Earleville, MD Vacation Rentals

Escape to 'The North Bay Cottage,' a charming 3-bed, 2-bath retreat in Charlestown's Waterfront Historical District! Just a 4-minute walk to coastal bliss, it offers easy access to Charlestown Public Beach & Ramp—perfect for sun-seekers and boaters. Explore Susquehanna State Park or the Chesapeake Bay Maritime Museum, then unwind at your home away from home, featuring a fully equipped kitchen, cozy living spaces, and a tranquil backyard. Make lasting memories at this coastal getaway! -- THE PROPERTY -- Newly Updated | Electric Fireplace | Free WiFi | 1,400 Sq Ft | Walk to Charlestown Beach Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: 2 Full Beds HOME FEATURES: Smart TVs, dining table, ceiling fans, covered front porch, outdoor seating KITCHEN: Refrigerator, stove/oven, drip & Keurig coffee maker, microwave, dishwasher, dishware & flatware, spices, Tupperware, baking sheets, cookware, blender GENERAL: Washer & dryer, towels, linens, complimentary toiletries, central heating & air conditioning, keyless entry FAQ: 1 exterior security camera (facing entryway) ACCESSIBILITY: 2-story home, exterior staircase to enter PARKING: Driveway (4 vehicles), trailer parking -- THE LOCATION -- ATTRACTIONS: Great Wolf Lodge Water Park (6 miles), Lock House Museum (8 miles), The Havre de Grace Maritime Museum (9 miles), Plumpton Park Zoo (12 miles), Turkey Point Lighthouse (15 miles) OUTDOOR RECREATION: Charlestown Public Boat Ramp (0.1 miles), North East River (0.7 miles), North East Community Park (4 miles), Kayak Ramp (8 miles), Perryville Boat Ramp (8 miles), Millard Tydings Memorial Park (9 miles), Marina Park (10 miles), Elk River Boat Launch (11 miles), Susquehanna State Park (14 miles), Iron Hill Park (14 miles), Bohemia River State Park (20 miles) LOCAL BITES: The Wellwood Restaurant (490 ft), Market Street Cafe (0.2 miles), Pier 1 Restaurant (3 miles), Bella Pizza (3 miles), Woody's Tacos & Tequila (3 miles), Nauti Goose Restaurant (4 miles), Steak & Main (4 miles) AIRPORTS: Philadelphia International Airport (52 miles), Baltimore/Washington International Thurgood Marshall Airport (54 miles), Ronald Reagan Washington National Airport (87 miles) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Early check-in and late check-out may be available upon request; please reach out to the Guest Contact to coordinate - Any check-in before 4:00 PM or late check-out after 11:00 AM is subject to an additional fee - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This 2-story home requires an exterior staircase to enter. Interior stairs are required to access all the bedrooms on the 2nd floor - NOTE: Your safety matters. This property features a Ring doorbell device with an exterior security camera facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video when motion is detected by the device

