Family-friendly vacation rentals in Northwest Harbor

We loved staying at this home - it was the perfect place for our group of ten. The outdoor space was definitely the highlight, with the pool & spa being our favorite part of the trip. The only thing to note is that we weren’t supplied quite enough toilet paper or paper towels, though I did not reach out for more - It was the last evening when we ran out and we were leaving early the next morning. The trash requirements were a surprise after booking, but going to the transfer station was easy enough, and it is listed on the house rules. Overall, an excellent stay and would absolutely return!

We had an event nearby and Brian’s place was a great base for us. Lovely and peaceful neighborhood. Brian was super responsive and reached out to us when the house was ready(before the official check-in time). Would def recommend to anyone!

Amazing! We really enjoyed our stay. Abby and David are extremely hospitable, responsive, and friendly hosts. The house is beautiful, clean, and well-located. The pool, hot tub, desk, and back garden are even larger and more beautiful in real life. We will definitely be back. Thank you Abby and David!

We had a fantastic girls weekend in Southampton and loved Anthony's cottage. It was so beautifully decorated and cozy. We throughly enjoyed mornings with coffee and books in the sun room.

This was one of the most thoughtful airbnb experiences I have ever had. The attention to detail was extraordinary. Cindy provided everything you could need -- a perfectly stocked kitchen, umbrellas, sunscreen, bug spray, first aid, yard games, pool floats etc. The house was just as charming -- if not more charming -- than the pictures. Super private but also great location with proximity to a CVS, grocery store and main street in East Hampton. Cindy was also very communicative and laid everything out super clearly with great recommendations etc. We are already planning our next trip!

This spot was a great find. Hadn't been to Shelter Island before. I found the location super convenient. Literally every place I went was 5 mins on GPS from her house. She was very clear about everything, responsive to emails, and everything was as described, however the pictures don't do it justice. Beautiful home and pool, people came to clean the pool early one morning during the stay and were not disruptive at all. There were beach chairs, umbrellas, pool floaties, games, netflix, literally everything you could want or need. Loved our stay!

We loved our stay at Chandra’s place, it was peaceful, super comfy and was close to everything we needed. It was great to enjoy a few runs locally and come back to the private garden and hot tub in the evening. The property was beautiful and well stocked with towels, soft bedding and kitchen equipment. I’d love to come back again in the future

🌟 A Perfect Hamptons Getaway – Highly Recommend! 🌟 We had the pleasure of staying at this beautiful Airbnb in the Hamptons for two days, and it was everything we hoped for and more. The home is a stunning blend of modern elegance and cozy charm. The interiors are tastefully decorated, creating a warm and inviting atmosphere. We especially loved the spacious living areas and the well-equipped kitchen, which made meal preparations a joy. Our host was exceptional responsive, accommodating, and genuinely kind. This Airbnb exceeded our expectations in every way.

Kate and Daniel are wonderful! Their beach cottage is a must for all families. The farmers markets within 2 miles have all the produce you need, while the fish markets within 5 miles have all the fresh caught seafood you need! There are several New York vineyards nearby and I’d recommend traveling to all the local towns like Greenport, Shelter Island, West/East/South Hampton, and Montauk to see how each one has its own identity. Overall, my wife and I loved our stay at the cottage and we spent most are days laying on the back porch with the beautiful views! Also, great kitchen for cooking and backyard grill with a view.

Had an amazing stay with my business partner. Farms around the area and proximity to multiple Hampton towns was ideal(5 mins from Southampton). Great stay, 10/10 recommend.

This was a lovely cottage and location, part of a private beach community, on a very quiet road, with partial views of the Long Island Sound. Gail was thoughtful to put out a nice welcome basket and some cold sodas and bottle water in the fridge. Perfect spot for two to three people. Close to Guilford main green, dock and nearby Stony Creek and Madison. We didn't make use of the bikes and kayaks bc it rained in the mornings, but we enjoyed one of the two beach just a few minute walk away. Jacob's cove area is a gem.

Michaels place was absolutely amazing. The location was fantastic and was only a short walk into the main part of town, but it was such a lovely neighbourhood and quiet. The place was exactly as described and was perfect for us. Michael made sure we had settled in and gave us plenty of recommendations, which were great! We’d come back in a heartbeat and stay here. Thanks so much!

We love staying at George’s place, it feels just like home away from home for us. We’ve visited this property several times over the years, most recently with our son who’s now old enough to fully enjoy the yard on his own. He had a fantastic time playing outside, talking to the deer and rabbits that came to visit. We even saw some turkey vultures! Overall a solid place to stay and it’s become somewhat of a family tradition. Thank you George!

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.

My girlfriend and I had an amazing time at Ron’s Cottage, it was beautiful and incredibly peaceful, very easy to get around steps from the beach. Listening to the waves crash on the beach from the kitchen was my favorite part. 10/10 wound stay again!

We loved staying at Steffen and Sara's and felt right at home the moment we arrived. Their place is exactly as the pictures suggest: clean, comfortable, full of wonderful art and a colorful design sense. The record player and records were an excellent bonus. We enjoyed a range of music while cooking fresh fish from a local fish market. We slept well and loved being close to town. We highly recommend Steffen and Sara's and hope to be back soon!

Everything was perfect for our girls weekend. This is the 3rd time we’ve used Laurie’s house and there’s obviously a reason we keep coming back. Can’t wait to go again.

Our family had an amazing stay at Colleen’s place. Communication and instruction leading up to our stay was excellent. The location was great. The house was spacious, comfortable, and the pool was beautiful. The house is close to the beach and a short drive to Sag Harbor and the Hamptons. We had a fantastic time.

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

Yvonne's place is wonderful, we spent six days there on a family vacation to celebrate a graduation and it was a perfect spot for a crowd. The description and pictures are spot on (maybe even better) and the place is very well maintained. The weather was not great - so we landed up staying in more than we anticipated and this was a great spot for that. The kitchen is well stocked, having a barbecue really helped, and the large windows and skylights kept us connected to the outside. Yvonne was also highly responsive in case we needed anything. Highly recommend.

Christine's place was nice and clean! We especially loved the fire pit and the pool. Upon arrival of the AirBNB Christine was waiting to meet us and show us around. This was something that was new to me in my AirBNB experience, but it was honestly so nice and so was she! Christine let me know that I could communicate with her for anything that was needed and asked for recommendations to make her place better. This place was so well-equipped, close to everything and it comfortably fit me and my 6 other friends! I would definitely book again with Christine.

We absolutely loved our stay at Milton & Megan's Montauk house! It was perfect for a group of 4 (2 couples) there for a 4 day trip. The house is very quiet & peaceful, with lots of outdoor space, but also very walkable to town. The house was super clean, and everything was very easy to find. The bedrooms had lots of closet space, the TV was easy to set up, and all the amenities listed on the website were accurate. We'd love to come back again and stay. Thanks!

John was a perfect host! Friendly, responsive and made us feel welcome. I took my 9 year old son and we had a great time fishing off the dock and kayaking. The kitchenette is lacking if you want to cook any meals but it didn’t matter in our case. Absolutely beautiful location!

We had a lovely stay at Eric's home. The home exceeded our expectations and we felt right at home. The decor was warm and inviting. Everything you could possibly need was in the stunning, modern kitchen. The beds were all comfortable and we slept very well. The property was very peaceful. We enjoyed seeing deer, turkeys and hawks each day. The fixtures in the home were modern, clean and high-end. It was great being so close to Greenport with it's wonderful restaurants and shops. We can't wait to return.