Vacation Rentals By Owner In Wittman, MD

Exceptional(122)

$247.5
/ Nightly

Cottage

Perfect Waterview Cottage - St. Michaels Getaway

Wittman, Maryland, United States
Shipwright Cottage is a fully-renovated idyllic getaway located in the Bay Hundred area of the Chesapeake Bay just 8 miles outside of St. Michaels, MD. Bikes and kayaks included!brbrShipwright Cottage is a fully-renovated 2 bedroom, 1 1/2 bath house that is a perfect getaway for couples or small families. The open concept main room on the second floor offers an queen-sized bed and reading nook, while the second bedroom has two extra long twin beds that can be combined to make a king. The living room offers an electric fireplace and pull out sofa. The full bath features a luxurious glass shower and water views accent every room. A screened porch offers space to relax and enjoy the views. The cottage is fully equipped with a fabulous kitchen, WiFi, DVD player, washer-dryer, and charcoal grill. Linens and bath towels are included. Two kayaks, Two adult bicycles, one child's bike, and one bike trailer are available for your use.brbrShipwright Cottage is located on Cummings Creek, just a short drive to St. Michaels, Tilghman Island, Oxford, and Easton.brbrThis property is a Talbot County licensed short term vacation rental (License #ST-228-HAB).

2
Bed

1
Bath

4
Sleeps

Exceptional(2)

$323.3
/ Nightly

Cottage

Lovely 2-bedroom waterfront cottage in charming Wittman

Wittman, Maryland, United States
Discover the beauty of Wittman from this 2-bedroom cottage. Guests will find a comfortable queen bed and a cozy twin bed, perfect for a small group or family. The bathroom features a refreshing shower and a handy hair dryer for convenience. With heating and AC, the cottage stays comfortable no matter the season. Whether you’re relaxing indoors or exploring nearby, this beautiful space offers an enjoyable retreat. We think our place will help you experience everything Wittman has to offer.

2
Bed

1
Bath

4
Sleeps

Exceptional(7)

$229.57
/ Nightly

Private Vacation Home

Cozy getaway! Centrally located between St. Michaels and Tilghman Island

Wittman, Maryland, United States
Unwind in Wittman at this welcoming house. With 3 cozy bedrooms including a queen bed, full bed, and bunk bed, guests will feel right at home. The living room offers an awesome additional space with a comfy sofa bed for extra sleeping arrangements. Stay connected with WiFi, keep clothes fresh with a washing machine, and stay comfortable with heating and AC. Enjoy your time in Wittman at our phenomenal house.

3
Bed

1
Bath

6
Sleeps

Exceptional(1)

$259.48
/ Nightly

Private Vacation Home

Charming 3 Bedroom Cottage – 6 Miles to St. Michaels

Wittman, Maryland, United States
Summary:brbrWelcome to Pot Pie Cottage — your charming, well-priced escape just minutes from the historic town of St. Michaels! Perfect for friends, family gatherings, or a peaceful solo retreat, this light-filled 3-bedroom home blends modern comfort with a serene coastal setting. Centrally located between St. Michaels and Tilghman Island, you’ll have easy access to waterfront dining, boutique shopping, and scenic fall foliage drives along the Eastern Shore.brbrbrbrTalbot County Licensure: STRN-25-31brbrbrbrThe Space:brbrEscape to Pot Pie Cottage, a bright and welcoming 3-bedroom home perfectly positioned between the charming towns of St. Michaels and Tilghman Island. Just 6 miles from the shops, restaurants, and waterfront of historic St. Michaels, this well-priced Eastern Shore retreat is ideal for families, friends, or couples looking for a peaceful getaway with easy access to local attractions.brbrbrbrInside, you’ll find a spacious, light-filled open floor plan with sleek furnishings, comfortable seating, and warm touches that make the home feel instantly inviting. The fully equipped kitchen is stocked with everything you need to prepare meals, from quick breakfasts before exploring town to cozy dinners at home. The dining area comfortably seats your group, and the living room features a Smart TV for movie nights after a day of adventures. For those who need to mix work with leisure, the dedicated workspace offers a quiet, comfortable spot to stay connected. Each of the three bedrooms is thoughtfully designed for restful nights, with plush bedding and plenty of natural light.brbrbrbrIn the fall, enjoy crisp mornings on the porch, scenic drives along the Chesapeake Bay, and nearby harvest festivals. In every season, Pot Pie Cottage delivers comfort, convenience, and excellent value.brbrbrbrWhat you'll love:brbr- Prime location — just 6 miles to historic St. Michaelsbrbr- Pet-friendly so you can bring your furry companionsbrbr- Affordable rates without sacrificing comfort or stylebrbr- Open, light-filled floor plan perfect for groupsbrbr- Fully equipped kitchen and Smart TVbrbr- Dedicated workspace for remote workbrbr- Quiet, peaceful neighborhoodbrbrbrbrCurated 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.brbrbrbrOther Things to Note:brbrStarter supply of paper towels, toilet paper, and basic toiletries provided. Please bring extra supplies if you prefer more than the starter set.

