Annapolis Vacation Rentals

Vacation Rentals in Annapolis

Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (3)
"Wonderful place to stay and Erin was great. Asked about a Grill on the property and the next day we had a grill. The young adults loved the pool and water activities while the older adults enjoyed sitting on the docks watching the sunrise with a cuppa coffee. Would highly recommend this property."
The price is $629
$1,417 total
includes taxes & fees
Jun 4 - Jun 5
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (180)
"Charming spot in the heart of Annapolis, just a few moments walk from anything you might need."
Directly Across from Gate One & Steps from the Waterfront
Property grounds
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun
10.0 out of 10, Exceptional, (60)
"We had a great stay here for my husband’s birthday. Pat and Ken were fantastic hosts and even decorated for this birthday. They provided everything we would need for our toddler and if the weather had cooperated we’d have spent hours and hours in the backyard. Really appreciative of all the attention to detail and would highly recommend this listing if you’re looking for a low-key, relaxing stay where you don’t need to worry about the details."
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun
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Beach
Cozy place close to the city dock
10.0 out of 10, Exceptional, (53)
"We were in town for a family wedding, and we also able to enjoy the atmosphere of downtown Annapolis."
Cozy place close to the city dock
Fridge, microwave, oven, stovetop
Recently Renovated Annapolis Home - Conveniently Located
10.0 out of 10, Exceptional, (44)
"This house was perfect for a group of friends celebrating a 50th birthday! The house was so clean and well cared for! The front porch and outdoor backyard space provided even more room for us to gather together. We will be back!"
Recently Renovated Annapolis Home - Conveniently Located
Exterior
Historic Annapolis Home!
10.0 out of 10, Exceptional, (1)
Historic Annapolis Home!
Property grounds
Popular Historic Firehouse fully renovated with Parking and Pet Friendly
10.0 out of 10, Exceptional, (50)
"I stayed at this property for a family wedding this last weekend with 5 other adult family members. The original spot we booked fell through last second and I found this unique property. It fit our needs perfectly. There was plenty of space. Everything was clean. The outdoor sitting areas were an added bonus. Plenty of parking. And the location in relation to downtown were perfect. I’d definitely stay here again."
Popular Historic Firehouse fully renovated with Parking and Pet Friendly
Property grounds
Pet Friendly - Stone's throw from Annapolis City Dock with private back patio
9.8 out of 10, Exceptional, (7)
"Super close to all downtown amenities. Would definitely return."
Pet Friendly - Stone's throw from Annapolis City Dock with private back patio
Fridge, microwave, oven, stovetop
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, (80)
"This is an absolutely fantastic place to stay!! The host Liz was so easy to work with and quick to respond to any inquiries we had. We booked for the Herndon climb (#plebenomore) and cannot say enough about how perfect this house was for us. It was an easy walk to DTA and gate #1. The kitchen was well stocked and had everything needed to make several home cooked meals for our son and his friends. The sun room is beautiful and the perfect spot to enjoy a cup of coffee or breakfast! The pool was...
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Interior
Cozy suite Located in Presidents Hill
10.0 out of 10, Exceptional, (7)
"This top floor apartment appeared to be recently updated and was immaculately clean. The hosts thought of all the little extras that make a short term rental special. It's located in the heart of annapolis and is easily walkable to soooo many good restaurants and bars. Beds were comfy! The kitchen has some awkwardly angled ceilings, so tall people will need to duck down, but as long as you aren't walking through looking at your phone (like I was), it's totally not a big deal. Even though it is...
The price is $338
$538 total
includes taxes & fees
Jun 3 - Jun 4
Cozy suite Located in Presidents Hill
Property grounds
Annapolis Condominium in the heart of the historic center
9.8 out of 10, Exceptional, (248)
"Great location"
Annapolis Condominium in the heart of the historic center
Property grounds
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (43)
"Beautiful house and views. Amenities and grounds were great. Loved the playground and beach. Peace and quiet at its finest in nature."
The price is $330
$676 total
includes taxes & fees
May 27 - May 28
Charming Annapolis WaterVIEW Home
Outdoor spa tub
Bay View Studio Apartment
10.0 out of 10, Exceptional, (25)
"If you are looking for a very spacious well-appointed one bedroom apt. style accommodation in a residential setting with lovely waterfront bay views, I highly recommend this place!"
Bay View Studio Apartment
Terrace/patio
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
10.0 out of 10, Exceptional, (19)
"Ingrid was a fabulous host. We already plan to return. Beautiful property inside and out. Thank you beyond words, Ingrid!"
The price is $485
$697 total
includes taxes & fees
May 27 - May 28
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Smart TV, Netflix, DVD player, streaming services
Amazing views, short walks to great dining!
10.0 out of 10, Exceptional, (65)
"Extremely responsive host and beautiful cottage. Incredible location with tranquil views of the water. 5 minute walk to ice cream and nice restaurants. Easy walk (20-25 mins) otherwise into more bustling downtown Annapolis."
Amazing views, short walks to great dining!
Property grounds
Charming Downtown 3rd Floor 1 Bedroom Apt
10.0 out of 10, Exceptional, (12)
"Nice place, nice owners, great location."
The price is $175
$306 total
includes taxes & fees
Jun 25 - Jun 26
Charming Downtown 3rd Floor 1 Bedroom Apt
2 bedrooms, free WiFi, bed sheets
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
The price is $239
$466 total
includes taxes & fees
May 27 - May 28
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Property grounds
Still Available for 2024 Commissioning Week! Dog-friendly beachfront home on the Chesapeake
9.8 out of 10, Exceptional, (20)
"The home was beautiful, the setting was stunning, and the check-in and check-out process was a breeze! Our group of 6 cousins had a fantastic time together enjoying the beautiful views and all that Annapolis has to offer. We are already planning a return trip next year!"
Still Available for 2024 Commissioning Week! Dog-friendly beachfront home on the Chesapeake
Exterior
Eastport Cottage .5 mi from Downtown Annapolis
10.0 out of 10, Exceptional, (52)
"Small but mighty Eastport house, super convenient to all thing Annapolis. Clean, equipped, comfortable. Mark is great at all things communication. Stay here….just not on the dates that I need it!"
Eastport Cottage .5 mi from Downtown Annapolis
Interior
Unique Listing! Entire Downtown Triplex w/Private Parking. Sleeps 12-18. Pets ok
10.0 out of 10, Exceptional, (3)
"We had a family reunion in Annapolis so we booked all three units. It was Thanksgiving week and we came from the West Coast. It has a large wonderful yard with lots of amenities to include a fire pit, gas plumbed and a grill. It is close to everything downtown yet not too close. We had everything we needed to have a Thanksgiving meal for our family. The hosts were helpful, responsive and amazing. It has super cute decor and felt very comfortable and cozy. I would highly recommend a stay here."
Unique Listing! Entire Downtown Triplex w/Private Parking. Sleeps 12-18. Pets ok
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See all available properties in 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.

