Deals on vacations and trips to Chester
Save when you book Chester package deals
Chester flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
InterContinental Washington D.C. - The Wharf by IHG
The Wharf
Save 100% on your flight
Price was $530, price is now $266 per person
$266
per person
Feb 13 - Feb 15
found 15 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Baltimore (BWI)
This smoke-free hotel features a full-service spa, a marina, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Unwind with a drink at one of the 3 bars/lounges and enjoy perks like a free area shuttle.
Sofitel Washington DC Lafayette Square
Downtown Washington D.C.
Save 100% on your flight
Price was $1,733, price is now $1,044 per person
$1,044
per person
Mar 11 - Mar 17
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Baltimore (BWI)
A restaurant and a bar/lounge are featured at this hotel. Families will appreciate the onsite laundry facilities and in-room childcare. WiFi in public areas is free.
Eurostars Saint Gregory Dupont Circle Georgetown
Downtown Washington D.C.
Save 100% on your flight
Price was $1,427, price is now $866 per person
$866
per person
Mar 14 - Mar 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Baltimore (BWI)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the express check-out, laundry service, and valet parking. A terrace, a lobby fireplace, and a computer station are also on offer.
Postcard Cabins Shenandoah North, Outdoor Collection by Marriott Bonvoy
Price was $902, price is now $557 per person
$557
per person
Jan 20 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Baltimore (BWI)
This cabin includes express check-out and a virtual front desk. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Take advantage of the free self parking.
Kellogg Conference Hotel at Gallaudet University
Northeast
Save 100% on your flight
Price was $1,449, price is now $896 per person
$896
per person
Mar 11 - Mar 17
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Baltimore (BWI)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a coffee shop, and a terrace are also offered.
Top Chester hotels deals
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Chester MD
This vacation home features free WiFi in public areas, a garden, and laundry facilities. Families will appreciate the playground and barbecue grills.
Kitchen
Washer
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Free Cancellation
Reserve now, pay when you stay
$75 nightly
The price is $85 total per night
$85 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy free perks like free self parking and an area shuttle.
Pet friendly
Parking included
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
Free Cancellation
$105 nightly
The price is $120 total per night
$120 total
Jan 3 - Jan 4, 2026
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
Pool
Parking included
Historic Inns of Annapolis
58 State Circle Annapolis MD
Free Cancellation
Reserve now, pay when you stay
$164 nightly
The price is $187 total per night
$187 total
Dec 28 - Dec 29
Total with taxes and fees
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. A terrace, limo/town car service, and a garden are also on offer.
Pet friendly
Free WiFi
Annapolis Waterfront Hotel, Autograph Collection
80 Compromise St Annapolis MD
Free Cancellation
Reserve now, pay when you stay
$195 nightly
The price is $222 total per night
$222 total
Dec 29 - Dec 30
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a rooftop terrace on site, and laundry facilities and concierge services are also offered.
Pet friendly
Free WiFi
Hilton Garden Inn Annapolis Downtown
174 West Street Annapolis MD
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $102 total per night
$102 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a snack bar/deli, and dry cleaning are also offered.
Pet friendly
Free WiFi
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.
Popular places to visit
Chesapeake Exploration Center
Learn about the events happening at Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.
Frequently asked questions
Photos of local treasures
Browse Chester vacation photos for more inspiration
