Vacation Rentals By Owner In Saint Michaels, MD

Cottage in Center of Historic St. MichaelsbrbrThis 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!).brbrHead 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!brbrPROPERTY FEATURES:brbrPet Policy: This is a pet friendly rental.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:brbrBunk Bed - Single over Single - 1 / Queen - 1 / Queen - 1 / Queen - 1 /

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Saint Michaels, Maryland, United States

3

Bed

3

Bath

6

Sleeps

$294.33

Welcome to our beautiful waterfront property, open for guests from March 25th to November 1st. We have a minimum stay of 2 nights, so you can fully enjoy our tranquil location. Our cottage is perfect for a small family or a couple and comes with a full kitchen, dining table, queen-size bed, and a pull-out coach. Enjoy the scenic views of the water. Please call our host, Elicia, upon your arrival.brbrPets are allowed, please review our pet policy. brLinens and towels are provided.brWe use well water, which is safe for cooking and showering but we recommend bringing your own drinking water.brbrAll guests are welcome to enjoy our common grounds, which include 2 small gazebos with a TV, and microwave. There is also an open fire pit for roasting marshmallows, piers for fishing and crabbing, a playground for children, and a hammock for both kids and adults. brIn case you forget your crabbing supplies, we have steamers available in our work shed. We also sell chicken necks and can bait your trout line with a 24-hour notice. Upon your return with the day`s catch, you can use our steam pots to prepare a delicious meal.brbrRelax in our waterfront chairs and take in the beautiful scenery and water views. We always interact with our guests and do our best to accommodate their needs. If you`re interested in some fresh seafood, we can provide you with the contact information of local fisherman who can deliver crabs right to our property.brbrFor those interested in shopping, St. Michael`s town is just 4 miles away and offers a variety of antique shops, as well as stores with new and old items. You can also visit the community pool with poolside chairs and lounge chairs available for a small fee.brbrWe are conveniently located just 4 miles from town, and Uber and Lyft services are available in the area.brbrPlease note that we do offer boat rentals at an additional cost. Our rates are $175 per day for a 14` boat with a motor, $875 for a week, and $90 for a half day. If you prefer a 14` boat without a motor, the rates are $40 per day, $200 for a week, and $25 for a half day. We also have a 16` boat without a motor available for $250 for a full 24 hours.brbrPlease take good care of our boats and cottages during your stay. Any damage or excessive cleaning needed may result in an additional fee. There is a 10% tax on your bill; 6% is collected by Airbnb and the remaining 4% will be collected upon arrival as the County Room Tax.brbrThank you for choosing us for your stay, we appreciate your hospitality and kind consideration in taking care of our property for the next guests. Check-in on the property is from 3pm to 9pm and check-out is at 11:00 am. We kindly ask that you adhere to these check-in and check-out times. We look forward to welcoming you to our lovely waterfront property.brNo parties.brNo unauthorized guests.brNo fireworks.brNo smoking.brNo trash outside.brbr Quiet hours: 10pm - 9ambrbr Please tidy up before check-out brbrAny house rule violated can result up to a $500 fine.

Cottage #4 Chesapeake Blue down the drive way.

Saint Michaels, Maryland, United States

Bed

Bath

Sleeps

$1611.83

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. brbrThe 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. brbrPerfectly 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.brbrTalbot County STR License STN-23-19

