Vacation Rentals By Owner In Royal Oak, MD

$997.98

Sunset Shores | an ESVR property

Royal Oak, Maryland, United States

Welcome to Sunset Shores, your perfect waterfront retreat near St. Michaels, Maryland! This stunning 4-bedroom, 2.5-bathroom home offers a luxurious escape for up to 8 guests. As you step inside, you'll be greeted by an open concept living area with a fully equipped kitchen, perfect for preparing delicious meals. The great room is cozy and inviting, with never-ending sunset views and a fireplace to keep you warm on cooler evenings. brbrThe primary bedroom features a plush king-sized bed, while a second bedroom also boasts a king-sized bed for ultimate comfort. The third bedroom has two full-sized beds, and the fourth bedroom offers a queen bed with a full-sized bunk bed for the kids. All bedrooms are tastefully decorated and provide a serene space to unwind after a day of exploration.brbrSunset Shores offers a range of premium amenities, including complimentary Wi-Fi, a private saltwater pool, waterfront access with a dock, kayaks, and numerous lawn games to enjoy on the expansive 4-acre yard. You'll also find a dishwasher, dryer, and all necessary kitchen essentials for your convenience. The property is an ideal choice for families with children.brbrSt. Michaels is a charming town with plenty to see and do. Explore the historic St. Michaels Harbor, visit the Chesapeake Bay Maritime Museum, or take a scenic boat tour. Enjoy delicious seafood at The Boatyard Restaurant or indulge in a sweet treat at the famous St. Michaels Fudge Company. With its picturesque setting and warm hospitality, Sunset Shores is the perfect place to create unforgettable memories.brbrBook your stay at Sunset Shores today and experience the ultimate in waterfront luxury. We can't wait to welcome you to our beautiful home! Talbot County STR License STN-25-18brbrPROPERTY FEATURES:brbrWaterfront: Bridge CreekbrDock: Water and electricity available for guest use. Guest can tie boat to dock but boat lift is NOT available for guest use.brWater Toys: 2 kayaks are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency.brPool: Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels.brGrill: Built-in propane grill. Propane is provided.brLand Toys: Basketball hoop available for guest use. Trampoline is NOT available for guest use.brPet Policy: Pets are not permitted.brWiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds.brbrBED SIZES:brbrKing - 1 / King - 1 / Double Bed - 2 / Bunk Bed - Full over Queen - 1 /

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Bath

Sleeps

$706.13

/ Nightly

Private Vacation Home

Minutes from Downtown Easton and St. Michaels | Private Dock | Kayak | Pet Frien

Royal Oak, Maryland, United States

Enjoy “the good old days” in style!brbrThis exceptional 4-bedroom, 3.5-bathroom home offers a character-filled interior and comes equipped with a formal dining room, large entertainment spaces and an expansive great room.brbrEnjoy the well-equipped kitchen that has been beautifully maintained and features a sprawling granite countertops island. The well-proportioned master suite is a secluded retreat that boasts an ensuite bathroom and waterfront views. The inviting interior features original hardwood flooring throughout.brbrThe tranquil backyard boasts a screened porch and private dock. A wonderful space for fishing, cycling, crabbing, entertaining or romantic cocktails for 2.brbrJust the rural atmosphere you've been looking for! Perfectly situated in a desirable Talbot County neighborhood. A rare opportunity. Early booking is recommended! Talbot County STR License STN-22-4brbrPROPERTY FEATURES:brbrWaterfront: Tred Avon RiverbrDock: Private dock. Owner keeps a boat at the dock. Guests are permitted to tie a boat to the dock.brWater Toys: 1 kayak is available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency.brGrill: Propane grill. Propane is provided.brFireplace: Wood burning. Wood is not provided.brPet Friendly: This is a pet friendly rental.brWiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds.brbrBED SIZES:brbrKing - 1 / Queen - 1 / Single Bed - Twin Sized - 2 / Crib - 1 / Single Bed - Twin Sized - 2 /

