Holiday rentals with a kayak in Gray

My family really enjoyed our stay at Justin's Cozy Lakefront Cottage on Little Sebago. It was exactly as advertised - a cozy lakefront cottage. We especially enjoyed the paddle boards, kayaks and a canoe (and plenty of life jackets) , as well as the dock and floating pier. This access made it easy to enjoy the lake all day. And the view of the stars from the dock at night was incredible. We enjoyed listening to the loons at night, and had many fabulous meals on the screened in porch. The inside of the cabin is very cozy and there are games to play and books to read. Justin gave us many great recommendations for places to enjoy in the area. In particular, we liked the lobster rolls at Fishermen's Catch and everything from The Good Life. It was easy to make day trips to Portland and Freeport. Overall, this was a very relaxing trip and everyone from age 12 to 60 thoroughly enjoyed themselves. Justin has thought of everything for you to have a wonderful vacation.

House was recently remodeled and they did a nice job. I only get one week of vacation a year and so I am pretty picky about things. The house was a great home base for exploring the south eastern part of Maine!

We had a great week at the cabin! The view is amazing and it was so relaxing. Courtney was very responsive and attentive. Highly recommend for a cozy getaway in a beautiful setting.

Such a beautiful and peaceful place!! my kids didn’t want to leave! Lovely cottage feel with a beautiful view to the lake. We had such a great time taking the kayaks and paddleboard out on the water and enjoying our coffee overlooking the water from the sunroom,. Thank you for the great family memories!

Our group was two small families with kids ages 6 and 8. Everyone had a great time. If you’re looking for a home to get out into nature, this is it. The private dock and lake gave us hours of time to play outside. Kayaks, paddle boards, and fishing off the dock was fun and all part of the house. Kids had a blast and so did the adults. Perfect for family summer vacation. We had a few rainy days but either played board games inside or went into Portland which is only 20-30 minutes away. Visited Mackworth Island in Casco Bay. Must do if you want to have a day excursion. The house well kept and easy to navigate. We spent more time outside on the lake than inside.

Our stay at Jordan’s beautiful place was wonderful. The house is exactly as pictured. The one addition is that along with the kayaks, there are also two paddle boards and a couple of pool noodles. We enjoyed everything from the spacious rooms to the fire pit outside (for s’mores) to the cozy indoor gar fireplace. We had a few questions and a concern during our stay and Jordan was very responsive and hospitable. He even came by to ensure everything was ok. Lastly, the neighbors are incredibly friendly and the neighborhood/lake is quiet and peaceful. Plus it’s about 45 minutes to Freeport (for great shopping) and Portland (for delicious meals). Whether you’re looking for a quick getaway or a longer stay, Jordan’s place is perfect for both couples and families.

We loved our stay (late May, 2025). The weather did not cooperate but the house was perfect. Thank you Debbi!

This was a wonderful stay! It was so cozy and peaceful. I wish I could have spent even more time in the cabin. Bethany was a wonderful host! Instructions were super clear and there were lots of activities and fun things to do!

we had the most peaceful and relaxing time. The cottage was adorable, clean and had everything you needed. The beds are so comfortable we have never slept so good away from home. the views of the lake are gorgeous 😍 we will be back for sure. The host was amazing as well giving recommendations of whats in the area and a sweet welcome basket.

A Perfect Waterfront Escape – 5 Stars My wife and I had an unforgettable stay at RK North Waterfront Cottage. From the moment we arrived, we were welcomed by breathtaking views, fresh coastal air, and a sense of peaceful seclusion that made this trip truly special. The cottage itself was spotless, beautifully maintained, and tastefully decorated with cozy touches that made it feel like a true home away from home. We especially loved the spacious deck overlooking the water — perfect for morning coffee or evening wine while watching the sunset. The hosts were thoughtful and responsive, ensuring we had everything we needed without ever being intrusive. Whether it was relaxing by the fire pit, walking along the shore, or just enjoying the tranquility of the surroundings, every moment felt effortless and restorative. If you’re looking for a quiet getaway with charm, comfort, and stunning waterfront views, this is the place. We’re already planning our next visit. — Eric & Juliet DiNoto

Janet’s place in Standish was great and we could not have asked for a better host. Apart from the home itself, Janet was very friendly and responsive. She even proactively offered early check in / late check out, extremely unexpected and appreciated! Would absolutely recommend this BNB 10 times out of 10.

