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.
Beacon Hotel & Corporate Quarters

Beacon Hotel & Corporate Quarters

3.5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $242, price is now $154 per person
$154
per person
Jan 10 - Jan 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Washington (DCA)
A 24-hour gym, valet parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the business center and free internet in public areas.
Embassy Suites by Hilton Washington D.C. – Convention Center

Embassy Suites by Hilton Washington D.C. – Convention Center

3.5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $895, price is now $560 per person
$560
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Washington (DCA)
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the express check-out, laundry service, and valet parking. Enjoy the free cooked-to-order breakfast each morning.
Le Meridien Arlington

Le Meridien Arlington

4 out of 5
Rosslyn
Save 100% on your flight
Price was $909, price is now $605 per person
$605
per person
Dec 30 - Jan 4
found 10 hours ago
Roundtrip flight included
Dallas (DFW) to Baltimore (BWI)
This hotel features a restaurant and 2 bars/lounges. Traveling on business? Take advantage of the business center and WiFi in public areas. There's a gym on site, and laundry facilities and concierge services are also offered.
Hilton Washington DC Capitol Hill

Hilton Washington DC Capitol Hill

4 out of 5
Northwest
Price was $849, price is now $581 per person
$581
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Baltimore (BWI)
This hotel features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a snack bar/deli, and luggage storage are also offered.
Hotel Revival Baltimore

Hotel Revival Baltimore

4 out of 5
Mount Vernon
Price was $1,649, price is now $1,136 per person
$1,136
per person
Jan 6 - Jan 13
just found
Roundtrip non-stop flight included
Dallas (DFW) to Baltimore (BWI)
This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A restaurant, a 24-hour front desk, and concierge services are also provided.

Top Chester hotels deals

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Chester MD
Get rates
This vacation home features free WiFi in public areas, a garden, and laundry facilities. Families will appreciate the playground and barbecue grills.
Kitchen
Washer
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
$154 nightly
The price is $175 total per night
$175 total
Dec 7 - Dec 8
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
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
$124 nightly
The price is $141 total per night
$141 total
Dec 21 - Dec 22
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 terrace 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
$59 nightly
The price is $68 total per night
$68 total
Dec 21 - Dec 22
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
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
$74 nightly
The price is $85 total per night
$85 total
Dec 7 - Dec 8
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
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Free Cancellation
$107 nightly
The price is $122 total per night
$122 total
Dec 1 - Dec 2
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
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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

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'll be pleasantly surprised — you can find yourself in Chester for a paltry $154. 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

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Photo by Patricia Knorr
Photo by Patricia Knorr