Minutes from Downtown St. Michaels | Pool | Kayaks | 350 Ft of Shoreline | Luxur

Saint Michaels, Maryland, United States

Bed

Bath

Sleeps

$294.33

Relax with the whole family at this peaceful place to stay. Great Sunset and Sunrises, located on Harris Creek, each cottages is on angle so no view is blocked. Open Studio style room with queen size bed one side, futon open to full size will sleep 2, other side is full kitchen incl: microwave, full sz refrigerator and stove, equipped with utensils, silverware, pots, pans, dishes, cups, glasses. Beds have quilts sets, pillows (4) plenty of seating on grounds, fire pit, steam station etc.brNo parties.brNo unauthorized guests.brNo fireworks.brNo smoking.brNo trash outside.brbrPet policy : br✅ Pet Fee: A $50 pet fee applies and should be paid before check-in.br✅ Crate Requirement: Pets must be crated when left alone in the rental.br✅ Clean-Up: Please clean up after your pet, both indoors and outdoors.br✅ Damage Responsibility: You are responsible for any damages caused by your pet. Additional charges may apply if extra cleaning or repairs are needed.brPlease confirm that you agree to these terms before your arrival. Let us know if you have any questions—we’re happy to help! brbr Quiet hours: 10pm - 9ambrbr Please tidy up before check-out brbrAny house rule violated can result up to a $500 fine.

#2 Egret Cottage Harris Cove

Saint Michaels, Maryland, United States

Bath

Sleeps

Exceptional(1)

$294.33

Welcome to our beautiful waterfront property, open for guests from March 25th to November 1st. We have a minimum stay of 2 nights, so you can fully enjoy our tranquil location. Our cottage is perfect for a small family or a couple and comes with a full kitchen, dining table, 2 queen-size bed. Enjoy the scenic views of the water. Please call our host, Elicia, upon your arrival.brbrPets are allowed, please review our pet policy. brLinens and towels are provided.brWe use well water, which is safe for cooking and showering but we recommend bringing your own drinking water.brbrGreat for any type of getaway, family reunions, intimate couples getaway, or family gatherings. All guests are welcome to enjoy our common grounds, which include two small gazebos with tv and microwave, horse shoes and corn hole, playground, hammocks, kayaks, canoes, and paddle boats to use for FREE. Keurig coffee machine , pots, pans, silverware, dishes, utensils for your convenience. Just pack food and drinks and head on down. We are water front but there is no beach area sorry.brIn case you forget your crabbing supplies, we have steamers available in our work shed. There are also fishing rods and kayaks available to use. Upon your return with the day`s catch, you can use our steam pots to prepare a delicious meal.brRelax in our waterfront chairs and take in the beautiful scenery and water views. We always interact with our guests and do our best to accommodate their needs. If you`re interested in some fresh seafood, we can provide you with the contact information of local fisherman who can deliver crabs right to our property.brFor those interested in shopping, St. Michael`s town is just 4 miles away and offers a variety of antique shops, as well as stores with new and old items. You can also visit the community pool with poolside chairs and lounge chairs available for a small fee.brWe are conveniently located just 4 miles from town, and Uber and Lyft services are available in the area.brPlease note that we do offer boat rentals at an additional cost. brOur rates are $175 per day for a 14` boat with a motor, $875 for a week, and $90 for a half day. If you prefer a 14` boat without a motor, the rates are $40 per day, $200 for a week, and $25 for a half day. brWe also have a 16` boat without a motor available for $250 for a full 24 hours.brAny boat returned uncleaned or not in condition as rented will be charged a $50 fee for cleaning. Same for the Cottages, if turned back over in unclean condition or not as you received the unit in there will be a cleaning bill minimum charge of $50 applied to final bill. There is a 10% tax on your bill 6% collected by ABB, the County Room Tax 4% will be collected upon arrival. Thank you for your hospitality and kind consideration and care of our boats and units for the next customer behind you. Check in on grounds 3pm -9PM Check out 11:00 Am or before required. No exceptions please don’t ask!brThank you for choosing us for your stay, we appreciate your hospitality and kind consideration in taking care of our property for the next guests. Check-in on the property is from 3pm to 9pm and check-out is at 11:00 am. We kindly ask that you adhere to these check-in and check-out times. We look forward to welcoming you to our lovely waterfront property.brNo parties.brNo unauthorized guests.brNo fireworks.brNo smoking.brNo trash outside.brbrPet policy : br✅ Pet Fee: A $50 pet fee applies and should be paid before check-in.br✅ Crate Requirement: Pets must be crated when left alone in the rental.br✅ Clean-Up: Please clean up after your pet, both indoors and outdoors.br✅ Damage Responsibility: You are responsible for any damages caused by your pet. Additional charges may apply if extra cleaning or repairs are needed.brPlease confirm that you agree to these terms before your arrival. Let us know if you have any questions—we’re happy to help! brbr Quiet hours: 10pm - 9ambrbr Please tidy up before check-out brbrAny house rule violated can result up to a $500 fine.

