$159 Roundtrip, found 2 hours ago
$159
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Thu, Dec 10 from Charlotte-Douglas Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Dec 15, priced at $159 found 2 hours ago
Southwest Airlines
Thu, Dec 10 - Tue, Dec 15
CLT
Charlotte-Douglas Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$159 Roundtrip, found 2 hours ago
$159
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Thu, Dec 10 from Charlotte-Douglas Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Dec 15, priced at $159 found 2 hours ago
United
Thu, Dec 10 - Tue, Dec 15
CLT
Charlotte-Douglas Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$179 Roundtrip, found 2 hours ago
$179
Roundtrip
found 2 hours ago
Select United flight, departing Thu, Dec 10 from Charlotte-Douglas Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Dec 15, priced at $179 found 2 hours ago