Deals on vacations and trips to Annapolis

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Annapolis flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Sonesta ES Suites St. Louis - Chesterfield

Sonesta ES Suites St. Louis - Chesterfield

3 out of 5
per person
Jul 17 - Jul 21
found 15 hours ago
Roundtrip flight included
Orlando (MCO) to St. Louis (STL)
This hotel features a 24-hour gym and a seasonal outdoor pool. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A 24-hour business center, a garden, and express check-out are also on offer.
Hilton Garden Inn St. Louis/O'Fallon MO

Hilton Garden Inn St. Louis/O'Fallon MO

3 out of 5
Save 100% on your flight
per person
Aug 17 - Aug 22
found 1 day ago
Roundtrip flight included
Orlando (MCO) to St. Louis (STL)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free self parking and free WiFi. A business center, a grocery/convenience store, and a lobby fireplace are also on offer.
DoubleTree by Hilton Hotel St. Louis - Chesterfield

DoubleTree by Hilton Hotel St. Louis - Chesterfield

4 out of 5
per person
Aug 17 - Aug 22
found 1 day ago
Roundtrip flight included
Orlando (MCO) to St. Louis (STL)
7 indoor tennis courts, an indoor pool, and a gym are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and perks like free self parking.
The Principal Hotel

The Principal Hotel

2 out of 5
per person
Jul 17 - Jul 21
found 15 hours ago
Roundtrip flight included
Orlando (MCO) to St. Louis (STL)
A restaurant, free self parking, and a 24-hour front desk are among this hotel's amenities. Dry cleaning and luggage storage are also provided.
DoubleTree by Hilton St. Louis - Westport

DoubleTree by Hilton St. Louis - Westport

4 out of 5
per person
Aug 17 - Aug 22
found 1 day ago
Roundtrip flight included
Orlando (MCO) to St. Louis (STL)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the gym and perks like free self parking.

Top Annapolis hotels deals

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This cabin featured laundry facilities and barbecue grills.
Kitchen
Washer
Completely Renovated in May 2023

Completely Renovated in May 2023

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This cabin includes free WiFi in public areas and barbecue grills.
Kitchen
Pet friendly
New Cabin Just Minutes from Black River

New Cabin Just Minutes from Black River

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This cabin featured laundry facilities and barbecue grills.
Kitchen
Washer
Rustic River Cabin Getaway

Rustic River Cabin Getaway

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This cabin features barbecue grills.
Kitchen
Pet friendly
Hillside Cabin #4 Annapolis, MO Black River

Hillside Cabin #4 Annapolis, MO Black River

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This cabin features free WiFi in public areas, laundry facilities, and barbecue grills.
Kitchen
Washer
Hillside Cabin #2 Annapolis, MO Black River

Hillside Cabin #2 Annapolis, MO Black River

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This cabin includes free WiFi in public areas and barbecue grills.
Kitchen
Pet friendly
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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

K Bridge Recreation Area

5/5(1 review)

Explore the great outdoors at K Bridge Recreation Area, a lovely green space in Annapolis. While you're in the area, stroll along the riverfront.

K Bridge Recreation Area

Walnut Hollow Lake

Commune with nature and explore the great outdoors at Walnut Hollow Lake during your travels in Annapolis. Wander the parks and riverfront while you're in the area.

Walnut Hollow Lake

Frequently asked questions

How much are vacation packages to Annapolis?
You can score a fantastic hotel and flight bundle from just $444. With one of our Travelocity vacation packages, a visit to Annapolis has never looked more irresistible! Save your time and money and then get a start on packing those bags.
How long should my Annapolis vacation be?
On average, people stay 5 nights in Annapolis. Although, that might not be anywhere near enough for you. If your aim is to explore some of the area’s off-the-beaten-path treasures, how about adding another few nights to your itinerary?
Where can I get the best vacation package deals for Annapolis?
You’ll come across a tempting selection of Annapolis package deals on Travelocity. With as many as 400 air carriers and 1,000,000 properties around the globe, piecing together the ultimate escape will be a piece of cake.
Why should I purchase my Annapolis vacation bundle with Travelocity?
Savings, support and a stress-free booking are just the tip of the iceberg. Collect lifelong memories and enjoy a fulfilling travel experience knowing you have access to 24/7 customer support. With the Travelocity Price Match Guarantee, you can rest easy knowing you’re getting the best deal available.
Can I save money on my Annapolis car rental if I combine it with a hotel or flight?
With an Annapolis vacation package, you can bundle your car, hotel and flight bookings and save a ton. If you’d love to uncover the best of this fabulous region, why not make tracks to Busch Stadium? This top attraction is 90 mi from Annapolis. With a rental car, you’ll be there before you know it.
Where should I stay when visiting Annapolis?
If you’re after somewhere to spend your nights, have a look at the FS Cabin #4 - Close to Black River. It’s the top choice for many travelers.

Photos of local treasures

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