The capital city of Maryland is also known as the sailing capital of the United States. The city has carefully preserved its heritage, the remains from the colonial era can be seen in various parts of the city. The beautiful brick row houses, cobblestone streets, and the traditional colonial architecture exude the typical feel of a past era. It has a long maritime history, along with the largest in-water sailboat show of the world. This city is the home of the U.S. Naval Academy, and you can take the historical USNA tours to know more about it. Downtown Annapolis is very interesting too, you can explore its typical colonial architecture, or walk till Ego Alley to see the boats. Take a sip of the classic rum cocktails in Pusser’s Caribbean Grille while watching the boats of Ego Alley. The most intriguing part of this town is most definitely the waterfront. Check out the waterfront Vrbo rentals in Annapolis, Maryland, to explore the town in detail.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, accommodation type, prices, availability of dates, decor, and a waterfront location. The image galleries get refreshed with the latest updates regularly. They were last updated on March 13, 2023.
1. Peaceful chalet with a private boat dock (from USD 714)
The spacious chalet is located in the banks of Severn River, offering an excellent view of the river. The chalet is seated on Mill Creek, close to the Chesapeake Bay. Its three bedrooms have assorted queen-sized, king-sized, and twin beds. Along with the futon and sofa bed of the living area, it can accommodate a group of up to 10. The bright and airy chalet projects an elegant décor, bright and colorful furniture complementing the light-colored walls. The living area includes a comfortable dining space. You can also dine in the patio, with the view of the outdoors. There is a private boat dock in front of the house.
2. Historic home in the old town (from USD 549)
The carriage house is full of character. It still has a historic charm. It stands in the waterside of Southgate Avenue ensuring complete privacy. The old carriage house architecture has remained the same, with age-old furniture and antiques. It has three bedrooms which can accommodate a group of eight. The waterfront patio has plenty of seating arrangements to enjoy the view of the water. Kayaks and canoes are also available if you prefer some adventure.
Top guest reviews
Amenities & Room:
air conditioning worked great to get through heat wave during stayi would recommend putting fans available to circulateCleanliness:
bathrooms were clean and beds were comfortablethe house is beautifully decorated has plenty of historic charm and was spotlessly cleanHost:
the owner was great and was available to answer our questionshost was great with communicating and providing local recommendationsthe property manager was very responsive and extremely nicehomeowner and property manager very accommodating and friendlyRead more reviewsLocation:
the location was great - close to everythingconvenient to the water taxi and easy walk to townthis was the perfect location for our mother /daughter getaway weekendthe place is in a very beautiful neighborhood of annapolis and right on the watermanagement gave us some parking garage tickets but its a good 15 min walk away one way
3. Upscale abode with a floating dock (from USD 656)
The amazing waterfront house is perfect for a family or a group of 13 people. The house has an amazing architecture, spread across three floors. The recently remodeled house has a colonial charm, with high ceiling and hardwood floors. There are huge glass doors and windows all through the property, which floods the house with natural light. The open-plan living area is on the main floor with various seating arrangements. The kitchen and dining area stand on one side. The bedrooms are spread across all three floors, including the loft. There is an indoor porch with a great view and an outdoor patio with a grill and dining area.
Top guest reviews
Cleanliness:
the house is clean very well equipped and was very easy to live in for a few daysit was so pretty very clean and in a perfect locationHost:
we were very please with the owner’s quit response to any concern we hadRead more reviewsLocation:
location was perfect to downtownwe loved the location on a little covethe house is very close to downtown annapolis and is a nice walk or an easy lyft ridegreat location kayak slip was a dream
4. Gorgeous townhome for a family of eight (from USD 560)
The amazing living area of this property is to give you a feeling of floating, its floor-to-ceiling windows practically open in the water. You can spend your time here counting the boats or watching the yachts passing by. The décor of this house is interesting, which projects lots of colors and interesting artworks. It has three bedrooms, comfortable enough for a group of eight. The private patio has a grill and seating area to enjoy a delicious barbeque with the view of the water.
