Large group vacation rentals in Royal Oak, MD

A Tranquil Contemporary St. Michaels Waterfront Cottage featuring a separate 1st floor newly renovated garage apartment with its own kitchen. This 6BR, 4.5 BA vacation paradise is conveniently located between the charming towns of St Michaels and Easton, Bayside The Point is just a stone’s throw away from numerous shops, boutiques, and dining experiences to please the entire family. The house is nestled among trees at the far end of a private road and provides a truly safe, peaceful and tranquil haven. With only birdsong and the gentle rustling of trees in the cool southerly breeze, you can be assured of a completely restful and private vacation. Set on a point, the aptly named Solitude Creek wraps around this lovely house, affording you water views from every room. The master suite benefits from a private deck where you can begin your day with freshly brewed coffee and a soul-warming sunrise. A large south-facing deck with ample outside dining area will enable you to make the most of outside living on your well-earned break. Take a dip in the pool, catch crabs and fish off the dock, relax by the firepit or just enjoy a delicious BBQ. This house is well-appointed, with a clean and modern feel. Glass doors line the whole back of the house, providing beautiful, uninterrupted views down Solitude Creek. The resident Ospreys are normally just a few feet offshore; these magnificent birds coupled with the shimmering waters will provide you with hours of viewing pleasure. Talbot County STR License STN-23-37 PROPERTY FEATURES: Waterfront: Solitude Creek Dock: 750 feet of shoreline with 80 ft of private dock with 4.5 ft MLW Guest House: 1st floor newly renovated garage apartment with its own kitchen. Water Toys: 2 kayaks, 1 canoe, 2 paddle boards and crabbing gear is available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Pool: 600 sq ft private swimming pool. Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels. Grill: Propane grill. Propane is provided. Hot Tub: 6 person hot tub is available for guest use. Firepit: Wood provided. Pet Policy: This is a pet friendly property. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds. BED SIZES: King - 1 / Queen - 1 / Queen - 1 / Double Bed - 1 / Single Bed - Twin Sized - 2 / Single Bed - Twin Sized - 1

O Say, Can You See Your Next Vacation? Don’t miss this truly exceptional 1950’s ranch style 3BR, 2.5BA waterfront on the Tred Avon River. The open floor plan features a character-filled interior and provides a sunroom, flow-through living/dining area, first-floor bedrooms and large entertainment spaces. Natural lighting creates the perfect ambiance in the comfortably sized main bedroom that enhances picturesque water views. Plenty of room for everyone in the sprawling backyard, which features a newly remodeled in-ground pool (opening May 17, 2023) and lush lawn. A wonderful space for fun and relaxation. Ideally located in a sought-after Talbot County neighborhood. Take advantage of the best rural vacationing around! Early booking is recommended. This vacation home will not be available for long. Talbot County STR License STN-22-24 PROPERTY FEATURES: Waterfront: Tred Avon River Dock: Private dock. Pool: Private pool. Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels. Pet Friendly: This is a pet friendly rental. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds. BED SIZES: Single Bed - Twin Sized - 1 / Single Bed - Twin Sized - 1 / Queen - 1 / Queen - 1 /

Enjoy “the good old days” in style! This 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. Enjoy 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. The tranquil backyard boasts a screened porch and private dock. A wonderful space for fishing, cycling, crabbing, entertaining or romantic cocktails for 2. Just 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-22-4 PROPERTY FEATURES: Waterfront: Tred Avon River Dock: Private dock. Owner keeps a boat at the dock. Guests are permitted to tie a boat to the dock. Water 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. Grill: Propane grill. Propane is provided. Fireplace: Wood burning. Wood is not provided. Pet Friendly: This is a pet friendly rental. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds. BED SIZES: King - 1 / Queen - 1 / Single Bed - Twin Sized - 2 / Crib - 1 / Single Bed - Twin Sized - 2 /

Begin your day at Riverview Retreat with a beautiful sunrise and be amazed with a stunning sky at sunset. As soon as you enter this charming cottage you are greeted with wide open vistas of the Miles River from the foyer, living room, sun room, kitchen and dining room. Freshly painted and appointed with modern and comfortable furnishings, bedding and a well-stocked gourmet kitchen, this three-bedroom two and a half bath home is sure to please. Located close (75ft) to the water’s edge, where you can fish or crab from the private dock. Crab cages are available for your use as well as 2 kayaks, 2 paddle boards, cornhole boards, and 2 adult bikes to mosey into St. Michaels for ice cream or a little shopping. Or simply relax in the Adirondacks and enjoy the sailboat races and wildlife that frequent, including osprey, turtles, rays and even the occasional pod of dolphin that make their way up the Miles River. St Michaels is a 15-minute walk or less than 5 minutes by bike with all the conveniences, including shopping, restaurants, wineries, the Chesapeake Bay Marine Museum and more! Talbot County STR License #ST-910