Other types of properties in Annapolis you may be interested in

Exterior
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1617)
"overall the room was very clean, very spacious and service with housekeeping was fabulous. The only complain we had was we kept hearing this noise coming from the wall like if there was some kind of machine that kept going off and on, humming sound"
The price is $148
$192 total
includes taxes & fees
Jun 2 - Jun 3
Historic Inns of Annapolis
Pool
Crowne Plaza Annapolis, an IHG Hotel
3.5 star property
8.8 out of 10, Excellent, (1004)
"Parking lot A little dark at night. Front desk was very welcoming Bartender was stale. Not very welcoming at all. Over all place is nice. Would recommend "
The price is $135
$154 total
includes taxes & fees
Jun 2 - Jun 3
Crowne Plaza Annapolis, an IHG Hotel
View from property
Graduate Annapolis
4.0 star property
9.4 out of 10, Exceptional, (1046)
"Hotel was convenient to the historic area. Parking lot was as too far from the main entrance."
The price is $195
$222 total
includes taxes & fees
Jun 9 - Jun 10
Graduate 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.

Everything you need to know about Annapolis vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Annapolis vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Annapolis vacation 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 low season months. For more hustle and bustle, you may prefer to visit Annapolis in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $175 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Annapolis rentals

At Expedia, we put the best Annapolis vacation 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 vacation.

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 vacation rentals in Annapolis?

Yes, there are vacation rentals in Annapolis near Annapolis Maritime Museum, or you can choose a secluded option if you're looking for extra privacy while you relax. Tourists who visit Annapolis speak highly of the college campus and array of shops. While you're in the area, you can also enjoy the top-notch restaurants and marina.

What's the top vacation rental in Annapolis?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: Visitors like this Annapolis vacation home rental. It offers a balcony, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the spa tub in this rental home to help you unwind. Some other top choices in Annapolis are Directly Across from Gate One & Steps from the Waterfront and Charming Annapolis WaterVIEW Home.

How many vacation rentals will I find in Annapolis?

Expedia has 439 vacation rentals for your stay in Annapolis.

What can I see and do in Annapolis?

Enjoy the outdoors at Maryland Quiet Waters Park and Sandy Point State Park, or simply take in cultural attractions like Annapolis Maritime Museum and Maryland Hall for Creative Arts. While here, Maryland State House and William Paca House are other places worth a visit.

What are vacation rentals like in Annapolis?

Vacation rentals are privately owned properties you can stay in for a short or long stay in Annapolis. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for families.

Recent reviews of Annapolis properties
Expedia verified reviews

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

5/5 Excellent
"Close to highways, ease into Annapolis proper and clean property. Staff are kind and the hotel is well maintained. "
A verified traveler stayed at SpringHill Suites by Marriott Annapolis
Posted 3 days ago
SpringHill Suites by Marriott Annapolis