Annapolis Holiday Rentals

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Holiday 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 NZ$2,321
includes taxes & fees
4 Jun - 5 Jun
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 NZ$951
includes taxes & fees
25 May - 26 May
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)
"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!
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 NZ$1,108
includes taxes & fees
27 May - 28 May
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)
"Super close to all downtown amenities. Would definitely return."
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 NZ$1,020
includes taxes & fees
27 May - 28 May
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 NZ$754
includes taxes & fees
4 Jun - 5 Jun
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
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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, (1613)
"Beautiful, central location, well appointed! Heating/cooling system is way loud."
The price is NZ$329
includes taxes & fees
9 Jun - 10 Jun
Historic Inns of Annapolis
View from property
Graduate Annapolis
4.0 star property
9.4 out of 10, Exceptional, (1045)
"Unique property, close to everything. Costly, but every hotel in the area is. "
The price is NZ$348
includes taxes & fees
9 Jun - 10 Jun
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 NZ$236
includes taxes & fees
4 Jun - 5 Jun
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Annapolis holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Annapolis. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Annapolis. Seeing all the best attractions is bound to make you fall in love with Annapolis. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Annapolis short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Annapolis?

Yes, there are holiday rentals in Annapolis close to Annapolis Maritime Museum, 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.

How many holiday rentals will I find in Annapolis?

Expedia has 439 holiday 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 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.

Recent reviews of Annapolis properties
Expedia verified reviews