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Waterfront vacation rentals in Annapolis

Find and book unique waterfront rentals on Airbnb

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Popular amenities for Annapolis waterfront rentals

Waterfront apartment rentals

Guest favorite
Apartment in Pasadena
5 out of 5 average rating, 15 reviews

Relaxing Waterfront Apartment!

MichaelRating, 5 stars5 days ago
Beautiful spot right on the water. Our whole family loved it. We would absolutely stay here again. Thanks Jeanne!
Top guest favorite
Apartment in Annapolis
4.98 out of 5 average rating, 113 reviews

One bedroom apartment in Annapolis

JensinaRating, 5 stars1 month ago
Great above-garage apartment. Fully equipped kitchen, large bathroom, and comfortable king bed with walk in closet. Location is directly off the highway but not at all noisy. Had a little trouble finding the location (I accidentally drove past it the first time) but eventually realized I was at the wrong place. 10 minutes to downtown Annapolis.
Superhost
Apartment in Dundalk
4.82 out of 5 average rating, 11 reviews

2 Bedroom on the Water Close to Baltimore and DC

VickiRating, 5 stars22 months ago
Ebony is one of the best hosts I’ve ever had through Airbnb. Very responsive and helpful! You want crab at 10pm? She’ll find it for you! The view from the home was gorgeous. Very nice and quiet which allowed us some relaxation. Pleasantly surprised by the fireflies in the backyard and the huge magnolias on the tree (neither can be found in Montana where we came from). Great place. Would stay again if I ever return to the area!
Superhost
Apartment in Inner Harbor
4.84 out of 5 average rating, 31 reviews

Beautiful 2 Bedroom Fully Furnished Apartment on H

BrianRating, 5 stars1 month ago
Overall great place. A few aspects missing (one light bulb out, 2/3 TVs not apparently hooked to cable or internet, only one lamp in master), but felt very welcoming and an easy and convenient place for a family with 2 bedrooms and 2.5 baths with full kitchen. Location was great.
Top guest favorite
Apartment in Stevensville
5 out of 5 average rating, 43 reviews

Heron Roost

TaylorRating, 5 stars2 days ago
We had the best stay. Couldn’t recommend more.
Top guest favorite
Apartment in Essex
4.97 out of 5 average rating, 264 reviews

A unique place on sue creek

MoniqueRating, 5 stars2 days ago
We stayed with Wayne and Kathleen for three nights and loved our stay. Its a cozy cottage that sits above a beautiful, whimsical garden. We actually bumped into Wayne a couple times - great guy who made us feel right at home if we needed something but didnt hover - the perfect balance! This couple has loaded this place with all the amenities you could ask for. We felt like we were staying at a upstate new england B&B. Highly recommended, we hope to stay again!
Top guest favorite
Apartment in Chester
4.97 out of 5 average rating, 262 reviews

Cozy Waterfront Apartment Chester, MD

BrettRating, 5 stars4 months ago
We needed a quiet and private space to relax. Jordan’s space was all of this. We stayed here for a month and hardly ever heard Jordan and her family. Jordan was quick to respond if we had any questions. The bed was very comfortable and the views of the water were nice.
Superhost
Apartment in Dundalk
5 out of 5 average rating, 3 reviews

Waterfront Romantic Studio

MariaRating, 5 stars2 days ago
This Airbnb definitely gives off “Romantic vibes”. I loved being able to sit outside and be within a few feet from the water ! The sea decor matches the water being right on the property. The Airbnb itself was decorated so nice and the bed was so comfortable! Also would love to know where you purchase your decor ? (Please and thx , lol). The host Michael and Melodie were so responsive , attentive and pleasant. My husband I enjoyed every second of our staycation there!

