Beach house holiday rentals in Middle River

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Popular amenities for Middle River beach house rentals

Beachfront house rentals

Top guest favourite
Home in Chestertown
5 out of 5 average rating, 24 reviews

Chestertown Watson Family Farm

AmyRating, 5 stars3 days ago
Words can’t describe how incredible this home/property is! You have the option to just sit by the water or in the hammock watching the birds play and fish jump, or you can do one of the MANY activities Molly has provided for you. Kayaks, canoes, paddle boards, pickleball, yards games, pool activities, etc are all provided. The family room is all windows so it not only provides the most incredible breeze- it is great for enjoying all the sights even if you’re not outside in it. Inside there are tons of toys for kids- you do not have to bring a thing if you have kids. They have inside toys, outside toys, kids life jackets, goggles, water balloons, rafts, floaties, pack and play…. Molly and her family have thought of it ALL. We are already talking about coming back. Molly was the best host- responsive, helpful and inviting.
Top guest favourite
Home in Annapolis
5 out of 5 average rating, 42 reviews

Peaceful Waterfront Home in Annapolis 3BR 2BA.

AndrewRating, 5 stars4 days ago
I would definitely come back here. If you want to unwind, decompress, or just slow-living for a couple of days, you won’t find a better place. The sounds of small waves all day and the birds chirping in the morning were almost as good as the break-taking ocean view. Better than advertised. I could sit in the cabana and read all day.
Guest favourite
Home in Shady Side
4.96 out of 5 average rating, 107 reviews

Waterfront w/ Private Pier, 35 Mins to Annapolis

LeilaRating, 5 stars5 days ago
We had a wonderful time, great location and loved reading about the house history.
Top guest favourite
Home in Perryville
5 out of 5 average rating, 25 reviews

Stay Anchored Chesapeake Bay, 5 bedrooms, 3 bath

Mrs. BrownRating, 5 stars2 months ago
We had a great time. There was plenty of space to move around so that everyone was not in each other's space. The place was very clean and well-stocked with some everyday items you would normally have in your house to cook, shower and clean with. Jen was very responsive with any questions we had. Even the small children loved the house, especially the bunk beds. It was easy to get to places we needed to go to. All 11 of us enjoyed our stay and everyone said they wouldn't mind returning for another family staycation.
Top guest favourite
Home in Chester
5 out of 5 average rating, 39 reviews

*Waterfront Sunset Bayview* sleeps 6

KellyRating, 5 stars2 weeks ago
The perfect mom and teen boy getaway! The house is on the water with gorgeous sunsets and super clean! My boys attempted fishing daily even without any luck. Altho we didn't kayak because of the choppy water, its great location (there's a ladder at the private pier or a public launch a few yards away) We cooked and ate in a few nights and also enjoyed a local spot on the water (The Narrows). The neighborhood was quiet, relaxing and peaceful. We enjoyed a visit to the Chesapeake Environmental center (abt a 12 min drive) which was a hidden treasure. The Chesapeake Outdoors (recommended by our host Jeremiah) was a great find for bait and info from the locals. Morning coffee on the patio and evening sunsets on the pier were some of my favorites, along with the spacious open floor plan (yet privacy with bedrooms). Jeremiah was super responsive and kind! We'll be back to kayak, fish more, enjoy the hot tub coming soon, the serenity and gorgeous sunsets! (maybe we'll even bring dad -LOL)
Guest favourite
Home in Joppatowne
4.95 out of 5 average rating, 40 reviews

Mac's Waterfront Wonder

IsaiahRating, 5 stars4 weeks ago
I’ve been to this location three (3) times now and each time was a pleasure. Communication was great and him allowing a late check out was fantastic (especially with multiple kids, trying to get them ready). I will continue to select this location when we have to come into town for the location, price, communication, and peace of mind knowing exactly what we’ll receive. The only issue with this last stay (and I can only assume it was due to holiday because never happened before) was the trash can being full. I do not suspect this is a regular occurrence as he is very transparent. I’d recommend this place to anyone and again, will be booking multiple times in the future as we will be traveling to MD a lot more.
Guest favourite
Home in Glen Burnie
4.97 out of 5 average rating, 38 reviews

Waterfront 5 Bedroom Near BWI/Annapolis/Baltimore

CarsynRating, 5 stars3 weeks ago
Patrick was deeply kind and helpful to my party. Anytime I had any questions, he was so quick to respond with helpful tips and information. Highly recommend
Top guest favourite
Home in Annapolis
5 out of 5 average rating, 42 reviews

Bay Home in Annapolis with Private Dock

ToddRating, 5 stars3 weeks ago
Beautiful place, beautiful location. Joel thought of anything you could want.

Beach house rentals with a pool

Guest favourite
Home in Annapolis
4.94 out of 5 average rating, 65 reviews

Naptown Suite

LilianRating, 5 stars2 weeks ago
Enjoyed her place and look forward to staying here again.
Home in Stevensville
4.92 out of 5 average rating, 12 reviews

Waterfront Escape with Pool Nature Lover Paradise

JessicaRating, 5 stars6 days ago
Beautiful spot right on the river. It’s a huge house with tons of space for a large group. The fenced in yard makes it ideal for furry family members. This was ideal for a multigenerational get together. Thank you so much!
Superhost
Home in Pasadena
4.87 out of 5 average rating, 61 reviews

Beautiful Home Near Beach and Patapsco River

KristinaRating, 5 stars3 weeks ago
Place was great and large enough to accommodate 2 families (9 total people). We were excited to have a place with a pool but didn’t end up using it because it was a little chilly. Neighborhood was quiet and early morning walks were pleasant. Beds were comfortable too.
Top guest favourite
Home in Edgewater
5 out of 5 average rating, 15 reviews

