Places to stay in Madison

Book unique places to stay, houses, and more on Airbnb

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Popular amenities for Madison places to stay

Stay near Madison's top sights

Hammonasset Beach State Park83 locals recommend
Chamard Vineyards Bistro28 locals recommend
Chatfield Hollow State Park15 locals recommend

Other great vacation rentals in Madison

Top guest favorite
Apartment in Westbrook
4.96 out of 5 average rating, 27 reviews

Meadowview & Pondside Retreat

LaurenRating, 5 stars1 day ago
We had a lovely stay at this beautiful home! We actually ended up having pictures taken in the backyard because of how gorgeous the scenery is. Becky was super responsive and friendly. Definitely would love to come back! :)
Top guest favorite
Apartment in Guilford
4.96 out of 5 average rating, 83 reviews

Cozy Private Lake Q Retreat

JenniferRating, 5 stars2 weeks ago
Great little spot. This rental has everything you need. Forget something-they got it. Very clean and modern with thoughtful touches. Had an extended stay here and extended for longer. 1 bedroom with loft that owner made into another bedroom for me. Loved it. Great deck, stunning lake view from all the windows. Owner very responsive to any needs. 100 percent recommend. Neighborhood lovely and quiet. Amazing respite.
Guest favorite
Home in Westbrook
4.96 out of 5 average rating, 25 reviews

Barnacle Bay Beach House

TiffanyRating, 5 stars5 days ago
It was easy to find, plenty of parking, nice backyard space, the house was as described and pictured. We felt right at home!
Home in Madison
4.75 out of 5 average rating, 4 reviews

Sea La Vie - Beachfront Private Home

NancyRating, 5 stars9 months ago
The setting right on the beach was perfect and very quiet and private! Loved being able to enjoy the views from inside as well as the great deck. The house was extremely comfortable and well equipped. It was the perfect setting for a great relaxing week and look forward to renting it again. It was also close to downtown Madison and great restaurants! Lori was very responsive to any questions etc!
Guest favorite
Cottage in Guilford
4.95 out of 5 average rating, 80 reviews

Direct Shoreline Long Island Sound Waterfront

ThomasRating, 5 stars9 months ago
Our visit was utilitarian. We needed accommodations for us, our grown children and grandchildren and a dog. But the site of the cottage, its charm, its comfort made us wish we were staying another week. James' thoughtfulness went beyond any other Airbnb hosts' that we've experienced. Everything we might need if we were staying 10 days was there, clean, labeled. Thank you, James.
Guest suite in Madison
4.88 out of 5 average rating, 8 reviews

Vintage Cabin Suite with full kitchen (No.2)

JerryRating, 5 stars6 months ago
There was a problem caused by skunk spray, hardly anything controllable by the innkeeper. Amanda handled our need to leave promptly, politely, and professionally.
Top guest favorite
Apartment in Clinton
4.99 out of 5 average rating, 69 reviews

Cozy Shoreline Getaway

HowardRating, 5 stars1 month ago
Second time staying at this Airbnb. Excellent hosts, conveniently located, and cottage had all the amenities.
Guest favorite
Home in Old Lyme
5 out of 5 average rating, 48 reviews

Beachfront Oasis

OliviaRating, 5 stars9 months ago
Joanne's waterfront home is an incredible oasis. Even the pictures do not do it justice. Our family had a wonderful week-long stay in her beautifully appointed home. Joanne's home is meticulously clean and decorated with wonderful touches. We had plenty of room and loved soaking up the sun every day on the fabulous wraparound porch (with built-in umbrellas) and jumping right into the water mere steps from the house. We cannot wait to return next year!

Quick stats about vacation rentals in Madison

  • Total rentals

    130 properties

  • Total number of reviews

    4.2K reviews

  • Family-friendly rentals

    80 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

Frequently Asked Questions

  • How much does it cost to stay in apartment rentals in Madison?

    Experience the best of Madison with our apartment rentals, starting at about $110 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there house rentals with a dedicated workspace in Madison?

    Yes! Work meets play with ease at over 20 house rentals in Madison featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • What are the most popular amenities for House Rentals in Madison?

    Enhance your stay in our House Rentals with the most popular amenities: over 60 homes with wifi, over 30 homes with a bbq area, over 20 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Madison have a bbq area?

    Absolutely! We offer over 30 house rentals with a bbq area in Madison. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Madison have self check-in?

    Absolutely! We offer over 20 house rentals with self check-in in Madison. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly house rentals in Madison?

    Four-legged friends are welcome in Madison. Choose from more than 20 house rentals for guests traveling with pets.

  • Do apartment rentals in Madison have wifi?

    Absolutely! We offer over 10 apartment rentals with wifi in Madison. Enjoy a tailored experience with all the comforts you desire.

  • Are there Madison vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Madison, available on Airbnb. Make a splash and soak up the sun in style!

Destinations to explore