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Chesapeake Bay Vacation Rentals With Private Pool

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Tilghman Time Tilghman Md

Kahana Sunset #B4B Beachfront Oceanview Vacation Rental Condo on a Private Bay in Kahana Maui

Bathrooms: 2 & 1 Half Baths

Minimum Stay: 3 nights

Within minutes of historic St Michaels this 4 BEDROOM waterfront home is located on Tilghman Island. A watermens community offering everything you need to relax and enjoy a REAL Eastern Shore vacation. A private dock on the Knapps Narrows is just the spot to launch your kayak or dock your boat. The kids will love fishing and crabbing right on the waters edge. When inside this tastefully decorated coastal property you will feel right at home. The first floor with wide open floor plan, well appointed kitchen and large island is perfect for gathering with family and friends. The first floor master en-suite with water view will be the room everyone fights over!. On the second floor there is 3 additional bedrooms, full bath and a cozy loft to sneak away to. Walking distance of marinas and restaurants this waterfront home is the perfect place to put your feet up and watch the boats cruising the Knapps Narrows. We call this home Tilghman Time because when your on Tilghman one does not pay attention to time. Your having so much fun and relaxing that time sort of stands still.

Stunning Waterscapes In Chesapeake Bay

Straddling both Maryland and Virginia, Chesapeake Bay takes the crown of the largest estuary in the United States. Its shoreline is dotted with rolling farmlands and lush wetlands, as well as a handful of state parks and sandy beaches. You’ll also find a handful of friendly towns and villages, each with their own unique personalities. Just across the Chesapeake Bay Bridge is the Eastern Shore, famous for its mouth-wateringly fresh seafood. If you want to reel in your own catch of the day, Chesapeake Bay vacation rentals unlock access to a stunning line-up of waterfront properties on the Eastern Shore.

Simply Relaxing The Shore Way

You will find Virginias Eastern Shore offers an opportunity for a unique coastal vacation experience amidst pristine, natural beauty, with a nearly endless list of great things to do. From A for Artists Galleries to Z for Zesty Clam Dip, youll have plenty to do in our beautiful rural, coastal setting. Long walks at sunset on uncrowded beaches, kayaking out to our unique chain of Barrier Islands, reeling in a fat tuna on a deep sea fishing expedition, crabbing & fishing in the Chesapeake Bay, trying out the fabulous new golf courses designed by Arnold Palmer & Jack Nicklaus, bird watching at one of our 4 wildlife refuges, finding a treasure at one of our antique shops, enjoying a sumptuous dinner at one of our gourmet restaurants, exploring our quaint little towns.

Rentals for the following homes are provided by Blue Heron Vacation Rentals the management and rental leasing agent representing the landlords of these properties. You can contact Blue Heron Vacation Rentals at 757-678-5277 or reach them by email at to book a reservation for one of their Simply Relaxing the Shore Way homes. So whether you want to simply relax with on the beach with some sun and sand or you want to be Busy-Busy, call them today at 757-678-5277 to get a unique Eastern Shore Vacation Experience started for your group.

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Chesapeake Bay Vacation Rentals & Rent By Owner Homes

There are more than 8367 vacation rentals that are available in Chesapeake Bay. These rentals, including vacation rentals, Rent By Owner Homes and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Chesapeake Bay.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Chesapeake Bay, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner , and other popular Airbnb-style properties in Chesapeake Bay. Places to stay near Chesapeake Bay are 1275.72 ft² on average, with prices averaging $390 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in Chesapeake Bay with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Chesapeake Bay Vacation Rentals

501 Chesapeake House Sea Colony
  • Plan your getaway & search Chesapeake Bay holiday rentals by owner

    Find the perfect Chesapeake Bay home rentals to stay, from beach homes to villas to condos and more.

  • No booking or services fees Chesapeake Bay vacation home rentals

    Save up to 20% over other Chesapeake Bay home rentals by owner website by booking directly.

  • Contact a few vacation rentals in Chesapeake Bay directly

    Inquire on 3 or more Chesapeake Bay vacation homes by owner to increase your chances of booking.

