14 Best Airbnbs in Annapolis, Maryland (Waterfront, Boats + More)

Planning a trip to Annapolis, Maryland? I’ve put together the ultimate list of the best Annapolis Airbnb rentals for you…

Famous for being the home of the United States Naval Academy, the Maryland capital of Annapolis has so much to discover, to explore and to experience.

The historic city, nestled on Chesapeake Bay, is home to nostalgic architecture dating back to the 18th century while at the same time buzzing with modern waterfront bars and a young, professional crowd. 

Annapolis Airbnb stays are as beautiful as their capital city home, and I’m sure you’ll be just as charmed by them as I am. 

From modern waterfront pads to historic homes, these are the 14 best Airbnb’s in Annapolis, Maryland…

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Quick Breakdown of Airbnb Annapolis

If you’re searching for the best Annapolis Airbnb’s to suit a range of budgets, styles and sizes – look no further! Before we dive into the main list, I’ve broken down the best top five below. If you don’t find what you’re looking for here, keep scrolling and I bet you will!

• Best Overall Annapolis Airbnb – Walk to Historic Annapolis from a Waterfront Apartment 
• Best Luxury Annapolis Airbnb – Luxury Waterfront Home Annapolis with beach & dock 
• Best Cheap Annapolis Airbnb – Private Annapolis Inlaw Apartment 
• Best Annapolis Airbnb For Families – Renovated Annapolis Row House a Minute’s Walk to USNA 
• Best Unique Annapolis Airbnb – Condo Houseboat

Throughout this list, I’ve included a variety of Annapolis Youtube guides to give you a tour of the Maryland capital. I’ve also included at the end of the list some other travel content for this part of the USA. If you’re heading to Maryland, I recommend checking out THE 14 BEST BALTIMORE AIRBNB STAYS FOR A “CHARM CITY” GETAWAY. 

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1) Walk to Historic Annapolis from a Waterfront Apartment

Best Overall Annapolis Airbnb

Location: Eastport 

Airbnb Plus: Yes

Superhost: Yes

Price: $250+ USD per night 

https://www.airbnb.com/rooms/10876158

This stunning one-bedroom waterfront apartment is easily my choice for the best Annapolis Airbnb. The beautiful pad is modern, stylish and sparkling clean, with light-filled interiors and a marina view from the private balcony. You’ll be located in the upmarket Eastport waterfront neighborhood, with incredible views and just a short stroll to Main Street, The Naval Academy and the Historic District at your doorstep. 

Guest review: “We booked this place as a last-minute change of scenery after months of working from home and could not be more pleased. I love this condo! The location is less than 10 minutes from anything you can need- shops, parks, restaurants, The Naval Academy etc. There is a bar/grill and park less than a block away. The patio was great we spent a lot of time just sitting out there watching the boats and relaxing. The home itself had everything you need and is beautifully decorated. We will for sure be back, hopefully when we can stay longer!” – Gina & Andrew 

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2) Luxury Waterfront Home Annapolis with beach & dock

Best Luxury Annapolis Airbnb

Location: Wilshire 

Airbnb Plus: No

Superhost: Yes

Price: $800+ USD per night 

https://www.airbnb.com/rooms/34271923

Live it up in style in Annapolis and book your stay at the best luxury Annapolis Airbnb. This three bedroom waterfront home in the classy neighborhood of Wilshire is five-star rated by many thrilled guests, and has its own private beach and dock. The modern home has been recently renovated and is located on the Severn River, just minutes from downtown Annapolis (but it feels like a million miles away!)

Guest review: “Simply the best! This is my second stay here and the house is absolutely spectacular, the host is amazing, and if you’re thinking about staying here, do it. You will definitely not regret it.” – Allan 

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3) Private Annapolis Inlaw Apartment

Best Cheap Annapolis Airbnb

Location: Forest Villa 

Airbnb Plus: No

Superhost: Yes

Price: $75+ USD per night 

https://www.airbnb.com/rooms/14592012

Save those hard-earned pennies for sightseeing around Annapolis, and secure your stay at the best cheap Airbnb in Annapolis. This private guesthouse apartment is clean and neat, with a king bed, two air mattresses, a private entrance and a location a stone’s throw from downtown Annapolis and major highways. The budget-friendly pad also comes with a parking spot, handy for those arriving into Annapolis by car. 

