Vacation 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, 196 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, 140 reviews

A comfortable living area is framed by large windows showcasing a vibrant sunset over the water. Soft furnishings include two chairs with decorative pillows and a coffee table. Plants are positioned thoughtfully, enhancing the serene atmosphere.

Home in North Beach

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**

4.97 out of 5 average rating, 130 reviews

A waterfront view is presented at night, featuring a well-lit building along the shoreline. Reflections of surrounding lights dance on the calm water, and a small pier is visible in the foreground, adding to the serene atmosphere.

Apartment 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.

4.98 out of 5 average rating, 154 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.

The image captures a scenic boardwalk extending into the water, lined with ornate lampposts. A vintage-style clock stands prominently at the foreground, while wooden benches are placed along the walkway. The sky is filled with dramatic clouds, illuminated by warm colors of the sunset.

4.94 out of 5 average rating, 162 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.

5 out of 5 average rating, 167 reviews

Home in Shady Side

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silver Water is a serene 5 Star retreat for those who value tranquility over spectacle. Set along the Chesapeake, it offers front-row seats to breathtaking sunsets—where golden light dances across the water. Inside, Nordic-inspired design meets quiet luxury, featuring award-winning mattresses and bedding that promise restorative sleep. Here, time slows, and luxury isn’t just something you see—it’s something you feel. We invite you to read the reviews of so many happy guests.

4.92 out of 5 average rating, 66 reviews

A bright and airy living area features large windows providing expansive views of the Chesapeake Bay. A cozy blue sofa complements a sleek coffee table, while a small dining area with four chairs invites shared meals. Light tile flooring enhances the spacious feel.

Home in North Beach

A Little Piece of Paradise - Waterfront Home

With unobstructed views of the Chesapeake Bay, you can wake up to beautiful sunrises, go for a walk/run by the Bay, return for Pilates/yoga/meditation on our waterfront deck, and enjoy a cappuccino/coffee from the espresso machine. After, relax with your favorite book or walk/bike to charming North Beach, less than 5 minutes away, and enjoy the beach, jet skis/paddleboard rentals, restaurants, live music, spas, parks, and much more. Note: The fireplace is just decorative.

4.99 out of 5 average rating, 210 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!

4.91 out of 5 average rating, 34 reviews

A decor piece shaped like a crab is mounted on a neutral wall. The crab is created from wooden planks painted in varying shades of blue and white, adding a coastal touch to the space.

Home in North Beach

Light of North Beach

This 1 bedroom/1 bathroom apartment has it's own private entry. The house is in a residential neighborhood, but the area is incredibly quiet. A family lives upstairs, so there may be minimal upstairs sounds. However, there are NO shared spaces. It is approximately 1/2 mile to walk to the North Beach boardwalk and pier where you'll find restaurants, boutique shopping and coffee shops. Free on street parking.

Guest suite in Chesapeake Beach

A coastal outdoor space features comfortable chairs arranged on a stone patio, overlooking the calm waters of the Chesapeake Bay. Decorative elements include a fire pit, potted plants, and a fishing net, while a distant pier completes the serene waterfront scene.

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.

A wooden pier extends into calm waters, with posts lining the edges. The sky displays soft hues of pink and blue, while wispy clouds are scattered above. The tranquil scene invites relaxation and contemplation near the Chesapeake Bay.

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.

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Other great vacation rentals in Rose Haven

4.92 out of 5 average rating, 143 reviews

A serene swimming pool is featured in a private outdoor area, surrounded by a stone deck. Two white lounge chairs are positioned nearby, with trees providing a shaded atmosphere. The clear water glistens under a partly cloudy sky, inviting relaxation.

Home in Edgewater

House in Edgewater Maryland

NancyRating, 5 stars1 month ago

Leisa’s home suited our needs to a T!! We were in town to attend a wedding at the London Town and Gardens, which was just a half mile away. The rehearsal dinner in downtown Annapolis was also a short distance away. Everything was fresh and clean, the beds were comfortable, and the showers were really great. The lack of seating in the main room wasn’t a problem for us as we didn’t spend much time there during the day. The area around the pool looked really comfortable and inviting for guests staying during the summer season! Would stay there again.

