Beach house holiday rentals in Chesapeake Beach

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Top-rated beach house rentals in Chesapeake Beach

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Guest favourite

Home in Woolford

4.99 out of 5 average rating, 129 reviews

Starboard on McKeil Point, w/heated pool & hot tub

Starboard on McKeil Point is a beautiful 5 bedroom, 3.5 bath private waterfront home on five acres overlooking the wide water of Fishing Creek - the perfect compound for families & groups. The house features water views from every turn. Outdoor amenities include a generous screened-in porch, a private dock, a sandy beach, a heated salt water pool & a hot tub. There is also a one bedroom apartment on the second floor of the carpenter's barn which sleeps 6 and includes a full bath and kitchenette.

Guest favourite

Home in Lusby

4.98 out of 5 average rating, 101 reviews

Waterfront with sweeping bay view & private beach

Year-round private beach oasis on Chesapeake Bay! Perfect Fall & Winter Escape. An hour from DC beltway & world away. Recharge & relax to the sound of waves & sailboats. Spacious & fully renovated, with modern features, ample outdoor terraces. Enjoy long walks, nature spotting (bald eagles, rays, dolphins), shark tooth collecting. Kayaks provided! Short drive to Solomons Island, and local amenities: restaurants, bars, store, national parks & vineyards. No parties or events. Only relaxing.

Top Guest favourite

Home in Grasonville

4.95 out of 5 average rating, 281 reviews

River Front, Private Single Family Home

Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away

Superhost

Home in Saint Leonard

4.89 out of 5 average rating, 133 reviews

Perfect Bay and Beach Getaway one hour from DC!

Our waterfront home with sweeping views of the Chesapeake Bay is close to beaches, the Flag Harbor Marina, Solomon's Island, Flag Pond Nature Preserve and Calvert Cliffs State Park. You’ll love the spectacular sunrises/sunsets over the Bay, diving ospreys and eagles, and exploring the bay by kayak, canoe, or paddle board. Our house is great for families (with kids), groups, and well-mannered dogs. New in 2023: we will be replaced the upstairs HVAC system, baby proofing, and fall 2023 paint

Top Guest favourite

Home in Montross

4.98 out of 5 average rating, 169 reviews

Beach Please! River cottage w/private beach & dock

Come unwind at "Beach, Please!" Our renovated cottage on the river with a private beach and dock is waiting for you! What's there to do? There's boating, fishing, crabbing, bird watching, tanning, and hammock-napping. Need more? Ok, antique shops, breweries, wineries, live music, crab boils and oyster fests. Still need more? Cornhole, can jam, horseshoes, hiking, and swimming and tennis at the community pool. That's not all, so just trust us - you will LOVE your time in Montross, Virginia!

Guest favourite

Home in Shady Side

4.96 out of 5 average rating, 112 reviews

Waterfront w/ Private Pier, 35 Mins to Annapolis

Located 35 minutes from Annapolis and 45 minutes from Washington DC, Shady Side is a quaint town. This waterfront home is perfect for families or small groups looking to enjoy a relaxing getaway on the Chesapeake Bay. Enjoy the large wrap-around screened in porch and private pier with ladder for easy access for swimming. Large yard, and an incredible view of the Bay Bridge. Free public boat ramp 5 min away in Parish Creek. Listed for 8 people max but contact us for approval of 1-2 more.

Top Guest favourite

Home in Lusby

4.95 out of 5 average rating, 178 reviews

Waterfront Home on the Chesapeake Bay-Pvt Beach

A commanding view of the Chesapeake Bay. Enjoy walking the beach to Calvert Cliffs, bike to parks, art and cultural events. Enjoy the private beach with plenty of fine sand and gentle waves, great for teaching little one's water skills, playing with your canine companion or fishing/crabbing off the beach. You’ll love this waterfront hideaway because of the location, views, and the ambiance. My place is suburb for couples, solo adventurers, business travelers, families, and canine friends.

Top Guest favourite

Home in Piney Point

5 out of 5 average rating, 129 reviews

Living on Island Time

Relax with the whole family and spend life on Island Time. Full bar set up with ice maker and wine refrigerator. Private pier, paddle boards and firepit. Unwind on St Goerge Island or head out to one of the local eateries for some southern Maryland faire. Inside you have 2 spacious rooms, 2 bathrooms. A massive island for cooking, card playing or just great conversations with endless views. Crabbing, fishing. The Neighbors have 2 Great Danes and a cat that you may see occasionally

Guest favourite

Home in Solomons

4.89 out of 5 average rating, 148 reviews

Perfect spot for a Vacay!

Be an Islander! This incredibly well-positioned home has 6-car parking and views of the Patuxent River and Solomons Island. Enjoy year-round life on the water. This is the dream vacation spot with so much to offer. Watch fireworks, fish, crab, enjoy beautiful sunrises & sunsets from the private pier or while relaxing in the gazebo. The local marina, shops, bars, and restaurants are within walking distance. Enjoy the best seafood Southern Maryland has to offer, a crab cake to die for!

Top Guest favourite

Home in St. Leonard

4.92 out of 5 average rating, 186 reviews

Cozy Cottage on the Chesapeake Bay

Tranquility supreme. Sit on the terrace and gaze at the Chesapeake Bay. Sandy beach -- just 50 steps from front door; quiet residential area; nearby antiquing & fishing; Only 75 min. from DC. Finish your book or just replenish your spirit. Enjoy. Oh, one more thing — looking for the perfect place for a retreat for your small DC team? Strategic planning will be even more creative and enjoyable when you have the Chesapeake Bay as your muse. Note: This property is for non-smokers.

Top Guest favourite

Home in Tracys Landing

4.99 out of 5 average rating, 231 reviews

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!

Top Guest favourite

Home in Cambridge

4.99 out of 5 average rating, 137 reviews

Waterfront, Private Pier, Sleeps 10, 4 bedrooms

Escape to our charming & serene waterfront retreat, perfectly situated on the picturesque Choptank River. This 4-bedroom home accommodates 10 guests w/ 7 comfortable beds & offers the ideal blend of relaxation & adventure for everyone. Our property comes fully equipped with bikes, kayaks, paddleboards & yard games for endless fun. Unwind and relax on the new pier. The river offers gorgeous sunrises and sunsets. Your perfect waterfront getaway awaits you!