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Kent Island Beach House Llc

We rented the KIBH I, II, and Golf House for our bridal parties for our wedding on 9/18/21. They had a 3-night minimum which was awesome for the timing for us. Donna discussed the pros/cons of booking direct vs through VRBO or AirBNB. She was so incredibly helpful with my questions about the house and also giving suggestions for food and things to do in the area. The houses were more than reasonably priced, the accommodations were perfect – beds definitely exceeded our comfort expectations, everything was in great working order, and the houses were just perfect for our needs. The location was very close to our wedding venue and there was plenty of parking at each. We even blew a fuse and Donna answered and walked us through finding the circuit breaker.The lighting in house I was perfect for getting the bridesmaids hair and makeup done. The boys even hung out outside and played volleyball while we got ready. Lots of DoorDash options available to the house addre…

We had an amazing time at the Kent Island Beach house! We celebrated a 30th birthday with family and friends, enjoyed a lovely dinner and the beach at Kentmorr, had a impromptu beach volleyball tournament, and had delicious crabs . Donna was there for any questions I had leading up to the trip and the house itself was even better than I expected. Would love to return in the future.

Happy Placetilghman Island Md

Bathrooms: 2 & 1 Half Bath

Minimum Stay: 3 nights

Peaceful retreat with breathtaking sunsets located on Tilghman Island. Kayaking, sailing, fishing, are all with in 100 feet of this beautiful home. Take a walk or a Bike ride to explore this unique island community. Visit Phillips Wharf Environmental Center and the Watermens Museum to learn all about life on the Chesapeake Bay. Enjoy dining in one of the islands many restaurants, rent a jet ski or paddle board at the marina. But then again, you may want to just sit on the waters edge and enjoy the tranquility of this unique property.

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Can I Find Short Term Rentals In Chesapeake Bay

If you have itchy feet but not a whole lot of time, there are short-term rental properties in Chesapeake Bay where you can spend a few days or so seeing the sights. Here are just two getaways that’ll help you quench your wanderlust:

  • “Brand New Renovation In Historic District With 2 Parking Spots” in Puerto de la Cruz is an excellent place to base yourself if you love sightseeing. Stay here and you’ll be within reach of epic sights including U.S. Naval Academy.
  • Another popular option is “Water Front Retreat – Sunrise And Sunset Water Views” in Chestertown. After dropping off your bags and settling in, venture out for some sightseeing. Rock Hall Harbor is one thing to see around here.

Enjoy Seclusion At Its Best

The Outer Banks’ First Private Lazy River Pool

Dameron Farm offers over 1,200+ feet of private shoreline, private mini-beaches, a swimming pool, classic fishing pier and a boat ramp for you to enjoy all to yourself.Dameron Farm sits upon its very own peninsula on the majestic St. Jeromes Creek. Just inside the mouth of the Chesapeake Bay in historic St. Marys County.Whether youre looking for a temporary escape from it all or want to take working remotely to the next level, Dameron Farm is a vacation rental far enough away to disconnect yet close enough to stay connected .

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What Are The Best Large Group Vacation Rentals In Chesapeake Bay

If you’re planning a getaway to remember, don’t go by yourself bring the whole gang. It’s always more fun to share your experiences with your friends and family. These vacation rentals in Chesapeake Bay are perfect for larger groups:

  • “Very Private Riverfront, Beach”: This popular retreat is a terrific choice for large groups wanting to stay in Bohannon. It has 6 bedrooms and many great amenities, including a firepit and a nearby river.
  • “Ultraclean Waterfront Home Annapolis Area”: You’ll get your squad’s tick of approval at this Severna Park option which comes with a water view, a nearby waterfront and more. It has 5 bedrooms that will comfortably accommodate your loved ones.

Ideal Time To Visit Chesapeake Bay

The peak season for travelers to Chesapeake Bay is the summer period between June and August. Thousands of holidaymakers visit during this time for the hot weather and fun water-sports, including fishing, boating, and swimming.

If you specifically want to avoid the peak crowds, travel to Chesapeake Bay in either spring or fall . During these seasons, you will be able to observe dolphins, explore salt marshes, and go hiking.

