Cottage vacation rentals in Chatham

We loved our short but sweet stay at Casa Sebastian. The ambience and decor are so thoughtful and we immediately felt at home. The Duplo blocks were an instant mood booster to our frustrated toddler (as was looking out the windows in the loft). The walk to the beach along the wooden boardwalk and path was short and a fun activity for our son. Even on a rainy day, we felt cozy and at ease listening to the rain and watching movies. We would love to stay again in the future! Thank you Mikhail and Erin!

Carl’s cottage was the perfect little get away! It was just the right size for me and my husband and very close to the beach. The yard was a bit overgrown but other than that, a great place!

Teagan’s place was exactly as described. Had a girls trip memorial day weekend and the spot didn’t disappoint. There were enough beds to accomodate us, it was spacious and very clean. We could see the beach path through the sliders and we were able to walk right down to the beach. Unfortunately there was a huge storm during half our trip but the cottage was such a cute spot to just chill and relax while waiting out the storm.

Mazie was great host and her place was perfect for our family. Walkable to beach. The kids could ride their bikes on the dead end road and they had a little candy and Icecream store they liked to bike to not far. The inside was great. We had four kids and our two youngest loved the little loft area as their room. The backyard was great for relaxing grilling and the outdoor shower was perfect to have for back and forth trips to the beach all day. Mazie was a great host and we are grateful for our stay at her beautiful home.

Really enjoyed this stay!! The hot tub was perfect for the chilly nights during the weekend, the kitchen was furnished with snacks, the bed was supremely comfortable, and the windows brought in great sunlight. Would absolutely recommend it, and hope to stay again in the future.

A wonderful place to relax, soak in the hot tub, and enjoy the nearby beaches and amenities.

Art is simply amazing to deal with for a host very responsive, home is beautiful right on the lake plenty of room for 2 -3 families..this is our 3rd year staying and hands down our favorite airbnb.

Very good place Cousy my husband and I love the jacuzzi my favorite part!❤️ ..I didn’t really like the patio kinda of simple but other wise everything was good well recommended for a couples!

This was the perfect stay for us to explore Cape Cod and Boston. It was central and only about an hour to two hour drive for all the activities we were hoping to do. The place was clean and so cute and comfortable. We would highly recommend!

Sweet, cozy house that’s perfect for 2-3 people. Very comfortable bathroom and kitchen, esp for a smaller house. Great outdoor space and loved the rope swing!

We had such an amazing time at Anne’s beachfront cottage. My girlfriend, pup and I spent about a week there to celebrate my birthday and staying here while on the island made it such a stress free trip. The house was well-stocked with supplies, towels, and pantry items that we would have otherwise forgotten to bring. The LOCATION was unbeatable, close to everything while still being secluded from the main road. The backyard views were immaculate, sitting on the beach for the sunset and enjoying the breeze, playing in the water with the dog. We all loved it! My only minor complaint is that the beach got a bit dirty with seaweed by the end of our stay, but I know that’s unavoidable due to the position within the cove. We would definitely come back for a future stay on the Vineyard!

We will definitely stay with Brian again on our next visit to MV. He was very responsive, friendly, great recommendations. The place was new, clean, comfortable. FYI, a new restaurant across the street is Black Joy. Can't recommend it highly enough. Please let guests know how tucked away the property is so they can find it better. We came at night so we were a bit confused. Once we figured it out, all good. Loved the location, easy to get everywhere. And Brian is a great host. Thanks so much for a great weekend.

A beautiful cottage. Our dogs loved the beach and we loved hearing the ocean at night. Best of all, we saw North Atlantic Right Whales at Long Point. In a world where it can be difficult to sleep well - I slept like a baby!

This was our second stay and though it rained and was very windy , we enjoyed our neighbor walks during the brief periods of sunshine. The cottage was perfectly clean and had everything we needed. Both of our stays were planned so we could visit with family that lived just two streets away. Proximity to the beach and great restaurants made our stay very relaxing. We will definitely plan another stay.

Despite the door’s un-latching issue due to a fault door knob, Michael and John were very easy to reach, and provided a fast solution. This place is in a wonderful section of P-Town that was both close to all of the action, and also felt remote and private. For my family (gf and two kids; 9yrs old & 18mo old), this cottage was the perfect size for us. To take advantage of the exceptional off-season price, we cooked all three nights of our stay. The place was stocked with all of the essentials, and there was even a packet of taco seasoning that we forgot to grab during our grocery run. We had such a wonderful time, that we’re planning on returning this time next year as a new family tradition. Thank you Michael and John for providing us the opportunity to have a wonderful escape for the week.

We had a wonderful stay at Bonnie’s cottage! It was quaint and cozy. Very clean and comfortable for our family of 3 and our doggie ! Bonnie was extremely helpful and responsive providing clear instructions and videos. We loved the location being so close to the beach and many other great restaurant spots/ desserts. Check-in/out was very easy. We would recommend this place to anyone planning a small trip to the cape!

Andrew was an excellent host. The beds and couches exceeded our expectations. You usually have to stay at a Marriott for that level of bed comfort.

Lovely cottage on a quiet street. Great location for walking into town and to several beaches. Nicely arranged backyard with comfortable chairs and dining table. And Ahhh the sun drenched outdoor shower was such a treat. I’d highly recommend this little gem.

My girlfriend and I stayed here for a few days during MDW and it was great. Andrew is a very responsive and friendly host and the cottage itself was perfect. It’s steps away from the nearby pond, which is a beautiful spot to have your morning coffee. The cottage is also in walking distance to Mac’s Chatham Fish & Lobster, good ice cream, bike rentals, downtown Chatham, etc. Definitely would recommend this spot and stay here again.

Absolutely sparkling fresh and clean. Beautifully designed and decorated. Bed was so cozy and comfortable. Stairs are tricky and steep But it is expected in this style cottage. Convenient to downtown yet very secluded. We had a nor easter through our visit. So sad that our outdoor plans were ruined but this cottage had lots of room to move around. Could not imagine being in a small hotel room. We loved handing out at Chatham Bars Sacred Cod for drinks and dinner! Coming home to our cottage was half the hotel price but twice as cool!

We love this house so much it was actually a second time booking it for our family getaway to cape cod. The house is immaculate upon arrival. The host(s) are extremely responsive with communication and curated a gorgeous spacious house for us to enjoy for our time in Ma. The house is in such a wonderful location within a quick drive to a cute Main Street, and a short drive away from all surrounding towns in cape Cod. We are already looking forward to another stay next year. -Allison

we stayed for a week in August and had a fantastic time!!. the cottage is located a few stairs away from a beautiful private beach..my kids had a lot fun playing on the beach.the cottage has all what you need for a relaxing week in cape cod. short drive to restaurants and local amenities. Bruce has been very helpful and always available.we will.come back for sure.

Betty was very friendly and responsive! The cottage was the perfect size for two people with so many amenities so we didn’t have to bring much. Would recommend this and stay again!

Cottage was adorable, home-y, very relaxing. Deidre was very responsive to any question or concern. And what was especially helpful was that she made sure that everything was provided-coffee, tea, ziploc bags, shampoo and conditioner, laundry detergent, etc.