We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Vacation rentals in Wittman

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Wittman

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

A panoramic view of the Chesapeake Bay Bridge spans across the calm waters, framed by a soft gradient of pink and orange hues in the evening sky. The silhouettes of the bridge's towers and cables create a striking contrast against the tranquil backdrop.

Home in Stevensville

4.93 out of 5 average rating, 224 reviews

Relax on Kent Island in 3 Bedroom Home w/Waterview

Enjoy your vacation in this Beautiful & Stylish 3 Bedroom Home with a view of the Chesapeake Bay from living room & kitchen! Perfect for Families & Wedding Groups. We are conveniently located to many areas/cities: Annapolis- 20 miles Baltimore- 45 Wash. DC- 50 Easton- 35 Enjoy a Self-Check-in to this Beautiful Home that is perfectly situated near all the local Kent Island Restaurants, Shops, Attractions. This is a Non-Smoking House. Also No Pets, Parties or Large Groups (11 max). Book Today!

Top guest favorite

A spacious backyard features a sizable in-ground pool surrounded by lounge chairs and a shaded canopy. Lush greenery provides a serene backdrop, while a colorful mat adds a decorative touch to the outdoor space. Floating devices are visible on the water's surface.

Apartment in Stevensville

4.98 out of 5 average rating, 278 reviews

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

Top guest favorite

An inviting living space features a comfortable sofa and a wall-mounted television. A modern kitchen area includes dark cabinetry and light furnishings, while large glass doors lead to a covered deck with scenic water views. Natural light enhances the airy atmosphere.

Houseboat in Kent Narrows

4.97 out of 5 average rating, 150 reviews

Cass-N-Reel Luxury Houseboat

Kent Narrows Rentals Welcomes you aboard Cass-N-Reel! A 432sqft luxury getaway in the Kent Narrows. With 1 bedroom, 1 bathroom, and a gorgeous covered rear facing deck; this is the ultimate couples retreat! 9 waterfront/waterview bars/restaurants within walking distance! Get a taste of what the eastern shore has to offer. Minutes from the Chesapeake Bay Bridge and a short drive to Annapolis, D.C., St. Michaels, and Ocean City. Come stay and live like a local! NO Fishing/Crabbing on property

Top guest favorite

Home in Shady Side

5 out of 5 average rating, 169 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silver Water is a serene 5 Star retreat for those who value tranquility over spectacle. Set along the Chesapeake, it offers front-row seats to breathtaking sunsets—where golden light dances across the water. Inside, Nordic-inspired design meets quiet luxury, featuring award-winning mattresses and bedding that promise restorative sleep. Here, time slows, and luxury isn’t just something you see—it’s something you feel. We invite you to read the reviews of so many happy guests.

Top guest favorite

A view from the front porch shows a quiet street with traditional homes across the road. A round wooden table is placed under the overhang, accompanied by white metal chairs. The brick pathway leads towards the tranquil surroundings, offering a welcoming setting.

Home in Saint Michaels

5 out of 5 average rating, 101 reviews

Shipwrights Cottage in Town!

Charming historic cottage within walking distance to all St. Michaels has to offer! Relax & enjoy the sights of town from your front porch! Once a working shipwrights cottage, this home is 2 stories with a 1st floor full kitchen, combo living-dining room, den with queensize pullout couch & full bath. The 2nd floor has 2 bedrooms & a full bath. Both bedrooms have vaulted ceilings & ceiling fans. The primary bedroom has a private sitting balcony. Walk to shops, restaurants & waterfront!

Top guest favorite

A glass table holds a coffee cup and a paper bag from a local café, alongside a pastry and a muffin. Two white Adirondack chairs frame the scene, set against a backdrop of lush greenery and a garden statue.

Guesthouse in Easton

4.99 out of 5 average rating, 602 reviews

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for ONLY TWO INDIVIDUALS (No children under 8 years of age.), and please limit your visit to one vehicle only.

A modern guesthouse is illuminated by soft light under a starry night sky. The silhouette of the structure is bordered by the Milky Way, creating a serene and captivating backdrop.

Cottage in Saint Michaels

4.97 out of 5 average rating, 164 reviews

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

Top guest favorite

A grassy area extends toward calm waters, where a small sailboat is visible on the shore. Wooden docks line the water's edge, leading into the distance. Soft clouds hover above, contributing to a peaceful outdoor setting.

