
Holiday rentals with outdoor seating in Madison
Find and book unique rentals with outdoor seating on Airbnb
Top-rated rentals with outdoor seating in Madison
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for outdoor seating rentals in Madison
House rentals with outdoor seating

Stunning Artisan Waterfall Escape, Walk Downtown
This is our second visit in the Recycle House. It’s such a lovely oasis. We love all the unique touches and creative uses of materials throughout the house. The location just steps from the charming town of Chester could not be better. The perfect CT weekend getaway!

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
My husband and I stayed at Peter's lake house from June 9th to the 12th. We found the home to be clean and bright, as well as spacious. The bed we slept in was comfortable with soft linens, and both bathrooms were clean with plenty of towels. It's a quiet neighborhood and although we didn't use the backyard, we found it to be private with a nice patio. The last minute tasks before check out were very basic. Peter was a great host, very welcoming and communicative. We felt right at home staying at his house and we would definitely book it again!

Charming home, easy access to everything Branford
super nice place. comfortable beds. Great backyard. super responsive and friendly hosts. Will book again!

Cozy Comforts!
We stayed here while attending a friend’s wedding celebration. It was conveniently located for our purposes, right in between each day’s events. It is a quiet area. The space itself was spacious and comfortable and clean. It is a newer place with all you need for a good stay. Helpful and convenient touches included having a few snacks and drinks available which was a big plus with our late arrival.

Field of Dreams Hot Tub - Fire Pit Retreat
Field of Dreams is a beautiful, spacious, well-appointed home. Brenda is an attentive, gracious, and thoughtful host. My family and I stayed there for four stellar days over Memorial Day for my daughter’s college graduation. We hosted a big family dinner with a private chef that was excellent. And Brenda really helped us with some of the details. This is a lovely home and I highly recommend it.

The ARLO - Walk to Brewery & Restaurants
Lovely home and communicative hosts! The house was very clean and comfortable as well as the back deck and yard. Felt very comfortable and very close to beach (though ended up being a rainy weekend so we didn’t get to go to beach). Close to Dockside Brewery which had great views and tons of tables and a few little stores within walking distance for convenience items

Stunning, peaceful and private home
The house was great and we were able to get Ubers to go to dinner. Beautiful house and stocked with everything you would need. We were on a girls weekend and had trouble with the locks but we just used the key. It could have just been us. We had a wonderful time and enjoyed the home.

Summer by the Beach,Outlets,Golf at the GlassHouse
This home was very spacious and clean. It was great to have the pool table, foosball and air hockey tables. This house had everything we needed and was only a 5-10 minute drive from restaurants, shopping and beaches. Great location!
Apartment rentals with outdoor seating

The Boathouse, private downtown Harborside suite
⭐️⭐️⭐️⭐️⭐️ Clean, Comfortable, and Thoughtfully Prepared! We had a great stay! The place was spotless, quiet, and exactly what we needed for a few nights of good sleep and hot showers. It was clear that the host put thought into making guests feel welcome—there was a mini chocolate bar and a bottle of water waiting for each of us when we arrived, which was such a kind touch after a long day of travel. Check-in was smooth, the bed was comfortable, and everything worked perfectly. While we didn’t spend much time there beyond resting, it was the perfect place to recharge. Highly recommend for anyone looking for a clean, convenient, and cozy spot!

The Federal Suite at the Wisteria Rest
Very nice apt and perfect for a quick weekend getaway.

Tranquil Apartment with Waterview, Walk to Beach!
I love this place. Perfect but what we were looking for. Walking distance to access beach. Overlooking the pier. Very clean and check in with.

Ridgeview Suite at Stony Creek Depot
Barbara’s place reminded me of the way airbnbs used to be. It felt like home-away-from-home. The accommodations were high quality and clean, and there were even some tasty snacks! We loved our stay. Everything was as pictured. Stony Creek was wonderful, and we look forward to visiting again next year!

