Vacation rentals in Madison

4.98 out of 5 average rating, 128 reviews

Home in Church Creek

Church Creek Charm (close to Blackwater Refuge)

Charming Eastern Shore home built in 1900, located in CHURCH CREEK, MD, less than 10-15 mins from Cambridge, Blackwater National Wildlife Refuge & the Harriet Tubman Underground Railroad museum. Ideal spot for cycling, birding, fishing, canoeing, relaxing, or exploring the many cute towns of Maryland's Eastern Shore. Just over an hour from Ocean City & Assateague Nat'l Seashore. Pet-friendly with a fenced backyard. The Eastern Shore is famous for its seafood, history, nature & fresh produce!

4.98 out of 5 average rating, 198 reviews

Farm stay in Madison

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.

4.98 out of 5 average rating, 201 reviews

A driving tour map and welcome guide for the Harriet Tubman Underground Railroad State Park are displayed on a wooden surface. The map features prominent colors and outlines routes. The welcome guide has an image of flags flying in front of a red brick visitor center, with text indicating its relevance to the park.

Tiny home in Cambridge

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!

4.99 out of 5 average rating, 172 reviews

Sunset Breezes - quiet waterfront retreat

Enjoy our waterfront home styled after historic bay lighthouses. Relax by the water in a hammock under the tall pines. Gather with family and friends around the fire pit. Take in the beautiful water sights while paddling in a kayak, canoe, or paddleboard. Laugh with family and friends while playing corn hole, croquet, or bocce ball waterside. Photograph abundant wildlife - bald eagles, blue herons, osprey, deer, turkey and numerous waterfowl. Dine on the deck while enjoying beautiful sunsets.

4.98 out of 5 average rating, 347 reviews

A cozy bedroom features a wooden bed adorned with soft linens and decorative pillows. Warm string lights drape along the sloped ceiling, creating a gentle glow. Framed artwork and bedside lamps add character to the space, while the walls exhibit a calming blue hue.

Guest suite in Lusby

Riverfront Chalet Kayak/Canoe, pier, breakfast!

This is a two room above the garage apartment with a dedicated side entrance for guests separate from the main house by screens down and a barn door up. Once upstairs you have your own private space. Your mini fridge will always be stocked with an assortment of beverages and snacks as well as breakfast items. Enjoy, our kayaks, fire pit or sunset viewing on the pier. Lots of hiking and water sports abound in the area. A short drive south is Solomon’s island. This is a safe space for all🥰

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.

4.94 out of 5 average rating, 141 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.

4.99 out of 5 average rating, 122 reviews

Guesthouse in Cambridge

Rosses Chance Guest House

This lovely guest cottage is located on a historic 16 acre waterfront estate on Hudson Creek that includes a main house, barn, pool, dock and pond. Built in the 18th century tidewater style, the guesthouse is charming and well decorated and completely self efficient. A special place for your romantic getaway at any season of the year. Recently cell phone service has improved and is reliable. However, in the country, WiFi internetl can be slow at times as well as the Wifi TV streaming.

4.89 out of 5 average rating, 603 reviews

Tiny home in Cambridge

Blackwater Tiny Cabin on Snakehead Creek

The Solar Powered Tiny Cabin is located on a farmette, making your visit even more memorable! Just a 5 min drive from Blackwater Refuge! It's an affordable and unique way to visit and enjoy all that Cambridge and Blackwater Refuge have to offer! The Tiny Cabin is located 50 steps away from Pitcher Dam Creek which leads to the Little Blackwater! Kayaks on site! Bring your fishing rod to catch popular Snakeheads! 15 minute drive to Route 50, downtown Cambridge, shopping and dining!

Apartment in Church Creek

A historical sign marking Cambridge is displayed prominently, detailing its origins as part of the Choptank Indian Reservation and its designation as a port of entry in 1684. The sign features bold text and the State Roads Commission emblem at the top, surrounded by grassy fields.