3
Bed

1
Bath

6
Sleeps

$2747.46
/ Nightly

Private Vacation Home

Bayview 2.0 | an ESVR property

Wittman, Maryland, United States
Escape to Bayview 2.0, a stunning waterfront retreat within a few miles of charming St. Michaels. Designed for unforgettable getaways, this expansive estate comfortably hosts up to 12 guests on a property that spans more than twelve acres. This home was crafted to deliver comfort, privacy, and relaxation.brbrWake up to sweeping views of the Chesapeake Bay and end your evenings with breathtaking, golden sunsets right outside your door. This expansive waterfront property boasts six beautifully appointed bedrooms each designed to provide a serene and comfortable escape. Four of the bedrooms have an ensuite full bathroom. Four bedrooms have king size beds, another bedroom has two king size beds and the sixth bedroom has a queen bed. All are equipped with premium linens and modern amenities. The first floor master bath provides a spa like experience. There are also two ½ baths and an outdoor shower. This home has majestic views of Chesapeake Bay and the sunsets are picturesque and unforgettable. Step into the open concept living and dining areas, where you will find an elegantly designed kitchen complete with top of the line appliances, extensive counter space and a cozy waterfront breakfast nook. The screened in porch offers comfortable seating with views of the Chesapeake Bay and the beautiful patio and pool. The living room is perfect for unwinding after a day of swimming and exploration with plush sofas, a smart TV and fireplace available for guest use.brbrOutside you will find a beautifully landscaped waterfront with a dock, ideal for fishing or simply soaking in the tranquil surroundings. This property also features a heated pool, hot tub and BBQ area perfect for gatherings and outdoor entertaining.brbrThe historic town of St. Michaels is a short 10 minute drive away and offers an array of shopping with fine and casual dining. Spend a day exploring the Chesapeake Maritime Museum, the St. Michaels nature trail and the historic downtown walking tour. You are within driving distance of the historic Harriet Tubman Underground Railroad Scenic Byway and the Blackwater National Wildlife Refuge. The town of Easton, a 22 minute drive from the home, has extensive shopping, dining and attractions that include the Academy Art Museum, Prager Auditorium and the Pickering Creek Audubon Center. The Avalon Theater provides dynamic arts, education and cultural programming. There are public and private golf courses in the area as well as public tennis courts.brbrWhether you are seeking a relaxing family vacation or a fun filled getaway with friends, Bayview 2.0 promises an unforgettable stay. Book now and make this luxurious waterfront haven your home away from home. Talbot County STR License STRN-26-11brbrPROPERTY FEATURES:brbrWaterfront: Eastern Bay - part of Chesapeake BaybrDock: Dock with 3ft MLW, water and electricity available for guest use.brWater Toys: Crabbing gear is available for guest use.brPool: 20’ x 45’ salt water pool. Pools are open from May 15 - October 15. Be sure to bring your own pool towels.brHot Tub: Open year round and available for guest use.brGrill: Propane grill with pizza oven. Propane is provided.brPet Policy: Pets are not permitted.brWiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds.brbrTHIS IS A LUXURY RENTAL:brbrGuests that stay at one of our luxury rentals unlock private access to a world of privilege. Benefits include:brbrUpon request an ESVR representative greeting you at your 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.

6
Bed

6
Bath

12
Sleeps

Exceptional(70)