StayAhoy! | Swim spa | Fishing

AlvaroRating, 5 stars2 months ago
Perfect place to explore DC while also being close to the water (and with an amazing hot tub to relax in)
Top guest favourite
Home in Rock Hall
5 out of 5 average rating, 15 reviews

The Mariner's House

ErinRating, 5 stars1 month ago
Wonderful property with lots of amenities!
Top guest favourite
Home in Edgewater
4.98 out of 5 average rating, 60 reviews

Entire Beach House with Pool and Hot Tub

LisaRating, 5 stars1 week ago
Peggy’s house is beautiful! The inside and the outside are just wonderful! The pool, hot tub are just perfect! Wishing only that the house could sleep 6 adults plus a couple of kids. The location is just perfect!
Top guest favourite
Home in Stevensville
5 out of 5 average rating, 5 reviews

Bay Bliss House

IanRating, 5 stars1 week ago
Beautiful property and well maintained. Unique views and plenty to do when the weather is not so good. Great proximity to Annapolis and the Eastern Shore and plenty of great dining spots on the water.
Guest favourite
Home in Chester
4.95 out of 5 average rating, 96 reviews

Waterfront Farmhouse Meets Modern Luxury

EricaRating, 5 stars6 days ago
Beautiful house! Clean, well maintained, and exactly as described. The host was easy to communicate with and very responsive throughout our stay. The space felt comfortable and welcoming, and everything we needed was thoughtfully provided. We had a great experience and would definitely love to come back!

Private beach house rentals

Guest favourite
Home in Stevensville
4.97 out of 5 average rating, 71 reviews

Cozy home with Screened Porch, Min from Weddings

GregRating, 5 stars1 month ago
Great little place. Convenient to the island and the venues
Guest favourite
Home in Annapolis
4.99 out of 5 average rating, 76 reviews

Captain’s Retreat! Newly Renovated - Beach House!

AmyRating, 5 stars2 weeks ago
This is our second time staying at this property. It is beautiful and has all the amenities you could ask for. The inside and outside living areas are so welcoming that we barely wanted to leave the house! The beds were all very comfortable and the bathrooms are beautiful. Thanks for an amazing stay!
Top guest favourite
Home in Stevensville
4.92 out of 5 average rating, 84 reviews

Cheerful & Spacious Shore Life Beauty!

JaclynRating, 5 stars3 days ago
Our stay at Micheal’s place was wonderful! The home was spotless, and smelled amazing. It was great to walk into the home and smell fresh flowers. I personally loved all the cool plants around the home and decor too. This home had everything we needed, and was so clean and comfortable. It was our first time staying in an Airbnb, and it was really cool. We are hoping all stays can be as awesome as this one. The location was perfect for what we needed also. Micheal was the best host, very responsive, helpful with local recommendations and very kind. We would definitely stay here again. Very thankful we found this home, don’t waste any more time- and book your stay!!
Top guest favourite
Home in Stevensville
5 out of 5 average rating, 21 reviews

Chessie Cottage - Chesapeake Bay

CarolineRating, 5 stars1 month ago
We had the BEST time staying at this beautiful home this past weekend while we were in town for a wedding. The location is absolutely perfect for a peaceful weekend on the water and this house is a DREAM. Thank you so much for letting us stay at your incredible home!
Guest favourite
Home in Rock Hall
4.9 out of 5 average rating, 30 reviews

Spacious Victorian close to everything in RH!

LisaRating, 5 stars1 month ago
Lovely immaculately clean home close to rock hall marinas. The beds were really comfortable and hosts super responsive. Loved all the books and board games they had. Kitchen very well stocked. Highly recommend staying here.
Superhost
Home in Grasonville
4.83 out of 5 average rating, 6 reviews

Relax - Eastern Shore Creek Home - 3 Br, 3.5 Ba

GinnyRating, 5 stars6 days ago
Holly and Nash's home was clean, beautiful, and very spacious for 3 couples. Complete renovation and all new furnishings inside. As listed, all 3 bedrooms are downstairs, along with 2 1/2 bathrooms. The beds (3 queens) were comfortable. The kitchen is gorgeous for meal prep. Kuerig and coffee pods, Nespresso and pods, salt, pepper, dish soap and some spices were provided. Bring anything else you need. Beautiful new grill on deck. Upstairs (using a tight, spiral staircase) housed more seating another TV, pool table, wet bar and another full bath--basically, an adult entertainment area. Beautiful neighborhood. Bridges Restaurant in Kent Narrows (12 min drive) had very good food and service. We visited the cute town of St. Michaels (49 min drive). Communication with Holly was excellent. She was super responsive and helpful, provided suggestions and went the extra mile. Great stay
Top guest favourite
Home in Chester
5 out of 5 average rating, 74 reviews

Chester Delight- Fireplace/Deck&Patio+fenced yard

JessicaRating, 5 stars1 week ago
Had a great stay here with a large group for a local wedding! Would absolutely recommend for anyone needing a comfy spot for multiple guests on the island.
Superhost
Home in Rock Hall
4.94 out of 5 average rating, 35 reviews

Rock Hall Sharp Street Retreat

MicheleRating, 5 stars3 weeks ago
We had a great stay in Rock Hall at Rick’s place for our triathlon race weekend. The house was very clean in a quiet neighborhood. It has a fully equipped kitchen and stocked with extra toiletries; which is always helpful. It’s located in a lovely area by the water with great local restaurants and shops. Communication with Rick was excellent and he’s a very responsive and helpful host.

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