4.97 out of 5 average rating, 417 reviews

Church Creek Natures' Rest

Nature's Rest is ideally located, just minutes to Blackwater Wildlife Refuge The Harriet Tubman Museum, as well as boat ramps for easy access to the Chesapeake Bay and it's 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.

4.93 out of 5 average rating, 152 reviews

A spacious hammock is gently draped between two trees, providing a restful spot with views of lush green grass and a calm waterway in the background. Surrounding tall grasses sway lightly in the breeze, framing the serene scene.

Home in Woolford

Waterfront Getaway with Dock

Bicyclist's and outdoorsman's dream! Beautiful rancher on two waterfront acres just 4 miles from Blackwater Wildlife Refuge and Harriet Tubman National Park. 10 minute drive from downtown, the Hyatt, and the Ironman starting point as well. Ironman and Eagleman races actually pass right by! Bright, sunny, and newly renovated, it's a great place to hang your hat after a day of hunting, fishing, bicycling, or triatholon-ing! Or just take a weekend to relax on the water!

4.96 out of 5 average rating, 148 reviews

A gravel lane is bordered by sparse greenery and trees, where a family of five deer is seen crossing. The deer appear serene as they pause and look in different directions, creating a tranquil scene in this natural setting.

Cottage in Cambridge

Church Creek - waterfront cottage & pool - private

Close to Blackwater NWR and the Harriet Tubman Center, enjoy peaceful days at our secluded waterfront cottage on Church Creek. Our closest neighbor is across a cove. Our estate offers 50 acres of privacy and one of the best waterfront views on the Chesapeake. Enjoy a view from every window and nature all around you. Excellent walking, swimming (in-ground pool-May 3-Oct 1), great birding and bicycling. Launch your kayak from the backyard. Perfect private getaway!

Superhost

A bright screened-in porch features comfortable seating, including a light-colored sofa with teal accents and a simple dining table. Large windows provide views of the waterfront and the grassy yard, with outdoor lounge chairs visible in the distance, creating a serene atmosphere.

4.9 out of 5 average rating, 110 reviews

Waterfront Oasis! Hot tub! 2+ acres - Sleeps 8

HOT TUB!! WATERFRONT!! Relax with the entire family at this peaceful 3 bedroom fully remodeled private waterfront cottage on a quiet cove off the Choptank River/Chesapeake Bay. Enjoy the incredible views from your bed, from the large screened-in porch, from the oversized deck, from the hammock or double swinging chair out by the water! Launch a kayak right from the property and watch the gorgeous sunrises from the comfort of your bed!

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 Madison vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Madison

A modern kitchen features sleek white cabinetry and a central island with a light-colored countertop. Four bar stools are positioned at the island. Stainless steel appliances are visible along with a dark backsplash, providing a contemporary contrast.

5 out of 5 average rating, 22 reviews

Aurora Blue - A stylish experience

JanetRating, 5 stars1 month ago

Aurora Blue is stunning, no detail was left out of the planning. The space is well planned to allow privacy and quiet when resting. Each room has a en suite bathroom and the master suite is beyond 5 star. The home was immaculate, having coffee and paper products available was an extra bonus. Great patio for sitting outside and quiet at night without any disturbances. We locked ourselves out and the host came onsite quickly to address the problem we created. Excited to go back one day.

4.88 out of 5 average rating, 52 reviews

Waterfront, amazing views, pier, fishing/crabbing

SandyRating, 5 stars9 months ago

The house are clean, bright with a great view. We had a wonderful time and were lucky to have wonderful weather during our stay! We also had a lot of fun playing Mad Gab and other games in the games chest. We were successful in catching some fish and plenty of crabs. It was a great vacation. We enjoyed it very much.