5

Bed

3

Bath

8

Sleeps

$663.22

/ Nightly

Private Vacation Home

The Farm at Cedar Cove | an ESVR property

ROYAL OAK, Maryland, United States

Waterfront Eastern Shore Retreat | 18 Acres | Private & SecludedbrbrSleeps 6 · 3 Bedrooms · 3 Bathrooms · Completely Renovated 2026brbrEscape to this quintessential Eastern Shore retreat, where nearly 18 acres of pristine waterfront farmland meets modern comfort. With over 1,000 feet of private waterfront, breathtaking sunset views, and complete seclusion, this is the getaway you've been dreaming of. Talbot County STR License STN-25-20brbrThe Space brbrCompletely renovated in 2026, every inch of this property has been thoughtfully updated. The bright, open living spaces feature warm hardwood floors throughout, fresh décor, and water views from nearly every room. Three queen bedrooms and three fully renovated bathrooms mean everyone travels in comfort. The primary bedroom enjoys its own en suite bathroom, a second full bathroom is conveniently shared between the other two bedrooms, and a third is located just off the family room. Families with little ones will appreciate that one bathroom features a full tub.brbrThe stunning new kitchen is the heart of the home, anchored by a large island perfect for meal prep and casual gathering. Start your mornings at the charming banquette dining nook, where you can sip your coffee and catch the news on the mounted TV.brbrWhether you feel like cooking, dining out, or staying in with takeout, the choice is entirely yours. The kitchen is fully equipped and local seafood options make it easy to bring the catch of the day home. Or head out to the world-class restaurants of St. Michaels and Easton, two of the Eastern Shore's most celebrated dining destinations, just minutes away.brbrFor evenings in or rainy days, the spacious living room and a dedicated entertainment room with a 75 TV and a table perfectly sized for mah jong, puzzles, board games, and more (all of which are available at the property!) make it the perfect place to settle in and stay a while.brbrStep outside to the screened-in porch, the ideal spot for happy hour as the sun dips below the water, or head down to the waterfront and relax into the comfortable Adirondack chairs with expansive waterfront views.brbrThe Grounds brbrThe property is truly special. Nearly 1 acre of manicured yard and an 800-meter walking path around the perimeter invite you to slow down and breathe. Deer, waterfowl, and other wildlife are frequent visitors. The waterfront is perfect for boating, fishing, kayaking, and hunting, or simply sitting and watching the world go by. Your four-legged family members are welcome too. With nearly 18 acres to roam, this is a dog's paradise.brbrPet Policy: We are happy to consider well-behaved pets! To ensure the home is a good fit for your companion, all pets must be pre-approved by the owner before booking. A non-refundable pet fee will apply to your stay. Please message to discuss your pet's details before finalizing your reservation.brbrThe LocationbrbrTucked away yet surprisingly convenient:br15 min to St. Michaelsbr20 min to Eastonbr15 min to the Oxford-Bellevue Ferrybr10 min to The Oak Waterfront Hotel / Wedding VenuebrMinutes from the Oxford/St. Michaels bike trail, recognized as one of the top cycling routes in the countrybrbrAmenities Include: All-new fully equipped kitchen · Brand new appliances · Large kitchen island · New washer/dryer · High-speed WiFi · 55 and 75 TV · 3 queen beds · En suite primary bathroom · Full bathtub · Screened-in porch · Adirondack waterfront seating · 1 km walking path · Private waterfront access · Games and board games provided · Dogs welcome (fee applies)

3

Bed

2

Bath

6

Sleeps

$11258.33

/ Nightly

Private Vacation Home

Moofy's Farmhouse: Main Lodge ; Private Waterfront Retreat Center, New Reno on 18 Acres