I had a wonderful 4 night stay at the lake house and couldn't have asked for a better place to spend the little getaway. It is beautifully located on the lake and has this huge window in the living room from which you have an amazing view. The house has everything you need, even washing machine and dryer in the basement. I would 100% recommend this unique place! Christine has been super helpful throughout my stay.

My wife and I wanted to have a lakeside getaway to kick off the summer! The weather was a bit colder than we had hoped, so we ended up enjoying the cottage to its fullest, which was a much needed and relaxing stay with everything we needed right there. It was very cozy and the lakeside view was wonderful, especially in the mornings. The owner was also very responsive to messages, making the experience seamless. We hope to visit again!

The cottage was so wonderful! The pictures did not do it justice, we appreciated the welcome bouquet made from her farms flowers! The grounds were so beautiful and peaceful. We wanted a relaxing getaway and that’s exactly what we got. The bed was so comfortable and we enjoyed the kayaks, fire pit, and bird watching! The location was far enough way for the privacy but a close drive to Portland and other must see locations. Jessica was responsive and communicative with any concerns. We cannot wait to come back and visit every season and cannot recommend the cottage enough!

Helen was actually wonderful. She returned calls and everything. It was a great place to stay beautiful and hope to stay there again someday.

This riverside retreat was the perfect weekend getaway! It was so peaceful and we felt right at home. It was a bit cozier than the pictures made it seem but it was perfect for two of us and a big dog. Everything was clean and it was easy to find things such as extra towels and plates. It was raining almost the whole weekend but there was still so much for us to do between games, the game shed, and the screened in portion of the shed where we could sit, watch the river, and listen to the rain. We hope to go back again someday!

We have stayed at Jackies place twice now and enjoyed it just as much this time as the last. Even though it rained for two days the house is plenty big enough to spread out. We had to change our reservation days twice because of circumstances and Jackie was very accomidating..

This was my second time staying at Terrill’s place and it was just as lovely as I remembered! It’s such a peaceful place, surrounded by natural beauty, to relax and unwind. I’ll definitely be back again!

Beautiful place. Lovely decorated. I would say that it is probably a little expensive for staying there in the winter/ fall time. Only one of us could sit on the couch at a time due to its location by the tv. The shower is really small and there is no room for toiletries in the bathroom at all. There is a rack but I had to keep all my bathroom stuff in bags the entire time because it is just lacking in space. I would think The price is worth it if you’re staying there in the summer and get to use the lake.

Does the cabin look perfect in the photo? It's better. Does the yard look like the perfect place to forget the rest of the world exists? It is. Are the White Mountains a place that make you feel like the psychological mountains in your life are just a little smaller? They are. We don't have enough good things to say about the Cabin or communicating with Cassouki. It's rare to step into a space that feels like it was designed with intention on every level - from the scents in the air to the textures of the cabin to the quiet confidence in every object's placement. The Conscious Cabin doesn't just reflect a designers eye, it reflects a storyteller's heart. I've stayed in more than a few retreats, but this is the first one that felt like it had something to say--and somehow said it quietly enough to let us hear ourselves again. Stay here.

Wonderful Stay in a Great Location! Zak and Emily’s house was exactly as described. It has a fully equipped kitchen, a grill, and a fire pit outside, making it perfect for relaxing evenings. The house is stocked with towels and other essentials, so we had everything we needed. There’s also a ping pong table, which was a lot of fun, and a great collection of movies for entertainment. Check-in was super easy, and the house is conveniently located across from Crystal Lake, offering a peaceful and scenic setting. Communication with Zak and Emily was excellent—they responded quickly and were very accommodating. Overall, it was a fantastic experience, and I would highly recommend staying here for a peaceful getaway. Thanks again, Zak and Emily!

We absolutely loved our stay at Alexa’s cabin. We enjoyed the hot tub, fully stocked kitchen, and truly felt like we could disconnect from the world to connect with those around us. Alexa was a great communicator, provided detailed instructions and local recommendations that were spot on. Don’t hesitate to book this Bridgton escape!

When you are out exploring a new area, the perfect way to end each day is in a cozy, relaxing secluded cabin in the woods, and this is just what Destie and George provide at The Little River Retreat. Their cabin, with its wide, inviting front porch with a sunrise view of mist over the pond, is just the place for morning coffee. They have thought of everything in terms of stocking the cabin, including rainy day and evening entertainment for all ages. I definitely overpacked as so much was provided by them! It is so nice to go to a place where you can take a step back from daily life and it's stresses, and just relax. Thank you for 6 wonderful days.

Third visit in three years for a weekend fishing getaway. Great location, beautiful property. Excellent hosts. Looking forward to a return visit.