Home in Woolford

4.63 out of 5 average rating, 43 reviews

The Blue Heron-Spacious Waterfront house w/ kayaks

KaitlynRating, 5 stars2 weeks ago

We stayed here for the Ironman 70.3 Eagleman race. The bike route goes right by the house at about mile 15. Beautiful house with plenty of room for everyone. The kids were outside fishing and kayaking constantly. When they were inside they were playing ping pong. Only thing I wish we would have brought is bug spray and itch ointment. We’d definitely stay here again for an Ironman.

An inviting living area is showcased, featuring a round glass table set on a patterned rug. Two chairs provide comfortable seating, while large windows frame a stunning view of the water, allowing plenty of natural light to brighten the space.

5 out of 5 average rating, 9 reviews

Magical Waterfront Home Dock, Firepit, Family Fun!

JoyceRating, 5 stars1 week ago

This was our second stay at Heron’s Rest with our extended family—siblings, partners, and one teen—and we’re already planning our return. It truly feels like our home away from home. Claire and Dominique could not be lovelier. From the moment we booked, everything felt seamless and welcoming. Their thoughtfulness shows in every detail—from the beautiful kitchen and quality linens to the heartfelt notes and local recommendations. The house and outside space is designed for comfort and peace, with stunning views of the Choptank River and soothing bird melodies. We love to cook, and Heron’s Rest is a dream—fully stocked, complete with cookbooks and even an ice cream maker. Their crab chowder recipe is now a favorite at home. And the art! Each room features something special—sophisticated yet cozy. Dominique’s eye is truly inspiring. Heron’s Rest is more than a rental—it’s a space to unwind, reconnect, and savor. We can’t wait to come back. We all already miss Heron's Rest!

Superhost

5 out of 5 average rating, 5 reviews

Drop Anchor on Brannocks Bay!

LaurenRating, 5 stars3 weeks ago

We absolutely loved our stay at Djr’s place! The home is on a beautiful waterfront property. Sitting outside or on the dock was incredibly serene and peaceful - we could have spent all day outside relaxing. The home itself was spacious and well equipped. While it was a bit too windy during our stay to use the kayaks and paddle boards, we appreciated that they were provided. Host Djr was very easy to communicate with and so kind. We will definitely be back to stay here again!

A red picnic table sits on a grassy area near the water's edge, with a wooden pier extending into the river. The sky above features a mix of clouds in shades of gray and blue, while the horizon reflects warm tones of sunset.

4.86 out of 5 average rating, 7 reviews

Choptank Riverside Retreat

WayneRating, 5 stars3 weeks ago

This is our favorite play to stay when we come home to visit. As soon as we make the left turn into the wooded driveway we get excited. One we get past the woods the view is always stunning. Very large property and beautiful home makes us feel like we're getting our moneys worth. Absolutely no neighbors in sight. We love seeing the wildlife around the property. There were plenty of games, seating and space. My grand daughter was excited about the slide. My family loves to go to the dock. There's something for everyone to do. I wish we could stay longer every time. We'll be back for sure.

A box filled with freshly caught crabs is displayed. The blue and green crabs are arranged closely together, resting on a layer of newspaper. The shells exhibit a vibrant mix of colors, highlighting their freshness and bounty from the Chesapeake Bay.

4.9 out of 5 average rating, 165 reviews

Jewell on the Chesapeake

NicoleRating, 5 stars6 months ago

We really enjoyed our stay. The house was very comfortable, clean, and well appointed. While the property shares part of the driveway with another house, the house itself, given the trees, still feels very private. And you can't beat having the water/dock access. The kitchen is well stocked with most everything you need. And the drive into Cambridge for groceries, etc. takes only about 15-20 minutes. We were there in November, so couldn't take advantage of the water, but we did enjoy a great bonfire and the hiking trails nearby. Joshua was super responsive and easy to deal with, even offering early and late checkouts since the property was open. We'd definitely love to come back in the warmer weather.

A bright blue paddle boat is situated against a gray metal shed, positioned near a tree. Surrounding grass is visible, and the area appears calm with a pond in the background.