Holiday rentals with beach access in Wainscott

Nice little Bungalow! Perfect for up to 4 people. Very private and clean. The Location was Great. Right across the street from the Beach with a beautiful view. Has a small Firepit. Only a mile or 2 to Downtown. Would definitely go back.

My girlfriend and I stayed here for a weekend in late May. The complimentary beach pass parking is nice, would love to have been here in the summertime. Cozy bed and very clean place. TV has all the apps. Food in the area was a bit hit or miss but I suppose it is the Hamptons.

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.

Jason was a great host. Very responsive to any questions we had while staying on Shelter Island. The location is great - easy walk from the North Ferry and central to great restaurants. Airbnb was exactly as pictured. Would definitely stay again! Thanks again Jason!

Alisa and Lena's place was really cute, private and comfortable. We had everything we needed for our 2 night stay. Also you can walk a few short blocks to a bird sanctuary!

Claire's place was the perfect spot for a weekend getaway. It was very clean, cozy and nicely situated on a peaceful street in walking distance to the LIRR train station, the main street in Southold, and a lovely beach with stunning views of the Shelter Island Sound and its surroundings. I would definitely book again!

Dawn and Bob’s place is one of the top Airbnb’s we have stayed in! Top notch in every way. It was spotless, comfortable and had everything we needed. And on top of that Dawn and Bob were the most friendly hosts we have met! I would recommend this Airbnb without reservation and will be back whenever we are back in CT!

Wonderful and cozy apartment! We were in town for a wedding and needed a clean and safe space to make home base. This was perfect. Would absolutely stay again!

Marta could not have been more accommodating! She was responsive and provided everything we needed. She even went the extra mile and insta cart-ed garbage bags and paper towels when we ran out. She could not have been a kinder host! We had the best weekend and would HIGHLY recommend staying at Marta’s place! We will definitely be back!

This place checked all the boxes. Very clean and comfortable home and a short uber ride to downtown Sag Harbor. Nice big yard for relaxing after a long day on the boat. Will definitely stay here again. Great host and a great place

John’s cottage is situated on a beautiful piece of land with a substantial water view and a lovely place to walk. The cottage was comfortable with lots of amenities and well cared for. Driving around the property one late afternoon, we came upon four large deer who arose one by one, glanced at us and went on their way. Very nice. John was a personable, friendly and helpful host. We’d definitely stay again.

I have never stayed in an Airbnb before. Bc I like a clean pristine place and prefer a hotel. I am converted after our stay. This house is so amazing pristine and clean. We enjoyed the fabulous design and comforts of home while being there for 5 night for our son’s wedding. I would stay at the house again in a heart beat. And to our surprise it was way bigger than it looks in photos. Thank you Ashley for having us.

Mike is a great host with helpful recommendations and plenty of advice. The house is amazing. Well located, calm, clean and so convenient. The pool is huge and very deep. Everything is perfect. Felt like at home. We will be back

Peace & tranquility! If you’re looking for some privacy with a view, I highly recommend!

Beautiful home, really well stocked and super comfortable. Warm, clean and lots of amenities. Comfortable beds, good showers, big lovely kitchen. Lots of space. We had a great stay. Thanks :)

We arrived to an absolutely spotless and welcoming cottage. Both Lucie & Chris responded immediately to any message/email and per their recommendation we enjoyed a fabulous meal at Il Buco Al Mare (cocktails & dinner), tasty fish taco lunch at Bostwick’s Chowder House and fantastic pastries & coffee for breakfast at Carissa’s Bakery. Ocelot cottage was well positioned for exploring the island (this was our 1st time) and we so enjoyed our sunrise & sunset beach walks on Indian Wells beach (also recommended)! 5 stars for absolutely everything except the cost of our 2 night stay - $1,231.23 we thought a bit pricey compared to other 4-star hotels we stayed at on Shelter Island and NYC.

This was a wonderful place to stay! The rooms were clean, and the ocean view was absolutely beautiful. 10/10 — I would definitely return!

Met all of our needs to be close to family in the area for an event. It's very spacious and the beds are comfortable. The spiral staircase was steep and narrow, but we made it work. Thanks for a great overall stay!

Great stay for a quick weekend getaway! Highly recommend as you are right by the beach, Montauk's downtown, and have access to a pool area.

Mia’s place is excellent. Exactly what the listing describes and more — Mia is a great host and super attentive despite us being a last minute booking, she even helped us through a tough time late in the day when I thought my daughter’s stuffie had been picked up by the maid service. Above and beyond!

We really enjoyed staying at Lynn’s place! Very clean and had a great view of the ocean from the deck. Lynn was very responsive and made the experience seamless. We would definitely stay with Lynn again.

If we don't give a good review, can we keep this to ourselves?! Patti was a perfect host; the views were fantastic, whether from the outdoor porch or inside through the French doors looking out on the water. Access to the small beach and pool were excellent and we were close to several good restaurants (many of which Patti suggested, including some on the water) for take-out during the pandemic. Wifi was great and everything was very clean and as advertised. We generally fly for vacations and long weekends but had to stay closer to home this year and this was a perfect choice.

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!

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!