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 ...
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 ...
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 ...
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 ...
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 ...
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. ...
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 ...
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 ...
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

2.5 out of 5
3101 Main Street Grasonville MD
4.18 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 ...
The Tidewater Inn

The Tidewater Inn

3 out of 5
101 E Dover St Easton MD
29.07 km from city center
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 ...
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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
Tue, Oct 20 - Sat, Oct 24
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$98 Roundtrip, found 3 hours ago
$98
Roundtrip
found 3 hours 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 hours ago
Delta
Tue, Aug 18 - Tue, Aug 25
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$117 Roundtrip, found 4 days ago
$117
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Aug 18 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Aug 25, priced at $117 found 4 days ago
Southwest Airlines
Tue, Aug 18 - Tue, Aug 25
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$134 Roundtrip, found 4 days ago
$134
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Aug 18 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Aug 25, priced at $134 found 4 days ago
JetBlue Airways
Wed, Sep 16 - Tue, Sep 29
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$217 Roundtrip, found 6 days ago
$217
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Wed, Sep 16 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Sep 29, priced at $217 found 6 days ago
American Airlines
Wed, Sep 16 - Tue, Sep 29
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$237 Roundtrip, found 6 days ago
$237
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Sep 16 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Sep 29, priced at $237 found 6 days ago