Caroline County Vacation Packages 2025/2026 from $321

Caroline County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

InterContinental Washington D.C. - The Wharf by IHG

The Wharf

Save 100% on your flight

$321

per person

Dec 26 - Dec 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Washington (DCA)

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.

Sofitel Washington DC Lafayette Square

Downtown Washington D.C.

Save 100% on your flight

$529

per person

Jan 4 - Jan 10

found 24 hours ago

Roundtrip flight included

Boston (BOS) to Washington (DCA)

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.

Washington Hilton

Northwest

Save 100% on your flight

$451

per person

Jan 4 - Jan 10

found 24 hours ago

Roundtrip flight included

Boston (BOS) to Washington (DCA)

This hotel's 4 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and laundry facilities.

Pendry Washington DC - The Wharf

The Wharf

Save 100% on your flight

$1,521

per person

Nov 17 - Nov 23

found 5 hours 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 luxury hotel. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. You'll appreciate the seasonal outdoor pool, poolside bar, and concierge services.

Hotel Arboretum

Northeast

Save 100% on your flight

$340

per person

Jan 4 - Jan 10

found 24 hours ago

Roundtrip flight included

Boston (BOS) to Washington (DCA)

This hotel doesn't skimp on freebies - guests receive free buffet breakfast and free WiFi. Traveling on business? Take advantage of the 4 onsite conference rooms. A gym is on site, and self parking and a 24-hour front desk are also offered.

Top Caroline County hotels deals

Bally's Dover Casino Resort

1131 N Dupont Hwy, Dover, DE

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$107 total

Oct 16 - Oct 17

Total with taxes and fees

A casino, 5 restaurants, and an indoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at one of the 5 bars/lounges and enjoy perks like free self parking.

Pool

Parking included

Tru by Hilton Georgetown

301 College Park Lane, Georgetown, DE

Free Cancellation

Reserve now, pay when you stay

$107 nightly

$119 total

Oct 27 - Oct 28

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

Hampton Inn Milford

100 Lighthouse Estates Dr, Milford, DE

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$108 total

Oct 23 - Oct 24

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A business center, a snack bar/deli, and express check-out are also on offer.

Pool

Breakfast included

Hyatt Regency Chesapeake Bay

100 Heron Blvd, Cambridge, MD

Free Cancellation

Reserve now, pay when you stay

$233 nightly

$265 total

Oct 19 - Oct 20

Total with taxes and fees

This smoke-free resort features a private beach, a golf course, and a full-service spa. Bring the family and enjoy the children's club, mini golf, and children's pool. Enjoy the 2 outdoor pools and perks like free self parking and free WiFi.

On private beach

Pool

Hyatt Place Kent Narrows & Marina

3028 KENT NARROW WAY S, Grasonville, MD

Free Cancellation

Reserve now, pay when you stay

$144 nightly

$160 total

Oct 21 - Oct 22

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

Pet friendly

St Michaels Inn

1228 S Talbot Street, St. Michaels, MD

$92 nightly

$102 total

Oct 22 - Oct 23

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

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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.

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Frequently asked questions

How much are vacation packages to Caroline County?

Packages, which provide both flights and hotels in Caroline County, start at just $321. Make your travel dreams come true and secure your trip with Travelocity today.

Where can I get the best vacation package deals for Caroline County?

No matter how you like to travel, Travelocity can help you score an unbeatable Caroline County package deal. The only thing you need to do is select a combination from our 400 airlines and 1,000,000 properties worldwide.

Why should I purchase my Caroline County vacation bundle via Travelocity?

We've got destinations and experiences to suit every type of traveler, top-quality service and 24/7 customer support. To top that off, we'll match any better price you come across with our Price Match Guarantee.

Will I save money on my Caroline County car rental if I combine it with hotels and flights?

Certainly. And our Caroline County vacation packages are the ideal way to do it. In only a few clicks you can save money as well as time by booking everything in one place. Pick up the keys to your rental car then chart your own course. Searching for things to do? Add some activities or experiences to your package and save on those too.

Which airport is best for Caroline County?

Your Caroline County trip will likely start at Baltimore Washington Intl. Thurgood Marshall Airport (BWI) or Salisbury - Ocean City Wicomico Regional Airport (SBY).