Cottage in Center of Historic St. Michaels This lovely in-town cottage is close to all the amenities and charms of historic St. Michaels. Enjoy outstanding restaurants and boutiques, ice cream parlors, coffee shops, art galleries and more, all within a few steps of this beautiful home! Try the local winery, distillery, and brewery for tastings of hand-crafted spirits (no driving required!). Head toward the Miles River waterfront for freshly caught and steamed crabs. If you want to venture farther, within just a couple of blocks you can easily rent bikes, kayaks, or paddleboards and let your adventurous side soar. Offering modern conveniences in a quintessential Eastern Shore village, Carpenter Alley Cottage is a fabulous place to stay! PROPERTY FEATURES: Pet Policy: This is a pet friendly rental. Grill: Propane grill. Propane is provided. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds. BED SIZES: Bunk Bed - Single over Single - 1 / Queen - 1 / Queen - 1 / Queen - 1 /

This 1-bedroom home is jam-packed with amenities & has EVERYTHING you need for an amazing vacation in St. Michaels, MD! • Prime Downtown Location: Walk to Dining, Shopping, & Waterfront Area! • Stocked Kitchen w/ Coffee Bar • Gas Fireplace • Plush Sofa & Smart TV • King Bedroom w/ Smart TV, Sitting Area • Ensuite Bathroom w/ Marble Shower • Family/Kid Friendly • Designated Parking (2 Spots) • High Speed WIFI • Washer & Dryer Step into Flat 207, a bright and stylish 1-bedroom, 1.5-bath flat designed for relaxation and comfort. Perfect for couples or solo travelers, it comfortably sleeps up to 4 guests. Located on the second floor, you’ll enjoy peace, privacy, and sun-filled rooms that set the tone for a serene escape. The open-concept living area invites you to relax with comfortable seating, a cozy gas fireplace, and tasteful modern décor. Whip up meals in the fully stocked kitchen, enjoy a glass of wine at the dining table, or head out to explore the local downtown scene. When you return, the spacious bedroom features a king bed with premium linens, while the sleek bathroom boasts a spa-like marble walk-in shower. Located just steps from the harbor, shops, and award-winning restaurants, this bright and modern flat offers both comfort and convenience. Whether you’re here for a romantic getaway, a wedding weekend, or a peaceful escape on the Eastern Shore, you’ll love coming home to this stylish space. MAIN SPACES OF THE HOME: – 1 BEDROOM & 1.5 BATHROOMS – BEDROOM 1: * King-sized Bed * Smart TV * Nightstand & Lamps * Ensuite Bathroom – 1.5 BATHROOMS – * Ensuite Bathroom with Walk-in Shower * Half Bathroom – CHEF’S KITCHEN – * Fully Stocked * High-end Stainless Appliances * Ample Cabinetry & Cooking Space – LIVING ROOM – * Smart TV * Pull-Out Sofa * Indoor Fireplace * Open Floor Plan The guest has access to the entire home minus the locked cleaners’ closet. By Car: Renting a car is a convenient option to explore the area at your own pace. Having a car makes it easy to visit the many shopping centers, restaurants, and other points of interest in the area. Rideshare Services: Services like Uber and Lyft are readily available in the area, providing a convenient alternative to driving. Simply book a ride through the app, and you’ll be on your way to your destination in no time. Check-in is at 4pm Check-out is at 10am - No pets allowed. - Stays of 28 days or more may incur an additional cleaning fee - No parties allowed—violations may result in immediate termination of the stay. We aim to maintain a respectful environment for our neighbors. - An exterior camera is installed solely to monitor our cleaning team for quality and security purposes. - Parking is available for 2 vehicles in the driveway. Please note that street parking is not allowed. - If you’re interested in a long-term stay, please reach out to inquire about availability - Guests must be 21 years or older to book this property. GUEST VERIFICATION: To help ensure a smooth and secure stay for all guests, the primary guest listed on the reservation may be asked to complete a quick verification process within 48 hours of booking, depending on the platform used to book the reservation. Prior to check-in, guests may also be asked to sign a Rental Agreement that includes agreeing to our rental terms and conditions and, on certain booking platforms, providing a valid government-issued ID and matching credit card before arrival. Included with your booking is our damage waiver coverage, which helps protect against accidental, self-reported damage during your stay when reported prior to check-out.

