Holiday rentals with outdoor seating in Chatham

Serene and charming riverfront hideaway. In a residential neighborhood but very quiet. You are 5-10 minutes from great restaurants, shopping, Dennis Beach but it all feels very secluded. We went kayaking every day from the private dock, saw swans, sea lions, and hawks. The space is clean, boho-chic, very comfortable beds, easy to use gas fireplaces. Primary bedroom sitting area/sunroom is dreamy for reading. Kitchen has everything you need. We thought we might miss an ocean/bay view but we didn't at all. Very reasonably priced for the quality. Meg replied to all messages within minutes. We would absolutely come back. Great for a couple or small family.

The team was very responsive and the home was exactly like the photos! Also, it was very close to town which was really nice!

You won't find more responsive hosts - literally within minutes. Check-in and communication throughout was great. And it's the first rental I've ever seen that had REAL toilet paper! IYKYK! They were super clear about everything. The only small issue we had was with the AC. It's listed as Central AC, which it has but only on one floor. This wasn't a big deal because it was later in the season but if it was in the middle of the summer it would have been an issue. The first floor didn't get any of the AC and just cracking the door from the upstairs wasn't really sufficient to cool it down, even at night. Again, not a problem around Labor Day when we were there but in mid-July I don't think it would have been very comfortable to sleep there. But other than that, a great stay in a great location.

We had a nice stay at Chuck's place in Cape Cod. The house was in a quiet neighborhood. It was clean and comfortable. We did feel like the $225 cleaning fee was a bit steep for only a couple of nights in a small house.

We had such a lovely stay at Paula’s! The kitchen was even stocked with some snacks and brekkie which is above and beyond!! My kids loved the fire pit and it’s a great spot to let them run around as it’s a quiet property. 10/10!

The cottage is beautiful, extremely comfortable and well equipped. The surroundings are peaceful and the location is conveniently at walking distance from the beach. We loved our stay there and spent an amazing week.

We had a great time staying at this Airbnb! If I find myself returning to Cape Cod I will be sure to look if this house is available again.

The Happy Yellow House was all I hoped for and more. Clean and well equipped, and very comfortable. The location couldn't be beat! Right down the street from a beautiful Nantucket sound beach and close to the amenities of Chatham. The house is in a quiet neighborhood of summer homes and was very peaceful. Caitlin is a superb host and responded promptly when there was a little snafu with a faulty smoke detector (at 10pm!), offering to have an electrician out on an emergency basis. (The electrician had just serviced the smoke detectors. As Host, Caitlin couldn't have been more pro-active or responsive) Luckily, I was able to solve the problem by simply removing and replacing the batteries. I would not hesitate to book this rental again.

Songbird Studio was the perfect b&b for me and my partner during our 3 days on the Cape. Private and peaceful, yet centrally located made getting anywhere of interest within 45 minutes extremely easy. The space was both clean and comfortable while also being very affordable compared to other listings. Ann was also such a gracious and hospitable host. The coffee shop right across the street was an added bonus in the mornings! Overall could not recommend this location enough and would 1000% stay here again.

I had a fantastic stay at Tara’s place! Everything was exactly as described—clean, comfortable, and thoughtfully set up. Tara was a wonderful host: super responsive, welcoming, and respectful of privacy. The space had everything I needed, and little touches made it feel like home. I’d definitely stay here again and highly recommend it to anyone visiting the area. Thanks again, Tara!

My son and I had a wonderful weekend visit to Eastham. Min's place was very clean, comfortable, and cosy. Coffee bar was well stocked and much appreciated!

If I could give 100 stars I would!! Out of all the airbnbs I have stayed at Jennifer’s listing has outdone them all!! First of all, Jennifer was the most amazing host and treated us like family! Secondly, the house was spotless, not a speck could be found (and I am usually picky about cleanliness) — it was absolutely exceptional!!! I will definitely be coming back multiple times. Thank you Jennifer for hosting us!

Diana and Greg's place is a wonderful place to stay, brimming with nature, quaint and comfortable living space and wonderful hosts. A nice walk to the beach, enjoyed the birds and frog sounds were the highlights and Orleans allows the entire Cape Cod to be accessible under an hour drive. An awesome weekend adventure and appreciate Diana and Greg opening up their doors! Cheers!

Beautiful little condo with great views and everything within walking distance. The photos do not do it justice! Will definitely be back and would recommend for anyone looking for a relaxing vacation on the cape

We had such a great stay! The hosts were super accommodating and really attentive to anything we needed. The place was spotless, cozy, and fully stocked with all the essentials (and then some). They went out of their way to make us feel at home, and it honestly made the whole experience so relaxing and enjoyable. We loved everything about our stay and are already looking forward to making this an annual tradition! Tracy Thomas and Drenary Gwynn Baltimore Maryland

The apartment is just perfect for a week on the Vineyard, and Jennifer has thought of all the details. So easy to use and find everything. And it is a lovely space.

Kevin's place is perfectly located in Angels Landing across from the library. It’s a quiet, safe location at night. The proximity to abundant dining and shopping options made exploring Provincetown incredibly convenient. The home was well-stocked with coffee and sweetener, which we appreciated each morning. The peaceful setting allowed for great rest after busy days exploring the town. Kevin was a thoughtful host and we'd definitely stay here again!

Anna’s place was exactly what we needed to have a peaceful and relaxing Memorial Day weekend stay. We knew the weather might be on the cooler side, so purposefully wanted to stay where there was the possibility of using the indoor pool – the sponsored guest passes were a huge benefit here, and Oceans Edge staff even went above and beyond, adding an extra day to our pool access since we were picking them up so late in the day. The condo was clean and filled with all the essentials, in a very quiet area of the property. Would definitely stay again!

Airbnb virgin….. but NOT ANY MORE! When I couldn’t figure out how to get in, at first I felt alone, scared, betrayed, abandoned, and almost closed my eyes to self sooth. But I forced myself to keep my eyes open, figured things out. All of a sudden I didn’t feel alone, I even felt loved/protected. Everybody was really nice. Even when I wasn’t. Thank you for letting me into your home!!

We had the BEST stay at Ingas place! It was so cute and perfect. We could walk places and it was so comfortable. Inga was amazing about being flexible with checkin and checkout. She also responded right away. The pricing was awesome. We will be back!

Loved my stay! Amazing location and comfortable, neat place. Will definitely be coming back!

We had a beautiful stay at Anil's, and would book it again. The thoughtful use of space made the interior feel expansive, and the views to the bay are inspiring from every area. The kitchen was well-appointed and we really appreciated all the storage in the bedroom loft allowing us to unpack our clothes neatly. This is a great location just after the end of all the shops and restaurants on Commercial St.-so it's quiet and mostly residential. Loved it, thanks Anil!

Amazing stay. Didn’t have to get an Uber once, everything was walkable. Brian communicated consistently.

This was our second stay at Steven’s place, and it continues to be the best spot to stay at. We love the location, it’s close to everything but still on a quiet part of Commercial St. And you can’t beat the friendliness and ocean view at the bayside condominium complex!