An aerial view of a coastal town with a prominent church, dense residential area, and a marina with boats.

Holiday Rentals in Anne Arundel County

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Our top choices for Anne Arundel County holiday rentals

1. Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (87 reviews)
"Location, amenities, cleanliness, parking all great!"
United States
Nancy N.
The price is €375
includes taxes & fees
16 Nov - 17 Nov
Cozy 2br home w/ parking in downtown Annapolis

2. Luxe downtown Annapolis condo! On the harbor, rooftop views, cozy fireplace, memory foam beds, free parking & fully stocked home. Walk to shops, dining, USNA!

Luxe downtown Annapolis condo! On the harbor, rooftop views, cozy fireplace, memory foam beds, free parking & fully stocked home. Walk to shops, dining, USNA!
Eastport
10.0 out of 10, Exceptional, (2 reviews)
"Excellent place to stay!"
United States
Michaell M.
Luxe downtown Annapolis condo! On the harbor, rooftop views, cozy fireplace, memory foam beds, free parking & fully stocked home. Walk to shops, dining, USNA!

3. 18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.2 out of 10, Wonderful, (16 reviews)
"Property description is accurate, host is quickly responsive."
United States
Bradford R.
The price is €388
includes taxes & fees
13 Dec - 14 Dec
18th Cent. Charm in Historic Downtown Annapolis

4. Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
Historic District
10.0 out of 10, Exceptional, (6 reviews)
"Very nice, comfortable, convenient property. Host was very communicative. "
United States
Brian L.
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

5. Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (24 reviews)
"The cottage was perfectly located in the heart of Annapolis. It has many eclectic decorations throughout out it. We enjoyed our stay."
United States
Bridget C.
Secluded Cozy Cottage in Historic Downtown

6. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (9 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is €422
includes taxes & fees
14 Nov - 15 Nov
Pool Loft Suite | Bay Access & Beach Passes

7. Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.8 out of 10, Exceptional, (31 reviews)
"Great stay"
United States
Guillaume P.
The price is €183
includes taxes & fees
15 Nov - 16 Nov
Cute, Cozy 2-bedroom house near Annapolis with water access

8. Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (44 reviews)
"This was a lovely place for my mom and I to stay - we were dealing with a challenging situation and Solmaz was very kind and was easy to communicate with. The community is nice and parking was easy. "
United States
Linda B.
The price is €288
includes taxes & fees
15 Nov - 16 Nov
Large 2 bedroom house with private parking in a nice neighborhood

9. Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Admiral Heights
10.0 out of 10, Exceptional, (56 reviews)
"Yes! Enjoyed our stay. Perfect setting and location to enjoy are time in Annapolis."
United States
Maureen D.
The price is €416
includes taxes & fees
15 Nov - 16 Nov
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

10. Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (14 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
United States
Diane D.
The price is €474
includes taxes & fees
14 Nov - 15 Nov
Renovated Bungalow | Walk to Beach | Dog-Friendly

11. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (19 reviews)
"Super clean, well furnished and in a nice quiet neighborhood close to downtown Annapolis. Great place to stay!"
United States
Ryan C.
The price is €430
includes taxes & fees
16 Nov - 17 Nov
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

12. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (24 reviews)
"Excellent Property"
United States
Buu T.
The price is €570
includes taxes & fees
16 Nov - 17 Nov
Chesapeake Cottages- 2 Quaint Waterfront Retreats

13. Chapel Gate 3BR Steps to City Dock & Naval Academy

Chapel Gate 3BR Steps to City Dock & Naval Academy
Historic District
10.0 out of 10, Exceptional, (1 review)
"Very cute home in great proximity to naval academy"
United States
JENNIFER E.
The price is €508
includes taxes & fees
15 Nov - 16 Nov
Chapel Gate 3BR Steps to City Dock & Naval Academy

14. Houseboat Suite for Two near Annapolis

Houseboat Suite for Two near Annapolis
Arnold
9.8 out of 10, Exceptional, (14 reviews)
"Beautiful location! Amazing restaurant down the street. Best crab dip and cream of crab soup you’ll ever have."
United States
Anonymous traveller
The price is €328
includes taxes & fees
15 Nov - 16 Nov
Houseboat Suite for Two near Annapolis

15. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
9.0 out of 10, Wonderful, (4 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is €474
includes taxes & fees
14 Dec - 15 Dec
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

16. Lakefront Home Firepit BWI Marleycreek River

Lakefront Home Firepit BWI Marleycreek River
3.0 star property
Marley
The price is €293
includes taxes & fees
15 Nov - 16 Nov
Lakefront Home Firepit BWI Marleycreek River

17. Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Homewood
9.8 out of 10, Exceptional, (10 reviews)
"The house was great and the host was better! She was super responsive and helpful, and everything went well on our stay!"
United States
Dan B.
The price is €543
includes taxes & fees
17 Nov - 18 Nov
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

18. Luxe Row Home Steps to USNA Gate 3!

Luxe Row Home Steps to USNA Gate 3!
Historic District
10.0 out of 10, Exceptional, (8 reviews)
"Great property, great location. Host was super responsive and accommodating! Highly recommended."
United States
Remy S.
Luxe Row Home Steps to USNA Gate 3!

19. Dean Street's Lower Deck House!

Dean Street's Lower Deck House!
Historic District
10.0 out of 10, Exceptional, (4 reviews)
"We had a great time—the location is fantastic and our dog loved the backyard! A great base to rest and recover between adventures in Annapolis. "
United States
Nathaniel R.
The price is €432
includes taxes & fees
15 Nov - 16 Nov
Dean Street's Lower Deck House!
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

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, apart-hotels, 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 €183 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.