Annapolis Vacation Rentals

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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 CA $861
CA $1,940 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
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 CA $541
CA $794 total
includes taxes & fees
May 25 - May 26
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
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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
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
Fridge, microwave, oven, stovetop
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, (80)
"Excellent stay."
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
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
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 CA $452
CA $925 total
includes taxes & fees
May 27 - May 28
Charming Annapolis WaterVIEW Home
Pool
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
10.0 out of 10, Exceptional, (34)
"The host was so friendly and easy to communicate with. The accommodations were very clean and organized. The location was perfect; cute shops only miles away, beach access, beautiful views, and short drive to downtown Annapolis!"
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Fridge, microwave, oven, stovetop
Historic Annapolis Home!
Historic Annapolis Home!
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
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!
Fridge, microwave, oven, stovetop
Cozy 1st Floor King George one bedroom apartment right across from USNA
10.0 out of 10, Exceptional, (17)
"Our home is over 100 years old so staying here was like being home. Great location to the main st shopping and food."
Cozy 1st Floor King George one bedroom apartment right across from USNA
Property grounds
Pet Friendly - Stone's throw from Annapolis City Dock with private back patio
9.8 out of 10, Exceptional, (7)
"Visted Annapolis to see my cousin attending the Naval Academy. Perfect location to walk to restaurants, bars and shopping. Absolutely recommend!!!!! Loved sitting outside with coffee. Such a cute spot."
Pet Friendly - Stone's throw from Annapolis City Dock with private back patio
Property grounds
Charming Cottage with Hot Tub 1 Block from the Bay
10.0 out of 10, Exceptional, (6)
"Was a super comfortable spot my 5 friends and I. Super comfy couches and beds, nice TV, well appointed kitchen. Took a nice walk down to the water in the am. Would stay again!"
The price is CA $418
CA $852 total
includes taxes & fees
May 27 - May 28
Charming Cottage with Hot Tub 1 Block from the Bay
Fridge, microwave, oven, stovetop
USNA home Downtown Annapolis
10.0 out of 10, Exceptional, (4)
"Nice relaxing getaway space. It served as a homebase for our vacay to MD/DC. It had all the amenities a family would need. The proximity to Annapolis harbor and access to the highway made staying local or heading to the city easy. The host was prompt and responsive on any question which arose. We were thoroughly satisfied with our experience."
The price is CA $281
CA $631 total
includes taxes & fees
May 28 - May 29
USNA home Downtown Annapolis
Fridge, microwave, oven, stovetop
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
9.6 out of 10, Exceptional, (99)
"Our daughter was married at the Annapolis Maritime Museum and the property is literally right around the corner. The house is spacious and included everything we needed for a wonderful weekend. Would highly recommend staying at this property to anyone looking to visit Annapolis/Eastport!!!"
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
Fridge, microwave, oven, stovetop
Pristine Downtown 1-Bedroom Steps from State House
10.0 out of 10, Exceptional, (16)
"The place was immaculate. It is small, but the space utilization is amazing. It doesn't feel small at all. It is just steps from a dining, drinking, boating, shopping. There was a lot of attention to detail and I would love to stay there another weekend."
Pristine Downtown 1-Bedroom Steps from State House
Fridge, microwave, oven, stovetop
Anchor's Away in the Heart of Eastport!
9.8 out of 10, Exceptional, (30)
"Great communication with the owner. Location was great and close to the Naval Academy. Parking spot was a plus, especially in the area where parking was tight. The place was clean and comfortable. Everything needed was on site. Would definitely recommend."
Anchor's Away in the Heart of Eastport!
Property grounds
Walk to Main Street from Waterfront Condo with pool and parking
10.0 out of 10, Exceptional, (7)
"In an older apartment building, this condo is situated over the creek with views to the bridge and beyond. Everything is new and I would highly recommend."
Walk to Main Street from Waterfront Condo with pool and parking
Don't see what you're looking for?
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, (1612)
"Beautiful, central location, well appointed! Heating/cooling system is way loud."
The price is CA $214
CA $275 total
includes taxes & fees
Jun 9 - Jun 10
Historic Inns of Annapolis
View from property
Graduate Annapolis
4.0 star property
9.4 out of 10, Exceptional, (1044)
"Unique property, close to everything. Costly, but every hotel in the area is. "
The price is CA $267
CA $304 total
includes taxes & fees
Jun 9 - Jun 10
Graduate Annapolis
Lobby
DoubleTree by Hilton Hotel Annapolis
4.0 star property
8.6 out of 10, Excellent, (1001)
"I was sadly visiting for a funeral and was there for a 4 nite stay. The staff was so kind and very helpful. The room was clean and comfortable. Perfect location to everything I needed. I will 100% stay at this double tree when I come back into town. "
The price is CA $173
CA $198 total
includes taxes & fees
Jun 4 - Jun 5
DoubleTree by Hilton Hotel 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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Annapolis vacation rentals we have selected for you start as low as CA $281 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 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

Red Roof Inn Annapolis

Red Roof Inn Annapolis

5/5 Excellent
Value
"Friendly service and a nice and clean basic room "
A verified traveller stayed at Red Roof Inn Annapolis
Posted 2 days ago
Red Roof Inn Annapolis