Beachfront holiday rental in Rose Haven

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Popular amenities for Rose Haven beachfront rentals

Pet-friendly beachfront home rentals

Guest favourite
Home in North Beach
4.93 out of 5 average rating, 67 reviews

A Little Piece of Paradise - Waterfront Home

LisaRating, 5 stars1 week ago
It was a great stay and a perfect location for our quick family back east. It was very comfortable, clean and a the right size for our family of 4. It was nice to have our own place to stay and not to far from our family. We didn’t spend much time in the town but it looked cute with shops, cafes and restaurants. We had great communication with Maria, she was very quick to respond. Thanks for a great and comfortable stay!!
Superhost
Apartment in Cambridge
4.91 out of 5 average rating, 129 reviews

Little Slice of Cambridge. Newly listed, 2 bedroom

JoanRating, 5 stars1 week ago
We rented A Little Slice of Cambridge because of the Iron Man competition held that weekend. It was convenient to the venue...and allowed to walk to the competition and nearby restaurants. Pamela was a wonderful host...communicating easily. The rental was well stocked with toiletries, dishes, pots and pans and extras. The house was comfy and the beds comfortable. An enjoyable stay...unfortunately, we weren't able to stay for more sightseeing...although I did walk down to the Lighthouse and beautiful wharf.
Guest favourite
Cottage in Pasadena
4.97 out of 5 average rating, 175 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

EmilyRating, 5 stars3 weeks ago
Keith’s water view cottage is so beautiful and peaceful. My husband and I had a lovely long weekend stay with our little dog. Even with the storms that passed through the bay we felt extremely safe and cozy throughout our stay. Keith was very responsive and flexible with checkin /checkout. Would definitely stay again!! Thanks Keith !
Guest favourite
Guesthouse in Annapolis
4.86 out of 5 average rating, 101 reviews

Chesapeake Bay Escape | Cozy Retreat

JacquelineRating, 5 stars4 weeks ago
We loved our weekend stay at Melanie’s place!! It was clean, easy to access and a lovely location!! She was super helpful with our questions about the areas and places she recommended. Definitely recommend!!
Superhost
Cottage in Port Republic
4.79 out of 5 average rating, 185 reviews

Shewell’s Cottage by the Shore

NoraRating, 5 stars2 months ago
What a gem of a place! So cute and cozy. A great location! Loved all the natural light that came in through the big windows. Everything was so clean yet very comfortable. Enjoyed walking the beach. Found sharks teeth and sea glass! Such a great surprise to find such treasures! Lisa was so very kind and accommodating. Appreciated the extras like coffee, bottled water, shampoo etc and she brought some wood for a cozy fire. They really worked hard at making our stay very comfortable. Definitely will be coming back. But plan on a longer stay because there is so much more in the area to check out!
Top Guest favourite
Home in Tilghman Island
5 out of 5 average rating, 18 reviews

Panoramic water views

MeganRating, 5 stars3 weeks ago
This was one of the loveliest Air BnBs I’ve had the pleasure of staying at. The photos don’t do it justice. A warm, welcoming and cozy home, filled with sunlight and stunning water views from every window. You literally feel like you’re on a boat! Comfortable furnishings and beds, a super well-stocked kitchen with lovely dishes and decor, bikes, kayaks, gas grill… everything you could want. The Tilghman Island General Store was just a short walk through a lovely neighborhood with the friendliest people. Breakfast at Two if by Sea was amazing! And crab cakes at Gina’s on the Bridge were delish. My dog loved the stay too! Tilghman Island is a peaceful treasure in today’s crazy world.
Top Guest favourite
Cottage in North Beach
4.94 out of 5 average rating, 50 reviews

Cozy Waterfront Cottage - Pet Friendly

LisaRating, 5 stars3 days ago
This was a fantastic vacation rental- the kids’ favorite yet! You can’t beat the views and the proximity to the beach and shops. There is also a playground, library, ice cream shop, and pizza just a block away. The host had snacks, water, and milk available for us and the kids when we arrived, which was very welcome after a long car ride! And having beach chairs and beach umbrellas for use made our beach days so much better! We brought our paddle board and launched it off the local beach which was quite fun. Annapolis and DC are both far drive and, when we weren’t enjoying the local amenities, we found plenty to do just an hour drive or less away. I highly recommend this rental. Thank you for allowing us to rent your lovely home and we will definitely be back
Top Guest favourite
Cottage in Lusby
4.98 out of 5 average rating, 278 reviews

Gettin to the point. ( Cove Point Beach)

BarbRating, 5 stars2 days ago
Have now stayed here twice and love it so much we just booked our next visit. It's a lovely and comfortable home!

