Holiday rentals with outdoor seating in North Beach

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!

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

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.

Luxe Winter Retreat- 5 Star

Winter at The Cottage at Silver Water is calm, clear, and quietly beautiful. Snow-dusted views and crystal-blue skies frame the Chesapeake as migrating waterfowl glide across the water. As the day ends, golden hour washes the bay in soft light, often finishing with a vivid winter sunset—quiet and unforgettable. Inside, Nordic-inspired design, a cozy fireplace, and sumptuous bedding create a warm retreat for deeply restorative rest. Discover why so many guests return by reading our reviews.

Calico Cottage Guest House, king bed, free parking

Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.

Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces

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 dates**

Cozy Cottage, Winter Promo, Hot Tub, BlockToBeach

Fall/Winter promo: Book two nights, get one free on midweek stays (Monday thru Thursday)! Book two nights, get 50% off third night on weekend stays. Send a message after booking, and the promo night will be added. Relax at this renovated cottage with views of the Chesapeake Bay! Features large screened deck, hot tub, around corner from private community beach where you can find fossils and shark teeth! (4 min drive to larger community beach.) Message for multi-night and monthly rates.

Annapolis Garden Suite

Welcome! We’re tucked away on a forested residential street, roughly a 7 minute drive from restaurants, coffee shops and all that Annapolis has to offer. 15m from the coast, 30m from Baltimore and 35m from DC. Tl;dr: this is a private ground-level guest suite with 3 beds, 2 bedrooms, 1 desk (optional standing desk), 1 kitchen with oven, dishwasher + Nespresso/pour over, 2 tvs, laundry room with washer/dryer, fast wifi, a pool, patio and a forest view. We live on the top floor.

Chic Loft | Rest and Relax l Private Beach Access

Outage worker welcome: 1 guest. orefer night sleeper as we will come and go thru garage during the day and the dog will bark..We cant guarantee quiet daytime sleeping conditions Relax in a chic, private loft just 5 minutes from Chesapeake beaches and 10 minutes from Solomons Island & Calvert Cliffs. Enjoy our private, above-garage hideaway with private beach access, fast WiFi, Smart TV, and cozy touches that make you feel at home.

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.

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, a basketball hoop, beach access, a canoe, a gas grill, a steam shower, and an outdoor redwood infrared barrel sauna.

Historic Downtown in-law suite

This special place is close to everything. One block to the Naval Academy and one block to all the historic and downtown attractions. This in-law suite has a queen bed, full bath, sauna, kitchenette, seating area, and desk/dining table. Welcoming separate, quiet entrance with access to a lovely patio with seating and firepit. Twin bed can be set up and made up at guest request.