
Vacation rentals with outdoor seating in Madison
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Top-rated outdoor seating rentals in Madison
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House rentals with outdoor seating

Welcome To Piper's Rest
It was wonderful stay and I’d go back anytime

Stylish Beach Getaway: pool & walking location
Maher’s house was an amazing peaceful experience. I enjoyed my time there and he had great recommendations to restaurants and activities! He was very responsive with all questions we had. I will totally stay here in the future if I can get the chance again!! Thank you Maher!!

Serene Country home 24 mi Mohawk ski area
A beautiful home- super comfortable and spacious. It is outfitted with everything you could need. Peaceful location (we stayed in spring/winter- can’t speak to what it would be like in season). Lovely views. Easy to get into town by car (3-5 minutes!). Host was excellent - responsive to any questions or inquiries

Maritime Village Getaway with Backyard
We had such a wonderful stay here over New Years. Like many other reviews have stated, pictures do not do this home justice. It’s so much larger and more spread out than we expected. Perfect layout for two couples where we each felt like we had our own place, with plenty of cozy spaces to hang out too. The kitchen is SO well equipped for anything and everything. Beds and sofas were super comfortable and the we loved all of the charming touches of this historical home. The location is fantastic too. Walking distance to everything you could need and a quick drive to so many beautiful areas. I can imagine spending hours in the backyard when the weather is warmer too!

Long Island home w/ large pool
My stay here was phenomenal! From the host’s response time, down to the amenities that were placed throughout the house. As soon as you walk in, it felt like home. The house is spacious and highly functional. The design of the house offers a perfect blend of modern mixed with nostalgic elements. The best stay by far. Would love to book again!

Farm house with vineyard views
We had an amazing time here! The home is very charming, in a great location on the North Fork close to our favorite vineyards and restaurants. Paul was kind enough to offer us an early check in so that we may accommodate our guests traveling to visit! We really enjoyed our stay & made great memories.

Bright and Breezy Cottage by the Sea
My family and I have stayed at a ton of different airbnbs, vrbos and vacation rentals both stateside and abroad and I have to say Anne’s property is among one of the best we’ve stayed in. We were traveling with twin toddlers and the space was perfect. Anne is very friendly, the place is larger than we expected, very clean and you can tell Anne cares to the make the best experience possible. All the little touches were so wonderful - she has beach chairs, reusable beach bags, sunscreen, books, kids toys, coloring accessories, balls and toys, an outdoor game, hammock, lanterns, lights, fire pit and wood, you name it - it’s there. It was one of the most convenient stays we’ve had. We’d love to return and I couldn’t recommend it enough!!

Private vacation home, close to beach
We loved our stay in Westbrook! Mia's lovely home exceeded our expectations in terms of decor, furnishings, cleanliness, comfortable beds, and well-stocked kitchen and bath ... all in a quiet and private setting. The house was especially well-situated for us. We had tickets for a special theater performance at Gillette Castle one evening, and then had to be in New Haven on the next day. All were easy drives. And, there are amazing fine dining options nearby. We'll definitely try to book this wonderful place any time we have events in the area. Thank you, Mia, for a magical Autumn weekend in Connecticut!
Apartment rentals with outdoor seating

The Mystic Surfside Getaway 1-BD Apt
Our stay at Jennifer's place was excellent. We wish we could have stayed much longer. The apartment is in a quiet neighborhood just a few minutes drive from all the Mystic attractions (and a short walk from the very necessary wine shop and pizza joint! ) We loved our little balcony just outside the living room. My wife and I would absolutely stay here again!

Lakefront Luxury on Pattagansett
Kevin is a great Host - very responsible and accountable. We fully enjoyed staying his place. He was always willing to help while needed. The AirBnB is clean and has full of required amenities. We left some stuffs while checking out, he communicated quickly and shipped it out very fast. I highly recommend to stay at his place at East Lyme, CT.

Upscale Newly Constructed Apartment
Our 3 time staying at Amanda’s home. Beautiful and spacious within walking distance to village. Looking forward to coming back next year!

Squire Chase House
Great spot! Very walkable. It's also a great layout if traveling with small children - there is a separate meditation room upstairs that was perfect for setting up our travel cribs. Would stay again!

