Naval Academy Holiday Rentals

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Holiday Rentals in Naval Academy

Upscale Condo in Annapolis

Historic District
10.0 out of 10, Exceptional, (1)
"The host family was incredible to work with. Patient with details. Easy location walking distance to USNA and the stadium. "
United States
Jennifer H.
The price is AU$808
includes taxes & fees
16 Dec - 17 Dec
Upscale Condo in Annapolis

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Rock Hall
10.0 out of 10, Exceptional, (17)
"I loved the welcome basket! This place was extremely clean and had all the amenities that we needed. Much larger in person than even in the pictures. Walkable to town! "
United States
Tracy S.
The price is AU$438
includes taxes & fees
4 Dec - 5 Dec
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to Beach! King Bed & Free Beach Passes

North Beach
10.0 out of 10, Exceptional, (16)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
The price is AU$544
includes taxes & fees
4 Dec - 5 Dec
Walk to Beach! King Bed & Free Beach Passes

Charming Coastal/Country Home w/3 Acres & Sauna!

Stevensville
9.6 out of 10, Exceptional, (32)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
The price is AU$400
includes taxes & fees
9 Dec - 10 Dec
Charming Coastal/Country Home w/3 Acres & Sauna!

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Grasonville
9.6 out of 10, Exceptional, (12)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is AU$649
includes taxes & fees
4 Dec - 5 Dec
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Stevensville
9.8 out of 10, Exceptional, (42)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is AU$385
includes taxes & fees
4 Dec - 5 Dec
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Waterfront Oasis of Annapolis Star

Annapolis
10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is AU$636
includes taxes & fees
4 Dec - 5 Dec
Waterfront Oasis of Annapolis Star

Chesapeake Bay Harbor View in a central location to events/restaurants

2.5 star property
Rock Hall
10.0 out of 10, Exceptional, (2)
"House was clean, great location. Furniture needs a little updating but overall our stay was great! Would definitely stay here again."
United States
Todd W.
The price is AU$417
includes taxes & fees
12 Dec - 13 Dec
Chesapeake Bay Harbor View in a central location to events/restaurants

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Shady Side
10.0 out of 10, Exceptional, (4)
"Would stay here again "
United States
Thomas D.
The price is AU$659
includes taxes & fees
4 Dec - 5 Dec
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

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

Arundel on the Bay
9.8 out of 10, Exceptional, (11)
"Very clean - well equipped - perfect for our relaxing weekend."
United States
Chris J.
The price is AU$702
includes taxes & fees
9 Dec - 10 Dec
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Arnold
10.0 out of 10, Exceptional, (6)
"Enjoyed the stay"
United States
Kedra B.
The price is AU$559
includes taxes & fees
4 Dec - 5 Dec
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

New! Stylish downtown home w/awesome outdoor area!

Stevensville
9.8 out of 10, Exceptional, (26)
"The house was spacious, clean, and in a great location. The owners were available, and easy to communicate with."
United States
Marjorie N.
The price is AU$818
includes taxes & fees
25 Dec - 26 Dec
New! Stylish downtown home w/awesome outdoor area!

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

2.0 star property
Stevensville
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
United States
shannan t.
The price is AU$1,361
includes taxes & fees
6 Dec - 7 Dec
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Charming Pet-Friendly Stay - Near Bay & Beaches.

Annapolis
10.0 out of 10, Exceptional, (6)
"The property provided the space I needed for my family. It is located in a cute neighborhood. The property was clean and the owner was very responsive to any questions that I had. I really enjoyed staying here."
United States
Kristina
The price is AU$865
includes taxes & fees
7 Dec - 8 Dec
Charming Pet-Friendly Stay - Near Bay & Beaches.

Neptune by the Water - Pet Friendly Fenced Yard

Cape Saint Claire
9.8 out of 10, Exceptional, (11)
"Very nice home, location, close to our family and activities. Enjoyed our stay and would recommend to other renters looking for spaciousness and holiness that a hotel cannot provide! "
United States
Lisa S.
The price is AU$780
includes taxes & fees
4 Dec - 5 Dec
Neptune by the Water - Pet Friendly Fenced Yard

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

Homewood
9.8 out of 10, Exceptional, (8)
"This house was perfect for us! We love the ease of getting into town without having to drive and park in a parking garage. I would 10/10 recommend this house!"
United States
Elaina H.
The price is AU$710
includes taxes & fees
8 Dec - 9 Dec
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Cute bungalow blocks to Stadium

Admiral Heights
9.8 out of 10, Exceptional, (7)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
United States
Tammy L.
The price is AU$805
includes taxes & fees
9 Dec - 10 Dec
Cute bungalow blocks to Stadium

BAYSIDE BUNGALOW

Rock Hall
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is AU$465
includes taxes & fees
1 Jan - 2 Jan 2026
BAYSIDE BUNGALOW

Historic Row Home 1 Block from Gate 1 at USNA!

Historic District
10.0 out of 10, Exceptional, (5)
"Wonderful location. Easy walking to downtown restaurants, shops, city docks and USNA. Enjoyed spending time on front porch and swing.Comfortable beds and home like atmosphere.No need for a vehicle, but if you have one, parking garage is just a few blocks away. "
United States
Katie S.
The price is AU$1,090
includes taxes & fees
8 Dec - 9 Dec
Historic Row Home 1 Block from Gate 1 at USNA!

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

Pasadena
The price is AU$649
includes taxes & fees
18 Dec - 19 Dec
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
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 Naval Academy

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

Naval Academy holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Naval Academy. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Naval Academy 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 Naval Academy holiday rentals we have selected for you start as low as AU$194 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Naval Academy rentals

At Expedia, we put the best Naval Academy 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 Naval Academy 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 Naval Academy 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 Naval Academy. 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

Can I find a holiday rental in Naval Academy?

Yes, there are holiday rentals close to the most popular sights in Naval Academy, or you can select a more secluded option if you're looking for a relaxing stay. Naval Academy is known for its university setting and architecture. Make sure you have time to check out the cathedral and sporting events during your trip.

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

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !: This holiday home rental outside of Naval Academy is located on the beach, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. It has 5 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 garden and a selection of games.

What’s there to see and do in Naval Academy?

Enjoy the area's cultural attractions such as Maryland Federation of Art, or get outdoors into nature at a spot like Peters Cove. While here, Alumni Hall and Annapolis Harbor are other places worth a visit.

What’s a holiday rental in Naval Academy like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Naval Academy. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family trips.