#3 Mallard Cottage (located 3rd down drive)

Saint Michaels, Maryland, United States

Bed

Bath

Sleeps

$1107.4

Summary:brbrWelcome to The Kipsy, your private waterfront oasis on Porters Creek, just minutes from charming St. Michaels. With a pool, hot tub, fire pit, and private dock, this home is the perfect balance of relaxation and adventure for families and groups.brbrbrbrTalbot County Licensure: STRN-24-49brbrbrbrThe Space:brbrInside, The Kipsy features an open, light-filled layout with modern furnishings and panoramic creek views. The gourmet kitchen is fully equipped for entertaining, while the large dining area and cozy living room invite family meals and movie nights. Three comfortable bedrooms provide restful retreats. With multiple indoor and outdoor spaces, the home easily accommodates families, friends, or groups celebrating special occasions.brbrbrbrThe Kipsy is tucked away in a quiet setting, yet only minutes to St. Michaels. Explore award-winning restaurants, boutique shops, museums, and harbor cruises. It’s the perfect home base for weddings, family reunions, or a peaceful Eastern Shore getaway.brbrbrbrWhat you'll love:brbr- Sparkling private pool with sun loungersbrbr- Hot tub overlooking the creek for year-round relaxationbrbr- Evening gatherings around the fire pit under the starsbrbr- Private dock ideal for fishing, crabbing, or launching kayaksbrbr- Spacious, open-concept living areas with water viewsbrbr- Just minutes to St. Michaels restaurants, shops, and harborbrbrbrbrCurated 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:brbrThe Kipsy is tucked away in a quiet setting, yet only minutes to St. Michaels. Explore award-winning restaurants, boutique shops, museums, and harbor cruises. It’s the perfect home base for family reunions, or a peaceful Eastern Shore getaway.brbrbrbrOther Things to Note:brbrWe provide a starter supply of toilet paper and paper towels, although we recommend bringing extra for longer stays.brbrbrbrThe private pool is scheduled to open for the season on April 15, 2026.

St. Michaels Escape | Pool, Hot Tub & Fire Pit

Saint Michaels, Maryland, United States

Bed

Bath

Sleeps

$290.4

brDiscover your home away from home in the heart of historic St. Michaels. Located on a peaceful residential street, this cottage offers a quiet sanctuary while putting the town’s best coffee shops, restaurants, and the harbor just steps from your front door.brbrThe Space:brbrEffortless Main-Level Living: All guest spaces are on the first floor, featuring a bright, spacious bedroom, 1.5 baths, a fully equipped kitchen, and a cozy family room.brbrOutdoor Serenity: Sip your morning coffee on the quiet front porch or retreat to the privacy of the fenced backyard and airy enclosed back porch.brbrExclusive Privacy: You have the entire first floor to yourself; the second floor is closed during stays to ensure a private, intimate experience.brbrUnbeatable Walkability:brLeave the car keys on the counter—you are perfectly positioned to explore everything on foot or by bicycle:brbrCoffee & Pastries: Stroll just 2–3 blocks to local favorites like Blue Heron Coffee or Sprout for your morning fix.brbrDining & Drinks: You’re minutes from the vibrant Talbot Street scene, including Bistro St. Michaels, Ava’s Pizzeria, and the legendary Carpenter Street Saloon.brbrThe Harbor & Museum: A short, scenic walk leads you directly to the Chesapeake Bay Maritime Museum (CBMM) and the waterfront, where you can watch the skipjacks come in or catch a sunset cruise.brbrLocation & Logistics:brPark your car in the driveway and forget it! Whether you’re here for a festival weekend, a wedding, or a quiet escape, our cottage is the perfect base camp for experiencing the magic of the Eastern Shore.

Charming Intown Cottage – The Ultimate Walkable Getaway steps from Downtown!