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Located Where The Earth Meets The Seaon The Chesapeake Bay Of Marylands Eastern Shorecan Accommodate 35

856-981-6612 215-350-1165 609-975-8127 609-257-3719

Ransomes Chesapeake Retreats, LLC is in the business of bringing families, friends, loved ones together from around the country! Are you looking for a unique and unbelievably stunning Chesapeake Bay setting for your family vacation, reunion, wedding destination, corporate seminar or club retreat and special event? Our Retreat is a peaceful refuge to relax in beautiful and pristine surroundings, yet be “close to it all”. Our 250-acre waterfront Chesapeake Bay estate offers the perfect vacation rental location for all occasions and many group activities. View some of our many rental uses.


Ransome’s Chesapeake Retreats is a multi-generational family vacation complex. RCR has several facilities, in close proximity to each other, on and near this exclusive and secluded bay estate. It’s an ideal situation for your special gathering, where you are close together but can still have your own space.

RCR has been called a “rare find”, as there are few, if any, large estates for your use that are situated on the Bay. This captivating estate is available for your enjoyment and pleasure.

New 10’x 60′ screened in porch/gazebo

Another fun day boating in the water and exploring the Bay shore

Conference / game room in Fun Center

A family’s schedule of fun eventsPlaying outdoor gamesMaking sweet memories at RCR

Sunset with Egret

Swimming pool view of the fishing pond and bay beyond

Are There Large Vacation Rentals That Sleep 30 Or More In Chesapeake Bay

anthonykingdesign: Maryland Vacation Home With Indoor Pool

Planning a trip to Chesapeake Bay with all your favorite people doesn’t have to mean crowding everyone into one room. If you want someplace comfy where you and your crew can stretch out and unwind, one of these large vacation rentals might be perfect for you:

  • “New ‘highlands Cottage’ Upscale Getaway W”: With 3 bedrooms accommodating up to 100 people, this property in Middle River will give you all the space you need. A kitchen and games are just some of the amenities on offer here.
  • “5eastern Shore/cambridge 250 Acres On Chesapeake Bay Vacation”: Sleeping up to 40 guests and with great amenities like a kitchen and a firepit, this is another winner. It has 12 bedrooms and is located in Mid-Atlantic.

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Best Vacation Home Deals In Chesapeake Bay

Using our filters will help you find the perfect vacation rental in Chesapeake Bay. HomeToGo’s data highlights that “Internet” and “TV” turn out to be the most frequently offered features in Chesapeake Bay. Plan your vacation in advance if you want a rental with a sauna or you enjoy soaking in the hot tub. There are just 192 listed accommodations providing “Sauna” and 278 properties including “Hot tub.”

Revel In The Laidback Atmosphere Of Chesapeake Bay Vacation Rentals

Chesapeake Bay, Marylands most famous estuary, is actually quite big approximately 200 miles long. It is home to historical attractions such as Fort McHenry and Chesapeake Bay Maritime Museum, as well as natural attractions such as Blackwater National Wildlife Refuge and Calvert Cliffs.

Chesapeake Bay vacation homes are available in different types and sizes. From luxury townhouses and waterfront cottages to apartments and farmhouses, vacation rentals in Chesapeake Bay are available to suit your every need and desire.

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What Are The Top

Walk out of work on Friday and then completely forget about those sales targets and spreadsheets. Get ready for a few days of good old-fashioned R& R â with adventure on the side â at one of these top-rated weekend getaways in Chesapeake Bay:

  • Experience relaxation and adventure all rolled into one at “Brand New Renovation In Historic District With 2 Parking Spots”. This cozy retreat in Puerto de la Cruz is an excellent base for visiting nature hot spots such as Laurel Museum and Triton Beach. If you want to do something a little more active, spend your days cycling or kayaking.
  • “Water Front Retreat – Sunrise And Sunset Water Views” in Chestertown is also suited to a quick getaway. Stay in with your feet up or get out and enjoy some cycling and fishing. If you’re eager to do a bit of sightseeing, Chesapeake Bay Environmental Center and Downs Park Dog Beach are must-do’s.