Guest review: “Great to place to stay . Rich and Pam provided a home away from home experience for us . The value of this place is awesome!! Very private and a roomy clean place . We’ll be back again and look forward too it !!” – Jeff

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4) Renovated Annapolis Row House a Minute’s walk to USNA 

Best Annapolis Airbnb For Families

Location: Historic District 

Airbnb Plus: Yes

Superhost: Yes 

Price: $150+ USD per night 

https://www.airbnb.com/rooms/27138859

Annapolis is a great family-friendly destination with a lot to see and do. This renovated two bedroom rowhouse has space to sleep up to six, and is located just one minute’s walk from The Naval Academy – ideal if you’re coming to Annapolis for an event here. This stunning family home is modern and stylish, with new kitchen and bathrooms, a charming porch and a cute as a button exterior. 

Guest review: “I highly recommend Ami & Sean’s home. The location is perfect, the space is designed well, clean and I like all the upgrades that came with the home like the soft towels, washer / dryer, amenities in the bathroom. Ami & Sean offered excellent customer service, responded quickly with great recommendations and the communication was detailed and made our trip easy. I highly recommend this home.” – Erika 

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5) Condo Houseboat

Best Unique Annapolis Airbnb

Location: Eastport 

Airbnb Plus: No

Superhost: Yes

Price: $300+ USD per night 

https://www.airbnb.com/rooms/42191569

If you’re keen for a unique stay in Annapolis, this stunning two-bedroom condo houseboat will blow you away. The sparkling clean and modern houseboat is brand new and luxurious, moored on Back Creek with views of Chesapeake Bay. The fully-equipped home on the water even has an epic rooftop deck to enjoy the sunsets from. Impeccable in every way. 

Guest review: “We had such an amazing time, will 100% book again and have friends asking about the listing too! Everything was sparkling clean, easy to use/ find. Beds were brand new and beyond comfy, she did not skimp on mattresses!!! Location was excellent. Design of the space was perfect. I didn’t want to leave my deck where we made friends all weekend with boaters, kayakers, etc!” – Heather 

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6) The Bennett House 

Location: Murray Hill

Airbnb Plus: No

Superhost: Yes

Price: $125+ USD per night 

https://www.airbnb.com/rooms/28657359

With a perfect five-star guest rating and so much to offer, this two bedroom upstairs detached home is private and hosted by some of Annapolis’ best Airbnb hosts. Within walking distance to downtown, USNA and City Dock, the apartment is fashionable, light-filled and welcoming, and equipped with all the necessary amenities and facilities you could need for a great stay. 

Guest review: “This house is even more charming than the description and photos provided. It’s delightful! Raiff and Regina provided prompt and specific advice and instructions, they were flexible with check-in and check-out, they left thoughtful little touches and generally made sure that absolutely every need was addressed. I don’t know when I’ll next be in Annapolis, but I would definitely stay here again.” – Anita 

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7) Charming Row House in Historic District

Location: Historic District 

Airbnb Plus: Yes 

Superhost: Yes 

Price: $150+ USD per night 

https://www.airbnb.com/rooms/19848436

This two bedroom home in the central Historic District of Annapolis is one of the city’s most highly-rated stays and an Airbnb Plus offering that you’ll fall in love with. The stylish home, with decor and artwork paying homage to the nearby United States Naval Academy, is modern, pristine and immaculately presented. There’s even a rear garden with a outdoor deck, and a front porch with a cozy rocking chair. 

Guest review: “Ami and Sean’s place was great! We really enjoyed the outdoor space and the furniture and beds were very comfortable. Our favorite part was the proximity to Main Street and to Acton Cove Park. We paddle boarded from the dock every morning and enjoyed the park at sunset every evening. We enjoyed the neighborhood so much we started looking at real estate.” – Thomas 

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8) Wright’s Cottage- No cleaning fees! Pets! River!

