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.
Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $835, price is now $560 per person
$560
per person
Jun 17 - Jun 21
found 14 hours ago
Roundtrip flight included
Boston (BOS) 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.
Eaton DC

Eaton DC

4.5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $1,061, price is now $688 per person
$688
per person
May 15 - May 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A bar/lounge, a 24-hour front desk, and a terrace are also provided.
Tysons Corner Marriott

Tysons Corner Marriott

4 out of 5
Save 100% on your flight
Price was $1,008, price is now $681 per person
$681
per person
May 17 - May 21
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Washington (IAD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 9 conference rooms, 24-hour business center, and express check-in. Self parking, a coffee shop, and a snack bar/deli are also offered.
The Jefferson, Washington, DC

The Jefferson, Washington, DC

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $1,561, price is now $1,081 per person
$1,081
per person
Jun 17 - Jun 21
found 14 hours ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
This luxury hotel features 3 restaurants, a bar/lounge, and a gym. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A library, luggage storage, and laundry facilities are also on offer.
Placemakr Buzzard Point

Placemakr Buzzard Point

4 out of 5
Southwest
Save 100% on your flight
Price was $1,132, price is now $791 per person
$791
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
A 24-hour gym, self parking, and laundry facilities are featured at this aparthotel. WiFi in public areas is free. A communal living room and luggage storage are also provided.

Top Chester hotels deals

Waterfront Sunset Bayview: sleeps 6

Waterfront Sunset Bayview: sleeps 6

Chester MD
Get rates
This vacation home features laundry facilities.
Kitchen
Washer
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.
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
$182 nightly
The price is $208 total per night
$208 total
Apr 19 - Apr 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 free WiFi in public areas, conference space, and valet parking. Self parking, a coffee shop, and a snack bar/deli are also offered.
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
$174 nightly
The price is $198 total per night
$198 total
Apr 19 - Apr 20
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
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Free Cancellation
$114 nightly
The price is $130 total per night
$130 total
Apr 14 - Apr 15
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
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
$128 nightly
The price is $146 total per night
$146 total
Apr 12 - Apr 13
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.
Don't see what you're looking for?
See all available properties in Chester
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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 $560. 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.

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