Royal Oak, Maryland, United States

Summary:brbrEscape to our stunning waterfront Main Lodge at Moofy's Farmhouse, a private 25-bedroom house with 25 ensuite bathrooms, ideal for retreats and family gatherings. Enjoy breathtaking Eastern Shore views, a spacious living room, and a game room with a pool table, darts, and karaoke. Cook in the fully-equipped kitchen, dine in the large dining area, and relax on the screened-in porch. Located near Easton and St. Michaels, offering a perfect blend of seclusion and convenience. (private chef options available)brbrbrbrThe Space:brbrThe Main Lodge at Moofy's Farmhouse offers a luxurious stay on a stunning waterfront estate, sharing grounds with three charming cottages. Guests enjoy complimentary access to a range of amenities, including a swimming pool, jacuzzis, private dock, tennis court, volleyball court, fishing and crabbing equipment, bikes, a gym, a library, a fire pit, and a delightful ice cream shop and more. Explore the beautiful gardens (in season), visit the chickens, and discover the art barn. For those seeking a private conference space, we offer a fully equipped room for $500/day, complete with seating, tables, AV equipment, complimentary coffee, a kitchenette, and a restroom. Enhance your stay with our private chef services, additional cleaning options, and premium activity experiences, available upon reservation.brbrbrbrGuest Access:brbrWhile the Main Lodge will be private to you and your guests during your stay, you might see other guests around the property and shared amenities. Private property option is available for additional cost.brbrbrbrThe Neighborhood:brbrWe are located on the waterfront, tucked away for a remote and peaceful private retreat. The property is only 15 minutes from Easton and St. Michaels for a quick trip into town for shopping and dining. The Oxford ferry is also 10 minutes away for a fun trip across the water for more local dining and shopping in Oxford. You can also take our bikes to the ferry for a fun bike trip instead of driving! Please check out our map of the property in the photos section for everything we have to offer for your retreat.brbrbrbrGetting Around:brbrWe have free parking on the property. It's best to have a car and or shuttle to get around if you are leaving the property. St. Michaels, Easton and the Oxford ferry are a short car ride away! Please do not rely on Ubers from Moofys' Farmhouse. We can provide a list of transportation vendors as well once reserved.brbrbrbrInteraction with Guests:brbrUpon arrival, you will be greeted by our caretaker, Mark. He will do a walkthrough of the Main Lodge and give more information about the property. For additional questions and maintenance urgencies, we will give you our on-site phone number to help out. You may also see our small team working on some projects around the property to keep it up and in good condition.

1

Bed

50

Sleeps

Exceptional(1)

$2724.17

/ Nightly

Private Vacation Home

Waterfront Farmhouse Retreat on 18 Acres, Pool

Royal Oak, Maryland, United States

Summary:brbrOur newly renovated Brick House at Moofy's Farmhouse is nestled on an 18 acre waterfront private retreat with access to a swimming pool, gym, tennis court & private dock! The kitchen is fully-equipped with stainless steel appliances and laundry located in house. The house shares the grounds with a few other of our private cottages. Guests also have access to kayaks, fishing equipment, the fire pit, ice cream shop, library and more! Quiet and remote but very close to both Easton and Saint Michaels.brbrbrbrThe Space:brbrThe Brick House at Moofy's Farmhouse is located on a beautiful waterfront private retreat that shares the grounds with 2 other cottages and our main lodge. Guests have access to the swimming pool, private dock, tennis court, fishing equipment, bikes, gym, the library, fire pit and the complimentary ice cream shop on the property! You can also walk through our gardens and visit the petting zoo and art barn on the property as well. Please check out our map of the property in the photos section for everything we have to offer for your retreat. The Brick House is an 8 bedroom house. The kitchen is fully-equipped with stainless steel appliances and laundry in the unit.brbrbrbrGuest Access:brbrThe caretaker will show the guests around the grounds and how to access the amenities on the property.brbrbrbrThe Neighborhood:brbrWe are located on the waterfront, tucked away for a remote and peaceful private retreat. The property is only 10-15 minutes from Easton and St. Michaels for a quick trip into town for shopping and dining. The Oxford ferry is also 10 minutes away for a fun trip across the water for more local dining and shopping in Oxford. You can also take our bikes to the ferry for a fun bike trip instead of driving! Please check out our map of the property in the photos section for everything we have to offer for your retreat.brbrbrbrGetting Around:brbrEasy to get around. We have free parking on the property. It's best to have a car to get around if you are leaving the property. St. Michaels, Easton and the Oxford ferry are a short car ride away!brbrbrbrOther Things to Note:brbrThe guest count is confirmed and agreed upon booking the reservation. If the guest count increases, there will be a fee per each additional guest at the nightly room rate.brbrbrbrInteraction with Guests:brbrWe have a caretaker who lives on the property and can help with whatever you need for your stay.