Book a tranquil East Coast getaway at this 60-acre vacation rental in Millington, MD. This secluded waterfront property offers the ultimate escape for you and your crew. Take the 2 included kayaks out on the Chester River, have a backyard cookout, and soak in the rejuvenating private hot tub while you’re here. Made up of two 120-year-old houses with 7 bedrooms and 4 bathrooms on-site, this expansive vacation rental is one of a kind. Take some much-needed time off and stay at this serene retreat! -- THE PROPERTY -- Private Hot Tub | 60-Acre Property | Chester River Access On-Site Bedroom 1 (Main House): Queen Bed, Full Bed | Bedroom 2 (Main House): 2 Full Beds | Bedroom 3 ( Main House): Full Bed | Bedroom 4 (Main House): Twin Bed | Bedroom 5 (Guest House): Queen Bed | Bedroom 6 (Guest House): Queen Bed | Bedroom 7 (Guest House): Twin Bed OUTDOOR LIVING: Fire pit (wood provided), cornhole, paddle board, 3 kayaks, gas grill, porch w/ swing GUEST HOUSE: Fully equipped kitchen, electric fireplace, deck w/ seating INDOOR LIVING: TVs w/ cable/satellite, board games, fireplace (decorative only), books, exposed wood interior KITCHEN: Stove/oven, fridge, microwave, dishwasher, coffee maker, cooking basics, dishware & flatware, toaster, complimentary coffee, tea & snacks, spices GENERAL: Lockbox entry, complimentary toiletries, free WiFi, central A/C & heat, hair dryer, iron/board, trash bags & paper towels, linens & towels, washer/dryer, laundry detergent FAQ: Stairs required, 1 exterior security camera (facing entryway of Main House) PARKING: Driveway (6 vehicles) -- THE LOCATION -- SUN & SAND: Betterton Beach (17 miles), Woodland Beach (27 miles), Fraland Beach (28 miles), Augustine Beach Access Area (34 miles) WINE TASTING: Crow Vineyard & Winery (9 miles), Casa Carmen Wines (11 miles), Broken Spoke Winery (20 miles), Chateau Bu-De, LLC Bohemia Manor Farm (20 miles) NATURE ESCAPE: Unicorn Lake (3 miles), Sassafras NRMA (14 miles), Fork Branch Nature Preserve (24 miles), Ferry Park (25 miles), Brecknock County Park (29 miles), Sandy Point State Park (42 miles) SET SAIL: Georgetown Yacht Haven (12 miles), Duffy Creek Marina (13 miles), Chesapeake Boating Club (51 miles), Salem Boating Club Inc (55 miles), Baltimore Boating Center (82 miles) ANIMAL SANCTUARY: Woodland Beach State Wildlife Management Area (18 miles), Pelot Bird Sanctuary Trailhead - MD Ornithological Society (24 miles), Bombay Hook National Wildlife Refuge (26 miles), Augustine Wildlife Area (33 miles), ABA’s Heron Watch (35 miles), Supawna Wildlife Refuge Observation Point (53 miles) AIRPORTS: Philadelphia International Airport (66 miles), Baltimore/Washington International Thurgood Marshall Airport (72 miles) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: The property requires stairs to access - NOTE: The fireplace is not for guest use - NOTE: Your safety matters. This property features 1 exterior doorbell camera located next to the front door of the Main House facing the front entryway. It does not look into any interior spaces. The camera records video and sound when activated by motion. It will record when it first senses motion and 30 seconds after the last motion is detected

Family Friendly | Private Yard w/ Fire Pit | Near Wineries & Vineyards Craving river days, adventurous hikes, and local flavors? Book this 3-bed, 3-bath North East vacation rental house! Rent a boat at a nearby marina and coast along the shore, lounge in the sand at Charlestown Manor Beach, or explore Elk Neck State Park. Traveling with kids? Check out Plumpton Park Zoo! After fun-filled days, grab a bite at a nearby restaurant, then unwind on the porch or around the fire pit. -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 twin bunk bed, 1 twin daybed - Bedroom 2: 1 queen bed - Bedroom 3: 1 queen bed INDOOR LIVING - 3 Smart TVs w/ cable - Dining table - Board games OUTDOOR LIVING - Deck w/ seating - Fire pit, private yard - Furnished porch KITCHEN - Refrigerator, stove/oven, dishwasher - Dishware/flatware, cooking basics - Keurig coffee maker (pods provided) - Microwave, toaster GENERAL - Free WiFi - Keyless entry - Central A/C & heating - Linens/towels, iron/board - Washer/dryer (detergent provided) - Trash bags, paper towels - Hair dryer, complimentary toiletries FAQ - Exterior security camera (facing out) ACCESSIBILITY - 2-story home, 4 steps to enter - 1st-floor bedroom & full bathroom - Bedroom 2 & 3 on 2nd floor PARKING - Driveway (3 vehicles) - Street parking (first-come, first-served) -- THE LOCATION -- - Walk to North East Town Pier, Anchor Marina, Bay Venture Outfitters - Waterfront Rentals - Near wineries & vineyards: Turkey Point Vineyard, Blue Elk Vineyard, Dove Valley Vineyard, The Vineyard Wine Bar, Mount Felix Vineyard & Winery - 4 miles to Charlestown Manor Beach & North East River Marina - 9 miles to Elk Neck State Park - 10 miles to Plumpton Park Zoo - 25 miles to Wilmington Airport, 47 miles to Philadelphia International Airport, 58 miles to Baltimore/Washington International Thurgood Marshall Airport -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Must be at least 18 years old to book - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - Your safety matters. This property features an exterior security camera next to the front door facing the front entry area. This camera is outward facing and records video when activated by motion - This 2-story home requires 4 steps to enter; there is a bedroom and a full bathroom on the 1st floor. Bedrooms 2 and 3 are on the 2nd floor