4.87 out of 5 average rating, 60 reviews

A backyard area features a spacious inground pool, enclosed by a wooden fence for privacy. Comfortable loungers are arranged around the pool, alongside a cozy seating area with a table. Surrounding trees provide a natural backdrop, and the sky is filled with scattered clouds.

Home in Pasadena

Beautiful Home Near Beach and Patapsco River

AmberRating, 5 stars2 weeks ago

We had a great time! Beautiful home in a peaceful beautiful beach town. You can see and hear the ocean from the front of the house. The pool and grill outside were a HUGE plus! We didn’t realize the adjacent house was unavailable and lost 2 queen beds. However, Hieu was more than willing to help resolve the issue. Would definitely stay here again! Thanks!

Cottage in Colonial Beach

An outdoor grilling area is featured with a stainless steel grill positioned beside a wooden staircase. Colorful flowerpots hang nearby, adding a touch of greenery. A hose is coiled beside the grill, with nearby picnic tables visible in the background.

4.93 out of 5 average rating, 169 reviews

Bayside Cottage- In the Town with views

KimberlyRating, 5 stars1 month ago

We thoroughly enjoyed our stay at this AIRBNB. It was walking distance to a nice Mexican Restaurant as well as to a brewery. We spent hours on the front porch in the nice rocking chairs. The back of the property overlooked the water which was beautiful! It was close to everything in town! The house was clean and had all of the necessities. We also enjoyed the front sitting area during the morning. The owner was responsive and helpful! We would definitely recommend this property.

4.98 out of 5 average rating, 128 reviews

Home in Cambridge

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

AnneRating, 5 stars1 month ago

This was a great house for our teammates to stay in for the weekend!

4.88 out of 5 average rating, 124 reviews

A spacious wooden pier extends over the calm water, furnished with five gray Adirondack chairs arranged in a semi-circle. Surrounding rocks add natural texture, while the distant waterfront landscape is visible, featuring additional structures and boats moored along the shore.

Cottage in Pasadena

Chesapeake Cottages- 2 Quaint Waterfront Retreats

JasonRating, 5 stars1 month ago

Great place and nice host. Would stay again definitely worth the price. The property was awesome, great place for a fire pit and barbecue.

4.97 out of 5 average rating, 106 reviews

The exterior of the house is showcased with a charming wrap-around porch, flanked by neatly trimmed landscaping. A three-story structure features shingle siding and multiple large windows that allow ample natural light. The front entrance is accessed via a set of stone steps.

Home in Arlington

Entire family size house steps to ANC & metro walk

SarahRating, 5 stars2 weeks ago

Given graduation on the East coast, location in Arlington/proximity to Georgetown, size and location of Tyler’s home, the value was worth the price! Coming from the Midwest, all was intimidating at first, but we wanted a comfortable, substantial place that would provide true bedroom spaces and adequate bathrooms for each pairing in the family. Tyler’s place did that plus offered two living areas, a large dining and spacious kitchen for conversation, food spread, cooking, mingling, celebrating, etc. We couldn’t have been more pleased with all of the spaces!

4.88 out of 5 average rating, 234 reviews

The house is positioned among leafy trees, featuring numerous large windows that brighten the interior. A spacious deck is visible, along with a hot tub. A stone fire pit surrounded by wooden chairs is located in the foreground, inviting outdoor gatherings.

Home in Montross

Lakefront/Dock, Woods, 3 Beaches, Kayaks, Hot tub

KelliRating, 5 stars1 month ago

I can't express enough how wonderful this home is. We loved it so much that we extended our stay by an extra day! The location was absolutely perfect and met all our family's needs. The private dock quickly became a family favorite, along with the hot tub. It's a quiet, peaceful retreat and the ideal place to recharge with your loved ones. We will definitely be back!