8

Bed

7

Bath

16

Sleeps

$1073.33

/ Nightly

Cottage

Newly Renovated Summer Paradise-Pool-Tennis-Garden Retreat

Royal Oak, Maryland, United States

Summary:brbrOur newly renovated garden cottage is nestled on our 18 acre waterfront private retreat, Moofy's Farmhouse, with access to a swimming pool, gym, tennis court & private dock! The cottage shares the grounds with a few other of our private cottages. Guests also have access to kayaks, fishing equipment, the fire pit, ice cream shop, library and more! Quiet and remote but very close to both Easton and Saint Michaels for a perfect retreat.brbrbrbrThe Space:brbrThe garden cottage is located on a beautiful waterfront private retreat, Moofy's Farmhouse, that shares the grounds with our 2 other cottages and our main lodge. Guests have access to the swimming pool, private dock, tennis court, fishing equipment, bikes, gym, the library, fire pit and the complimentary ice cream shop on the property! You can also walk through our gardens and visit the petting zoo and art barn on the property as well. The garden cottage is a 4 bedroom cottage with a fully-equipped kitchen with stainless steel appliances and laundry in the unit. There is one king bed, 2 queens, and a twin over twin bunk beds. This cottage is attached to the barn. Please check out our map of the property in the photos section for everything we have to offer for your retreat.brbrbrbrGuest Access:brbrThe caretaker will show the guests around the grounds and how to access the amenities on the property.brbrbrbrThe Neighborhood:brbrWe are located on the waterfront, tucked away for a remote and peaceful private retreat. The property is only 10-15 minutes from Easton and St. Michaels for a quick trip into town for shopping and dining. The Oxford ferry is also 10 minutes away for a fun trip across the water for more local dining and shopping in Oxford. You can also take our bikes to the ferry for a fun bike trip instead of driving! Please check out our map of the property in the photos section for everything we have to offer for your retreat.brbrbrbrGetting Around:brbrEasy to get around. We have free parking on the property. It's best to have a car to get around if you are leaving the property. St. Michaels, Easton and the Oxford ferry are a short car ride away! There are no Ubers in the area available so please plan accordingly.brbrbrbrOther Things to Note:brbrThe occupancy for this cottage is 6 guests.brbrbrbrInteraction with Guests:brbrWe have a caretaker who lives on the property and can help with whatever you need for your stay.

4

Bed

2

Bath

6

Sleeps

$930.32

/ Nightly

Private Vacation Home

Waterfront Paradise | Pool, Views & Serenity

Royal Oak, Maryland, United States

Summary:brbrGather your favorite people and escape to a spacious waterfront haven in Royal Oak. From coffee at sunrise on the private dock to evening swims under pastel skies, this home blends Chesapeake Bay charm with resort-style amenities. Designed for families and friends, every space invites connection, comfort, and unforgettable memories.brbrbrbrTalbot County Licensure: STRN-26-33brbrbrbrThe Space:brbrAt the end of a quiet road, where trees give way to endless water, you’ll find Overlook Farm — a luxurious waterfront retreat made for connection and calm. The open-concept layout flows from a chef’s kitchen with an oversized island into inviting dining areas indoors and out. Multiple living spaces offer room to gather or spread out, while a game room sparks friendly competition and tucked-away nooks invite a good book. Four serene bedrooms each frame a private view of the water, bringing golden sunrises and gentle evening breezes to your stay. Outside, the private pool, sun loungers, and shaded seating create the perfect setting for long, lingering days on the shore. brbrbrbrWhat you’ll love: brbr- Unmatched waterfront views from every bedroombrbr- Chef’s kitchen with oversized island & premium appliancesbrbr- Multiple living rooms & cozy nooks for relaxation or playbrbr- Game room for friendly competition & late-night laughterbrbr- Private pool overlooking the bay with loungers & dining spacebrbr- Indoor & outdoor dining areas for memorable mealsbrbr- Quiet corners perfect for reading, journaling, or reflectionbrbr- Spacious lawn & gathering areas for sunrise coffee or sunset drinksbrbrbrbrOverlook Farm is more than a home — it’s a place for reconnection, restoration, and creating lasting memories.brbrbrbrCurated by Flaneur, this experience is designed in the spirit of slow travel — where comfort is intentional, beauty surrounds you, and every moment is yours to truly savor. Your peace and privacy are our priorities, but we're always here to enhance your experience. From insider tips on local gems to ensuring every comfort, consider Flaneur as your waterfront hosts.brbrbrbrGuest Access:brbrThis property features keyless entry for your convenience. Check-in instructions are sent 72 hours prior to arrival. To receive these instructions, guests must sign the county-required lease agreement provided at booking confirmation.brbrbrbrThe Neighborhood:brbrRural waterfront, peaceful and private.brbrbrbrGetting Around:brbrCentrally located between downtown Easton and historic St Michaels.brbrbrbrOther Things to Note:brbrWe provide a starter supply of toilet paper and paper towels, although we recommend bringing extra for longer stays. Personal care items are not supplied and must be brought by guests. We can welcome your dog for a nonrefundable pet fee of $200.brbrbrbrThe private pool is scheduled to open for the season by Memorial Day.

