Holiday rentals in Rose Haven

4.9 out of 5 average rating, 102 reviews

Quiet Coastal Cottage Escape with Water Views

Want to get away? Come relax and escape in our updated bay view cottage. You'll enjoy stunning sunsets, warm surroundings, and all the amenities you could want in our cozy, peaceful cottage home. You'll find plenty of comfortable spots to relax, inside and out. Located on a quiet street, while still close to the small-town charm and offerings of North Beach, Chesapeake Beach, and Herrington Harbor. Walk along the bay, enjoy the local restaurants, and get ready to relax. Stay a week and save!

4.96 out of 5 average rating, 198 reviews

Townhouse in North Beach

Walk to Beach! King Bed & Free Beach Passes

Welcome to Bay Haven at A Haven Away! Relax in a fully-equipped, plant-filled oasis with a king bed primary suite that our guests love. Its prime location is in walking distance to the beach, restaurants, fresh seafood, and wetlands. We’ll share our beach passes and lots of local recommendations so you can enjoy our little slice of heaven. 12 min walk to the beach, boardwalk, restaurants, and kids play areas in cute North Beach, MD 7 min drive to Herrington Harbor 14 min drive to Tacaro Estate

5 out of 5 average rating, 142 reviews

Waterfront, Dog-friendly, Hot Tub, Peleton

A spectacular, spacious 2 bed, 2.5 bath, pet friendly, waterfront home with stunning, unobstructed views located directly on the Chesapeake Bay. Short walk to beach and pier and several bars and restaurants. A large gourmet kitchen provides everything you'lli need. Workout on the in-house Peleton bike & treadmill. Two cruising bikes are yours to explore town or bike to dinner. Enjoy the private hot tub and 2 gas fireplaces. Solo stove on back deck. **Message host for add’l winter dates**

4.96 out of 5 average rating, 131 reviews

Flat in North Beach

Bayside Oasis of Southern Maryland

1 1/2 blocks from the beautiful Chesapeake Bay. Walk to boardwalk, restaurants and shopping. Beach opens, with some restrictions, May 28, 2021. Free beach pass provided. Quiet friendly town where everyone knows your name. King bed, private bath with shower (no tub). Free WiFi, private off street parking, 45” TCL-Roku TV, Echo Dot, Keurig w/pods for coffee and tea, full kitchen (no dishwasher), beach chairs, beach towels, dishes, flatware, pots pans. Chesapeake Beach is 1-mile south on Rt 262.

4.96 out of 5 average rating, 156 reviews

Bell Estates I Beautiful Cottage I *Beach Passes*

Bell Estates is a newly built corner lot across the street from the bay with minimal views of the water from Master bedroom and front yard. Located in the heart of North Beach in the exclusive Holland Point neighborhood, our home provides a cozy get-a-way for a family looking to escape the hustle and bustle of life. Home is 2 minutes away from Herrington Harbor, Ketch 22, North Beach Boardwalk & more. Enjoy local accessibility to fishing from the boardwalk dock or rent a boat to go crabbing.

4.94 out of 5 average rating, 163 reviews

Club Carp North Beach - Steps to the Bay!

Calendar open for bookings in April 2025! Welcome to Club Carp North Beach. A charming and cozy cottage just 3 blocks to the Boardwalk/Beach. Renovated throughout with 3 bedrooms and 2 full baths. Perfect place for a relaxing, family vacation! This kid-friendly home has a large fenced side yard with swing set, play area for the kiddos, and lots of extra amenities with families in mind. Comfortable outdoor dining area with fire pit and gas grill. Just steps to restaurants, shopping, and bars.

Guest house in Galesville

4.95 out of 5 average rating, 171 reviews

Nautical Charm and relaxing waterview!

Our comfortable and relaxing studio is a quiet retreat with a fantastic view while still in close proximity to Washington DC, Annapolis and Baltimore! Situated in a charming waterfront and sailing community, this separate and private unit has: parking, 1 bath, queen bed, kitchen (limited), TV, high speed WiFi and Bluetooth speaker. Wake up to the cluck cluck of our four resident chickens who are tucked away in their attractive coop. Sit on the porch and take in the view!

4.98 out of 5 average rating, 124 reviews

Home in West River

Cozy waterview home in West River!

Your family will be close to everything when you stay at this centrally-located place. This home is located just 15 miles to Annapolis, 18 miles to the Naval Academy, and 30 miles to the heart of Washington, DC. Less then 8 miles to Rt 214, providing direct access to beltway, and other major highways. This charming home has as spacious fenced in yard, High Speed Internet, TV (Netflix & Hulu), outdoor seating and a fire pit. Want to get away? Bring the whole family!

4.99 out of 5 average rating, 214 reviews

Home in Tracys Landing

The Little Gypsy BoHome

Welcome to our Little Gypsy BoHome on the bay! The house is situated in Southern Anne Arundel County, MD in the quaint waterfront town of Tracy's Landing. Our home sits directly on The Chesapeake Bay with breathtaking views from every window. We offer a saltwater swimming pool, two corn hole game sets, a basketball hoop, beach access, canoe, 2 Paddle Boards, a gas grill, and a steam shower, an outdoor redwood panoramic barrel sauna and a redwood cold plunge!

