Anne Arundel County Holiday Rentals

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Top Holiday Rentals Destinations in Anne Arundel County

Our top choices for Anne Arundel County holiday rentals

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (32)
"We had 14 family members join us to celebrate my son’s graduation from the Naval Academy. The house is clean, the rooms were great, the property was beautiful, and it was close to USNA. Our family loved the open concept. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (78)
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."
The price is NZ$836
includes taxes & fees
2 Sept - 3 Sept
Waterfront Oasis of Annapolis Star

The Heron's Nest at Atlantic Marina

9.8 out of 10, Exceptional, (302)
"Nice weekend getaway!"
The Heron's Nest at Atlantic Marina

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat

9.8 out of 10, Exceptional, (63)
"Awesome place!"
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat

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

10.0 out of 10, Exceptional, (230)
"Loved everything! Parking garage included, close to everything, very comfortable. Would stay there again!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Bay views with kayaks, bikes, fire pit, crabbing and more

9.6 out of 10, Exceptional, (21)
"The host were helpful and easy to work with. Property was thoughtfully outfitted with everything we needed. Great location."
Bay views with kayaks, bikes, fire pit, crabbing and more

Large 2 bedroom house with private parking in a nice neighborhood

9.4 out of 10, Exceptional, (28)
"We stayed here for about a month while we found and bought a house. It was very comfortable, near shopping, near a dog park, and a great place to relax after work as well as make our meals and do laundry. Owners were quick to respond to questions or issues, friendly and easy to get along with."
The price is NZ$644
includes taxes & fees
1 Sept - 2 Sept
Large 2 bedroom house with private parking in a nice neighborhood

Private Cottage on gated estate

10.0 out of 10, Exceptional, (29)
"Excellent location, Excellent property, Excellent owners!"
Private Cottage on gated estate

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (46)
"Beautiful views and a lush backyard. Jacob was excellent with communication. The house was clean and had all amenities needed for a wonderful stay. Please note there are a lot of stairs in the house as well as get to the dock. It was a good workout for us!"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Waterfront Getaway, Dock Your Boat & Play!

10.0 out of 10, Exceptional, (2)
"Lovely stay, don't let the RV aspect.of it scare you. Nicer than most other bnbs ice stayed in. Quiet, clean and beautiful view of the water. "
The price is NZ$527
includes taxes & fees
1 Sept - 2 Sept
Waterfront Getaway, Dock Your Boat & Play!

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (164)
"Easy checkin/checkout. Cute cottage. Scenic and comfortable."
The Yellow Cottage on Harness Creek

Luxury Waterfront Executive Family Home Annapolis with All Amenities

10.0 out of 10, Exceptional, (2)
"Very beautiful, uniquely designed home on the water. There were 2 bedrooms on the first floor making in it easy for our elderly quests. The main suite was great for our young adults to stay in together with 2 kings, sectional and multiple love sacs. Plenty of seating throughout the home both inside and out. "
Luxury Waterfront Executive Family Home Annapolis with All Amenities

Charming Historic Townhouse Steps From USNA

10.0 out of 10, Exceptional, (27)
"It was great!"
Charming Historic Townhouse Steps From USNA

Romantic Two Bedroom Condo

10.0 out of 10, Exceptional, (83)
"Excellent stay. We look forward to returning."
Romantic Two Bedroom Condo

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

9.4 out of 10, Exceptional, (11)
"Three generations of family gathered here for a holiday together. The beautiful historic home is located in the heart of downtown Annapolis - activities for everyone within blocks. We opted for the chef-prepared breakfast,- a highlight!"
The price is NZ$2,592
includes taxes & fees
8 Sept - 9 Sept
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

Large Home with Pool & 7 bedrooms; sleeps 21

9.6 out of 10, Exceptional, (25)
"We did a guys golf trip hitting courses around both Baltimore and Washington DC. We didn’t spend much time at the property but plenty of rooms and beds and perfect to get a few families together and meet up for a vacation"
The price is NZ$1,649
includes taxes & fees
2 Sept - 3 Sept
Large Home with Pool & 7 bedrooms; sleeps 21

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

9.8 out of 10, Exceptional, (77)
"Great location, comfortable stay!!"
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

USNA Getaway: Heated Pool, Hot Tub, Indoor Grill!

9.8 out of 10, Exceptional, (23)
"Great location, great host! "
The price is NZ$1,720
includes taxes & fees
1 Sept - 2 Sept
USNA Getaway: Heated Pool, Hot Tub, Indoor Grill!

Waterfront Annapolis Home: Fire Pit & Fishing Pier

9.2 out of 10, Wonderful, (38)
"Great location"
Waterfront Annapolis Home: Fire Pit & Fishing Pier

Annapolis Home Near Beach & Quiet Waters Park!

Annapolis Home Near Beach & Quiet Waters Park!
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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Top Anne Arundel County Hotel Reviews

Find out more about Anne Arundel County

Find out more about Anne Arundel County

Everything you need to know about Anne Arundel County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Anne Arundel County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Anne Arundel County holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Anne Arundel County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Anne Arundel County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Anne Arundel County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Anne Arundel County holiday rentals we have selected for you start as low as NZ$527 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Anne Arundel County rentals

At Expedia, we put the best Anne Arundel County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Anne Arundel County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Anne Arundel County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Anne Arundel County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Explore a world of travel with Expedia

Explore a world of travel with Expedia