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Bath

Sleeps

$1336.67

/ Nightly

Cottage

Spacious 6-bedroom house/cottage in charming Royal Oak with WiFi, AC

Royal Oak, Maryland, United States

This charming house/cottage in Royal Oak offers 6 cozy bedrooms, including 2 king beds, 1 full bed, 2 twin beds, and 1 queen bed. With 4 bathrooms featuring a mix of showers, jetted bathtub, and regular bathtub, guests will feel pampered during their stay. The property also includes amenities like a hair dryer, washing machine, dryer, iron, heating, WiFi, and AC. Our adorable house and cottage will help you feel at home while you're traveling around Royal Oak and the Eastern Shore. We are easy 15 min drives to both St Micheal’s and Easton.brbr3 night minimum required by Talbot County Short term rental license.brLicense number 24-22.brThe property may not be used for any weddings, banquets, corporate retreat, fundraiser or similar activity that would exceed the maximum persons permitted to be on-site.brNoise levels shall comply with Talbot County code.brFireworks are prohibited.

6

Bed

4

Bath

14

Sleeps

$539.49

/ Nightly

Private Vacation Home

Loon Cottage on Irish Creek

Royal Oak, Maryland, United States

Waterfront living at its best on Irish Creek! Nestled along the peaceful shores of Maryland’s Eastern Shore, Loon Cottage offers the rare combination of a private deep-water dock, a private tennis court, and expansive waterfront grounds designed for relaxing coastal living.brbrSet on a large private estate in Royal Oak, this charming 3-bedroom, 2-bath waterfront cottage blends classic Eastern Shore character with comfortable coastal style. Inside, vaulted ceilings with exposed beams, abundant natural light, and inviting gathering spaces create a warm and airy atmosphere perfect for reconnecting with family and friends after a day on the water.brbrThe open living and dining areas flow seamlessly into cozy sitting spaces, while large windows frame serene creek views throughout the home. Whether you’re enjoying morning coffee indoors or winding down beside the firepit in the evening, the cottage is designed to make every moment feel relaxed and effortless.brbrOutside, the property truly shines. Spend your days boating, kayaking, crabbing, or fishing from the private deep-water dock, or simply soak in the peaceful waterfront setting. Gather around the fire pit in Adirondack chairs for sunset cocktails as bald eagles soar overhead and the creek glows in the evening light. The expansive waterfront views and outdoor entertaining areas create the perfect backdrop for family gatherings, al fresco dinners, and quiet afternoons by the water. For guests seeking both relaxation and convenience, Loon Cottage feels wonderfully secluded while remaining just minutes from the shops, restaurants, and charm of St. Michaels and Easton.brbrProperty Highlights:br• Waterfront location on Irish Creekbr• Private deep-water dock ideal for boating and water activitiesbr• Private tennis courtbr• Expansive waterfront lawn and outdoor living spacesbr• 3 bedrooms | 2 bathroomsbr• Vaulted ceilings with exposed beamsbr• Light-filled interiors with fireplacebr• Minutes from St. Michaels and EastonbrbrAdditional Property Information:brLoon Cottage is located on a large private estate and sits approximately 150 yards from the main estate residence, separated by the tennis court.brbrGuests are welcome to enjoy:br• The entire waterfront areabr• Walking trails near the paddock and barn areabrbrPlease note:br• The swimming pool is not available for guest usebr• Guests may not enter any other estate structures, including the main house, barns, or greenhousebrbrThe main estate residence is not occupied full-time. On occasion, the owners may be staying onsite with their two dogs during your visit. We kindly ask guests to respect the owners’ privacy if they are present. Tidewater Vacations is available to assist with any questions or concerns 24hrs a day during your stay.brYou are staying in someone’s home, so please treat it with the same care and respect you’d expect for your own place. brbrLoon Cottage is located on a large private estate. The cottage is situated approximately 150 yards from the main estate home, with a tennis court separating the two properties.br• The pool is not available for guest use.br• Guests are welcome to enjoy the entire waterfront area of the property, as well as the paddock and barn area trails.br• Guests may not enter any other structures on the estate besides the cottage, including but not limited to the main estate house, barns, or greenhouse.brbrThe main estate is not occupied full-time; however, if the estate owners are staying onsite during your visit, please be aware they may have two dogs with them on the property. We kindly ask all guests to respect the owners’ privacy during their stay. Please direct any questions or concerns to Tidewater Vacations.brbrUse of property, tennis court, dock and any other amenities is at individuals own risk. Owner and agent shall not be held responsible for any accidents or injury that occurs on the property during staybrbrNo Fireworks or sparklers are allowed on property at any timebrUse of pool on property is prohibited. brbrDue to the rural nature of the area, this property may experience slow internet speeds, limited access to email, web browsing and streaming servicesbrbrDue to local zoning ordinances weddings and special events are not permitted at this property. No parties or events are permitted on this property during staybrbrDue to the local `Noise Ordinance` no parties are allowed at our properties and quite hours are between 10:00 PM & 7:00 AMbrbrThis property does not allow group rentals to guests under the age of 25. Any group rental made by an individual under the age of 25 will not be honoredbrbrEvery effort has been made to ensure the accuracy of the images, descriptions, and amenities. Although they are deemed reliable, they cannot be guaranteedbrbrNo refunds will be given due to amenity discrepancies or area event closures/cancellationsbrbrCheck-in / Check-out dates and times are strictly followedbrbrAll Trash is to be bagged and placed in outside trash receptacles. Please do not leave trash on ground as animals will get into it.

