Vacation rentals in Wittman

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Top-rated vacation rentals in Wittman

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Guest favorite

Apartment in Stevensville

4.97 out of 5 average rating, 239 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.

May 5 – 12

R3,281 ZAR per night

Guest favorite

Cottage in Saint Michaels

4.98 out of 5 average rating, 425 reviews

St. Michaels-Historic Dist. Margaret Wells House

The Margaret Wells House is in the heart of the Historic District between the main street and water. Enjoy a total renovation of this charming home. A short walk to the water's edge, Inn at Perry Cabin, Chesapeake Bay Maritime Museum, restaurants, shops, winery, brewery and local market. A perfect spot for a couple's Shore weekend getaway or attending a wedding, nearby. Our nightly pricing includes coffee, tea, fresh linens on beds, hand-milled natural soap, fresh bath towels and wash cloths.

Nov 15 – 22

R3,928 ZAR per night

Guest favorite

Farm stay in Madison

4.98 out of 5 average rating, 162 reviews

Madison Nature Getaway

We're on 106 acres minutes away from Cambridge, Blackwater NWR, Harriet Tubman URR State Park and two public boat ramps for access to Chesapeake Bay. Hike our trails and enjoy bird watching, wildlife photography and fishing on our award winning tree farm and relax by our pond. Bring your bikes, binoculars and kayaks and enjoy the surrounding area. We have a gas grill and a screened pavilion for our guests for parties and meals. FRIENDS OF BLACKWATER NWR MEMBERS & MILITARY RECEIVE A 10% DISCOUNT.

Mar 7 – 14

R2,372 ZAR per night

Guest favorite

Guesthouse in Annapolis

4.9 out of 5 average rating, 206 reviews

Calico Cottage Guest House, king bed, free parking

Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.

Jan 10 – 17

R1,878 ZAR per night

Guest favorite

Guesthouse in Easton

4.99 out of 5 average rating, 545 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 two individuals (No children under 8 years of age.), and please limit your visit to one vehicle only.

Jan 25 – 30

R2,756 ZAR per night

Guest favorite

Cottage in Saint Michaels

4.99 out of 5 average rating, 136 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.

Sep 15 – 22

R10,271 ZAR per night

Guest favorite

Guest suite in Tilghman Island

4.96 out of 5 average rating, 114 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

Oct 23 – 30

R2,772 ZAR per night

Guest favorite

Apartment in Lexington Park

5.0 out of 5 average rating, 315 reviews

Adorable Waterfront Apartment Weekend Getaway

Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!

Oct 1 – 8

R1,687 ZAR per night

Guest favorite

Guesthouse in Stevensville

5.0 out of 5 average rating, 207 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.

Jan 10 – 17

R5,515 ZAR per night

Guest favorite

Cottage in Saint Michaels

4.98 out of 5 average rating, 174 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.

Aug 13 – 20

R5,049 ZAR per night

Guest favorite

Tiny home in Cambridge

4.99 out of 5 average rating, 156 reviews

Blackwater Refuge House on The Farm, water access

The Little House on The Farm is located on a beautiful family farm in rural Dorchester County! Located just 1.5 miles from the Blackwater Wildlife Refuge and Harriet Tubman National Park, This space is quaint,yet provides all the basics for a cozy welcoming getaway! Bring your bikes and cycle to the refuge and kayak in the Blackwater River. Kitchen is fully stocked for cooking. Coffee, tea and basic condiments and all linens and towels are provided.

Aug 21 – 28

R2,052 ZAR per night

Guest favorite

Guest suite in Saint Michaels

4.78 out of 5 average rating, 330 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

Oct 21 – 28

R2,679 ZAR per night