Vacation Rentals By Owner In Easton, MD

Showing 32 Of 32 Vacation Rentals

$1539.2

Thorneton Point Estate

Easton, Maryland, United States

Summary:brbr**HEATABLE SPA** Nestled on the tip of an idyllic private 5-acre peninsula, minutes from historic St. Michaels, Thorneton Point Estate represents the very best of the Durham-Hythe Experience property collection. This 6-bedroom, 5-bathroom home was designed to exceed guest expectations. The Games House features billiards, table tennis, foosball, arcade games, and the fitness center.brbrbrbrThe Space:brbrSpoil your loved ones with beautiful views and being surrounded by water. Like all Durham-Hythe Experience properties, you will have access to an abundance of amenities suitable for all ages and all energy levels!brbrbrbrDon't forget to ask about our elevated experiences!brbrbrbrOther Things to Note:brbrWhile our pool is closed between October and April, the outdoor spa remains open all year round. There is an additional fee of $100 per day for heating the hot spa. So relax and soak away those aches and pains while star gazing! brbrbrbrPlease note that due to insurance and county guidelines a property specific rental agreement will have to be completed prior to your stay. brbrbrbrPets are welcome but incur a $50 per pet per night charge. There is a maximum of 2 pets allowed due to county guidelines. Please ensure pets are kept off furniture and beds. Pets are also not allowed to enter the pool as this seriously destabilizes the chemicals and damages the filter system. Violations of these rules will incur additional fees and/or penalties.brbrbrbrShort-term rental license: STRN-25-42

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$709.81

/ Nightly

Private Vacation Home

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

Easton, Maryland, United States

O Say, Can You See Your Next Vacation brbrDon’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.brbrPlenty 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.brbrIdeally 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-22-24brbrPROPERTY FEATURES:brbrWaterfront: Tred Avon RiverbrDock: Private dock.brPool: Private pool. Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels.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:brbrSingle Bed - Twin Sized - 1 / Single Bed - Twin Sized - 1 / Queen - 1 / Queen - 1 /

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Sleeps

$1051.41

/ Nightly

Private Vacation Home

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

Easton, Maryland, United States

Talbot County MD Short Term Rental License #STRN-23-12 brbrArrive at your beautiful, 4000+ sq. ft, 2 story waterfront 5-bdr, 3.5-bth retreat with its own private pier near the historic and charming town of St. Michaels. Enjoy breathtaking waterfront views from the expansive decks, complete with a gourmet grill for al fresco dining and a cozy backyard fire pit perfect for relaxing with a cold brew or glass of your favorite wine. Your private pier awaits you for fishing, crabbing, kayaking and paddle board (all provided)brbrThere are multiple cozy entertainment spaces for your enjoyment. Relax and unwind in the large living room, featuring a large screen TV with high-speed WiFi and 180-degree water views. Enjoy the natural light and serene ambiance of the sunroom, overlooking Oak Creek. Take in the stunning water views from the comfort of the 2nd floor ensuite bedroom and gathering area with a panoramic view of Oak Creek also with a wide screen TV. Retreat to the front reading room of the house for a quiet moment, conversation or to read a book and look out over the serene landscape.brPlease be aware that the swing adorning our tree at the front of the house is for decorative purposes only and is not to be used as such. brbrYou will be in the most convenient of locations. Just a 2 minute walk to the Oaks Resort with dining and jazz several times a week. Historic St. Michaels is a 5 minute drive with its charming stores, multiple dining venues and the Chesapeake Bay Maritime Museum. Explore the beauty of Oxford and the many activities, unique shops, and restaurants in Easton.br brOur Talbot County License #STRN--23-12 permits 10 GUESTS in our house and property at any given time. Please note that our Talbot County Short Term Rental license requires a three night minimum and does not allow any events to be held on the property. We are located in a serene, residential community in Royal Oak and Talbot County has a noise ordinance - no noise after 10 PM No pets permitted. brbrHighlightsbro 5 min drive to historic St. Michaelsbro 2 min walk to the Oaks Resortbro beautiful water viewsbro large deck areasbro private pier for fishing, crabbing & kayaking/boatingbro custom coffee & tea bar; complimentary whole bean coffee, grinder, coffee selectionbro fully equipped kitchenbro gas fireplacebro outdoor fire pitbro outdoor gourmet(new Weber Genisus) barbecuebro 2 large screen TV, Cable & Disney Channel for the kidsbro high speed internetbro game collection box and kids room with DVD's and playerbro horseshoes, cornhole, badminton and other gamesbro fishing rods and tackle boxbro TESLA charging portbro 240 v, NEMA EV charging port bro Two main bedrooms - one on first floor and one on second floor with three additional bedrooms and large sitting room with window wall overlooking the water.bro Spaces for gathering and spaces for quiet reflections and/or me time.