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Bath

Sleeps

$527.06

/ Nightly

Cottage

Cottage at Goose Neck Point

Royal Oak, Maryland, United States

Charming newly renovated cottage at the end of a private drive. Direct access to the Tred Avon River. Spectacular view of the Tred Avon River, as well as Plaindealing and Tar Creeks. Charming house boasts a large eat in kitchen, screen porch and sun porch. Living room is spacious and airy with a wood burning fireplace. brHouse has fiber optic Wi-Fi. brbrLocated between Easton and St. Michaels(and a quick ferry ride to Oxford) in Talbot County. Close to restaurants and shops. House includesbrpaddle board, kayaks, and bikes

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Bath

Sleeps

$2388.25

/ Nightly

Private Vacation Home

Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Luxury

Royal Oak, Maryland, United States

Only a 15 Minute Drive to Downtown St. Michaels and Easton!brbrJewel of the Tred Avon | an ESVR propertybrbrThis 7,700 sq ft magnificently renovated nantucket style coastal home offers 5 BR, 5 and a half baths and is situated on 9 acres of landscaped grounds along the Tred Avon River with views to Oxford.brbrThe ideal open-design floor plan concept features a sprawling interior with a formal dining room, expansive great room, pool table with bar, first-floor and second floor master bedrooms, flow-through living area and a home gym. No expense was spared in the chef-inspired kitchen that has been beautifully updated and boasts Viking appliances, granite countertops, an oversized kitchen island and a kitchen table that seats 10. All bedrooms offer picture perfect water views and were designed for relaxation. 4 out of the 5 bedrooms also offer a private master bathroom.brbrEnjoy the indoor/outdoor lifestyle while vacationing at this wonderfully secluded property which includes a private pond for morning strolls while sipping on your morning coffee, an expansive outdoor entertaining area, climate-controlled screened in porch, private pier, 350 ft of shoreline and a 50 x 25 x 9 ft heated waterside pool. Ideally positioned in a desirable Talbot County neighborhood. Take advantage of the best waterfront living around!brbrThis premier property will book fast, so be sure to secure your paradise vacation today. Talbot County STR License STRN-23-7

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Sleeps

$2868.06

/ Nightly

Private Vacation Home

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

Royal Oak, Maryland, United States

TREMEZZO STAY - RANCH AT ROYAL OAKbrOur properties are owned, managed, and hosted by us. We deliver personally hosted luxury rental experiences in St. Michaels, MD.brbrIf you do not see availability for your dates please visit our other exclusive listings!brChesapeake Mansion:brhttps://www.vrbo.com/2207416 unitId=2771970brPunch Point:brhttps://www.vrbo.com/3887202 dateless=truebrSpencer Creek Cabin:brhttps://www.vrbo.com/1342430 unitId=1900766brbrOver the years we have had so many guests inquire about the Royal Oak area. Our response, of course, was to investigate what was generating of of the buzz. The results are in- exclusivity! This majestic peninsula is private yet so proximate to St. Michaels and Easton. After spending time at The Ranch at Royal Oak, believe me, you will understand. We're excited to offer this one-of-a-kind property to our guests!brbrTalbot County rental license ST-644-LYTbrbr

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Bath

Sleeps

$761.71

/ Nightly

Private Vacation Home

Book Now for 15% Off. Waterfront, Dock, Hot Tub, Sandy Beach, Elevator!

