Holiday rentals in Secretary

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Top-rated holiday rentals in Secretary

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Top guest favourite
A cozy living space features a brown reclining sofa paired with a black accent chair. A wooden coffee table centers the room, and a large art print is mounted on the wall. A full kitchen showcases modern appliances and ample counter space, illuminated by overhead lighting.
Guest house in Cambridge
5 out of 5 average rating, 16 reviews

Cozy Guest House Near Park

This lovely guest house is located in the historic district of Cambridge within 3 blocks to the Great Marsh/Gerry Boyle waterfront park. This cozy space includes a full kitchen with dishes, living space with reclining sofa, new Bedstory medium firm bed separated by an antique armoire as well as a large bathroom. You will have a private parking area and separate entryway through a private courtyard. Less than 1 mile to historic Cambridge. Near the start of annual races and waterfront activities.

Guest favourite
A cozy living area features a dark leather sofa and two blue chairs arranged around a round coffee table. Soft lighting is provided by stylish lamps on both ends. Framed artwork lines the walls, and natural light streams through the curtains.
Flat in Cambridge
4.9 out of 5 average rating, 146 reviews

Little Slice of Cambridge. 2 bedroom, pet friendly

You’ll be staying right in the center of the Historic district, close enough to walk to town and enjoy shopping or some of the great restaurants. Just two blocks from the water, a short stroll to the lighthouse or down to the water front and enjoy the park. This newly listed 2 bedroom , pet- friendly apartment has everything you will need to explore the history, food and waterfowl found in this area. Park your boat here. We can’t wait for you to experience Cambridge and relax in the “West End”.

Top guest favourite
A bright dining area features a wooden table surrounded by four chairs, illuminated by natural light from the sliding glass doors. A cozy armchair with a soft throw blanket is present, with a clock and decorative art pieces on the walls, creating a welcoming atmosphere.
Flat in Church Creek
4.97 out of 5 average rating, 429 reviews

Nature's Rest in Church Creek

Nature's Rest is located just minutes from Blackwater Wildlife Refuge, The Harriet Tubman Museum, Blackwater Adventures! Boat ramps are close by for easy access to the Chesapeake Bay and its tributaries for enjoying Maryland's Eastern Shore. We have plenty of parking, so bring your boat, bikes, and binoculars. Just mins from downtown Cambridge for dining & shopping. Discover the many quaint towns the area has to offer, come for a night, or stay as long as you'd like, look forward to meeting you.

Top guest favourite
The sun is seen shining through the branches of a tree, casting rays of light over a calm river. The water reflects the sunlight, creating a sparkling effect. A wooden pier extends into the water, surrounded by lush greenery.
Tiny home in Saint Inigoes
4.98 out of 5 average rating, 378 reviews

Historic St.Mary's City at the Lazy Bear Cottage

Inquire first on pets, there is a 50 lb. weight limit total, can be split up between 2 small dogs or 1 at 50lbs or less,must be house broken and friendly. Close to Saint Mary's historic city, Pt. Lookout State Park, Sotterley Plantation. Great hiking trails, restored colonial village,a replica of the Maryland Dove. Tour a lighthouse. Great restaurants , or spend a day over in Solomons Island, about 20 miles from us. Peaceful settings for relaxing right on the water,or kayak on the river.

Top guest favourite
The little house is nestled in a serene rural setting, surrounded by greenery and farmland. A gravel pathway leads up to the front door, flanked by simple flower pots. The landscape features open fields in the background, enhancing the peaceful ambience.
Tiny home in Cambridge
4.98 out of 5 average rating, 216 reviews

The Little House on the Farm, Water Access

Peaceful, Quaint & located on the Little Blackwater River, & 1.5 miles from the Blackwater National Wildlife Refuge & The Harriet Tubman Underground Railroad State Park & Museum. A bird watching, kayaking, and bicycling paradise awaits. Perfect for a couples retreat, girls getaway or a solo vacation to relax & unwind. Hunters and Fishermen are welcome also! Route 50 & downtown Cambridge are 10 mins away for local eateries and shopping! This is the perfect location to explore the Eastern Shore!