Beachfront home rentals with a pool

Top Guest favourite
Home in Chestertown
5 out of 5 average rating, 23 reviews

Chestertown Watson Family Farm

LukeRating, 5 stars1 day ago
We had a great time. The view is one of the best we have stayed at. The hosts have thought of almost everything you could need or want to do. Our kids wanted to come back just to do more of the activities. The interior is obviously dated but it is thoughtful, functional, and clean. We felt cozy and at home! We will be back!
Home in Stevensville
4.88 out of 5 average rating, 8 reviews

Waterfront Escape with Pool Nature Lover Paradise

AnaRating, 5 stars2 weeks ago
Hosted my intimate wedding at Nancy’s home and we had an amazing weekend! My family & closest friends loved the home, location, amenities & the coziness of the house. Perfect for a lil vacation with friends & family and very kid friendly. Absolutely loved my stay. Thanks for letting us stay at your place, view was incredible and so much space for a big group. Will definitely come back and recommend 100%
Top Guest favourite
Home in Lusby
5 out of 5 average rating, 16 reviews

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

DeniseRating, 5 stars7 months ago
The area and view are beautiful and the home's decor is welcoming. The home was very comfortable for our family group and had a VERY well-stocked kitchen. The master bed was VERY comfortable as were the rest of the beds. My husband and I slept well. We all felt at home. MJ was very responsive when I had questions and communicated about the property in clear, concise language. The host provided many outdoor recreation opportunities, which included paddleboards, kayaks, and life jackets. There was a nice sized pool but we were visiting out of season so we did not use it. The exercise room downstairs has a lot of equipment. We all enjoyed our time together. Our family is asking to come back again next year. Thanks for a great stay!
Top Guest favourite
Place to stay in Annapolis
4.94 out of 5 average rating, 121 reviews

Chesapeake Bay View 3BR/2BA Duplex*Hot Tub*

PaulRating, 5 stars1 month ago
We found Paul’s home very comfortable and accommodating. Paul was accessible when we reached out to him and he communicated well with us. It was a very nice location with a fantastic view of the bay, as we hoped for.
Superhost
Home in Royal Oak
4.67 out of 5 average rating, 3 reviews

Waterfront, Pool, Dock, Hot Tub.Stunning Views! A

HeatherRating, 5 stars3 weeks ago
We had a fantastic stay at this Chesapeake Bay home for our annual family trip! The outdoor space is a total standout—beautiful views, a great pool, and everything we needed for kayaking, crabbing, and making memories by the water. We especially loved the roomy layout, the well-stocked kitchen, and the big dining table that made family dinners a highlight each night. The house is full of personality, with tons of unique decor and interesting items throughout—definitely made for a fun and memorable stay, though we did find ourselves having to keep a very close eye on the kids around all the treasures! Overall, it was a wonderful trip and we’d absolutely book again!
Guest favourite
Cottage in Neavitt
4.88 out of 5 average rating, 24 reviews

Grandview - Cottage 1B, Queen Bed, Pool, Bay, WIFI

HeatherRating, 5 stars4 weeks ago
A cozy and quiet cottage right along the water. The kitchen is very well stocked. You can find any pot or utensil you may need. The best part of the cottage is the sun room, it was a great place to enjoy a glass of wine in the evening or enjoy a cup of coffee in the morning and soak in the sparkling water and peaceful surroundings. A peaceful spot away from everything, but a short 15 minute drive into St. Michaels. The road to the cottage is a bit rough, a small car has to navigate it with some care.
Superhost
Home in Woolford

"Endless Summer" on the Chesapeake!

JeannineRating, 5 stars1 month ago
great location and very clean!
Superhost
Home in Saint Michaels
4.58 out of 5 average rating, 12 reviews

10 Minutes to St. Michaels with a Private Pool

SarahRating, 5 stars1 day ago
This home gave us something we hadn’t experienced before: a vacation with two small children that actually felt like a vacation! From the moment we arrived, we were blown away by how perfectly suited the home is for families with young kids. The pool has a shallow platform area that our toddlers could safely enjoy, and the expansive, beautifully maintained yard gave them plenty of space to run and play freely along with a swing and hammock. Inside, the house is just as exceptional. The layout is thoughtfully designed, with a separate bedroom wing that allowed us to put the kids to bed and then relax in the evenings without worrying about noise. Every detail felt intentional and welcoming, and the water views were absolutely stunning. The home is just a short drive from the charming town of St. Michael’s, which we loved exploring. This trip was such a joy for our entire family, and we’re already talking about when we can come back. Highly, highly recommend!

