Compare Annapolis Vacation Rentals

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Annapolis Rentals

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

0.36 mi from city center
This vacation home offers a water park, laundry facilities, and local meal delivery service. This family-friendly vacation home also has barbecue grills.
Kitchen
Washer
Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock

Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock

0.26 mi from city center
$1,465 nightly
The price is $1,670 total per night
$1,670 total
Jun 2 - Jun 3
Total includes taxes and fees
This vacation home offers an arcade/game room, laundry facilities, and local meal delivery service. Friendly staff can provide concierge services, and also offer advice about sightseeing. Additional amenities include barbecue grills, a water dispenser, and a garden.
Kitchen
Washer
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

2.5 out of 5
0.63 mi from city center
At this vacation home, guests have access to barbecue grills.
Kitchen
Air conditioning
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

1.4 mi from city center
Guests staying at this vacation home have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Cozy place close to the city dock

Cozy place close to the city dock

2.36 mi from city center
This apartment is a smoke-free apartment building.
Kitchen
Free WiFi
Wright's Cottage- Pet's Welcome & EV Charging

Wright's Cottage- Pet's Welcome & EV Charging

5.21 mi from city center
$330 nightly
The price is $376 total per night
$376 total
Jun 9 - Jun 10
Total includes taxes and fees
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has barbecue grills.
Kitchen
Washer
Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!

Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!

0.51 mi from city center
$406 nightly
The price is $463 total per night
$463 total
May 31 - Jun 1
Total includes taxes and fees
Guests staying at this vacation home enjoy a hot tub, laundry facilities, and a garden.
Historic Annapolis Home 1.5 blocks from center of town.

Historic Annapolis Home 1.5 blocks from center of town.

0.17 mi from city center
At this vacation home, guests have access to laundry facilities, local meal delivery service, and barbecue grills.
Kitchen
Washer
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis

Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis

3.62 mi from city center
At this apartment, guests have access to a sauna, a hot tub, and laundry facilities. Additional amenities include barbecue grills and a garden.
Hot Tub
Kitchen
Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star

2.61 mi from city center
$389 nightly
The price is $443 total per night
$443 total
May 26 - May 27
Total includes taxes and fees
Guests staying at this apartment enjoy features like a water park, an outdoor pool, and barbecue grills.
Pool
Kitchen
Recently Renovated Annapolis Home - Conveniently Located

Recently Renovated Annapolis Home - Conveniently Located

0.72 mi from city center
At this vacation home, guests have access to an arcade/game room, laundry facilities, and barbecue grills. This family-friendly vacation home also has a garden.
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity

COZY DOWNTOWN APARTMENT-Naval Academy Vicinity

0.35 mi from city center
At this apartment, guests have access to features like laundry facilities.
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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.

Annapolis Large Group Rentals

How to Book Vacation Rentals in Annapolis



🏠 What is the best price for Annapolis vacation rentals?

Annapolis vacation rentals range in price, starting at $376 total per night.


🏠 What types of vacation rentals in Annapolis can I rent?

Orbitz offers a wide range of Annapolis rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Annapolis condo rentals.


🏠 Is it free to cancel my Annapolis vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Annapolis vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Annapolis. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Annapolis?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Annapolis apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Annapolis?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Annapolis package deals will get you even more savings.

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