Deals on vacations and trips to Chester

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Chester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Churchill Hotel near Embassy Row

The Churchill Hotel near Embassy Row

4 out of 5
Northwest
Save 100% on your flight
Price was $506, price is now $337 per person
$337
per person
Nov 14 - Nov 17
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 limo/town car service are also offered.
Club Quarters Hotel White House, Washington DC

Club Quarters Hotel White House, Washington DC

3 out of 5
Downtown Washington D.C.
Price was $794, price is now $446 per person
$446
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
A 24-hour gym is featured at this hotel, along with free WiFi in public areas and a communal living room. Business travelers can take advantage of the business center. Express check-in, express check-out, and a computer station are also on offer.
Arlo Washington DC

Arlo Washington DC

4 out of 5
Northwest
Save 100% on your flight
Price was $655, price is now $406 per person
$406
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
The hotel's 24-hour gym, seasonal outdoor pool, and 2 bars/lounges are among the featured amenities. Enjoy a meal from the restaurant and perks like free WiFi. Self parking, a coffee shop, and dry cleaning are also offered.
Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
Price was $576, price is now $358 per person
$358
per person
Nov 11 - Nov 15
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.
Crowne Plaza Crystal City-Washington, D.C. by IHG

Crowne Plaza Crystal City-Washington, D.C. by IHG

3.5 out of 5
Crystal City
Save 100% on your flight
Price was $655, price is now $438 per person
$438
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Self parking, a coffee shop, and a terrace are also offered.

Top Chester hotels deals

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
Free Cancellation
Reserve now, pay when you stay
$147 nightly
The price is $167 total per night
$167 total
Oct 26 - Oct 27
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.
Pet friendly
Free WiFi
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
Free Cancellation
Reserve now, pay when you stay
$111 nightly
The price is $126 total per night
$126 total
Oct 19 - Oct 20
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

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Free Cancellation
$105 nightly
The price is $120 total per night
$120 total
Oct 25 - Oct 26
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

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Free Cancellation
Reserve now, pay when you stay
$128 nightly
The price is $146 total per night
$146 total
Oct 31 - Nov 1
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
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
$95 nightly
The price is $105 total per night
$105 total
Nov 1 - Nov 2
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.
Pool
Breakfast 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
$106 nightly
The price is $121 total per night
$121 total
Oct 25 - Oct 26
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
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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 $337. 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.