Royal Oak, Maryland, United States

Another Luxury VIP Vacation Rental Property License # STRN-22-25 brCan't do stairs No Problem! This home has an ELEVATOR!brbrStay in Comfort Just Minutes from the festivities in St. Michaels and Easton, MDbrbrMake this beautiful waterfront property your home base for the holidays in Easton, MD. brbrJust minutes from all the festivities, you’ll also enjoy everything Easton has to offer year-round—fantastic dining, art galleries, boutique shops, live theater, and even a plush movie theater. Nearby St. Michaels is another must-visit, with its wine tasting, great restaurants, charming shops, and the famous Chesapeake Bay Maritime Museum.brbrFor a unique adventure, take your bikes or car on the Oxford-Bellevue Ferry (just up the street), in season, to explore the storybook village of Oxford. Ride through tree-lined streets of Victorian homes, stop at the sandy beach, or treat yourself to handmade ice cream at the beloved Scottish Highland Creamery.brbrProperty Highlights:brbrSpacious kitchen and family room with fireplace, perfect for gatherings of up to 8 guestsbrbrElevator access to all three levels, including 4 comfortable bedroomsbrbrLower-level family room for extra relaxation spacebrbrHot tub overlooking the riverbrbrWaterfront gazebo for crab feasts, picnics, or simply enjoying the breeze and sweeping water viewsbrbrPrivate dock for fishing, crabbing, or soaking in spectacular sunsetsbrbrActivities & Experiences:brbrKayaking, boating, crabbing, fishing, and water sports (kayak rentals can be delivered to the property)brbrMiles of flat, scenic biking routes perfect for casual rides or competitive events like the IRONMAN racebrbrLocal excursions for birthdays, anniversaries, and girls’ getawaysbrbrEasy access to cultural attractions like live theater and the Chesapeake Bay Maritime MuseumbrbrLocal Secrets to Try:brbrChesapeake Landing Restaurant & Seafood Market—fresh, down-home cooking just outside St. MichaelsbrbrPicnic at Oxford’s waterfront park with swings for the kids and gorgeous Tred Avon River viewsbrbrWhether you’re here for the Waterfowl Festival, a family gathering, or a quiet Eastern Shore escape, this property offers endless opportunities for relaxation, exploration, and unforgettable memories—all year round.brOwners found a rejuvenating spot to escape the hustle and bustle of New York City.brUnique BenefitsbrbrElevator, Hot Tub, Waterfront Gazebo, Dock.brAccommodations Summarybrbr4 Bedrooms, 4 Full BathsbrLocation ActivitiesbrbrCheck out Tour Talbot at https://r.search.yahoo.com/_ylt=Awrhe0.COR9lVwgG9QwPxQt.;_ylu=Y29sbwNiZjEEcG9zAzIEdnRpZAMEc2VjA3Ny/RV=2/RE=1696573955/RO=10/RU=https%3a%2f%2ftourtalbot.org%2f/RK=2/RS=BFJQDUvw1v.Wk0WS4G1Wlsia1BE-

Bed

Bath

Sleeps

$1044.5

/ Nightly

Private Vacation Home

20% Off 5 Night Min. Waterfront, Hot Tub, Pool,Minutes to St.Michaels.

