Cottage holiday rentals in Plainedge

Louise's place was perfect. Louise was so easy to communicate with, super responsive, kind, thoughtful and truly appreciated that she had the option of flexible dates (instead of so many sat to sat or sun to sun requirements in summer). The cottage was cozy, cute, spotless & well stocked. My teenage kids loved the hot tub (as it was a bit chilly in the evenings) and I loved the outdoor shower. We loved having the bikes to take rides around the Island and loved the location. Our only regret is that we didn't get to stay there longer! We will definitely try to stay at Old Snuggler again!

My friend and I stayed here for a quick two-night getaway and had a great experience. The space is quiet, cozy, and super well taken care of. The view of the water from the living area is beautiful, and we spent both mornings sitting outside with coffee, and afternoons enjoying the view from the hot tub. We appreciated that the kitchen was fully stocked with all the cooking equipment we needed for nights in—and that Mary had a whole list of spots to check out for adventures out (local shops, antique spots, and really solid lobster rolls!) If you’re looking for a low-key, clean, calm place to relax, recharge, and still have easy access to town, this is a great pick. We’d absolutely come back.

What a wonderful experience! I wanted to celebrate my wife’s birthday and this was a fantastic place to do it! We had a terrific time. The house is beautiful and well appointed. Location was great . Visited 2 Farmer’s market and enjoyed the beauty in general. We will return! Thank you for being a gracious host!❤️

Tabitha's place was perfect for our group stay. Right in the middle of town and perfect for what we needed for the week!

beautiful house, great location and very nice and peaceful neighborhood close to the beach and the vineyards the house is very well equipped ! Richard was very nice and even find a little bed for our baby boy ! thanks !

Ivana and John are the most wonderful hosts! This was truly like staying at a family cottage and everything was just beautiful. John greeted us upon arrival and even had a bottle of wine for my husbands birthday! We loved staying here from the city because it was only a little over a hour to arrive and less than a hour to South Hampton where we had dinner. Also the little town is so so cute and we were able to walk over so quickly! We can’t wait to stay here again. Thank you again Ivana and John!

Lil Nauti was perfect for our family. The bedrooms were adequate, with very comfortable beds and plenty of pillows. The wardrobe space and drawers were great as we had a long stay with a lot of baggage! Jason has absolutely everything you could possibly want or need for a stay. The kitchen is really well equipped. Cute cottage and delightful private garden.

Brenda’s home in Lake Como was a fantastic stay! The place was spotless, comfortable, and had everything we needed. The kitchen was especially well-equipped, which made cooking super convenient. The highlight for us was definitely the hot tub—such a perfect way to unwind and enjoy the beautiful surroundings. Brenda was a great host, responsive and thoughtful throughout our stay. Highly recommend for anyone looking for a peaceful, well-kept home in a stunning location!

Absolutely loved our stay with Michelle. She was an amazingly thoughtful host to us and our dogs, her place was in a great location, and it was great value! Definitely recommend!

I love the fresh air flowing throughout this entire little cottage. Every room invites dappled sunlight filtered through lush summer foliage. It is truly cozy, whether enjoying a coffee on the back porch, journaling at the desk or chilling on the big comfy couch. Walk out the door and the lake and charming downtown are steps away. I find myself thinking I could truly spend a happy month, here. Stay. Return. I know I will.

Great place and great location. Lots to do in walking distance. Host was responsive and flexible with our check in requests.

Lovely little cottage with all the necessary amenities. Really enjoyed our stay!

We enjoyed our stay at the cottage. I had reached out to Lisa numerous different times and she was very understanding and quickly responsive. The home itself was clean, walking distance from the beach, and I loved it was nice and cool inside from the AC.

Jim’s place was an absolute gem for my inaugural trip to Black Rock! The Loft is incredibly spacious and equipped with everything you could possibly need for a perfect stay. From the moment I arrived, I was impressed by the meticulous cleanliness, attention to detail, and beautiful furnishings. Jim's communication was top-notch, making the entire experience seamless. One of the highlights was the extensive music collection, perfect for setting the mood during my downtime. The bed and furniture provided a level of comfort that made it hard to leave. Nestled on a serene, tree-lined street, the location couldn’t be better; it’s just a leisurely stroll away from delightful restaurants, charming shops, food markets, and more. I can’t wait to return for another stay whenever I’m in the area!

Jeanne's place was perfect for my trip to Guilford. Excellent location, close to the Green and to the water, quiet, peaceful. The house had everything I needed and more, Jeanne was super responsive and kind, and the bed was comfortable.

One of the best air bnbs we’ve had the pleasure of staying. Was even more comfortable, spacious and well appointed than the photos portray. Walking distance to the three villages historic museum and so close to port Jeff and the university. Everything we needed and more, and Lise was incredibly thoughtful and accommodating. Stayed with two small dogs , so easy. Love this historic home!

Wonderful place to stay with everything you need for a fire island getaway! Was very responsive and helpful with any questions we had. I always look forward to staying at this house!

We had a great stay! The cottage is so close to everything, has a nice outside area to sit and enjoy the weather, and has everything you could need. Karen was super responsive and even left us a few snacks and drinks in the cottage, which was very nice! We would not hesitate to stay here again in the future.

The proximity to the beach is unmatched. Additionally, a short drive or bike ride to Post Road provides an unlimited amount of food and culture to enjoy. The space is comfortable and clean with all you need for a short or long stay.

Susan is a fantastic host and the cottage is a lovely place to stay. Steps from the beach and a quick drive into town plus pool access right out your door. Susan was great to interact with. We definitely plan to come back.

We absolutely loved this little house. It's super-stylish, light and airy, clean and modern and a perfect place for a couple to stay. Mark is a very helpful and charming host - he came round to welcome us, when we arrived, and to tell us where the local restaurants & shops are. There are great facilities nearby - in particular a coffee shop which sells the most amazing freshly cooked donuts (which we very indulgently had for breakfast). The little house has everything you need for a very comfortable stay, and we highly recommend it.

Beautifully decorated place with tons of personal touches and attention to detail. Great location to go explore the north and south fork from. But we’d also recommend coming just to stay at the cabin! Woke up to a little rabbit rolling around in the yard and the neighboring plot had a horse that was curious about our presence. Located close to train tracks but very quiet in practice.

Crystals Cottage is very charming..very clean..safe area… Crystal was a great host…would stay there again if ever in the area!!!!

Stay was perfect, it’s shows the at the owner cares about the guest experience! Perfect spot right on the lake and freshly renovated.