Top guest reviews
Amenities & Room:
we really appreciated the extra efforts including fresh flowers on the kitchen countervery comfortable home with great views and easy to walk to bars and restaurantsthe house was wonderful especially the living room with comfortable seating for all and such a beautiful viewCleanliness:
the townhouse was well stocked and very cleanbeautiful townhouse great layout and very cleanHost:
gil was a great host as wellRead more reviewsLocation:
great location within walking distance to restaurants and shopsgreat property close to downtown and comfortablegreat location - easy walk to usna downtown annapolis eastporteasy walk to downtown annapolis and convenient to many restaurants in eastportso many great restaurants and bars within walking distance
5. Beach-themed home with a seasonal pool (from USD 350)
The bright and beautiful remodeled home is minutes away from downtown Annapolis. It has a colonial charm with lots of natural light entering through the grand window. Its hardwood floors combine with light-colored walls and colorful furniture with a beach theme. There are two bedrooms with double and king-sized beds, along with the sleeper sofa in the living area it can accommodate a group of six. The spacious living has a fully equipped kitchen on one side. Its dining area offers an excellent view of the marina. A seasonal pool is located beside the marina with plenty of space to sit and relax.
Top guest reviews
Amenities & Room:
cozy and comfortable minutes from amenities and down townCleanliness:
so quaint and very cleanabsolutely beautiful cottage clean perfect locationvery neat and cleanRead more reviewsLocation:
it is in a great location for trips to annapolis and the surrounding areasand clean as a whistle the location is just perfect-so relaxing and beautifulquiet clean great views close to great shopping and restaurants
6. Refurbished house with a pool and hot tub
The house sits just in front of the Chesapeake Bay offering an enchanting view. The sunroom, waterfront living area, offers an enchanting view of the water. The house is quite big, with five bedrooms and lots of places to sit and relax. It is comfortable enough for a group of 12. A large outdoor pool is on the lawn, along with a hot tub. There is a cozy place to dine outdoors, along with a view of the water.
9.13 km (5.7 mi) from Sandy Point State ParkAccommodates: 12
Minimum Nights: 0
Refund Policy : 100% refund if you cancel at least 30 days before check-in.
Top guest reviews
Amenities & Room:
the house is even nicer than the pictures and the pool/yard is beautifulHost:
we recommend the owners reconnect the cable if possiblethe young lady caretaker was very helpfulvery helpful rental agentRead more reviewsLocation:
location is so great and having a pool is a must for usfantastic location on the water with its own poolthe neighborhood is quiet and safe which made it perfect for walking running and bike ridingthe location is great for heading to annapolis or over the bridge to kent narrowsthe neighborhood is ideal for walking jogging bicycling-all passersby are friendly and unobtrusive
7. Lavish residence with a private pier
This grand luxurious home stands in front of Lake Ogleton with two decks to enjoy the view. The interior combines a mix of traditional and modern décor, with hardwood floors and matching furniture. The bedrooms are huge, the master bedroom even has its private patio. The large outdoor pool is in front of the lake, located beside the hot tub and a patio with a grill. There is a deep-water dock if you are planning to rent a boat.
9.24 km (5.8 mi) from Sandy Point State ParkAccommodates: 18
Minimum Nights: 0
Refund Policy : 100% refund if you cancel at least 30 days before check-in.
Top guest reviews
Amenities & Room:
we had a fantastic weekend there was plenty of space and the pool was perfectkitchen stuff but nothing that would stop us from going backRead more reviewsHost:
kate with aha was super responsive and the surrounding community seemed friendly
Experience a mix of history and waterfront living
The blend of history in waterfront living makes the town Annapolis unique. You can explore the native architecture of this town if you visit Maryland State House, Banneker-Douglass Museum, Anne’s Episcopal Church, or just hire a boat and spend your entire vacation on water.
History
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