Cozy Apartment with Water View of Brook
Our stay was extremely quiet until the upstairs neighbors returned. We don't have kids or pets so we're very used to quiet. Getting used to hearing upstairs neighbors took getting used to for me. The place was chock full of supplies, coffee, Scrabble and welcoming decor. The bed was outstandingly comfortable. The bathroom was modern and creative! The outdoor patio, activities and view of the creek were impressive. This is definitely on our "to return to" list.

Lovely Garden-Level Apartment in Heart of Town
My girlfriends and I stayed for a girls’ weekend. The place was so clean and lots of personal touches. Beautiful flowers and a well stocked kitchen. We even had yummy chocolates available to us. The beds and lines were very comfortable. Fun games and lots of books and magazines to choose from. The home had a lot of character and antique charm. It is a quick walk to restaurants and shops. We had dinner at the Red Door and would highly recommend. Deep River roasters was our destination for breakfast. Coffee was sensational. And bagels tasty. Liz was so responsive, kind, and helpful for any questions we had. We will definitely be returning to stay.

Sperry House one bedroom private apartment
I had the pleasure of staying at Rosaria’s apartment for two months, and it was an amazing experience. The place was spotless, well-equipped, and had everything I needed for a comfortable stay. Rosaria herself was incredibly kind and helpful, always making sure everything was perfect. I highly recommend staying here to anyone looking for a great place. Thank you, Rosaria!

Recharge at our Renovated ocean front unit
Great place ideally located next to town and the view is amazing. highly recommend in particular for short term stay.
Condo rentals with outdoor seating

CASiNO, Spa, Hot Tub, Pool, Private Villa, Kingbed
Kim’s place was perfect for what me and my daughter needed. We were in the area celebrating her 15th birthday. The villa was clean, and quaint. The decor of the room was peaceful and warm. And most importantly it was CLEAN, no complaints! Kim was responsive and proactive in her communication. Will definitely visit again in the future and recommend to any friends and family who might travel that direction.

Seaside Summer Escape: 2BR Waterfront Condo w/Pool
We had an amazing stay! We stayed off peak season, although alot was closed we felt right at home and were more than happy to spend family time at this condo! The views were stunning, and the condo was immaculate. We were close to everything and was still within very reasonable driving distance to the surrounding towns. Julie was a pleasure to work with and was always very responsive and accomadating throughout the process. Hoping to stay again next year!

Montauk Waterfront Condo w/ Sunset Views
Absolutely wonderful stay and host. I've stayed at dozens of Airbnbs and this is one of my favorites! Doug's place is even better in person than the photos. We were a little nervous taking our first trip away with our baby, but it was extremely clean and comfortable, and Doug was so kind and responsive. The condo complex has a lovely boardwalk for taking walks, and the deck furniture was so comfortable to lounge in and take in the beautiful view. We hope to be back!

Peaceful Oasis steps from Mohegan Sun
We loved our time at Christina’s villa! I mentioned to her that it was a mini honeymoon getaway and Christina left us a bottle of wine, chocolates, a nice card and some other snacks! The villa smelled extremely clean and nice upon entry. The extra amenities such as toothbrushes, and everything else you might have forgotten was a great added touch! We will definitely be back for another stay and will be recommending to others as well!

The Vacay Villa
Krista place is very clean and welcoming. It had perfect personal touches. From coffee creamer for our morning coffee, to shower essentials. I find the small personal touches so nice and it is welcoming. Christa offered east check in and extended my check out time with no questions ask. This was a very nice place for a weekend trip and we will def be booking again!

Beachside Waterview 2Br Condo w/ Pool in Greenport
The place was perfect nice and clean what I like the best is the it was close to the beach to go for a walk.

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!

Coastline View Studio
This was absolutely perfect for our wedding weekend in Montauk. We were so close to everything which made it very convenient. The room was perfect and loved the clothing rack perk! Everything was clean and loved the skylights in the unit and the patio overlooking the water. 10/10 woud definitely stay here again!
Quick stats about vacation rentals with outdoor seating in Madison
Total rentals
60 properties
Nightly prices starting at
ﺩ.ﺇ257 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
Destinations to explore
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- Rentals with outdoor seating New Haven County
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- Beach
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Foxwoods Resort Casino
- Napeague Beach
- Ocean Beach Park
- Cooper's Beach, Southampton
- Quotonset Beach
- Walnut Public Beach
- Shinnecock Hills Golf Club
- Woodmont Beach
- Giants Neck Beach
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- Blue Shutters Beach
- TPC River Highlands
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- Sunken Meadow State Park
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