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Waterfront holiday rentals in Annapolis

Find and book unique waterfront rentals on Airbnb

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Popular amenities for waterfront rentals in Annapolis

Waterfront apartment rentals

Guest favourite
Flat in Springfield
4.89 out of 5 average rating, 114 reviews

Lg 2bd/1ba | Chef's Kitch | Peaceful Parklike Yard

JodyRating, 5 stars1 month ago
Our stay was awesome. Amy and Owen were friendly, super responsive, and very helpful. They also helped us out with kids things and other items we needed, even brought us down sleds when it snowed for the kids to use. It was also very comfortable there and it had all the amenities we needed for a month long stay. We would definitely stay here again!
Guest favourite
Flat in Pasadena
5 out of 5 average rating, 15 reviews

Relaxing Waterfront Apartment!

MichaelRating, 5 stars4 days ago
Beautiful spot right on the water. Our whole family loved it. We would absolutely stay here again. Thanks Jeanne!
Top guest favourite
Flat 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
Flat 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
Flat 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 favourite
Flat in Stevensville
5 out of 5 average rating, 42 reviews

Heron Roost

AdamRating, 5 stars2 weeks ago
We had a fantastic stay! The place was spotless, exactly as described, and in a great location on Kent Island. Easy access to rest of MD. The host was super responsive and made check-in a breeze. Definitely recommend and would love to stay again!
Top guest favourite
Flat in Essex
4.97 out of 5 average rating, 264 reviews

A unique place on sue creek

MoniqueRating, 5 stars1 day 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 favourite
Flat 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.

Waterfront house rentals

Guest favourite
Home in Woolford
4.93 out of 5 average rating, 145 reviews

Waterfront Getaway with Dock

TysheraRating, 5 stars1 month ago
Went to location as a family get-away. The views were breathtaking, who knew we would find such peace so close to home. Literally sat on the couch and stared outside for hours. The home was small enough to enjoy each other's company but large enough to allow everyone the time and space to do their own thing. The price was more than reasonable and we can't wait to return.
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!
Superhost
Home in Rosedale
4.88 out of 5 average rating, 16 reviews

Waterfront Retreat close to Downtown Baltimore

AkishaRating, 5 stars6 months ago
Beautiful home!! Pictures don’t do it justice! Lake view every morning was serene and gorgeous. Very updated. Large bathroom and VERY clean home overall. Carlene was a great responsive host and was very accommodating. Our new fav rental option in Baltimore!!
Top guest favourite
Home in Woolford
5 out of 5 average rating, 218 reviews

Newly Renovated Modern 3 bed 2 bath Water Front

SarahRating, 5 stars4 months ago
The Riverhouse exceeded our expectations and deserved the 5 or more rating! The place was immaculate, had a gorgeous river view, and the hosts were extremely accommodating and responsive! Highly recommended!
Top guest favourite
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 favourite
Home in Shady Side
5 out of 5 average rating, 164 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

DeanneRating, 5 stars3 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!!
Superhost
Home in Shady Side
4.88 out of 5 average rating, 181 reviews

Cattail Landing- Photographer's Waterfront Retreat

AshleyRating, 5 stars6 months ago
We had a wonderful time during our visit. The peaceful environment on the water was just what our group needed. Thank you!
Top guest favourite
Home in Cambridge
4.98 out of 5 average rating, 46 reviews

WaterfrontHotTubPvtPierFirePitKayakGrillQuietHouse

KatieRating, 5 starstoday
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.

Waterfront apartment rentals

Guest favourite
Apartment 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
Apartment 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 favourite
Apartment 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 favourite
Apartment in Annapolis
4.99 out of 5 average rating, 74 reviews

Charming Annapolis Waterfront Condo

BobRating, 5 stars5 days ago
Nice place. I’ll be coming back for sure.
Superhost
Apartment 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.
Superhost
Apartment in Annapolis
4.6 out of 5 average rating, 5 reviews

Book for CW25 Walk to Main St w pool & parking

George And MicheleRating, 5 stars18 months ago
A beautiful location with plenty of room for two couples. Nice balcony and panoramic view of the historical Annapolis waterfront and state capital. Fantastic restaurants and attractions within easy walking distance. Super parking too!!!
Superhost
Apartment in Georgetown
4.7 out of 5 average rating, 82 reviews

Historical Georgetown Modern Penthouse 12 min DCA

OksanaRating, 5 stars2 weeks ago
This flat is right in the heart of Georgetown. Walking distance to all restaurants and bakeries if you are into that kind of thing :) This place is located in an old area and is part of a historic building, so be mindful of that and don’t expect modern elevators or wide space parking lots. You are in historical area :) I stayed here with my almost 80 year old parents and they did well on stairs to get to the apartment, no problem. The apartment is clean and has all you need for a short stay. There is no real living room there, it’s a combination of super nice kitchen and high chairs at the bar area. I found this place very cozy and well laid out. The host is the best! Super helpful, very responsive and very kind! Thank you so much for everything and we will be back again!
Top guest favourite
Apartment 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.

Quick stats about waterfront rentals in Annapolis

  • Total rentals

    30 properties

  • Nightly prices starting at

    £112 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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