Location: Bon Haven 

Airbnb Plus: No

Superhost: Yes

Price: $100+ USD per night 

https://www.airbnb.com/rooms/24062720

This one bedroom Annapolis cottage is not only hella cute on the outside, but on the inside as well! The freestanding tiny home is budget-friendly and cozy, with interiors that blend modern and rustic design elements. You’ll be staying on an acre of private land, with an RV hookup, a fire pit, private yard, grill and boat slip on the river that are all yours to use. The quiet community of Bon Haven is just 10 minutes from downtown Annapolis and also an easy drive to Baltimore and Washington DC. 

Guest review: “Cute little house with everything you need. Wonderful nautical and Chesapeake decor thought. Enjoyed the fire pit and the grill was there but we didn’t use because there’s a great Italian deli nearby. Walked to the river. lovely in the fall colors.” – Margaret 

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9) Crab Cakes and Football Historic District

Location: Arts District  

Airbnb Plus: Yes

Superhost: Yes

Price: $300+ USD per night 

https://www.airbnb.com/rooms/18747637

The Annapolis Arts District is a humming neighborhood with galleries, restaurants, bars and cool locals, and this charming two bedroom home is right at the heart of it. The five-star rated home has open concept, eclectic interiors, a master suite balcony, a front garden and a rear BBQ area, and the best offerings of the Arts District is just minutes on foot away. 

Guest review: “This is the perfect getaway house if you’re staying in Annapolis! It’s right downtown, close to everything you need and such a nice home. Liz went above and beyond to make us feel welcome! Highly recommend!” – Courtney 

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10) Beautiful and Tranquil Carriage House

Location: West Annapolis

Airbnb Plus: Yes

Superhost: Yes

Price: $200+ USD per night 

https://www.airbnb.com/rooms/18347729

Nestled in a quiet and friendly neighbourhood in West Annapolis, this two bedroom historic carriage house has been transformed into a luxurious modern dream. The sparkling space features open and airy white interiors, a living room balcony and plush beds and furniture. The family-friendly abode is just minutes from downtown Annapolis, Route 50 and USNA. 

Guest review: “Kristin’s place was fantastic! Even better than what the photos show. They were lovely hosts and they made us feel like home. The apartment was spotless, with brand new features, very comfy beds and thoughtful details. We cannot wait to go back!” – Margarita 

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11) Private Art-Filled Guesthouse near Naval Academy

Location: West Annapolis 

Airbnb Plus: Yes

Superhost: Yes

Price: $150+ USD per night 

https://www.airbnb.com/rooms/28153838

This dreamy Annapolis studio guesthouse is just five minutes drive from downtown and a range of cafes, restaurants and bars. The artistic Airbnb Plus is colorful, bright and eclectic, with unique decor and design elements and a modern kitchen and bathroom. This entirely private guesthouse also boasts air-conditioning, black-out blinds and kid-friendly add-ons should you need them, and the neighborhood borders the Severn River. 

Guest review: “Lovely studio, full of nice cute details, great taste. It is not located in the middle of downtown, but 5 minutes drive by car, in a quite area close to cafes and a couple of terrific bakeries. The hosts were very gracious. We couldn’t have been happier. Thanks Linda!” – Jorge 

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12) Historic Victorian home 7,016 sqf, built in 1875!!

Location: Downtown Annapolis 

Airbnb Plus: No

Superhost: Yes

Price: $800+ USD per night 

https://www.airbnb.com/rooms/11081525

This beautiful historic home is ideal for a family reunion or group getaway, and is sure to enchant even the most discerning guest. The seven bedroom home is a sprawling Victorian abode that was built in 1875, and today boasts classic towering ceilings, antique furniture and a lovely garden. With space to sleep up to 16 guests, this stunning home is located in the heart of downtown Annapolis, five blocks from the waterfront and a block from the Naval Academy. 