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Exceptional(6)

$1194.04

/ Nightly

Private Vacation Home

Travelers Rest Spacious 5BR Pool riverfront Pier charming Easton Saint Michaels

Easton, Maryland, United States

Travelers Rest Spacious 5BR Pool riverfront Pier charming Easton Saint MichaelsbrbrPOOL OPEN May to OCTOBER brbrRelax with the whole family at this peaceful place to stay. Welcome to Travelers Rest! A quiet and secluded neighborhood true to its name where homes are tucked away on large waterfront lots. Be prepared for frequent wildlife sightings, including osprey, eagles, deer, rabbit, fox, and much more. A quiet, peaceful respite awaits your family at this beautiful waterfront home. The home boasts five bedrooms with two additional pullout sofas sleeping up to ten very comfortably.brbr5 Bedroom, 3.5 Bath, Pool, Dock Private Retreat.brbrWelcome to Travelers Rest! brbrA quiet and secluded neighborhood true to its name where homes are tucked away on large waterfront lots. Be prepared for frequent wildlife sightings, including osprey, eagles, deer, rabbit, fox, and much more. A quiet, peaceful respite awaits your family at this beautiful waterfront home. The home boasts five bedrooms with two additional pullout sofas, sleeping ten very comfortably.brbrInside, enjoy the open floor plan living with comfortable areas for entertaining and lively discussion. Sit out by the sunroom and enjoy the sunrise and sunset all while surrounded by the beauty of nature. The bathrooms and kitchen were recently upgraded by the owners according to their love for preparing gourmet meals. brbrMultiple fireplaces, open floor plan, and surrounding windows highlight your experience in the outdoors.brbrBut the true beauty of this property is the environment surrounding the home. Enjoy the unique natural shoreline at the Tred Avon River while relaxing by the pool or outdoor fire pit. The dock comes with a canoe and sailboat ready to easily launched. Fishing, crabbing, and dinghy gear is complementary. Bring your bikes to explore the quiet, secluded community.brbrKids are welcome, and be sure to enjoy the expansive book collection in the library, learn new games and take advantage of many children's activities you'll find included in this warm home of a family of six. They are currently off on an adventure sailing the far seas and look forward to sharing their eastern shore retreat with your family!brbrThree Bedrooms on Main Level.brbrMaster bedroom facing the Tred Avon River with king bed and large master bath with large soaking tub and stand- up shower. Private toilet with bidet as well.brbrSecond suite features a queen bed, baby crib and attached full bath.brbrThird bedroom off entry has a queen-size sleeper sofa with comfy memory foam mattress. Also adjacent to the half bath off the living area.brbrSecond floor fourth bedroom has a double bed, fifth bedroom includes two twin beds and an additional baby crib. brbrTop of stairs has a bonus loft space with large TV and queen sleeper sofa.brbrGet ready to relax in this fabulous five-bedroom house in Easton. This amazing property boasts one king bed, two queen beds, two cribs, one full bed, and one twin bed, perfect for families or groups. With four bathrooms featuring a shower, bidet, hair dryer, and bathtub, guests will feel right at home. The loft living room even has a cozy sofa bed for extra sleeping space. Fall in love with Easton and enjoy the magic it has to offer.brbr

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Exceptional(49)

$1485.0

/ Nightly

Private Vacation Home

Beautiful Tidewater home between Easton & ST Michaels!

Easton, Maryland, United States

Quintessential charming Eastern Shore waterfront home stocked with all the amenities to make your stay stress free and relaxing. During the day you can enjoy the pool , tiki bar,gazebo; kayak on the quiet creek, play games or simply lounge on the new deck and soak in the views. A comfortable screened porch opening from the large dining room is also a great place to kick back or enjoy a bushel of crabs. The open kitchen/family room includes all you need (no need to bring spices, paper goods, condiments as we will provide) and is perfect for entertaining . Relax in adirondack chairs by the fire pit and when it's time to turn in you'll find comfortable beds and lush towels and sheets in each room.brLocated in between Easton and St. MIchaels, visitors can tour the towns and shop at a host of wonderful stores or visit the many attractions such as The Maritime Museum, Art Academy, St Michaels harbor, and wonderful Farmers Markets.brThere are also fabulous restaurants to choose from and many are waterside. All information will be here to welcome you.brSTR License : ST-723-CAR

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Exceptional(11)

$1414.57

/ Nightly

Private Vacation Home

Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.

