Holiday rentals with a pool in Delaware Bay

The Mint Cottage in Chesapeake City

The Mint Cottage is new to the air bnb market. It is a 3 bedroom Cape Cod on .5 acre lot in Charming Chesapeake City! The 1st floor features a master bedroom suite with updated amenities, large living room and kitchen, PLUS a full hair and makeup station (great for bridal parties). The 2nd floor has two bedrooms- a queen and 2 twin beds. The house features 3 full baths.The back yard has a private swimming pool, fire pit and patio. Terrific location to walk to waterfront, shops, and restaurants!

Boutique suite, Palace in the Woods

⚽️⚽️ WELCOME FIFA ⚽️⚽️ The Palace in the Woods is a “ NO CHORES STAY AIRBNB “ just what you need for a peaceful visit to Cape May County BEACHES & BOARDWALKS . Located in the woods, just ten to fifteen minutes from Sea Isle, Avalon, and Stone Harbor, and the Cape May County ZOO - a little bit further to Ocean City, Wildwood and Cape May. A perfect location for beachgoers, birders, cyclists, and foodies. Please read house rules ( additional rules ). If you have any questions, feel free to ask.

Hot Tub Backyard Oasis! Private Beach, Local Pool

Start your morning soaking in the hot tub or curled up on a heavenly chaise lounge in the sunroom. Just 9 houses from the beach, toss in a fishing line at the ferry jetty, while steps away, your group soaks up the sun on the beach. Enjoy the local pool or a beachfront eatery, both just a few blocks away! Spot a school of dolphins under a red-sky sunset before heading home for grilling & corn hole by the fire, or watching movies on the screened porch! Click our icon for our other Cape May homes!

-The Pool Cottage at The Roundtop Estate-

Experience the ultimate private, romantic retreat tucked away from the hustle and bustle. Our unique hideaway offers over a mile of seclusion from the nearest road, immersing you in nature’s quiet beauty. Relax in the Brand-new Saltwater pool and hear the gentle hums of a train rolling along on the other side of the river. Indulge in the luxurious amenities our property has to offer. Rejuvenate in the hot tub, or warm up by the Breeo Firepit with a Latte from the Breville Espresso Machine.

Charming cottage

Welcome to this over 100 yr young charming cottage located betw New Hope Boro and Peddlers Village. Completely updated and renewed, this stylish open floor plan cutie has all new appliances, offering Bertazonni stove, Pfisher & Pakel fridge &much more! Two generously sized bedrooms on the upper level, full bathroom on first floor. Exquisite views of the professionally landscaped spacious rear yard and in ground pool with lg deck overlooking the grounds & charming paths to guide you thru

THE SORA with Disco, Hot Tub & Pool

Immerse yourself in the timeless beauty of this 12 acre riverfront property. Experience the peaceful beauty of 800+ feet of direct river frontage on the deep Cohansey River. This river leads to the Delaware Bay/ Atlantic Ocean. Situated on the site of the Prestigious Sora Gun Club, this historic 4 Bedroom, 2 1/2 Baths light-filled home with magnificent great room has classical details and distinctive appointments. One of the 4 bedrooms and the 1/2 bath is in the 2 story guest house.

Cozy Woodland Cottage

Enjoy the sounds of nature when you stay in this unique place. Located less than 5 miles from downtown Lewes and Delaware Beaches. The cottage guest house is nestled in the woods adjacent to a tree house overlooking a tranquil pond with a calming fountain sounds. On the main property guests have access to a in ground swimming pool (seasonal) with a 60 foot lap lane and slide, schedule times with hosts.. The backyard also includes an organic garden, playground and 🐔 chickens.

Bay Block Sunsets | Firepit + Zen Den + Cabin

Walk just 1 block to bay sunsets, then come home to a private backyard retreat with fire pit, outdoor kitchen, and bonus spaces you won’t find anywhere else. The main house offers 2 bedrooms, plus a separate camp-style cabin for extra sleeping. Enjoy your morning coffee in the screened-in Zen Den or unwind outside under the stars. A unique, laid-back Cape May stay—perfect for couples, families, and small groups who want space, character, and a true getaway feel.

Waterfront-View of Bay from your Bed-Steamy Sauna

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

Historic Rousby Hall, Waterfront, Pool, Beach

Rousby Hall is a stunning waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee is additional).

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.