Saint Michaels, Maryland, United States

Bed

Bath

Sleeps

$533.57

Summary:brbrStay in the heart of downtown St. Michaels in this charming, professionally managed studio apartment, perfectly located so you can walk to restaurants, shops, and the waterfront. Ideal for couples, solo travelers, this cozy retreat offers comfort, convenience, and a prime location in one of Maryland’s most beloved coastal towns. Pet-friendly and thoughtfully equipped, it’s an easy, stress-free place to settle in and enjoy the area like a local.brbrbrbrThe Space:brbrThis thoughtfully designed studio is the perfect home base for exploring downtown St. Michaels. Every detail has been intentionally curated to maximize comfort, functionality, and ease , whether you’re staying for a weekend or a longer stay.brbrbrbrInside, you’ll find:brbr- A cozy sleeping area with high-quality linens and a comfortable mattress for a great night’s sleepbrbr- A welcoming sitting area to relax, read, or enjoy a quiet evening after a day outbrbr- A practical kitchenette equipped with essentials for morning coffeebrbr- A clean, modern bathroom stocked with fresh towelsbrbr- Fiber Internet making for a great space for workbrbrbrbrThe layout is efficient yet inviting, offering everything you need without feeling cramped, ideal for guests who want comfort without excess.brbrLarge windows bring in natural light, creating a bright and calming space to unwind between adventures.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 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:brbrYou’re truly in the center of it all, quaint boutiques, delicious seafood spots, harbor strolls, and live music venues are just steps away. St. Michaels’ rich history and vibrant culture are yours to explore.brbrbrbrGetting Around:brbrWalk everywhere in town, or rent a bike for a scenic ride. Free private parking makes exploring the Eastern Shore a breeze.brbrbrbrOther Things to Note:brbrWe welcome your furry friends at an additional non refundable fee of $200 per pet. Starter supply of paper towels, toilet paper, and basic toiletries provided. Please bring extra supplies if you prefer more than the starter set.

Apartment

Downtown St. Michaels | Porch + Pet-Friendly

Saint Michaels, Maryland, United States

Bed

Bath

Sleeps

$474.9

Less than a mile to the town center, this property is a perfect location for those seeking a tranquil Eastern Shore escape that is still within walking distance to historic downtown Saint Michaels. This home boasts a newly renovated interior and exterior, and includes a full-size kitchen that is equipped with all essential appliances, a full-size dining room and living room with a flat screen tv, three upstairs bedrooms and two full baths. In addition, there is a large backyard for privacy. There is one noise monitoring device in the house: it is located in the office and only monitors noise decibel levels as well as the number of IOS devices in the home. This device monitors noise and decibel levels 24/7 but it does not record audio or video and is for safety and security purposes. brbr* A signed contract is required after booking. No pets. No one under the age of 24 will be allowed to book. No parties. No smoking. No parking on grass. brbrTalbot County STR License #ST-242-LOU

Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels

Saint Michaels, Maryland, United States

Bed

Bath

Sleeps

$1021.84

Location , Location, LocationbrbrEscape to this stunning cedar Lindal home on the Eastern Shore, just a short drive from historic St. Michael's. Perfect for friends and family, this spacious 3-bedroom, 2.5-bathroom retreat boasts a top-to-bottom renovation with an open floor plan, chef inspired kitchen, loft, and expansive entertainment areas. Floor-to-ceiling windows frame breathtaking views of Broad Creek, creating a tranquil backdrop for cocktails and conversation in the screened patio, outdoor dining and poolside relaxation. brbrEnjoy the wrap-around porch, heated swimming pool, and a cozy propane fire pit under the stars. Don't miss this unique opportunity to unwind in luxury. Talbot County STR License STN 24-13brbrPROPERTY FEATURES:brbrWaterfront: Broad CreekbrDock: Private dock with 4ft MLW, water and electricity available for guest use.brPool: 18 x 38 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. brWater Toys: 2 kayaks, 2 stand up paddleboards, pool toys and crabbing gear are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency.brLand Toys: Badminton or corn hole are available for guest use.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:brbrKing - 1 / Queen - 1 / Double - 2 /

