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.
Baltimore executive Furnished rentals

Baltimore executive Furnished rentals

4 out of 5
Downtown Baltimore
Price was $508, price is now $379 per person
$379
per person
Jul 3 - Jul 6
found 6 hours ago
Roundtrip flight included
Minneapolis (MSP) to Baltimore (BWI)
A 24-hour gym is featured at this apartment, along with free parking. Business travelers can take advantage of the business center. There's dry cleaning and multilingual staff can provide around-the-clock assistance.
Pendry Baltimore

Pendry Baltimore

5 out of 5
Fells Point
Save 100% on your flight
Price was $2,635, price is now $1,913 per person
$1,913
per person
Jul 24 - Jul 29
found 8 hours ago
Roundtrip flight included
Orlando (MCO) to Baltimore (BWI)
This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. There's a 24-hour gym on site, and laundry facilities and concierge services are also offered.
Hilton Arlington National Landing

Hilton Arlington National Landing

4 out of 5
Crystal City
Save 100% on your flight
Price was $682, price is now $505 per person
$505
per person
Jul 24 - Jul 29
found 8 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Baltimore (BWI)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Guests will appreciate perks like free WiFi and a free airport shuttle. You'll appreciate the free area shuttle, self parking, and coffee shop/cafe.
Hilton Washington DC/Rockville Hotel & Executive Meeting Ctr

Hilton Washington DC/Rockville Hotel & Executive Meeting Ctr

4 out of 5
Price was $624, price is now $463 per person
$463
per person
Aug 15 - Aug 20
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) 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 and free WiFi in public areas. Self parking, a coffee shop, and limo/town car service are also offered.
InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
Southwest
Price was $964, price is now $720 per person
$720
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Baltimore (BWI)
This smoke-free hotel features a full-service spa, a marina, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Unwind with a drink at one of the 3 bars/lounges and enjoy perks like a free area shuttle.

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.
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
$159 nightly
The price is $181 total per night
$181 total
May 31 - Jun 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
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
$98 nightly
The price is $111 total per night
$111 total
May 31 - Jun 1
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
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3 out of 5
170 Admiral Cochrane Dr Edgewater MD
Free Cancellation
Reserve now, pay when you stay
$103 nightly
The price is $117 total per night
$117 total
May 25 - May 26
Total with taxes and fees
This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.
Pool
Breakfast included
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

3 out of 5
2559 Riva Rd Annapolis MD
Free Cancellation
Reserve now, pay when you stay
$105 nightly
The price is $120 total per night
$120 total
Jun 8 - Jun 9
Total with taxes and fees
This hotel features an indoor pool, a hot tub, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. There's a gym on site, and a 24-hour front desk and a coffee shop are also provided.
Pool
Hot Tub
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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 $379. 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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Chester