1/2 Mile to Historic District, Pickleball Court, 3 Private Suites! Step into this idyllic, uniquely Eastern Shore Nanticoke mid- century home, perfect for friends and family, especially for multiple couples looking to be a short drive into the historic town of St. Michael’s . This spacious 3-bedroom, 3.5-bathroom home was renovated top-to-bottom in 2022 with an open-design floor plan, formal dining room, and large entertainment spaces. Extra large windows through-out provide wonderful views open field farmland . The kitchen boasts commercial-grade appliances, granite countertops, and a center butcher block island to take entertaining to the next level. The outdoor space is the perfect place to relax and entertain, with an open air pavilion complete with lounge seating, large dining table, propane grill, outdoor shower , a built-in heated swimming pool and hot tub, as well as a propane fire pit- perfect for late night star gazing . Bikes are conveniently stored in the garden shed. Don’t miss out on the opportunity to celebrate in this luxurious yet easygoing property. Talbot County STR License STN-26-21 PROPERTY FEATURES: Pool: Private pool. Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels. Heat is available for an additional fee. Please contact us if you want to add this option. Hot Tub: Hot tub is available for guest use. Grill: Propane grill. Propane is provided. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds.

Love at First Sight Welcome to “Heron’s Roost,” an exceptional 3-bedroom, 2.5-bathroom haven nestled on 10 picturesque, wooded acres with 400 feet of waterfront on Grace Creek. This charming residence is designed for your comfort, featuring a thoughtfully laid-out floor plan that encompasses a charming living room, beautifully decorated bedrooms upstairs and down, and a seamless flow between the kitchen and dining areas. Step outside to discover a wonderfully secluded backyard oasis, complete with an outdoor dining area, gazebo, duck blind, grill, oversized outdoor chess/checkerboard, and a private 75 ft dock. Whether you’re enjoying a morning coffee amidst the calming water views or hosting a sunset get-together, this spacious estate offers the perfect backdrop for relaxation and exploration, surrounded by well-established trees that provide ample privacy and shade. Located in a quaint Talbot County neighborhood with shaded streets ideal for biking and walking, you’ll have kayaks and canoes ready for launch right from the sandy beach! Or bring your own small boat and use the boat ramp adjacent to the dock. Revel in the nearby charm of St. Michael’s, where you can explore mom-and-pop shops, specialty boutiques, farmers markets, wineries, local cafes, bars, and restaurants. Don’t miss your chance for ’love at first sight’—book your serene getaway today and experience the tranquility of waterfront living! Talbot County STR License STN 24-9 PROPERTY FEATURES: Waterfront: Grace Creek Dock: Private dock and 2’ MLW. Guests are permitted to tie a boat to the dock. Water Toys: 2 kayaks and 2 canoes are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Crabbing Gear: Crabbing gear is available for guest use. Grill: Propane grill available for guest use. WiFi: High speed broadband internet is available through Breezeline internet. BED SIZES: Queen- 1 / Full - 1 / Full - 1 / Twin - 2

Let go of your cares and enjoy the respite of this Covey Creek waterfront home. Let the kids play in the fenced-in yard and enjoy an easy getaway close to historic St. Michaels. Boasting two living areas, four spacious bedrooms, and a light-filled sunroom, this is a place for relaxing! You’ll certainly be comfortable while vacationing with family and/or friends. The waterside picnic table is perfect for crab feasts and alfresco lunches. Use the kayaks and paddleboards to explore the creek and beyond. The Landing provides a low-key, easy vacation experience on the Shore! Talbot County License #ST-236-HIN-2019

Talbot County STR License STRN-23-7 This 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. The 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. Enjoy 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! This premier property will book fast, so be sure to secure your paradise vacation today.

Talbot County STR License STN-22-27 This 4-bedroom, 1.5-bathroom waterfront getaway features a character-filled interior and features a separate dining room. A foodie’s dream, this well-equipped recently updated kitchen is space efficient. Retreat to the comfortably sized main bedroom that comes complete with spacious closets. Out back, you’ll find the ultimate rural retreat, equipped with a large outdoor deck, private pool and hot tub. The perfect location for outdoor fun. Your search for the finest vacation living is over. Nestled in a sought-after Talbot County neighborhood. Don’t miss out on relaxing at this fabulous home. Book your getaway today.