Minutes from Downtown St. Michaels | Pool | Dock

Saint Michaels, Maryland, United States

Bed

Bath

Sleeps

$724.13

Cranford on the Miles is an historic waterfront home located on 3+ acres, in St. Michaels, and 1+ mile from the beginning of town. Fully renovated, with WI-Fi, there is a Master Bedroom with king bed, sitting room, private bathroom and private balcony; Second Bedroom with a double bed; Third Bedroom with both a double and twin bed; and a Den with a trundle bed with 2 twins beds and a second balcony. Downstairs there is a queen sofa bed. Every room has a view of the water. brbrLinens, towels, beach towels, blankets and pillows provided.brbrProvided are two kayaks (one single, one double) for exploring the Chesapeake.brbrFrom the private dock you can watch wildlife, fish or crab. Roast marshmallows over the fire pit, or cook your fish on the grill. Bring your boat and launch from the public boat ramp within walking distance. brbrOr just relax on either the screened porch with ceiling fans, cushioned sofa and chairs, or the front porch rocking chairs. Indoors, every bedroom has a TV, large TV is genie ready, books, and music CDs for all ages. The second family room has a fireplace.brbrTalbot County Short Term Rental License Number STN-24-32.brbrThere is also a community pool about 1 mile from the house.

Waterfront Property, kayaks, private dock, near town

Saint Michaels, Maryland, United States

Bed

Bath

Sleeps

$519.05

Summary:brbrWelcome to Coco’s Nest, your intimate escape in the charming historic district of Saint Michaels, Maryland. Perfect for couples, friends, or small families, this two-bedroom retreat blends modern comfort with classic Eastern Shore charm. Located just steps from the harbor, boutique shops, restaurants, and art galleries, you can park once and explore the best of Saint Michaels on foot.brbrbrbrThe Space:brbrOur thoughtfully designed second-floor apartment combines clean, modern finishes with the character of a historic coastal town. Relax in the open living area, step out to the private balcony, or retreat to the plush comfort of two king bedrooms. The kitchenette includes essentials for light cooking—ideal for preparing breakfast, snacks, or coffee.brbrbrbrWhat you'll love: brbr- Prime Location: In the historic district, just steps from shopping, dining, and attractions.brbr- Spacious Comfort: 2 king bedrooms with luxury bedding for restful nights.brbr- Private Balcony: Sip coffee or wine while enjoying the peaceful small-town vibe.brbr- Spa-Like Bathroom: Walk-in shower, plush towels, and premium toiletries provided.brbr- Private Parking: Leave your car and explore Saint Michaels on foot.brbr- Keyless Entry: Smooth, secure check-in process.brbrbrbrWhether you’re here for a romantic weekend, sailing adventure, wine tasting, or a family getaway, Coco’s Nest is perfectly located for all Saint Michaels has to offer. Walk to harbor cruises, seafood restaurants, antique shops, and the Chesapeake Bay Maritime Museum. Short drive to Tilghman Island, Oxford, and other Eastern Shore destinations.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 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:brbrYou’re truly in the center of it all—quaint boutiques, delicious seafood spots, harbor strolls, and live music venues are just steps away. St. Michaels’ rich history and vibrant culture are yours to explore.brbrbrbrGetting Around:brbrWalk everywhere in town, or rent a bike for a scenic ride. Free private parking makes exploring the Eastern Shore a breeze.brbrbrbrOther Things to Note:brbrThere is stairs to enter the apartment.