Waterfront house rentals

Guest favorite
Home in Riviera Beach
4.95 out of 5 average rating, 137 reviews

Waterfront Cheerful 5 home

PolinaRating, 5 stars2 weeks ago
Excellent house for a family reunion, spotlessly clean and very comfortable. It features a huge, well-stocked kitchen, nice mattresses and bedding, and is situated in a quiet neighborhood with beautiful nature. I will definitely return soon.
Superhost
Home in Middle River
4.7 out of 5 average rating, 64 reviews

Waterfront Oasis w/ Private Dock, 3BR/2BA

ElaineRating, 5 stars1 month ago
Everything was very good bdrm, 2 baths, waterfront! Dock to fish from! love the Morning/all day room for us. We enjoyed fishing and Bird watching, Eagles and Osprey among other, I know why the call it Bird River! Will definitely stay again. Hosts were very understanding of our changing plans, quick response times!
Top guest favorite
Home in Middle River
5 out of 5 average rating, 113 reviews

Beautiful, quiet waterfront house. Lots of room!

HeatherRating, 5 stars3 weeks ago
Quiet and tranquil getaway. Felt like a secluded oasis without a long drive. Beautifully maintained home with comfortable and clean decor. Tons of room! Gordon was incredibly responsive and thorough in his communications.
Guest favorite
Home in Shady Side
4.96 out of 5 average rating, 105 reviews

Waterfront w/ Private Pier, 35 Mins to Annapolis

NicholasRating, 5 stars5 months ago
We had 6 people for a weekend retreat and this was a fantastic house and location for us. the host was super communacitive and easy/friendly to work with. We'll go back for sure next time we need a retreat space that is quiet, private and affordable.
Top guest favorite
Home in Grasonville
4.95 out of 5 average rating, 267 reviews

River Front, Private Single Family Home

JohnRating, 5 stars1 week ago
We were delightfully pleased with our stay here. The house was clean and comfortably fit our 3 adults and 2 kids. We were happy with the “extras” like having our linens and towels cleaned and wrapped in plastic, shampoo/conditioner, kitchen stocked with cookware, and the decor. The best part was the view and proximity to the water. The pictures do not do the sunset justice. We will definitely come back.
Top guest favorite
Home in Shady Side
5 out of 5 average rating, 164 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

DeanneRating, 5 stars4 days ago
Absolutely amazing house and location!! Our family had an incredible week spent enjoying the property & views, spending time watching the sunsets by the fire, and kayaking around the bay. It's a great spot to teach kids to paddle and our 7 and 9-year old both enjoyed learning on the still waters near the sandy beach. The property and house are both thoughtfully designed and have so many spots to relax, read, watch the birds, and take in the views - made it feel like there was never a reason to leave. We had an incredibly peaceful week and would love to visit again!!
Top guest favorite
Home in Cambridge
4.98 out of 5 average rating, 46 reviews

WaterfrontHotTubPvtPierFirePitKayakGrillQuietHouse

KatieRating, 5 stars1 day ago
We were so impressed with the property, amenities and host communications. The house was spotless, comfortable and packed with everything you could think of and MORE! Kitchen and bathroom were fully stocked, sunscreen, bug spray, books, games, even a karaoke machine!! The hot tub was amazing, with a stunning waterfront background. I wish we had stayed longer to enjoy the fire pit, paddle boards, kayaks and private pier. definitely adding this to our list of favorite homes. fabulous host was the cherry on top! We mentioned we were celebrating birthdays and were surprised with wine, chocolate and a note wishing happy birthday.
Top guest favorite
Home in Stevensville
5 out of 5 average rating, 109 reviews

Kent Island Waterfront Home with Amazing Sunsets

JoanRating, 5 stars1 week ago
Kelly's Kent Island Waterfront Home was the perfect location for a girl's get-away. Her home was incredibly cozy, the waterfront view amazing, and the location couldn't have been better in terms of access to great restaurants/things to do. Kelly was extremely quick to respond to communications and offered up helpful suggestions for local activities and restaurants. I would highly recommend Kelly's home for a girl's trip or a family gathering. I hope to make a return trip sometime soon!