Private beachfront home rentals

Top Guest favourite
Apartment in Broomes Island
5 out of 5 average rating, 42 reviews

Beautiful waterfront apartment in Broomes Island

LisaRating, 5 stars3 weeks ago
We loved our stay! Len and Shannon are incredible hosts! Every sunset from the deck was perfect! Having the convenience store below was also nice for grabbing a snack. We wish we could have stayed longer! I would highly recommend the stay! A++++++++++++++
Top Guest favourite
Home in Edgewater
5 out of 5 average rating, 56 reviews

Waterfront South River Edgewater Sunrises & Beach!

KatRating, 5 stars8 months ago
We had a lovely stay at Heather’s place. The house was clean, comfortable, and we felt taken care of. The porch with the view of the water and sunrises was so relaxing. Visiting during the off-season was peaceful, but there was still plenty to do in the area. We couldn’t have asked for a better getaway weekend.
Guest favourite
Home in Oxford
4.96 out of 5 average rating, 213 reviews

The Oxford House

GregRating, 5 stars1 week ago
This place is nicely furnished and the kitchen/dining area are very well supplied. We always enjoy our time in Oxford and the surrounding area and Suzanne Marie's place made it very comfortable. Walkable to the market, coffee shop, ice cream shop and 2 restaurants.
Top Guest favourite
Houseboat in Stevensville
4.94 out of 5 average rating, 53 reviews

Chesapeake Houseboat Getaway

RomaRating, 5 stars1 month ago
I loved Julia’s Arc. First time I Airbnb’d in a houseboat; won’t be my last. I loved this experience! Julia’s was inviting, comfortable, well appointed. I enjoyed sitting on the upper deck but even sitting inside with the blinds up and the windows open afforded the sounds of the water while enjoying the view of the marina and boats. I wish I had more time here to explore more. This was exactly what I needed for some time alone.
Guest favourite
Cottage in Annapolis
5 out of 5 average rating, 9 reviews

Wonderful Cottage Nestled On Chesapeake Bay

EdmondRating, 5 stars2 weeks ago
The cottage looks just like the photos. Very quiet and peaceful location. They provided a binder that catalogs anything you may need during your stay. EXCELLENT communication. Easiest Check out EVER. Would certainly book again if we return to the area.
Guest favourite
Home in Benedict
4.9 out of 5 average rating, 30 reviews

Bright airy waterfront getaway

StephanieRating, 5 stars4 weeks ago
The lake was the perfect serenity we needed and fun sea life to enjoy. The house felt a little crowded for 4 people but it had everything we needed and our host had plenty of “extras” to make our trip complete
Top Guest favourite
Cottage in Annapolis
4.98 out of 5 average rating, 47 reviews

Charming Waterfront Cottage on Historic Property

LizRating, 5 stars1 month ago
What an absolute treat to stay at the Cottage at Whitehall. We had such a lovely time, we stayed an extra day! Ty & Susie are gracious hosts and we were so excited to get a tour of the mansion and explore the grounds. The private beach at the back of the cottage is phenomenal, please take the canoe out - or even go for a swim. The sand is silky and soft, it was like a giant swimming pool nearly all to yourself. My husband enjoyed the canoe immensely (the waves scare me, so it wasn’t too much for me / but if you canoe out on the Meredith River it’s much calmer). If you fish - bring your fishing gear!! (Check local laws first, of course) Absolutely do not hesitate to book here if you have the chance, highly recommended 😍
Top Guest favourite
Home in Edgewater
5 out of 5 average rating, 14 reviews

Waterfront home on the Bay

Steven JayRating, 5 stars1 week ago
This is one of the best Airbnb experiences we have ever had. Teresa’s house was 10 out of 10. Everything was absolutely fantastic. Very clean with everything we needed. The view was spectacular!!!! We absolutely loved everything especially the bald eagle that flew by on our last morning. I highly highly recommend staying here and next time we make the trip up there from Texas it will be scheduled based on the availability of Teresa’s house. Thank you for being a great host!!

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