Charming Chester Retreat - Cottage
Wow!!! This is the nicest airbnb I have ever stayed in. The property is beautiful and peaceful, surrounded by trees with lots of privacy. The cottage itself is immaculate (I’m very particular about cleanliness). The dining area is stunning with skylights and beautiful trees outside and great light! The hosts were also so welcoming and friendly, they included so many nice touches for my baby including a pack and play/travel crib, diaper changing area, and toys! I hope to stay here again every time we come to this area!

Spacious Cozy Guest Suite
We booked this place to be close the the festival downtown and it was. 1.3 miles or 25 minutes walk. Perfect for us. The Airbnb was clean and spacious. Shower is a little small but ok. King bed is very comfortable. Yummy welcome treats on the table was a nice touch. Keurig pods and maker available for your pleasure. Well lit and very secure. Felt safe at all times. Great place to book if you need to stay in this area.

King 1BR Apt with Cozy Den and Luxury Amenities
Very clean and comfortable! Tatenda is so sweet and responsive. Walkable to Yale and great restaurants, but also includes covered, safe parking in the building. We had fun grilling a dinner by the outdoor pool. Well-equipped workout rooms and the coffeemaker in the lobby was amazing offering a variety of options. We enjoyed everything about this Airbnb and will likely be back! Thank you Tatenda and Hyatus!

Peaceful apartment on 3.5 acres w/ Artist studio.
The place was really nice and the host was great! Don’t get discouraged if the power goes out during your stay cause apparently that’ll happen 2-4 times a year according to the host. Other than that I highly recommend
Apartment rentals with outdoor seating

CASiNO, Spa, Hot Tub, Pool, King bed, sauna
The Villa was exactly as described! Easy communication with owner. A perfect getaway weekend, every amenity we could want or need! Look forward to visiting again in the near future!

Montauk Waterfront Condo w/ Sunset Views
We loved Montauk - low key, wild and upmarket at the same time. This apartment was perfect, super quiet yet near everything and loved seeing wild deer from the terrace

Peaceful Oasis steps from Mohegan Sun
We had a great time and the property was immaculate! The hosts came by with extra towels quickly upon request and it was a holiday. Recommended!

The Vacay Villa
This is a wonderful property that is close to everything we like to do! Krista is a wonderful host and I’m always excited if her place is available.

Seaside Summer Escape –2BR Waterfront Condo w/Pool
We had a great time at Julie’s place. Would love to visit again…perhaps in the Fall. Loved the balcony overlooking the Sound. Julie was very responsive to my questions. She got back to me immediately. I would highly recommend Julie’s home!

Beachside Waterview 2Br Condo w/ Pool in Greenport
We had a great stay! Instructions were clear and the home had everything we needed.

Deluxe Studio Apt@The Montauk Manor
Just had a wonderful stay at Robert’s place! The place was impeccably clean, and Robert was incredibly responsive and friendly throughout our visit. While the manor has a charmingly vintage vibe and could use a bit of modernization, we truly enjoyed our time there. The warmth of the atmosphere made it feel like a home away from home. We recommend for anyone looking for a cozy getaway!

KINGbed-Casino-HotTub-Pool-Sauna-Massagechair-golf
We recently stayed at Kelly’s place and everything was great! The place was clean, comfortable, and exactly as described. Communication was smooth, and check-in was easy. We really enjoyed our stay and would definitely recommend it to others. Thank you, Kelly!
Quick stats about holiday rentals with outdoor seating in Madison
Total rentals
60 properties
Nightly prices starting at
₹6,044 before taxes and fees
Total number of reviews
2.1K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
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- Beach
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Napeague Beach
- Shinnecock Hills Golf Club
- Walnut Public Beach
- TPC River Highlands
- Ocean Beach Park
- Woodmont Beach
- Amagansett Beach
- Blue Shutters Beach
- Jennings Beach
- Seaside Beach
- Silver Sands Beach
- Bushnell Park
- Quotonset Beach
- Heckscher State Park
- Ninigret Beach
- Sunken Meadow State Park
- Calf Pasture Beach