Apartment

Elegant 2-Bedroom Retreat in Historic Saint Michaels – Walk to Dining & Shops

Saint Michaels, Maryland, United States

Bed

Bath

Sleeps

$473.0

The recently renovated Carpenter St. Cottage is centrally located in village of St. Michaels. The house is a 2 bedroom 2 full bathroom house with plenty of living space and a large screened porch facing a large yard. Rates vary by season, and whether stay is weeknight or weekend. Stays of a week or longer are discounted, as are last minute bookings.brbrThe first floor of the house includes a front parlor (living room), a den (reading room) with a queen sleep sofa, a full bathroom, a first floor bedroom with a queen bed, a fully equipped new kitchen, and a large family room. Adjacent the family room is a large screened porch facing the large rear yard. The second floor of the house comprises the large master bedroom with a king bed and the master bathroom. br

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Saint Michaels, Maryland, United States

Bed

Bath

Sleeps

$1385.7

A Tranquil Contemporary St. Michaels Waterfront Cottage featuring a separate 1st floor newly renovated garage apartment with its own kitchen.brbrThis 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. brbrThe 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.brbrSet 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. brbrThis 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-23-37brbrPROPERTY FEATURES:brbrWaterfront: Solitude CreekbrDock: 750 feet of shoreline with 80 ft of private dock with 4.5 ft MLWbrGuest House: 1st floor newly renovated garage apartment with its own kitchen.brWater 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.brPool: 600 sq ft private swimming pool. Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels.brGrill: Propane grill. Propane is provided.brHot Tub: 6 person hot tub is available for guest use.brFirepit: Wood provided.brPet Policy: This is a pet friendly property.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 / Queen - 1 / Double Bed - 1 / Single Bed - Twin Sized - 2 / Single Bed - Twin Sized - 1

Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock

Saint Michaels, Maryland, United States

Bed

Bath

Sleeps

$332.81

The Dollhouse is a fully updated two story centrally located 1870s historic house with 2 bedrooms and 1.5 baths. The house was completely restored during 2016-2020. The house has a front porch as well as screened rear porch. There are TVs in living room (55) and master bedroom. Popular local outdoor activities include fishing, kayaking, paddle boarding, biking or simply relaxing. This is a wonderful property centrally located in St Michaels. Great restaurants and shops within blocks of the house!

Dollhouse in Central Historic St Michaels

Saint Michaels, Maryland, United States

Bed

Bath

Sleeps

$1518.7

Summary:brbrExperience a stunning waterfront escape just minutes from the charm and dining of downtown St. Michaels. This spacious, beautifully furnished home offers panoramic water views, your own private dock, and a sparkling pool, perfect for families, groups, or extended stays.brbrbrbrTalbot County Licensure: STRN-26-17brbrbrbrThe Space:brbrFrom the moment you arrive at Eventide Farm, the rhythm of life slows. The home is designed to draw you toward the water — with panoramic views from nearly every room and gentle breezes that flow through open French doors.brbrThe living room is a sun-drenched gathering place, anchored by plush seating, a warm color palette, and windows framing the pool and shoreline. It’s the heart of the home, perfect for late-night board games, coffee at sunrise, or curling up with a book after exploring town. The kitchen is both a chef’s dream and a family hub — featuring high-end appliances, generous counter space, and an oversized island for casual dining or wine tastings. Step outside to discover multiple terraces and patios — each with its own mood. Sunbathe by the pool, sip cocktails in the shaded garden lounge, or dine al fresco as the sky turns gold at sunset. For restful nights, the first-floor primary suite offers private pool access and spa-like amenities. Upstairs, four additional bedrooms are designed for tranquility — each thoughtfully decorated with soft linens, cozy textures, and serene lighting.brbrbrbrWhat you'll love: brbr- Unmatched sunset views over the private pool.brbr- Spacious open-plan design that flows effortlessly outdoors.brbr- Multiple lounge areas for cocktails, coffee, or simply watching the tide.brbr- Luxury bedrooms with plush bedding and curated décor.brbr- Proximity to St. Michaels — a charming harbor town full of dining, boutiques, and history.brbrbrbrWhether you’re here for intimate family time, a friends’ getaway, or a quiet retreat, every inch of Eventide Farm invites you to live slowly, connect deeply, and savor every season.brbrbrbrWhile this home is new to VRBO, it is professionally managed by Flaneur, an experienced vacation rental company with hundreds of 5-star reviews across our portfolio. 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:brbrLocated just minutes from St. Michaels — renowned for its historic waterfront, boutique shops, and acclaimed restaurants. Whether sailing, antiquing, or simply strolling, you’ll find a perfect mix of activity and relaxation.brbrbrbrOther Things to Note:brbrStarter paper goods provided; please bring any additional supplies you may need.brbrbrbrThe private pool is scheduled to open for the season by Memorial Day.