$1068.83
/ Nightly

Private Vacation Home

Waterfront Oyster Farmhouse Built 2018 with Pool/Fence and Dock-23 private acres

Wittman, Maryland, United States
Relax and absorb the beauty of living on the water at our 23 acre waterfront property on Harris Creek, in between historic St. Michaels and charming Tilghman Island. Our family has lived on this body of water for 10 generations and we would love to share the ambience with your family or group of friends. brbr The house was designed by DC architect, Richard Leggin and completed in October 2018 with 5,000 sq. ft. of awesome living space. There is a new 140 ft. dock and an outdoor pool with fence and tanning ledge installed October 2022. A 5 acre oyster aquaculture lease is located in the water cove behind the house. Guests of all ages enjoy fishing/crabbing/swimming off of the dock and beach area with a spacious lawn for croquet , cornhole, lawn golf, and fire pit. You may bring your own boat (or rent a boat at Tilghman Marina) to tie up at our dock. We invite you to observe the operations of our family owned oyster business, Harris Creek Oyster Company, and perhaps sample the product! Oysters are an ecological and sustainable product that benefit the Chesapeake Bay. brbrThe farmhouse has a spacious/open floor plan with adjacent breezeway and detached garage/exercise room and full bath. There is a Master bedroom wing on the main floor with an additional master suite located on 2nd floor. The bathrooms have all glass shower doors and tile. The kitchen is bright and spacious with an 8 ft. quartz island, porcelain tile, 2 ovens, farm sink and wine/coffee bar. Family/TV room has granite wet bar. 2nd floor observation deck provides wide views of Harris Creek. There are 2 fireplaces (wood and gas) and entire back of house is encompassed by a 90 ft. brick and bluestone porch. Wake up to the sounds of watermen catching crabs for your evening dining pleasure at home or at any of the fabulous restaurants in St. Michaels or Tilghman Island. Explore the area with bikes and kayaks that are provided. Enjoy the evening with after dinner S’mores at our fire pit.brbrbrTalbot County Short Term Rental License #brST-858 JOH 2019brTalbot County Taxes are listed as Property Fees

4
Bed

4
Bath

8
Sleeps

$352.27
/ Nightly

Cottage

Relaxing Waterfront Cottage Near St Michaels, Maryland

Wittman, Maryland, United States
Eastern Shore two bedroom cottage with dock on a quiet creek of the Chesapeake Bay in Wittman, Maryland. Surrounded by mature majestic shade trees. Beautiful water views on 3 sides and facing west with spectacular sunsets from the comfort of your screened front porch. Quiet street, ideal for relaxation and getting away from it all. brbrInterior remodeled/upgraded a few years ago. Bright living area incorporates: living room with two sofas and a recliner, TV with basic cable, VCR player and video collection; dining area which opens onto side deck; and a modern kitchen with silestone counter-tops, single oven, fully stocked with dishes and utensils, including toaster, coffee maker, electric kettle. Two modest sized bedrooms. Master with queen bed and sliding double doors opening directly onto front porch. Ensuite bathroom with shower and jetted soaking tub. Second bedroom with queen bed and connected bathroom with shower. Laundry room with washer and dryer. Grill (gas)on deck for use by guests, Private pool open Memorial Day thru Labor Day. Includes a portable Fire pit near private dock that has a bench to watch the wild life and sunsets.brbrWireless internet access.brbrEnjoy crabbing and kayaking (two kayaks with vests provided) from the large dock (bring your boat - draw about 4 feet) or just relax and read or watch the water from the newly screened porch furniture. Self-contained for everything you need for a relaxing time away from home, work and the madding crowd! brbrEnjoy riding our 2 bikes or take a ride just 7 miles into St Michaels along 322 where you can enjoy coffee at the Blue Heron Coffee Shop on Talbot St. as good as you can find anywhere or dine at any one of many fine restaurants after you amble through the shops and explore the harbor. Easy access to St Michaels, Easton, Oxford. brbrTalbot County Short Term License # STRN-26-35

2
Bed

2
Bath

4
Sleeps

$229.57
/ Nightly

Private vacation home

Cozy getaway! Centrally located between St. Michaels and Tilghman Island

Wittman, Maryland, United States

3
Bed

1
Bath

6
Sleeps

$1068.83
/ Nightly

Private vacation home

Waterfront Oyster Farmhouse Built 2018 with Pool/Fence and Dock-23 private acres

Wittman, Maryland, United States

4
Bed

4
Bath

8
Sleeps

$247.50
/ Nightly

Cottage

Perfect Waterview Cottage - St. Michaels Getaway

Wittman, Maryland, United States

2
Bed

1
Bath

4
Sleeps

$323.30
/ Nightly

Cottage

Lovely 2-bedroom waterfront cottage in charming Wittman

Wittman, Maryland, United States

2
Bed

1
Bath

4
Sleeps

$259.48
/ Nightly

Private vacation home

Charming 3 Bedroom Cottage – 6 Miles to St. Michaels

Wittman, Maryland, United States

3
Bed

1
Bath

6
Sleeps

$352.27
/ Nightly

Cottage

Relaxing Waterfront Cottage Near St Michaels, Maryland

Wittman, Maryland, United States

2
Bed

2
Bath

4
Sleeps

$2747.46
/ Nightly

Private vacation home

Bayview 2.0 | an ESVR property

Wittman, Maryland, United States

6
Bed

6
Bath

12
Sleeps