Deals on vacations and trips to Chester

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Chester flight + hotel vacation packages

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The LINE Hotel DC

The LINE Hotel DC

4.5 out of 5
Northwest
Save 100% on your flight
Price was $566, price is now $369 per person
$369
per person
Oct 7 - Oct 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
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. A coffee shop, dry cleaning, and luggage storage are also on offer.
The Poppy Georgetown

The Poppy Georgetown

4 out of 5
Northwest
Price was $1,585, price is now $830 per person
$830
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
This hotel features 2 outdoor tennis courts and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the free continental breakfast each morning.
Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
Price was $861, price is now $490 per person
$490
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Phoenix Park Hotel

Phoenix Park Hotel

3.5 out of 5
Northwest
Save 100% on your flight
Price was $973, price is now $560 per person
$560
per person
Sep 30 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a 24-hour business center, and express check-out are also offered.
Furnished Apartments

Furnished Apartments

3 out of 5
Ashton Heights
Save 100% on your flight
Price was $1,015, price is now $649 per person
$649
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
This apartment features laundry facilities.

Top Chester hotels deals

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
$98 nightly
The price is $111 total per night
$111 total
Aug 30 - Aug 31
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.
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
$159 nightly
The price is $181 total per night
$181 total
Aug 27 - Aug 28
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.
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
$107 nightly
The price is $122 total per night
$122 total
Sep 23 - Sep 24
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.
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
$155 nightly
The price is $177 total per night
$177 total
Aug 30 - Aug 31
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 free WiFi in public areas, conference space, and valet parking. Self parking, a coffee shop, and a snack bar/deli are also offered.
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $98 total per night
$98 total
Aug 31 - Sep 1
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the conference center and conference space on site. Enjoy the seasonal outdoor pool and conveniences like a terrace and laundry facilities.
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3 out of 5
2600 Housley Road Annapolis MD
$100 nightly
The price is $114 total per night
$114 total
Sep 16 - Sep 17
Total with taxes and fees
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. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
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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.

Stay near popular Chester attractions

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.
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Frequently asked questions

How much are vacation packages to Chester?
You'll be pleasantly surprised — you can find yourself in Chester for a paltry $369. At Travelocity, we save you time and money with our amazing vacation packages. With hotels, flights and tours all ready to go at our one-stop shop, what's holding you back?
Where can I get the best vacation package deals for Chester?
Travelocity is where to go to score an incredible Chester package deal. Select from 400 partner airlines and 1,000,000 properties worldwide and put together a vacation package that's perfect for you. With this amount of choice at your fingertips, it's time to start planning your next great escape.
Why should I book my Chester vacation bundle via Travelocity?
Because life is one big journey, and we offer all you need to help you on the way. With our top-notch service and Price Match Guarantee, you can book with confidence. What's more, you can sleep easy on the road knowing we're always available to chat via our round-the-clock support.
Will I save money on my Chester car rental if I combine it with my hotel or flight?
You most certainly can — combine your car, hotel and flight into a Chester vacation package and you'll save a ton. With so much to see in and around Chester, having your own wheels will more than come in handy. Once you're behind the wheel, put the stereo on and make tracks to White House, a renowned attraction around 40 mi from Chester.
Which airport is best for Chester?
Ronald Reagan Washington National Airport (DCA) is a main hub. You'll find it roughly 40 mi west of Chester. Other options worth checking out are Baltimore Washington Intl. Thurgood Marshall Airport (BWI) (25 mi away from central Chester) and Salisbury - Ocean City Wicomico Regional Airport (SBY) (60 mi away from central Chester).
Where should I stay when visiting Chester?
If you're looking for a place to lay your head, check out the Waterfront Sunset Bayview: sleeps 6. It's the top pick for many visitors.

Photos of local treasures

Browse Chester vacation photos for more inspiration

A boat docked at a pier during twilight with a city skyline in the background.