Guest suite in Tilghman Island

4.97 out of 5 average rating, 145 reviews

Black Walnut Cove Retreat, Tilghman Island

Our waterfront studio retreat is a birdwatchers paradise. Located on beautiful Black Walnut Cove at the southern tip of Tilghman Island, you will be in a quiet neighborhood surrounded by water. Enjoy a quiet walk or bike ride along the Chesapeake Bay shoreline. You will have access to our dock and small boat ramp. Crabbing and fishing are a delight. Please note: 1) There is a 3-nt. minimum on holiday weekends. 2) Children between the ages of 1 and 5 are not permitted

Top guest favorite

The kitchen features white cabinetry and stainless steel appliances, including a dishwasher and stove. A spacious countertop offers ample workspace, illuminated by natural light from the nearby window. The adjacent dining area is visible, showcasing a table and chairs.

Home in West River

4.98 out of 5 average rating, 124 reviews

Cozy waterview home in West River!

Your family will be close to everything when you stay at this centrally-located place. This home is located just 15 miles to Annapolis, 18 miles to the Naval Academy, and 30 miles to the heart of Washington, DC. Less then 8 miles to Rt 214, providing direct access to beltway, and other major highways. This charming home has as spacious fenced in yard, High Speed Internet, TV (Netflix & Hulu), outdoor seating and a fire pit. Want to get away? Bring the whole family!

Top guest favorite

Guesthouse in Stevensville

4.99 out of 5 average rating, 278 reviews

Waterfront Getaway - View of bay from your bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Top guest favorite

A countertop with a stainless steel sink is shown, featuring a water filtration system. The unit is clear and reveals layered filtration media. In the background, a boat-themed painting hangs above a wooden mantle, adding a coastal touch to the space.

Cottage in Saint Michaels

4.98 out of 5 average rating, 234 reviews

The Little Anchor Cottage, St. Michaels, MD

Welcome to the Little Anchor cottage in St. Michaels, Maryland! The cottage was built in late 1880s and is located in the charming Historic District, where you can enjoy the convenience of walking one block to the downtown shops and restaurants on S. Talbot street. And for another 5 to 15 minute walk, you can reach more waterfront dining on St. Michaels Harbor with its boat slips, boat ramps, the Chesapeake Bay Maritime Museum, Muskrat Park and Hollis Park.

An inviting loft space features two new twin beds with plush bedding accented by navy and white decor. A cozy window seat provides natural light and views, while light blue walls contribute to a serene atmosphere. The area rug adds a touch of warmth to the wooden floor.

Guest suite in Saint Michaels

4.78 out of 5 average rating, 358 reviews

Gorgeous Cottage: Easy Walk into St Michaels Town!

Gorgeous, sunny former artist loft with great views. Across from Miles River & harbor. Walk to town! Shopping, brewery, winery, museum, restaurants await! Located in historic Bentley Hay, the lodge is perfect for relaxing walks while runners and bikers explore spectacular sights, including the nearby St Michaels Nature Trail. Or rent a kayak and explore San Domingo Creek! NO PETS OR SMOKING. 4 GUESTS MAX BY LAW. Talbot Co License STR-716-KIM

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Wittman vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Wittman

Top guest favorite

Home in Grasonville

5 out of 5 average rating, 56 reviews

Bay Breeze - 3BR Waterfront Chester River Retreat

MollyRating, 5 stars2 weeks ago

This house was in a beautiful location. Everything was clean and comfortable, thoroughly enjoyed our stay. You cannot beat the views from the main level. Katie was communicative and we were even able to get an early check in!

An aerial view captures a spacious property surrounded by lush greenery. A rectangular pool is positioned in front of a two-story structure, along with multiple lounge chairs and a swing set nearby. The expansive lawn provides an open and inviting outdoor space.

Home in Sherwood

5 out of 5 average rating, 11 reviews

Punch Point boasts a sandy beach w/ pool and pier

ErickaRating, 5 stars1 week ago

Marissa’s place is always amazing. As usual, the house was very clean and equipped with everything a family with kids would need. We cooked multiple meals and had everything we needed in the fully stocked kitchen. The extra refrigerator upstairs came in handy for leftovers. The playroom and garage were packed with toys and games for kids of all ages. Marissa has truly thought of everything. Downtown St. Michael’s is only a short drive away and well worth the visit. We look forward to returning again soon!