Royal Oak, Maryland, United States

License No. STRN-24-4 Note: A Contract is Required to Be SignedbrbrThis lovely home offers a large main house with a downstairs bedroom, and a private apartment over the attached garage. All linens, towels and pillows are provided. It has the best of both worlds on a private point of land that has open vistas and also a quiet creek to dock your boat. Deep water dock will accommodate a 52' yacht! Catch fresh fish and go crabbing, and two kayaks are available. The views are wide open and can be enjoyed from most (Website hidden by Airbnb) sparkling pool is adjacent to a large porch where you can watch the kids, have a crab feast, or just enjoy the expansive water views. Celebrate the end of a perfect day by viewing the sunsets.You may arrive by water, MLW depth is 4 1/2-6 feet/end of the dock. Will accommodate 40 ' sailboats. brbrYour family can enjoy boating, swimming, fishing, crabbing, bike riding, and beautiful walks from this 4.6 acre private property located on a panoramic point of land. If you want to explore, you can ride your bike to the 9 car/passenger Oxford/Bellevue Ferry (just minutes away), which will take you to the quaint, and beautiful village of Oxford where there are some great restaurants, a park, and performances at the Tred Avon Theater. Biking through the town and beyond is very scenic with very little traffic. The larger town of Easton, 20 min. away, offers art galleries, golf courses, fine and casual dining, lots of shops, movies, and live entertainment at the fully restored, historic, art deco Avalon Theater. The Chesapeake Maritime Museum, gourmet/casual dining, antiquing, boutique shops, and golf are available in the nearby Victorian village of St. Michaels. You can also pamper yourself there with a spa treatment and fine dining at 'The Inn at Perry Cabin...fronting on the Miles River. ALL of this is located just 1 1/2 hrs. from Washington or Baltimore. Boat charters are also available at area marinas. brThe Oxford Bellevue Ferry is a few minutes walk which will deliver you to another charming town. You can access it by car, on foot, or your bike. Once there, you will love to bike ride around one of the most beautiful and quaint villages on the eastern shore. Must stop at the Scottish Creamery where you will find homemade ice cream in many flavors...a VERY popular stop for locals and tourists! brbrYou will need a car.

5

Bed

5

Bath

10

Sleeps

$1382.5

/ Nightly

Private Vacation Home

Waterfront Cottage Retreat on 18 Acre Farm, Pool

Royal Oak, Maryland, United States

Summary:brbrOur newly renovated point cottage at Moofy's Farmhouse is nestled on an 18 acre waterfront private retreat with access to a swimming pool, gym, tennis court, dock & more! This cottage features a private porch to enjoy the sunset, fully-equipped kitchen and laundry in unit. The cottage shares the grounds with a few other of our private cottages. Guests also have access to kayaks, fishing equipment, the fire pit, ice cream shop & library! Quiet and remote but very close to both Easton and Saint Michaels.brbrbrbrThe Space:brbrThe point cottage at Moofy's Farmhouse is located on a beautiful waterfront private retreat that shares the grounds with our 2 other cottages and our main lodge. Guests have access to the swimming pool, private dock, tennis court, fishing equipment, bikes, gym, the library, fire pit and the complimentary ice cream shop on the property! You can also walk through our gardens and visit the petting zoo and art barn on the property as well. The point cottage is a 4 bedroom cottage. The 4th bedroom is an open den/loft with a bunk bed (walk through). The cottage has fully-renovated bathrooms, rain shower with double sink in the master bedroom. If you need cribs, or additional beds we are happy to try to accommodate. The kitchen is fully-equipped with stainless steel appliances and has a laundry in the unit. Please check out our map of the property in the photos section for everything we have to offer on the property for your retreat.brbrbrbrGuest Access:brbrThe caretaker will show the guests around the grounds and how to access the amenities on the property.brbrbrbrThe Neighborhood:brbrWe are located on the waterfront, tucked away for a remote and peaceful private retreat. The property is only 10-15 minutes from Easton and St. Michaels for a quick trip into town for shopping and dining. The Oxford ferry is also 10 minutes away for a fun trip across the water for more local dining and shopping in Oxford. You can also take our bikes to the ferry for a fun bike trip instead of driving! Please check out our map of the property in the photos section for everything we have to offer for your retreat.brbrbrbrGetting Around:brbrEasy to get around. We have free parking on the property. It's best to have a car to get around if you are leaving the property. St. Michaels, Easton and the Oxford ferry are a short car ride away!brbrbrbrOther Things to Note:brbrThe guest count is confirmed and agreed upon booking the reservation. If the guest count increases, there will be a fee per each additional guest at the nightly room rate.brbrbrbrInteraction with Guests:brbrWe have a caretaker who lives on the property and can help with whatever you need for your stay.

4

Bed

3

Bath

8

Sleeps

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