Deals on vacations and trips to Chester

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Chester flight + hotel vacation packages

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Hamilton Hotel Washington DC

Hamilton Hotel Washington DC

4 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Jul 23 - Jul 27
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A terrace, dry cleaning, and luggage storage are also on offer.
YOTEL Washington DC

YOTEL Washington DC

4 out of 5
Northwest
Save 100% on your flight
per person
Jul 26 - Jul 29
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. You'll appreciate the seasonal outdoor pool, poolside bar, and concierge services.
Hyatt Place National Harbor

Hyatt Place National Harbor

3 out of 5
Save 100% on your flight
per person
Jul 26 - Jul 29
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A computer station, luggage storage, and laundry facilities are also on offer.
Element Arundel Mills BWI Airport

Element Arundel Mills BWI Airport

3 out of 5
Save 100% on your flight
per person
Jun 4 - Jun 9
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and free self parking.
Ulysses

Ulysses

3 out of 5
Midtown
Save 100% on your flight
per person
Jun 4 - Jun 9
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A coffee shop, a snack bar/deli, and dry cleaning are also on offer.

Top Chester hotel deals

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
Free Cancellation
Reserve now, pay when you stay
The price is $152 per night
$152
per night
May 13 - May 14
This hotel features a restaurant, 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
Parking available
Graduate Annapolis

Graduate Annapolis

4 out of 5
126 West St, Annapolis, MD
Free Cancellation
Reserve now, pay when you stay
The price is $195 per night
$195
per night
May 26 - May 27
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference space, and valet parking. Self parking, a coffee shop, and a terrace are also offered.
Pet friendly
Breakfast available
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3 out of 5
2600 Housley Road, Annapolis, MD
Free Cancellation
The price is $112 per night
$112
per night
May 27 - May 28
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pet friendly
Breakfast included
The Westin Annapolis

The Westin Annapolis

4 out of 5
100 Westgate Cir, Annapolis, MD
Free Cancellation
Reserve now, pay when you stay
The price is $169 per night
$169
per night
May 19 - May 20
A full-service spa, a 24-hour gym, and a restaurant are all featured at this Beaux Arts hotel. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and snack bar/deli.
Pet friendly
Breakfast available
Crowne Plaza Annapolis, an IHG Hotel

Crowne Plaza Annapolis, an IHG Hotel

3.5 out of 5
173 Jennifer Rd, Annapolis, MD
Free Cancellation
The price is $130 per night
$130
per night
May 5 - May 6
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. Free self parking, a terrace, and a grocery/convenience store are also offered.
Breakfast available
Parking included
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3 out of 5
174 West Street, Annapolis, MD
Free Cancellation
Reserve now, pay when you stay
The price is $139 per night
$139
per night
May 5 - May 6
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a snack bar/deli, and dry cleaning are also offered.
Pet friendly
Breakfast available
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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.

Popular places to visit

Image for Chesapeake Exploration Center

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.

Chesapeake Exploration Center

Frequently asked questions

How much are vacation packages to Chester?
You can score a great hotel and flight bundle for an affordable $408. With one of our Travelocity vacation packages, a getaway to Chester has never looked so tempting! Save both time and money and then start packing that suitcase.
Where can I get the best vacation package deals for Chester?
Travelocity has countless ways to score an incredible Chester package deal. Take your pick of 400 partner airlines and 1,000,000 properties all over the globe and put together a travel itinerary that suits your style. With almost endless choice, it’s easy to plan your next big adventure.
Why should I purchase my Chester vacation bundle via Travelocity?
From enticing destinations to fun experiences, we have everything you need to appease your wanderlust. Our 24/7 customer care will also make sure you’re being taken care of while you’re on your vacation. And don’t worry if you spot a lower price on your booking, we’ll match it. That’s our Price Match Guarantee.
Can I save money on my Chester car rental if I combine it with my hotel or flight?
With a Chester vacation package, you can combine your car, hotel and flight bookings and save a tidy sum. When you’re ready to explore the best of this impressive destination, why not head to White House? This popular attraction is 40 mi from Chester. With your own rental car, you’ll be there before you know it.
What is the best time of year to go to Chester?
That all comes down to whether you’d rather save money or visit Chester at its most exciting. The quietest time to see this part of the world is November, December and January. But if you’d like to experience this destination at its peak, consider May, June and July. Want to save your hard-earned money? The cheapest month is . typically has the most expensive prices.
Which airport is best for Chester?
Many visitors fly into Ronald Reagan Washington National Airport (DCA), 40 mi west of downtown Chester. Others prefer Baltimore Washington Intl. Thurgood Marshall Airport (BWI) (25 mi away from central Chester) or Salisbury - Ocean City Wicomico Regional Airport (SBY) (60 mi away from central Chester).
Where should I stay when visiting Chester?
The Waterfront home with private pier is A Shore Thing is popular with many visitors. Book as soon as possible before it’s too late.