Endless Sunset Claiborne Md

Sunny Solara | 9-Bed Private Pool | Vacation Rental in Orlando, FL

Bathrooms: 3 & 1 Half Bath

Minimum Stay: 3 nights

Come enjoy the quaintness of Claiborne, MD, just 5 minutes from historic St. Michaels, on the beautiful Eastern Shore of MD. Slow your pace and enjoy a leisurely bike ride into town or stroll the public beach for sea glass, unusual shells or driftwood. Lounge poolside with a good book or enjoy the ever-present cool breezes from the porches. Or, just do nothing at all. You wont believe the views from the double-decker waterside porches of this lovely 3 BR/3.5 BA home. Claiborne boasts some of the most beautiful sunsets youve ever seen over Eastern Bay! If youre looking for a quaint get-away spot with plenty to do or not!! Endless Sunsets is the place to spend your vacation days. Wed be honored to have you and youll be glad you decided to visit. We hope you have a pleasant stay and welcome you to return again with friends and family.

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Which Chesapeake Bay Vacation Rental Is Right For You

  • Combsberry of Oxford

  • Were starting off with one of the larger vacation rental properties we have here in Chesapeake Bay, Combsberry of Oxford. This adorable house on an historic estate dates back to 1730 and is blessed with 30 acres of manicured gardens, peaceful waterfront and picturesque farmland.

    This stunning property is large enough to sleep 12 across its 6 luxurious bedrooms, making it ideal for extended families looking for a long weekend away. Plus, you can even bring your furry friends, as this property is pet-friendly.

    Just imagine sitting on your private deck in the evening, surrounded by loved ones, and watching the sun go down with a glass of wine. Idyllic! And during the day when youre not exploring the surrounding countryside, you and your crew can enjoy the stunning outdoor pool.

    Savanna is one of Marylands oldest and most picturesque rental homes. It has sat proudly on the banks of the Miles River in Talbot County since 1659, and has certainly evolved through the years. Now, this beautiful home celebrates its storied past with a decor thats reminiscent of its major moments in time. The perfect property for those who love to step back in time, while also feeling like they have all the modern conveniences.

  • The Beach House

  • The Beach House can sleep 8 across 4 bedrooms, making it ideal for groups of friends who want a fun, luxury getaway, complete with private pool, dock, and BBQ area.

  • Aspen on the Tuckahoe

  • What Are The Best Tiny House Vacation Rentals In Chesapeake Bay

    Punching way above its weight when it comes to character and charm, a tiny house vacation rental in Chesapeake Bay puts you on the doorstep of big adventure. Turn off all your devices and switch your focus to outdoor fun at one of these pocket-sized escapes:

    • Take time off and enjoy a simpler way of life at “Annapolis Waterfront “tiny House” In Garden Setting”. Located in Parole, a microwave oven and off-street parking options are a couple of amenities offered here.
    • “Secluded Log Cabin Tiny House In The Woods And On Lake Russell” offers conveniences such as games and golf. Located in Elberton, you’ll be able to live large in this small but nicely designed abode.

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    Crosswinds Tilghman Island Md

    Welcome to Crosswinds! This newly renovated waterfront home is being offered for vacation rentals for the first time! We welcome you to start a tradition for your annual getaway where you will create memories of a lifetime!

    Located on Harris Creek on Tilghman Island, the views will take your breath away and transport you to a land of tranquility and relaxation. The kids will be ecstatic to swim in the indoor, heated pool and play foosball in the game room come rain or shine. Not to mention, crabbing, fishing, kayaking, and exploring “The Island” which are only a few of the treasured pastimes of the area.

    Historic St Michaels is a short drive away and offers exceptional dining opportunities, a gorgeous harbor, and one of a kind shops along Main Street.

    A private dock where you can catch crabs or fish, kayaks, a wrap-around deck for barbecues, 6 bedrooms, 5.5 bathrooms, an indoor pool with jacuzzi all secluded on a point surrounded by water….what more could you ask for! Come enjoy eastern shore hospitality at Crosswinds.

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