Annapolis Holiday Rentals

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Our top choices for Annapolis holiday rentals

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, (9 reviews)
"Our family gathered for a special celebration and loved the home! It was roomy and had everything we needed for our stay. The location was perfect for getting around."
United States
Jeanie W.
The price is NZ$1,051
includes taxes & fees
20 Apr - 21 Apr
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is NZ$782
includes taxes & fees
14 Apr - 15 Apr
Waterfront Oasis of Annapolis Star

Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking

Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
Cape Saint Claire
9.2 out of 10, Wonderful, (5 reviews)
"Dominick was a great communicator, he was very responsive and ensured we were comfortable during this stay. Highly recommend anyone to book this property!"
United States
Marissa F.
The price is NZ$975
includes taxes & fees
14 Apr - 15 Apr
Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking

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, (13 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is NZ$996
includes taxes & fees
21 Apr - 22 Apr
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

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, (51 reviews)
"Yes! Enjoyed our stay. Perfect setting and location to enjoy are time in Annapolis."
United States
Maureen D.
The price is NZ$776
includes taxes & fees
14 Apr - 15 Apr
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Historic Annapolis Charmer <1Mile to NMC Stadium

Historic Annapolis Charmer <1Mile to NMC Stadium
Homewood
9.8 out of 10, Exceptional, (7 reviews)
"We had 11 people in our group and this house was the perfect size for gathering and sleeping comfortably. Great accommodations, easy to get downtown and around. Definitely recommend"
United States
Priscilla M.
The price is NZ$2,300
includes taxes & fees
27 Apr - 28 Apr
Historic Annapolis Charmer <1Mile to NMC Stadium

Cozy 3BR Annapolis sleeps 10 Private Deck, Parking

Cozy 3BR Annapolis sleeps 10 Private Deck, Parking
Annapolis
The price is NZ$982
includes taxes & fees
27 Apr - 28 Apr
Cozy 3BR Annapolis sleeps 10 Private Deck, Parking

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Historic District
9.4 out of 10, Exceptional, (20 reviews)
"The owners were very good with pre and post-check in communications, and were on site to meet us and show us the property. It was an excellent stay with an excellent location. Kitchen was well stocked and lots of room for everyone."
United States
Ward U.
The price is NZ$2,519
includes taxes & fees
11 May - 12 May
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Eastport 4 Bedroom Spacious Gem on Jefferson

Eastport 4 Bedroom Spacious Gem on Jefferson
Eastport
The price is NZ$2,072
includes taxes & fees
3 May - 4 May
Eastport 4 Bedroom Spacious Gem on Jefferson

Historic Annapolis Home | 2 Blocks to Main St

Historic Annapolis Home | 2 Blocks to Main St
Historic District
10.0 out of 10, Exceptional, (16 reviews)
"Great house and location. Great communication. We had a great time there!"
United States
Barbara S.
The price is NZ$1,097
includes taxes & fees
19 Apr - 20 Apr
Historic Annapolis Home | 2 Blocks to Main St

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is NZ$817
includes taxes & fees
20 Apr - 21 Apr
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Admiral's Abode - Charming Retreat

Admiral's Abode - Charming Retreat
Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Great location, well appointed home and good communication."
United States
Andrea K.
The price is NZ$1,992
includes taxes & fees
26 Apr - 27 Apr
Admiral's Abode - Charming Retreat

Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (19 reviews)
"This cottage is a hidden gem. Beautiful decor, perfect for our family of 4 & right in the center of all the main attractions. Jennifer was an amazing host!"
United States
Linda Q.
The price is NZ$1,056
includes taxes & fees
14 Apr - 15 Apr
Secluded Cozy Cottage in Historic Downtown

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is NZ$902
includes taxes & fees
27 Apr - 28 Apr
Annapolis Retreat - 7 mins from downtown Annapolis!

2BR, 1BA Boutique Brick Beauty located in historic Eastport.

2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Eastport
The price is NZ$695
includes taxes & fees
10 May - 11 May
2BR, 1BA Boutique Brick Beauty located in historic Eastport.

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.8 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is NZ$959
includes taxes & fees
19 Apr - 20 Apr
Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Historic District
The price is NZ$870
includes taxes & fees
14 Apr - 15 Apr
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Stadium-Side Annapolis | Chef Kitchen | Sleeps 10

Stadium-Side Annapolis | Chef Kitchen | Sleeps 10
Admiral Heights
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful house & our hosts were very responsive to our questions. We had a wonderful experience!"
United States
JP Y.
The price is NZ$1,340
includes taxes & fees
27 Apr - 28 Apr
Stadium-Side Annapolis | Chef Kitchen | Sleeps 10

Fabulous 5-bedroom house with AC in charming Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
Annapolis
8.0 out of 10, Very good, (3 reviews)
"Everything was as we expected or better. Very clean well appointed property "
United States
Stuart P.
The price is NZ$662
includes taxes & fees
20 Apr - 21 Apr
Fabulous 5-bedroom house with AC in charming Annapolis

Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
The price is NZ$941
includes taxes & fees
14 Apr - 15 Apr
Historic Row Home in Downtown Annapolis
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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Find out more about Annapolis

Everything you need to know about Annapolis 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 Annapolis 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 Annapolis holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Annapolis holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Annapolis. 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 Annapolis 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 Annapolis holiday rentals we have selected for you start as low as NZ$682 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Annapolis rentals

At Expedia, we put the best Annapolis 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 Annapolis 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 Annapolis 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 Annapolis. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Annapolis?

Yes, there are holiday rentals in Annapolis close to Maryland Hall for Creative Arts, or you can select a more secluded option if you're looking for a relaxing stay. Tourists who visit Annapolis speak highly of the university campus and array of shops. While you're in the area, you can also enjoy the top-notch restaurants and marina.

What are some of the best holiday rentals that Annapolis has to offer?

Charming Annapolis WaterVIEW Home: This highly rated holiday home rental in Annapolis is located on the waterfront, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub. Some other top choices in Annapolis are Spacious Luxe USNA Home - Pool, Hot Tub, Grill and Charming Downtown Annapolis. Stroll to all the Historic District has to offer. .

How many holiday rentals will I find in Annapolis?

Expedia has 380 holiday rentals for your stay in Annapolis.

What can I see and do in Annapolis?

Enjoy the outdoors at Maryland Quiet Waters Park and Bay Ridge Beach, or simply take in cultural attractions like Hammond-Harwood House and Annapolis Maritime Museum. While here, Maryland State House and William Paca House are other places worth a visit.

What are holiday rentals like in Annapolis?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Annapolis. Holiday rentals offer amenities like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for a family trip or a small group gathering.