Annapolis Vacation Rentals

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Oct 31 - Nov 2
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Nov 14 - Nov 16
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Jan 9 - Jan 11

Vacation Rentals in Annapolis

Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (36)
"Fabulous place. We’ll be booking again next year. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Marina
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
10.0 out of 10, Exceptional, (236)
"This was a wonderful historic home to vacation in"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Interior
Charming townhome with AC and WiFi in delightful Annapolis
Charming townhome with AC and WiFi in delightful Annapolis
3.0 out of 10, (2)
"This is a room, property owner will be there during your stay. Mattress on The floor. Single pillow, comforter, no top sheet. No curtans, and in a mildly questionable part of town. Owner was very "
$68 nightly
The price is $77
Nov 6 - Nov 7
Total with taxes and fees
Charming townhome with AC and WiFi in delightful Annapolis
Outdoor dining
Luxury Waterfront Executive Family Home Annapolis with All Amenities
Luxury Waterfront Executive Family Home Annapolis with All Amenities
7.6 out of 10, Good, (4)
"Very beautiful, uniquely designed home on the water. There were 2 bedrooms on the first floor making in it easy for our elderly quests. The main suite was great for our young adults to stay in together with 2 kings, sectional and multiple love sacs. Plenty of seating throughout the home both inside and out. "
Luxury Waterfront Executive Family Home Annapolis with All Amenities
Fridge, microwave, oven, stovetop
18th Cent. Charm in Historic Downtown Annapolis
18th Cent. Charm in Historic Downtown Annapolis
9.0 out of 10, Wonderful, (12)
"Property description is accurate, host is quickly responsive."
$326 nightly
The price is $372
Oct 19 - Oct 20
Total with taxes and fees
18th Cent. Charm in Historic Downtown Annapolis
Interior
Historic Row Home 1 Block from Gate 1 at USNA!
Historic Row Home 1 Block from Gate 1 at USNA!
10.0 out of 10, Exceptional, (2)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
$595 nightly
The price is $678
Oct 16 - Oct 17
Total with taxes and fees
Historic Row Home 1 Block from Gate 1 at USNA!
Interior
Charming Historic Annapolis Home With Two Off-street Parking Places!
Charming Historic Annapolis Home With Two Off-street Parking Places!
10.0 out of 10, Exceptional, (198)
"Really lovely stay! Such a perfect location, and has lovely home-y touches, we thoroughly enjoyed our time. The extra parking was really helpful!"
Charming Historic Annapolis Home With Two Off-street Parking Places!
Fridge, microwave, oven, stovetop
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
9.2 out of 10, Wonderful, (15)
"Clean, affordable, and a great location that allowed us to easily walk downtown and to the naval academy."
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Exterior
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
2.5 star property
10.0 out of 10, Exceptional, (31)
"Absolutely the best Vrbo we have ever encountered! Beautiful, charming, accommodating, family friendly and in an excellent location. Our stay was exceptional. "
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
Microwave, oven, stovetop, dishwasher
Walk to the stadium! - Lighthouse on Glenwood
Walk to the stadium! - Lighthouse on Glenwood
10.0 out of 10, Exceptional, (1)
"5 star property with plenty of street parking. Everything was clean and had all of the ammendities"
$342 nightly
The price is $390
Oct 28 - Oct 29
Total with taxes and fees
Walk to the stadium! - Lighthouse on Glenwood
Interior
Private Waterfront Woods | Dock, Kayaks, Views
Private Waterfront Woods | Dock, Kayaks, Views
9.2 out of 10, Wonderful, (29)
"This place was great for 10 us (5 adults and 5 kids). Plenty of fun activities for the kids, and it was clean and comfortable for the adults. Check-in and communication was easy. No complaints. Thank you for sharing your wonderful property!"
Private Waterfront Woods | Dock, Kayaks, Views
Fridge, microwave, oven, stovetop
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, (122)
"My family had a great time staying here during a lacrosse tournament. Host was the best and the house was great. My boys loved the pool and adults loved the proximity to the restaurants and bars. Will stay here again in future. "
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Fridge, microwave, oven, stovetop
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
10.0 out of 10, Exceptional, (30)
"Great location for our team to stay during Annapolis sail show. "
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Fridge, microwave, oven, stovetop
Timeless Charm Meets Modern Comfort
Timeless Charm Meets Modern Comfort
10.0 out of 10, Exceptional, (2)
"We enjoyed being in walking distance of everything we needed for the stay, restaurants, shopping, marina, and history. "
Timeless Charm Meets Modern Comfort
Dining
Newly Updated EV Charger Ready Peaceful Home in Annapolis
Newly Updated EV Charger Ready Peaceful Home in Annapolis
9.0 out of 10, Wonderful, (6)
"Had a great time. House was clean and furnished well. Adequately stocked with the essentials. Great location...close to town but still far enough away for peace and quiet. Would definitely stay here again."
Newly Updated EV Charger Ready Peaceful Home in Annapolis
Dining
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis
10.0 out of 10, Exceptional, (110)
"Great property, convenient location, really nicely decorated. "
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis
Fridge, microwave, oven, stovetop
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
9.4 out of 10, Exceptional, (16)
"Our group had a great time! This house was super convenient location and easily walkable to Main Street. Thank you!"
$1,088 nightly
The price is $1,240
Oct 19 - Oct 20
Total with taxes and fees
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Marina
Charming brick home with patio, WiFi, AC, & W/D - walk to everything
Charming brick home with patio, WiFi, AC, & W/D - walk to everything
9.0 out of 10, Wonderful, (26)
"This was our second stay at The Little House. We enjoyed it just as much as the first. Take heed, though, of their description of the parking pad. My Escape barely fits but we love having a parking spot right there. We make it work. We will definitely stay here again."
Charming brick home with patio, WiFi, AC, & W/D - walk to everything
Terrace/patio
Annapolis Condominium in the heart of the historic center
Annapolis Condominium in the heart of the historic center
9.8 out of 10, Exceptional, (285)
"Very nice , convenient to downtown "
Annapolis Condominium in the heart of the historic center
Terrace/patio
Parking at Randall House Across from USNA Gate 1
Parking at Randall House Across from USNA Gate 1
9.8 out of 10, Exceptional, (49)
"Had a wonderful time in downtown Annapolis anchoring from the Randall House. The house is more spacious than it looks online. The hosts are good communicators and very responsive. Would definitely recommend it. "
Parking at Randall House Across from USNA Gate 1
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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Top Annapolis Hotel Reviews

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG

10/10 Excellent
"This hotel was a nice surprise tucked away in a quiet area, yet close to everything Annapolis has to offer. The woman who checked us in was very welcoming and helpful!"
Sharon 1-night trip
Posted 2 days ago
Candlewood Suites Annapolis by IHG

Find out more about Annapolis

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 $77 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.

Explore a world of travel with Expedia

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?

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! : Visitors like this Annapolis vacation home rental. It is located in the city center and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. Some other top choices in Annapolis are Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably and Charming garden row home, easy 4 block walk to the heart of Annapolis..

How many vacation rentals will I find in Annapolis?

Expedia has 403 vacation rentals for your stay in Annapolis.

What can I see and do in Annapolis?

Enjoy the outdoors at Carrs Beach and Maryland Quiet Waters Park, or simply take in cultural attractions like Maryland Hall for Creative Arts and Annapolis Maritime Museum. 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.