Vacation rentals in Madison

Find and book unique accommodations on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Madison vacation rentals

Other great vacation rentals in Madison

Top guest favorite
A serene backyard scene is captured at sunset, featuring a concrete patio with four chairs arranged around a small table. A shed is visible in the distance, alongside lush green grass and mature trees. The sky displays a gradient of colors as daylight fades.
Home in Fruitland
4.97 out of 5 average rating, 130 reviews

Amazingly convenient yet secluded.

MaryRating, 5 stars1 week ago
Keith was always prompt in responding to questions and was very friendly. The house was easy to get to and had plenty of things to do around the area. We were very happy with our stay and will definitely stay again.
Guest favorite
A serene swimming pool is featured in a private outdoor area, surrounded by a stone deck. Two white lounge chairs are positioned nearby, with trees providing a shaded atmosphere. The clear water glistens under a partly cloudy sky, inviting relaxation.
Home in Edgewater
4.92 out of 5 average rating, 143 reviews

House in Edgewater Maryland

NancyRating, 5 stars3 weeks ago
Leisa’s home suited our needs to a T!! We were in town to attend a wedding at the London Town and Gardens, which was just a half mile away. The rehearsal dinner in downtown Annapolis was also a short distance away. Everything was fresh and clean, the beds were comfortable, and the showers were really great. The lack of seating in the main room wasn’t a problem for us as we didn’t spend much time there during the day. The area around the pool looked really comfortable and inviting for guests staying during the summer season! Would stay there again.
Superhost
Two white Adirondack chairs are positioned facing a serene lake, surrounded by lush green trees. A small table sits between them, adorned with a vase containing fresh flowers. Soft sunlight filters through the leaves, creating a peaceful outdoor setting.
Home in Wye Mills
4.91 out of 5 average rating, 11 reviews

⇚Family Getaway⇛| Lakeside + A Nature View |

LisaRating, 5 stars12 months ago
Kevin is a great host to us year after year! we love staying at his place!
Guest favorite
Home in Deale
4.88 out of 5 average rating, 100 reviews

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home

CourtneyRating, 5 stars1 month ago
This air b&b is in a beautiful setting with plenty to do (kayaking, hot tub, fire pits, bird watching, etc). It's also very centrally located so we could easily get to more populated areas in no time. The most stunning part of the house is the master suite in my opinion which is on the upper level (the upper level is shared with another apartment, but you don't really hear the air b&b tenants of this suite and it's completely separate with a separate entrance). Stunning views from both the master bedroom and the bath tub in the master suite! The downstairs is also quite lovely with two regular bedrooms, one small bedroom, and a sun room that has a pull out couch (we didn't use it). It's a lovely house to entertain in. It has personal photographs to the owner downstairs that speak to the family's history. The owner is communicative. The overall experience was quite lovely. We'd be happy to return.
Superhost
The house is positioned among leafy trees, featuring numerous large windows that brighten the interior. A spacious deck is visible, along with a hot tub. A stone fire pit surrounded by wooden chairs is located in the foreground, inviting outdoor gatherings.
Home in Montross
4.88 out of 5 average rating, 233 reviews

Lakefront/Dock, Woods, 3 Beaches, Kayaks, Hot tub

SarahRating, 5 stars2 weeks ago
This cabin was everything we wanted and more! It’s in the perfect location, just a short drive to so many activities but also tucked away offering privacy. The house was so cozy it put us at ease as soon as we walked in. The owner was proactive and very quick to respond, including sending a great packing and local activity list a couple days in advance of our trip which came in very handy. Activities: This rental comes with guest passes to the private Shark Tooth Beach where our kids had so much fun finding real shark and manta ray teeth in the sand! Westmorland State Park and George Washington’s Birthplace both had great hiking and beaches for the kids. We visited Garners Produce twice where the kids fed animals and pedaled toy tractor’s while we picked up farm fresh milk and eggs. We spent our afternoons kayaking on the quiet lake soaking up the sunshine. We will definitely book another vacation at this cabin. You will not be disappointed with your stay at this little gem!
Superhost
A wooden deck is visible, surrounded by trees adorned with autumn foliage. The serene lake reflects the vibrant colors of the leaves, creating a peaceful outdoor space perfect for relaxation.
Cabin in Lusby
4.84 out of 5 average rating, 171 reviews

2-bedroom lake-house with a magnificent view

MohamedRating, 5 stars3 weeks ago
Beautiful house and beautiful view. Outdoor jacuzzi with the view is not to be missed! Gorgeous and clean home. The private site made it an amazing getaway from busy life. Thank you, we will be back soon!!!
Guest favorite
Home in Colonial Beach
4.94 out of 5 average rating, 68 reviews

The Heaven at Colonial Beach

MelissaRating, 5 stars3 months ago
I’ve stayed at a lot of Airbnb’s and this was easily one of the best. Everything was exactly as described, and maybe even better than described. It had tons of amenities and a well stocked kitchen perfect for our large family. Spotless and beautiful. I highly recommend this home and would gladly stay there again.
Guest favorite
A pair of glass French doors provides a view of the outdoor seating area and pool. Bright red chairs are positioned around a fire pit on a stone patio, framed by a lush green lawn leading to the water.
Home in Tilghman Island
4.97 out of 5 average rating, 30 reviews

Relax by the Water - Summer Dates Available!

RonnieRating, 5 stars3 months ago
Absolutely beautiful home! highly recommend!

Destinations to explore

  1. Airbnb
  2. United States
  3. Maryland
  4. Dorchester County
  5. Madison