Guest suite in Chesapeake Beach

4.96 out of 5 average rating, 115 reviews

Nice Guest Suite at Chesapeake Bay

Take it easy at this unique and tranquil getaway. Come and relax in our modern & comfortable guest suite to enjoy a small-town quiet setting with amazing Chesapeake Bay views. A short drive from Washington DC (45 min), Annapolis (30 Min), or Baltimore (1 hr). Groceries, boardwalks, restaurants are all within walking distance. Enjoy cable TV, high-speed Internet, and strong wifi through Xfinity.

4.97 out of 5 average rating, 329 reviews

Waterfront Cottage Near Herrington and North Beach

Escape to Osprey Cottage, a renovated oasis overlooking the Chesapeake Bay. Our home is a 1930s bungalow that has been tastefully updated with modern sensibility, while still preserving its original charm. Streamlined decor, gleaming wood floors, and stunning views from the common spaces, deck, and hot tub invite you to simply relax.

4.77 out of 5 average rating, 22 reviews

Safe Harbor at Herring Bay

Discover the enchanting allure of Safe Harbor at Herring Bay – an impeccably renovated haven tailored for group adventures! Whether you’re immersing yourself in the wonders of Chesapeake Bay or celebrating love at a Herrington Harbor wedding, this resplendent retreat beckons as your ideal home-away-from-home.

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Rose Haven holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Rose Haven

5 out of 5 average rating, 16 reviews

Stunning North Beach Getaway w/ Inground Pool

IsabelRating, 5 stars1 week ago

We had our wedding at the Herrington on the Bay venue Finding Patii’s place was a gem! I had the most wonderful stay—truly one of those rare experiences that stays with you long after you’ve left. It wasn’t just a trip or a few nights in a beautiful place. It was peace. It was comfort. It was healing. From the moment I arrived, I felt something different in the air—something warm, gentle, and full of care. The home was spotless, cozy, and filled with thoughtful details that made me feel instantly at ease. But beyond the beauty of the space, it was the feeling that made it unforgettable. Patti was so communicative and always responsive. She made sure that we will have the best weekend

4.83 out of 5 average rating, 204 reviews

Warm Home Overlooking the Chesapeake Bay

EdRating, 5 stars1 month ago

Pretty home in a great location. You can just park your car and walk everywhere. Well stocked with books, videos and games. Brian communicated well and was very responsive. Recommended.

4.88 out of 5 average rating, 34 reviews

Home in Riva

Waterfront Annapolis Getaway!

NicholeRating, 5 stars1 week ago

Beautiful place with a lovely spot on the south river. Loved the views and how the space allowed the views to really shine. Comfortable, clean, would stay again if I come back to the area. Very peaceful and what I was hoping for. (And not far to town/other things either!)

Holiday home in Chesapeake Beach

4.98 out of 5 average rating, 65 reviews

Chesapeake Bay Apartment w/Free Season Beach Pass!

PatriciaRating, 5 stars3 weeks ago

This was my third visit (second with my daughter and granddaughter). As always, we felt very comfortable. The Airbnb was spotless and had every amenity we needed to feel right at home. As a bonus, we got to meet Inna during our visit and were impressed with her warmth and hospitality. We really enjoyed the homemade cookies too!

4.96 out of 5 average rating, 26 reviews

Home in Shady Side

Ruby Of The Bay

StarlaRating, 5 stars2 weeks ago

Can’t say enough good things about our stay! Beautiful place with everything we could possibly need. The kitchen was well stocked and our host had thought of everything! Clear instructions, great recommendations for local spots etc. And the huge backyard and deck was perfect for us and our pups. Very comfortable beds and pillows too! Finally, host communicated so well and was incredibly accommodating.

4.87 out of 5 average rating, 180 reviews

Full house rental in Twin Beach. 1 bk from the Bay

CarolRating, 5 stars1 week ago

This little Chesapeake Cottage is a gem. Located on the border of restaurants on 7th St it's also a stone's throw to the Bay. I could see boats in the Bay while chilling on the wonderful porch. Everything is bright and beachy in the kitchen area. The LR is roomy and cozy. The front porch is a beach house must; it's bright and airy after the heat of the day. I slept soundly in the comfortable bed and luxuriated under the showerhead. I've visited North Beach for over 30 years living locally. I've always dreamed of renting a little cottage close to the Bay and staying a week. Mission accomplished with resounding success. Thank you Heather and Jan!

5 out of 5 average rating, 11 reviews

Home in Shady Side

The Wise Quack 2 - A Taste of the Chesapeake Bay!

ToddRating, 5 stars2 weeks ago

The Wise Quack 2 is a cozy, clean Airbnb steps from the Chesapeake Bay, perfect for a relaxing getaway. Sidco’s warm hospitality, comfy beds, and thoughtful touches like the deep tub and hammock make it a gem. The quiet Shady Side location and quick host responses ensure a delightful stay.