Waterfront condo rentals

Superhost
Condo in Inner Harbor
4.89 out of 5 average rating, 228 reviews

Historic Federal hills urban lifestyle

JohnRating, 5 stars1 week ago
We stayed here for one night while on a trip to Baltimore. The place was easy to find and clean and the host was responsive. As noted in other reviews, there is street noise in the living room. But that is expected when staying downtown and not in a high-rise. Another thing to note is the kitchen is downstairs and reached by narrow windy stairs. Again, nothing bad, but a little inconvenient. Finally, there is no bathroom on the main level. It was an excellent place to stay and we felt safe in the neighborhood with an easy walk to the inner harbor and stadiums. We would stay there again.
Superhost
Condo in Annapolis
4.77 out of 5 average rating, 81 reviews

Amazing Views from Spa Creek 2BD Condo with Pool

ShellyRating, 5 stars3 months ago
Loved our stay at Marie’s condo. The place was clean, well-stocked and cute. Comfortable beds. Unbelievable view of the water and State House. A 10!
Top guest favorite
Condo in Inner Harbor
5 out of 5 average rating, 50 reviews

Harbor Gem

TammyRating, 5 stars5 months ago
This property is in an excellent location in Federal Hill and is walking distance between the big stadiums and the harbor as well as great restaurants. The unit was VERY clean and well kept and we enjoyed an evening watching a movie with the great sound system and large TV. All in all - a fantastic stay!
Top guest favorite
Condo in Annapolis
4.99 out of 5 average rating, 74 reviews

Charming Annapolis Waterfront Condo

BobRating, 5 stars6 days ago
Nice place. I’ll be coming back for sure.
Superhost
Condo in Betterton
4.92 out of 5 average rating, 36 reviews

3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!

CaitlinRating, 5 stars7 months ago
A great sunset view from the balcony, such a nice quiet river/bay beach, peaceful community to walk around. Would stay in again! Would note there’s 1 flight of stairs up as it’s a 2nd floor condo of sorts; and a big hill/stairs down to the beach. However, also a parking lot if needed to drive to the beach. Beach chairs were nice to have. There was no cooking oil but I think we left some :) I would only ask they replace the dining room chair with the hole in the seat. The pool was closed and that was not expected! Adam was very responsive when we messaged.
Top guest favorite
Condo in Betterton
5 out of 5 average rating, 16 reviews

Beach Haven Hideout

TerryRating, 5 stars3 weeks ago
This apartment was perfect for our family get together. Although we had a short stay, every detail made us feel very welcome. Michelle was very helpful and promptly mer our needs.
Guest favorite
Condo in North Beach
4.95 out of 5 average rating, 21 reviews

Unbelievable beach views for 6

DavidRating, 5 stars1 month ago
Our stay at this Airbnb was absolutely wonderful. The location is fantastic right on the water across from the small beach that is available and right on the boardwalk. We used this for a getaway with my wife, and we spent a lot of time just sitting on the balcony people watching and enjoying the beautiful view of the water. The owners were very responsive answering questions and the instructions to get in were very easy. We were walking distance from anywhere you would like to go- restaurants, Café, ice cream, the boardwalk, and the small beach on the bay right across the street. We were also a very short car ride or a bike ride away from another boardwalk on the bay and the Chesapeake beach Railway Trail through the marshes. The condo was very clean and well equipped. Decorations were lovely and everything felt brand new and spacious. There were two bedrooms and while we didn’t use one of them, the bed that we slept in very comfortable. We definitely recommend!
Top guest favorite
Condo in Annapolis
4.96 out of 5 average rating, 274 reviews

Annapolis Waterfront Condo - Unit #: A-203

DavidRating, 5 stars3 days ago
We had a great stay at Jane’s. It’s lovely and comfortable place with a deck that looks out over the water. Location is excellent, walkable to Annapolis and destinations in Eastport. We especially appreciated the scones and wine ready upon arrival. Jane was also a very responsive and welcoming host. Great stay!

Quick stats about waterfront rentals in Annapolis

  • Total rentals

    30 properties

  • Nightly prices starting at

    ﺩ.ﺇ551 before taxes and fees

  • Total number of reviews

    2.4K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with a pool

    10 properties have a pool

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