Fantastic Family Compound Just 1/2 Mile to Historic District! Located just on the outskirts of St. Michaels, this fantastic family vacation compound provides everything you need for a true Eastern Shore getaway. The lovingly restored farmhouse has a brand new gourmet kitchen, five bedrooms, a cozy den, and a screened porch with a gas fireplace to warm you on those breezy summers or early fall mornings. There is plenty of room for everyone to spread out, play games, or enjoy coffee and plan the day while overlooking the formal garden. The grounds are lush with mature landscaping, plenty of privacy, centuries-old shade trees, and room to roam for the little ones. Enjoy the new gazebo: a perfect backdrop to capture some treasured family photos! The newly restored barn supplies endless opportunities for your kids or kids-at-heart with game tables, air hockey, and foosball. Work off the crab cakes and ice cream with the Vectra gym and rowing equipment! The pool is flanked by a pool house complete with a changing area and two full baths for showering, in addition to a kitchenette for your snacks and favorite beverages. The hot tub and pickle ball court are open year round for your enjoyment as well. The deep-water slip has easy access to the Miles River and St. Michaels harbor. Kayaks are included with this property to explore the smaller creeks and nature-watch on a peaceful morning. Like a good Captain, the owner has taken meticulous care to ensure your enjoyment of this home. Guests who have previously stayed here will appreciate the continual upgrades, including new pool furniture, restored steps in the barn and other improvements. This home offers something for everyone! Talbot County STR License ST-26-25 PROPERTY FEATURES: Waterfront: Long Haul Creek Dock: 100ft L-shaped dock with 6ft MLW, water and 30 amp electricity available for guest use. The owner keeps a sailboat at the long end of dock. Interior slips are available for guest use. Pickleball Court: Available for guest use. Water Toys: 1 tandem kayak, 2 medium-sized kayaks (175lbs or less) and 1 stand up paddleboard are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Pool: Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels. Hot Tub: Open year round and available for guest use. Grill: Propane grill. Propane is provided. Barn: The ground floor of the barn is not available for guest use between October and April. Pet Policy: Pets are not permitted. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds. THIS IS A LUXURY RENTAL: Guests that stay at one of our luxury rentals unlock private access to a world of privilege. Benefits include: Upon request an ESVR representative greeting at your arrival. They will ensure the rental meets our white glove standard, provide a tour of the property and answer any questions. Upgraded essentials package to include: paper towels, trash bags, toilet paper per bathroom, dishwasher pods, laundry pods, and full size (soap, shampoo and conditioner) per bathroom for your entire stay. Access to our proprietary app (A Day With ESVR) for guests that provides guests access to curated maps featuring all of the best places and experiences Maryland’s Eastern Shore has to offer. Access to our dynamic and fully integrated mobile-first welcome book designed to delight and support guests with property information and direct messaging with a guest service representative throughout your stay. Access to our concierge services to help with booking nearby activities, tours and more.

No expense spared! The impressive 6BR, 5.5BA St. Michaels waterfront getaway has recently been remodeled throughout with your comfort in mind. The open floor plan features a modern interior and provides large entertainment spaces. No expense was spared in this chef-inspired kitchen that comes equipped with dual ovens, wine fridge and island with butcher block countertop. The home boasts a master suite on both the first and second floors, each with a luxury ensuite bathroom and waterfront view. The 10-acre property has a resort-like backyard complete with a shady pergola, picnic tables, built-in swimming pool, and rolling green lawn. The westward facing screened porch provides a great spot for enjoying a morning cup of coffee or an evening cocktail with the sunset. Perfectly positioned close to downtown St. Michaels. Discover all the perks of this extraordinary property. A rare vacation opportunity for a large family. Early booking is recommended. Talbot County STR License STN-26-37 PROPERTY FEATURES: Waterfront: Rolles Creek with 300ft of shoreline. Dock: 75ft private dock. Water and electricity are available for guest use. Water Toys: 1 Kayak, 1 Canoe and 1 Paddleboard are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Pool: Private pool. Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels. Land Toys: 3 bicycles are available for guest use. Grill: Propane grill. Propane is provided. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds. THIS IS A LUXURY RENTAL: Guests that stay at one of our luxury rentals unlock private access to a world of privilege. Benefits include: Upon request an ESVR representative greeting at your arrival. They will ensure the rental meets our white glove standard, provide a tour of the property and answer any questions. Upgraded essentials package to include: paper towels, trash bags, toilet paper per bathroom, dishwasher pods, laundry pods, and full size (soap, shampoo and conditioner) per bathroom for your entire stay. Access to our proprietary app (A Day With ESVR) for guests that provides guests access to curated maps featuring all of the best places and experiences Maryland’s Eastern Shore has to offer. Access to our dynamic and fully integrated mobile-first welcome book designed to delight and support guests with property information and direct messaging with a guest service representative throughout your stay. Access to our concierge services to help with booking nearby activities, tours and more.