
Beach house holiday rentals in Middle River
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Top-rated beach house rentals in Middle River
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Popular amenities for Middle River beach house rentals
Beachfront house rentals

Chestertown Watson Family Farm
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.

Peaceful Waterfront Home in Annapolis 3BR 2BA.
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.

Waterfront w/ Private Pier, 35 Mins to Annapolis
We had a wonderful time, great location and loved reading about the house history.

Stay Anchored Chesapeake Bay, 5 bedrooms, 3 bath
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.

*Waterfront Sunset Bayview* sleeps 6
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)

Mac's Waterfront Wonder
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.

Waterfront 5 Bedroom Near BWI/Annapolis/Baltimore
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

Bay Home in Annapolis with Private Dock
Beautiful place, beautiful location. Joel thought of anything you could want.
Beach house rentals with a pool

Naptown Suite
Enjoyed her place and look forward to staying here again.

Waterfront Escape with Pool Nature Lover Paradise
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!

Beautiful Home Near Beach and Patapsco River
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.

StayAhoy! | Swim spa | Fishing
Perfect place to explore DC while also being close to the water (and with an amazing hot tub to relax in)

The Mariner's House
Wonderful property with lots of amenities!

Entire Beach House with Pool and Hot Tub
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!

Bay Bliss House
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.

Waterfront Farmhouse Meets Modern Luxury
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

Cozy home with Screened Porch, Min from Weddings
Great little place. Convenient to the island and the venues

Captain’s Retreat! Newly Renovated - Beach House!
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!

Cheerful & Spacious Shore Life Beauty!
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!!

Chessie Cottage - Chesapeake Bay
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!

Spacious Victorian close to everything in RH!
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.

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

Chester Delight- Fireplace/Deck&Patio+fenced yard
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.

Rock Hall Sharp Street Retreat
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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- Nationals Park
- The White House
- Betterton Beach
- National Mall
- Georgetown University
- Oriole Park at Camden Yards
- National Museum of African American History and Culture
- District Wharf
- Smithsonian National Museum of Natural History
- Dutch Wonderland
- Hampden
- M&T Bank Stadium
- Sandy Point State Park
- Georgetown Waterfront Park
- Patterson Park
- Arlington National Cemetery
- Washington Monument
- Great Falls Park
- National Air and Space Museum
- National Harbor
- Smithsonian American Art Museum
- Lincoln Park
- Maryland Renaissance Festival
- Crystal Beach Manor, Earleville, MD