Top guest favorite

Guesthouse in Stevensville

5 out of 5 average rating, 32 reviews

Private | Near BayBridge | Wedding Venue Proximity

SusanRating, 5 stars3 days ago

Karin war eine sehr freundliche und zuvorkommene Gastgeberin. Sie hat sich super schnell bei Fragen zurückgemeldet. Die Wohnung war sauber und gut ausgestattet und mit kleinen Aufmerksamkeiten sehr willkommende eingerichtet. Man kann von der Wohnung aus einen sehr schönen Naturpark und das historische Stevensville (mit tollem italienischen Restaurant) zu Fuß erreichen.

A charming outdoor seating area is set beneath a large tree, featuring a white wrought iron bench and a small table adorned with a potted flowering plant. The surrounding green lawn offers a tranquil and inviting space for relaxation.

Guesthouse in Grasonville

4.9 out of 5 average rating, 229 reviews

Eastern Shore Charm on Winchester Creek

FuadRating, 5 stars1 week ago

Judy's guest house was conveniently close to a weekend wedding getaway for us. she was a attentive and responsive host. checking in on us before, during and after our stay (thank you for letting us know about the purse we left!) her yard let's out to the water front and it's a short drive to anywhere you want on Kent Island. We appreciated her flexibility with checkin/out and the wonderful snacks and fresh muffins.

Top guest favorite

The exterior of a two-story residence is shown, featuring a light-colored siding and a blue metal roof. A paved walkway leads to the inviting front porch, bordered by neatly trimmed greenery and well-maintained landscaping.

Guesthouse in Saint Michaels

5 out of 5 average rating, 26 reviews

The Suite at Mostly Porches

StephenRating, 5 stars2 weeks ago

You won’t find a better apartment in St. Michaels. Great bed, clean and orderly with all the little things that make a stay memorable. This rental is a wonderful compliment to a special town. You will not regret your decision to visit St. Michaels nor your stay at mostly Porches.

Top guest favorite

Guesthouse in Cambridge

4.99 out of 5 average rating, 120 reviews

Rosses Chance Guest House

JoeRating, 5 stars4 days ago

I booked this quiet location for Eagleman 70.3 and it didn’t dissapoint. The cottage was the perfect spot since it was close to the race venue and a peaceful place to rest and relax before the event. The cottage was perfectly set up with everything I needed to make me feel right at home. The hosts were great at communicating with me leading up to my trip and very accommodating with my requested check in and check out times. This was a huge bonus on the last day since I didn’t have to pack up everything at 3:30am when leaving to get to the venue on race morning! I will be back for sure!

Top guest favorite

A two-story coastal cottage is illuminated by soft exterior lights, reflecting gently on the water. Surrounding trees are silhouetted against the evening sky, and a full moon casts a warm glow over the scene. The serene waterfront adds to the tranquil ambiance.

Home in Tilghman Island

5 out of 5 average rating, 18 reviews

Panoramic water views

MeganRating, 5 stars3 weeks ago

This was one of the loveliest Air BnBs I’ve had the pleasure of staying at. The photos don’t do it justice. A warm, welcoming and cozy home, filled with sunlight and stunning water views from every window. You literally feel like you’re on a boat! Comfortable furnishings and beds, a super well-stocked kitchen with lovely dishes and decor, bikes, kayaks, gas grill… everything you could want. The Tilghman Island General Store was just a short walk through a lovely neighborhood with the friendliest people. Breakfast at Two if by Sea was amazing! And crab cakes at Gina’s on the Bridge were delish. My dog loved the stay too! Tilghman Island is a peaceful treasure in today’s crazy world.

Top guest favorite

A sign for the Chesapeake Bay Maritime Museum is prominently displayed. The circular sign features a depiction of a building surrounded by water, with the text clearly stating the museum's name. Nearby, a stop sign and a wooden post are visible, set against a backdrop of greenery.

Cottage in Wittman

5 out of 5 average rating, 13 reviews

"Imagine Acre" on Maryland's Eastern Shore

ElizabethRating, 5 stars4 days ago

Earle’s place was very quaint and cozy!! It had everything you needed and more! The house had a lot of little special touches to it!! The beds were super comfortable. I never sleep that good at home!! The house is on a huge piece of property. My favorite plant in the world Gardenias ,were blooming outside the front door!!! You can walk to the water. We tried everyday to get there by sunset .. St Michael’s is close also. And Earle was very communicative. Would love to stay there again!

Destinations to explore