Easton, Maryland, United States

Talbot County Rental License STRN-23-19brbrStunning 22 acre property in prime location on the Tred Avon situated between St Michaels and Easton. Offering complete privacy, spectacular 1500 foot waterfront views and access, and all the luxuries of modern living within a carefully updated historic property, this home is large enough to comfortably accommodate multiple families. Considerable amenities are available for your outdoor enjoyment including the oversized pool, hot tub, beach and expansive yard. Pool House with updated covered outdoor lounging area with TV and bath. 5 Bedrooms 3.5 baths. Multiple indoor and covered outdoor seating and eating spaces. Gourmet Kitchen and Wet-bar. Amazing views and sunsets. All within 5 miles of high quality groceries, shops and restaurants. Have bikes, kayaks, etc delivered for your enjoyment while at Woodwind.

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Sleeps

Exceptional(2)

$2594.07

/ Nightly

Private Vacation Home

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

Easton, Maryland, United States

One Of A Kind!brbrTranquil and timeless, Fairview is among the great historic estates of Talbot County. Offering a total of 6 bedrooms, 4 full baths and 2 half baths, the home and property provide ultimate peace and privacy. The waterfront estate is located on the Eastern Shore and sits at the end of a peninsula on the Miles River, a 12.9-mile-long tributary of the Chesapeake Bay, and is equidistant to the towns of Easton and St. Michaels.brbrThe estate's picturesque grounds encompass 74 acres of private parkland, 19th-century formal gardens, and 1,500 feet of shoreline with a private beach. With 3 private golf holes, an 20’ x 47’ pool, basketball court with hoop, tennis court, a gym, and 50 acres of backyard, this vacation experience offers excitement for the whole family.brbrFairview Estate with its serene and private setting offers a rare rental opportunity to enjoy the best that the Eastern Shore has to offer. Talbot County STR License STN-23-10brbrPROPERTY FEATURES:brbrWaterfront: Miles River with 1500' of shoreline.brDock: Floating dock. Guests are not permitted to tie a boat to the dock.brWater Toys: 1 double and 1 single kayak are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency.brPool: 47’ x 20’ private pool. Swimming pools are open from May 15 - October 15. Heat is available for an additional fee. Please contact us if you want to add this option.brPool House: Pool house with bathroom and shower available for guest use.brPrivate Beach: Private beach with floating dock and water toys available for guest use.brGrill: 2 propane grills. Propane is provided.brGolf Course: Three hole (Par 3) golf course and practice area. Bring your own clubs. There will be practice balls available for guest use.brExercise Room: Exercise room available for guest use.brFire Pit: Available for guest use.brLand Toys: 8 bicycles are available for guest use.brPet Friendly: This is a pet friendly rental.brWiFi: Included for guest use.brbrBED SIZES:brbrKing - 1 / King - 1 / Queen - 1 / Double Bed - 1 / Single Bed - Twin Sized - 2 / Single Bed - Twin Sized - 2 /brbrTHIS IS A LUXURY RENTAL:brbrGuests that stay at one of our luxury rentals unlock private access to a world of privilege. Benefits include:brbrAn 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.brbrUpgraded 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.brbrAccess 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.brbrAccess 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.brbrAccess to our concierge services to help with booking nearby activities, tours and more.

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Exceptional(27)

$437.75

/ Nightly

Private Vacation Home

A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels

Easton, Maryland, United States

This luxury home is nestled on a spacious lot, offering peaceful water views overlooking a beautiful pond. The 3-bedroom, 2-bathroom home comfortably sleeps 6.brbrbrMaster Bedroom: Featuring a king-size bed, this spacious suite offers beautiful water views, two oversized closets, and a large smart TV. The en-suite bathroom includes marble accents, a dual-head shower, and separate vanity and shower areas.brbrBedroom #1: This room offers a full-size bed, a large closet, dresser, mounted smart TV, and tranquil front garden views.brbrBedroom #2: With a queen-size bed, closet, dresser, smart TV, and both garden and water views, this room is perfect for relaxation.brbrBathrooms: The master bath is elegantly designed with marble finishes and a dual-head shower, while the second bathroom features granite countertops and a full-size tub/shower.brbrThe Kitchen: The kitchen boasts a sleek all-white design, complete with upgraded appliances, including a double oven and a wine refrigerator.brbrLiving Areas:brbrFront Sitting Room: A cozy area with four plush leather chairs—ideal for working or enjoying a good book.brbrSunroom: This bright space includes a table for six and a ping pong table, perfect for entertaining or relaxing.brbrDeck & Outdoor Seating: The expansive deck features a dining table and Adirondack chairs right by the water's edge, making it the perfect spot for morning coffee or an evening glass of wine.brbrAdditional Amenities:brbrAll bed linens and bath towels are provided, and the beds will be made upon your arrival. Each shower is stocked with shampoo, conditioner, and body wash. A hairdryer is available in the master bath. We provide a limited supply of paper towels and toilet paper to get you started.brbrWiFi is available throughout the house, and all bedrooms and the living room are equipped with smart TVs that offer popular streaming apps.brbrA second refrigerator/freezer is available for use in the garage.brbrCheck-in and check-out are made easy with our smart lock system, eliminating the need for keys. The code will be provided to you prior to check-in.