Top guest favourite
The exterior of a two-story wooden structure is presented, featuring a staircase leading to a covered balcony. The building is surrounded by trees displaying fall foliage, creating a serene outdoor atmosphere. A gravel area is noted at the base, with a vibrant red and white camper positioned nearby.
Flat in Greenwood
4.97 out of 5 average rating, 634 reviews

Beach Highway Hobby Farm

We are a hobby farm with pygmy goats and free-range hens located along Beach Highway near Greenwood, Delaware, in the heart of the Mennonite Community (not to be confused with the Amish). We are centrally located in southern Delaware with many attractions within easy driving distance: Rehoboth Beach (35 minutes) Delaware State Fairgrounds (10 minutes) Dover Downs/Firefly (30 minutes) Ocean City, MD (50 minutes) Cape May/Lewes Ferry Terminal (30 minutes) DE Turf Sports Complex (20 minutes)

Top guest favourite
A spacious open-concept living area features large windows offering unobstructed views of the water and sunset. A comfortable sectional sofa is positioned near the windows, with a dining table visible in the background. Natural light fills the space, enhancing the tranquil setting.
Home in Leonardtown
4.99 out of 5 average rating, 105 reviews

Water's Edge Cottage | Luxury Retreat

We are thrilled to host guests at the newly renovated Water's Edge Cottage -- a serene oasis offering what may be the best views on the Potomac. The rural charm of St. Mary’s County is among Maryland’s best kept secrets -- 90 minutes but a world away from Washington DC (with no Bay Bridge traffic!). We are near historic Leonardtown, boasting one of Maryland’s few remaining town squares (we affectionately call it “Mayberry”). And be sure to visit our sister property, White Point Cottage!

Top guest favourite
A spacious backyard features a circular fire pit surrounded by Adirondack chairs. A picnic table sits to one side, and a hot tub is partially shielded by evergreen trees and a wooden fence, providing a serene outdoor retreat.
Home in Cambridge
4.94 out of 5 average rating, 161 reviews

Peaceful Historic House Near Water, with Hot Tub!

Peaceful 3 bedroom/1.5 bath Victorian house near the water. Located in Historic West End, this 1900 house has been recently renovated to accentuate its historic charm while delivering all the modern comforts. Just a short walk from Long Wharf Park, the Choptank River Lighthouse, and downtown Cambridge with great restaurants and shops. Amenities include air conditioning/heating, a hot tub, WIFI, a back deck and grill, front porch with rocking chairs, and a fire pit with Adirondack chairs.

Guest favourite
A waterfront farmhouse retreat is depicted, featuring a large porch that extends across the front. The structure is complemented by expansive windows and a well-manicured lawn. Tree lines frame the property, and the tranquil water reflects the setting, enhancing the serene atmosphere.
Home in East New Market
5 out of 5 average rating, 8 reviews

Warwick Farms waterfront Retreat

Bright, rustic, waterfront farmhouse retreat resting on over 9 acres. The water views can be enjoyed almost anywhere from this 5-bedroom, 3-bathroom home. Drift off to sleep in the Master suite overlooking the water. Enjoy rocking on the porch, relaxing by the large private pool, or mastering your skills at the endless opportunities on the water. A private pier for your crabbing, fishing, and boating pleasures awaits you. Catch dinner! There is a public boat ramp less than a mile away!

Top guest favourite
The exterior entrance of a converted corn crib features natural wood siding and a gabled roof. Large double doors framed by lantern-style lights open into a welcoming space, complemented by potted plants on either side. Lush green trees and a gravel path are visible in the surrounding landscape.
Guest house in Easton
4.99 out of 5 average rating, 630 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.

Guest favourite
The exterior of the 'She Shed' Tiny House is shown, featuring a pale yellow siding with a simple door and window design. Two metal chairs and a small round table provide a cozy seating area on a gravel surface, creating an inviting entrance.
Farm stay in Cambridge
4.79 out of 5 average rating, 405 reviews

Blackwater & Snakehead Farm "She Shed" Tiny House

The "She Shed" Tiny House is the best bargain & unique stay around! This Tiny House is made from a traditional 10'x18' shed and is solar powered! It's surprisingly spacious with a full size bathroom, kitchenette, lofted twin bed, day bed & trundle bed! The home borders a sheep pasture, barn, goat pasture & chicken coop! Snakehead fishing is just a short walk away! Kayacks & creek launch on site! Just a 5 minute drive from Blackwater Refuge! Relax and enjoy country living!

Top guest favourite
A serene view of a serene water landscape is showcased, featuring a double rainbow arching across the sky. Reflections of the rainbow are visible on the water's surface. A private pier extends into the water, surrounded by lush greenery.
Cottage in East New Market
4.96 out of 5 average rating, 72 reviews

Cottage on Cabin Creek

The cottage is the perfect getaway for couples. It is located on the water with two private piers for you to use. You may enjoy fishing, crabbing, kayaking, canoeing or bird watching from the piers. There is a charcoal grill available and a fire pit. The cottage is secluded enough for relaxation, but not far from local attractions and restaurants. Note the cottage is best suited for 1 to 2 people.

Popular amenities for Secretary holiday rentals

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