Soak up the small-town charm of North East, MD, at this lovely 5-bedroom, 3-bath home nestled at the head of the Chesapeake Bay! This idyllic vacation rental provides the perfect place for the whole crew to relax and have fun. Rent kayaks and go for a ride along the river, peruse produce at the local farmers market, or visit nearby wineries for tastings and tours. After your adventures, return to ‘Harbor Haven’ to unwind with a glass of wine by the fire pit. Book now! -- THE PROPERTY -- Furnished Deck & Patio | Fireplace | 1,990 Sq Ft Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: 2 Twin Beds | Bedroom 4: Queen Bed | Bedroom 5: Queen Bed | Additional Sleeping: Pack ‘n Play INDOOR LIVING: Flat-screen TV, dining table, en-suite bathrooms KITCHEN: Cooking basics, dishware/flatware, dishwasher, refrigerator, stove, microwave, drip coffee maker, blender, toaster GENERAL: Free WiFi, keyless entry, central A/C, electric heating, ceiling fans, complimentary toiletries, linens/towels, washer/dryer, iron/board, hangers, hair dryer, high chair, trash bags/paper towels FAQ: 2 exterior security cameras (facing out) ACCESSIBILITY: Interior & exterior steps required, 2-story home, bedrooms/full bathrooms on 1st floor PARKING: Driveway (1 vehicle), street (1 vehicle) -- THE LOCATION -- NORTH EAST RIVER: North East Town Pier (0.3 miles), Anchor Marina (0.3 miles), Bay Venture Outfitters - Waterfront Rentals (0.3 miles), Charlestown Manor Beach (4 miles), North East River Marina (4 miles), Elk Neck State Park (9 miles) LOCAL FUN: Cecil County Dragway (6 miles), Chesapeake Bay Golf Club (6 miles), Plumpton Park Zoo (10 miles), Turkey Point Lighthouse (11 miles), Friends-Concord Point Lighthouse (12 miles), Susquehanna State Park (20 miles), Leidos Field at Ripken Stadium (20 miles) WINE COUNTRY: Turkey Point Vineyard (5 miles), Blue Elk Vineyard (7 miles), Dove Valley Vineyard (9 miles), The Vineyard Wine Bar (11 miles), Mount Felix Vineyard & Winery (16 miles) AIRPORTS: Wilmington Airport (25 miles), Philadelphia International Airport (47 miles), Baltimore/Washington International Thurgood Marshall Airport (58 miles) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: While this 2-story home requires 3 exterior steps and 2 interior steps to access, it features bedrooms and full bathrooms on the 1st floor - NOTE: Your safety matters. This property features 2 exterior security cameras. Camera 1 is on the front door facing out toward the front entry, and camera 2 is on the sliding door facing out toward the deck. They do not look into any interior spaces. The cameras record video and sound when activated by motion

Secluded History - in the Land of Pleasant Living Located five miles from Chestertown, Thornton is a magnificent 6,000 square foot manor house built in 1815 and is currently owned and cared for by the twelfth-generation family. Having undergone two additions over the years, it was recently restored and renovated to include a modern cook’s kitchen. Thornton has a graceful combination of the finest finishes from both the past and the present. Thornton Farm comprises a 300+ acre traditional and organic crop farm with 2500’+ of shoreline on Morgan Creek. You will immediately get a sense of the grace and grandeur of Thornton as you drive down the long tree-lined lane leading to the high grounds of the farm. During the day you’ll enjoy the bucolic privacy while evenings will leave you awestruck by the twinkling stars overhead. It’s possible to believe that Thornton is where the earth stops and the night sky begins. Among other features of this exquisite, classic and charming house are manicured grounds, swimming pool, bass fishing pond, extensive walking paths, and a Merlot grape vineyard. The large library/family room has a gas burning fireplace and big screen television for everyone to enjoy. Although you may consider venturing into Chestertown to sample the local cuisine and flavors, Thornton promises to make the decision a difficult one, as would be expected when vacationing at a quintessential Eastern Shore Estate. PROPERTY FEATURES: Pool: Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels. Acreage: 300 +/- acres of complete privacy. Fireplaces: 1 gas. Firepit: Firewood is not provided. Grill: Propane grill. Propane is 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: Single Bed - Twin Sized - 1 / King - 1 / Queen - 1 / Queen - 1 / Queen - 1 / Single Bed - Twin Sized - 1 / Single Bed - Twin Sized - 2 / THIS IS A LUXURY RENTAL: Guests that stay at one of our luxury rentals unlock private access to a world of privilege. Benefits include: An ESVR representative greeting you upon 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.