Luxury Waterfront Home with Pool + Private Dock

Saint Michaels, Maryland, United States

Bed

Bath

Sleeps

$641.3

Welcome to Grace Street Cottage, a charming retreat in the heart of the historic district of St. Michaels. We are new owners of this lovely cottage and are committed to upholding the high standards set by the previous owners. Don't worry--if you have already booked through them, we saved your spot. If you are considering Grace cottage for the first time, we are thrilled to tell you that it is a guest favorite with a 4.99 rating.brbrGrace Cottage is a cozy home with a newly renovated kitchen in one of the most walkable locations in St. Michaels. Set on a large lot with a private yard at 100 Grace Street, you are moments from the heart of town—yet pleasantly set back from the main street for a calmer, more relaxed stay.brbrSpend your days strolling to local shops, restaurants, and waterfront charm, then come home to cozy evenings by one of the three fireplaces. Inside, you’ll find multiple living spaces—perfect for gathering with friends, spreading out with a book, or enjoying a quiet night in.brbrOutside, embrace effortless outdoor living on the Eastern Shore. Grill, dine, and unwind by the fire pit in your own private oasis. Surrounded by a high privacy fence, the oversized backyard offers total seclusion for stargazing and peaceful evenings.brbrYou will have the entire house to yourself. There is one bedroom on the first floor and another on the second (each with its own bathroom). Although you are in the center of in town, where parking is challenging, there is a private driveway that easily accommodates two vehicles. Nearby restaurants are some of the best in the area, and there is a great market in town if you prefer to whip up something on your own. The house is stocked with everything you need from cooking supplies to bedding and toiletries. brbrWith 2 bedrooms, 2.5 baths, beautiful character, and all the comforts you need for a getaway, Grace Street Cottage is an ideal home base for experiencing the very best of St. Michaels.

Grace Cottage, St Michaels Walk to everything!

Saint Michaels, Maryland, United States

Bed

Bath

Sleeps

$653.34

Step away from the rush of everyday life and into the cozy calm of our family's cabin. Nestled on acres of pristine forest just 3 miles from historic St. Michaels (and 8 miles from Easton). Here you can enjoy the feel of a true retreat while staying effortlessly close to the restaurants, historic sites, and waterfront activities that make the Eastern Shore so special.brbrbrbrOur log-built cabin overlooks a 1-acre freshwater pondbrbrSleeps 8 with multiple living and dining areasbrbrProvides Modern comforts including central heat/air, fully equipped kitchen and TVs in each bedroombrbrOutdoor enjoyment with our grill, fire pit, covered & uncovered decks for views in all directions. S’mores station, fire wood, and charcoal included.brbrWhether sipping your morning coffee on the porch or gathering at the fire pit under the stars, every moment is surrounded by quiet, peace, and the ever-changing backdrop of forest and sky.brbrTalbot County License #STN24-27brbrSubject to Talbot County Code. No Fireworks, Events, Parties, Violations of Noise CodebrbrMinimum 3 night stay

Cozy, Family Friendly, Log Cabin-St. Michaels, MD

Saint Michaels, Maryland, United States

Bed

3

Bath

8

Sleeps

$316.23

Stunning and completely renovated 1940s bungalow in the heart of Saint Michaels! Located just steps from shopping, restaurants, historical sites, and the harbor. Amazing chef's kitchen, hardwood flooring throughout, two cozy bedrooms, fantastic living room/dining room combo, full size W/D, cable/internet, and more! Screened in front porch PLUS backyard with fire pit and gas grill for entertaining or just relaxing. Parking for two cars. Don't miss this gem!

Stay in the HEART of Saint Michaels!

Saint Michaels, Maryland, United States

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Bath