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Sleeps

Exceptional(4)

$1470.15

/ Nightly

Private Vacation Home

Minutes from Downtown Easton and St. Michaels | Pool

Easton, Maryland, United States

Welcome to your dream retreat, nestled in a serene cove that feels like a page from a fairytale.brbrThis enchanting waterfront vacation home spans over 3.6 acres and boasts a private dock along 233 feet of pristine water frontage on the tranquil Edge Creek, complete with a rip-rapped shoreline for added beauty and protection. The elegant 5-bedroom, 4-bath rental is designed to maximize breathtaking water views, allowing you to savor the picturesque scenery from nearly every room. brbrStep inside to discover a meticulously maintained interior featuring an open-concept kitchen and dining area that flows seamlessly into the inviting waterside formal living room, adorned with a cozy fireplace. Bright and airy, the sunroom is framed by expansive Palladian and bay windows, offering panoramic views that change with the seasons. For added convenience, a separate in-law or au pair suite awaits, complete with its own full-sized kitchen for privacy and comfort. The primary suite is a true sanctuary, featuring a private balcony where you can unwind, as well as a luxurious bath equipped with double sinks, a corner jetted tub, and a separate shower. brbrOutside, the property continues to impress with a covered back porch, a charming balcony, and an in-ground pool, all surrounded by stunning landscaping that enhances the natural beauty of this idyllic setting. This is more than just a vacation rental; it’s a lifestyle waiting to be embraced. Don’t miss your opportunity to own this slice of paradise! Talbot County STR License #26-20brbrPROPERTY FEATURES:brbrWaterfront: Edge CreekbrPool: Private Pool. Swimming pools are open from May 22 - October 15. Be sure to bring your own pool towels.brDock: Available for guest use. Water and electricity are included.brGrill: Propane grill. Propane is provided.brWiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds.brbrTHIS IS A LUXURY RENTAL:brbrGuests that stay at one of our luxury rentals unlock private access to a world of privilege. Benefits include:brbrAn ESVR representative will ensure the rental meets our white glove standard, provide a tour of the property, if requested and answer any questions.brbrUpgraded 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.brbrAccess 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.brbrAccess 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.brbrAccess to our concierge services to help with booking nearby activities, tours and more.

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Sleeps

Exceptional(5)

$1119.82

/ Nightly

Private Vacation Home

Minutes from Downtown St. Michaels | Pool | Pickle Ball Court | Private Dock | K

Easton, Maryland, United States

Lovely and serene-the perfect spot to nurture your soul!brbrThis 5,000 square foot, 5-bedroom, 5-bathroom waterfront was designed with your comfort in mind, the open floor plan features a modern interior and incorporates a separate dining room, flow-through living area and a generous bonus suite. The appliances enhance this gorgeous recently remodeled kitchen, equipped with quartz countertops and sprawling island. Drift off to sleep each night in the opulent main suite that comes complete with an ensuite bathroom, private balcony, and water views. The wonderfully secluded backyard boasts a patio dining space and a 18’x39’ built-in swimming pool with tanning ledge.brbrYou will love this waterfront vacation home! Well placed in a sought-after Talbot County neighborhood. This unique home will book fast! Talbot County STR License STRN-22-36brbrPROPERTY FEATURES:brbrWaterfront: Leeds CreekbrDock: Private dock with bench and beautiful views. Guests are not permitted to tie a boat to the dock.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: Brand new 18’x39’ built-in swimming pool with tanning ledge. Guests swim in pool at their own risk.brPickleball Court: Pickleball court for guest use.brGrill: Propane grill. Propane is provided.brPet Friendly: This is a pet friendly rental.brWiFi: Available for guest use.brbrBED SIZES:brbrKing - 1 / King - 1 / Queen - 1 / Queen - 2 / Bunk Bed - Single over Single - 1 / Sleep Sofa - Queen - 1 /

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Bath

Sleeps

Exceptional(5)

$719.74

/ Nightly

Private Vacation Home

Arcadia Shores on the Cove.