Guest review: “Lovely house! We had such a nice time! Love the history of the house, and the authentic items that complement the period architecture. Very convenient location, just a quick walk to downtown Annapolis, the harbor, and the Naval Academy. The back yard is beautiful. Quaint little bookstore and coffee shop across the street. We brought our coffee back and sat on the front porch. Definitely will go back!” – Mary Jane 

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13) Midcentury Modern Getaway with Prime Location

Location: Historic District 

Airbnb Plus: No 

Superhost: Yes

Price: $200+ USD per night

https://www.airbnb.com/rooms/42505363

With a perfect five-star guest review score thus far, this three bedroom modern townhouse has space to sleep up to six and something to offer each and every guest. The entirely renovated home boasts midcentury modern interiors and a rooftop deck with breathtaking views. This upscale home is located in the stunning Historic District of Annapolis, with its colonial architecture, cozy laneways and endless restaurants and bars. 

Guest review: “Gorgeous townhome with impeccable interior design and amenities, close to everything Annapolis has to offer. We especially enjoyed a glass of wine on the rooftop deck. The property is even more beautiful than pictured/described and we will definitely come again. Thank you, Ryan!” – Jennifer 

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14) Moose’s Happy Place

Location: Eastport 

Airbnb Plus: No

Superhost: Yes

Price: $350+ USD per night

https://www.airbnb.com/rooms/35542579

“Moose’s Happy Place” is indeed one of Annapolis’ most happy places, with a perfect five-star overall guest score and an unbeatable spot near the water. The three bedroom townhouse is brand new and modern, with stylish, coastal-inspired interiors and front and back porches. Spa Creek and the Severn River are just steps away, and the hip neighborhood or Eastport’s best restaurants, bars and shops are right on your doorstep.

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Guest review: “Amazing place and location. We walked to dinner every night. Place is modern, well-appointed and very spacious and comfortable. We stayed at several very nice places this year and this was by far the best.” – Christopher 

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Annapolis Tours & Experiences

Eat up a storm or hit the bay on a yacht in Annapolis, these Annapolis tours and experiences are lead by expert locals and will give you an insider look at life in the Maryland capital. 

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Private Annapolis Sailing Charter

“There is no better way to see Annapolis than by the water on our 54 foot sailing yacht! We will meet you at the boat with your Welcome (non-alcoholic) Cocktail or non-alcoholic beverage of choice to enjoy while we prepare the boat for launch. Before we take off, we will have the safety briefing and tour of the vessel. Then leave the work to us and the fun to you!”

https://www.airbnb.com/experiences/860142

Price: From $300 USD per person (2.5 hours)

Review: “The most amazing dinner and fantastic people! Spectacular!” – Karen

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Historic Annapolis Food Tour

“Some history-focused city tours can feel stale. Spice up your visit to Annapolis on this guided tour that combines history with food. Visit historic sites and hear fascinating stories while enjoying a series of dishes from downtown restaurants, which may include a tavern frequented by Washington, Jefferson, and Franklin, and a local lobbyists’ favorite lunch spot.”

https://www.viator.com/en-AU//tours/Annapolis/Historic-Annapolis-Food-Tour/d40943-39348P7?mcid=61846

Price: From $70 USD per person 

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Did I miss any top Annapolis Airbnb rentals?

There’s so many top Annapolis Airbnbs, I couldn’t include them all on this list. However, if you have recently stayed at a five star Annapolis Airbnb that didn’t make the cut and think it should have – send me its details. I’ll check it out to see if it has the goods to be added to the ultimate list of the best Annapolis Airbnb stays. 

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Heading to Maryland?

The US state of Maryland is located on the mid-Atlantic, with so many neighboring states and cities to explore in close proximity. If you’re heading to Maryland, why not extend your vacation and take a road trip of these epic destinations nearby?

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Final thoughts on Airbnb Annapolis…

From charming historic row houses to eclectic downtown pads, I was so impressed with the range of Airbnb rentals in Annapolis. The Maryland capital is a hidden gem that is ideal for a long weekend away or a cozy city escape, and I’m sure you’ll fall in love with nostalgic Annapolis. 

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