Easton, Maryland, United States

Your home away from home in Easton with 4 bedrooms and 4 full baths. This sprawling rancher offers a tranquil and soothing atmosphere for guests to unwind and relax. Experience the ease of one-floor living with our array of amenities designed for your comfort. Whether you're unwinding in the spacious living area, preparing meals in the fully-equipped kitchen. Boasting panoramic views of the Miles River. Large 85' long dock. Outdoor firepit area for cozy evenings the ideal spot for roasting marshmallows, sharing stores, and creating cherished memories. Whether you're starting your morning with a breath of fresh air or winding down after a day of exploration, our inviting porch offer the perfect setting for relaxation and reflection Luxurious sleeping accommodations for every guest. Separate ensuite with king bed and luxury shower and separate soaking tub. A second king size suite awaits with private full bath. A queen bedroom, and additional room with bunk beds with a full, trundle and single bunk above, and a shared hall full bathroom with double sinks. The large living room also features a pull-out sofa and a full bathroom, which can be used as a 5th bedroom. There's a variety of space for everyone to get a good night's sleep. Whether you're exploring the town or simply enjoying the comforts of this lovely house, we'll be available to answer any questions while you stay at our place.brbrSTRN-25-8

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$1113.31

/ Nightly

Private Vacation Home

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

Easton, Maryland, United States

Welcome to The Helm, your perfect waterfront retreat nestled in the charming town of Easton. This luxurious five-bedroom, five-bathroom vacation rental is designed for comfort and style, offering a serene escape for up to nine guests. As you step inside, you'll find a thoughtfully laid out space where modern amenities meet classic elegance.brbrThe open-concept living area is a focal point, with a spacious living room that flows seamlessly into the kitchen, perfect for family gatherings or entertaining friends. The kitchen is fully equipped with modern appliances, including a refrigerator, oven, stove, microwave, and dishwasher, ensuring that your culinary adventures are both convenient and enjoyable.brbrFive beautifully appointed bedrooms provide a range of sleeping arrangements, including three queen-sized beds and three twin-sized beds, ensuring everyone has a comfortable place to rest. Each bedroom is designed with your relaxation in mind, featuring plush bedding and ample closet space.brbrThe three full bathrooms and two convenient half baths are stocked with all the essentials, from fresh towels to premium toiletries. High-speed Wi-Fi keeps you connected, while the smart TV offers endless entertainment options.brbrStep outside to the private pool, where you can unwind with a refreshing swim or relax on the waterfront deck, complete with a gas grill for those perfect outdoor meals. The private pool area is the ideal spot to soak up the sun or enjoy a quiet evening under the stars.brbrEaston is a vibrant town with plenty to explore. A short drive will take you to the historic Easton Town Center, where you can enjoy shopping and dining at unique local boutiques and restaurants. For outdoor enthusiasts, the Tred Avon River offers excellent kayaking and fishing opportunities. And don't miss a visit to the Easton Farmers Market for fresh produce and local crafts.brbrWhether you're looking for a family vacation, a romantic getaway, or a peaceful retreat, The Helm offers everything you need for an unforgettable stay. Book your perfect getaway today and experience the best of Easton. Talbot County STR License STN-24-23brbrPROPERTY FEATURES:brbrWaterfront: Peachblossom CreekbrDock: Private dock with 5’ MLW. Water and electricity is available for guests. Guests are allowed to tie a boat to dock with proof of insurance.brPool: Private pool. Swimming pools are open from May 15 - October 15.brGrill: Propane grill. Propane is provided.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:brbrQueen - 1 / Queen - 1 / Queen - 1 / Twin - 2 / Twin - 1 /

Bed

Bath

Sleeps

Sleeps

$1485.00

/ Nightly

Private vacation home

Beautiful Tidewater home between Easton & ST Michaels!

Easton, Maryland, United States

Bed

Bath

Sleeps

$1470.15

/ Nightly

Private vacation home

Minutes from Downtown Easton and St. Michaels | Pool

Easton, Maryland, United States

Bed

Bath

Sleeps

Vacation Rentals By Owner In Easton, MD

$1539.2

$709.81

$1051.41

$1194.04

$1485.0

$1414.57

$2594.07

$437.75

$1470.15

$1119.82

$719.74

$1113.31

Most popular vacation rentals in Easton

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