Chatham Vacation Properties

Chatham and Harwichport, Cape Cod year round vacation properties

be born again


Evelyn and I were married on Nantucket Island back in the summer of 1992.  We truly love the island, weather, shops and beaches and truly missed not being able to travel down on a regular basis.  In 2008, with our family of five, we decided to establish roots back in the Cape Cod and Islands area and chose the destination of Chatham!  It reminded us of all the similarities of Nantucket in regards to the scenic views, weather, shops and beaches – with the caveat that it took half the time to get to Chatham versus Nantucket from our permanent home in Lexington, Massachusetts!  

Over the course of the last decade we have been able to purchase additional properties and taken on the opportunity to develop a unique group of vacation rental properties that are situated within a mile from Chatham Harbor and Downtown Main Street.  We are well-established in the vacation rental business and understand first-hand the importance of providing both excellent customer service including clean and well stocked properties.   Our portfolio of properties come with many features and amenities to insure your perfect vacation is set up in the best way possible.  While we are available on the top rental platforms we also understand that in order to provide affordable options we maintain a direct book to guest business also.

it's a big world out there

Chatham and Harwichport, Cape Cod year round vacation properties.


Recommended Properties

$ 325

per night

Year-round, 4 Bedrooms Inside + Detached Loft, 2.5 Baths, (Sleeps 8 + depending on loft use in summer/shoulder season...

$ 395

per night

Year-round, 5 Bedrooms, 6 beds, + sleeper, 2.5 Baths, (Sleeps 10)


$ 325.00

per night

My family and I live full time in Lexington, ma. We decided to purchase a vacation home in Chatham, ma because of the...

$ 275

per night

This is a fantastic - location right off main street in Chatham downtown area - 5 minute walk to Oyster Pond Ocean Inlet...

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happy traveler

Karen D.

We had great time at this lovely house in Chatham! Lots of space.

Kristin A.

We had a sweet time in David and Evelyn's house. They were very responsive and helpful. The location was an easy drive to downtown Chatham, which had plenty of parking for our late June stay. The house was a littl...

Douglas W.

We really enjoyed our stay. Very nice house in a great location near downtown Chatham. The owners were very good about communicating with us. Highly recommend.

Michael S.

A true Cape Cod dream home. David and Evelyn could not have been more accommodating. My family throughly enjoyed our week on the Cape and my wife and I would highly recommend their home to everyone. Great fenced in ba...

Christopher R.

This gem was everything we needed. 4 comfortable bedrooms, with a beautiful master suite and needed privacy.

Kitchen and living room was very comfortable and had plenty of space for all 8 of us. Fenced-in ya...

Laura T.

Fantastic location! Walking distance to town, Oyster Pond and grocery/drug store. Comfortable home with gorgeous kitchen.

Owner is on top of every need or question.

Loved our stay there.

Cindy M.

Family members are still talking about our reunion at the Cape--which more than met our expectations! We chose the house because of its convenient location to beaches, park, ballfield, restaurants, and shopping (Chath...

Tomas W.

It is a very nice, clean and well maintained house - there is everything inside to spend a few nice days in Chatham, Cape Cod, MA. The rooms are well distributed, a lot of natural light, a large well equipped kitchen....

Tomas W.

It is a very nice, clean and well maintained house - there is everything inside to spend a few nice days in Chatham, Cape Cod, MA. The rooms are well distributed, a lot of natural light, a large well equipped kitchen....

Erin D.

This is a beautiful, well apointed home, within walking distance to shops, restaurants, and a lovely pond. Owner is very responsive to questions.

Barbara R.

Thank you Evelyn and David. The house is beautiful. It was perfectly located and so close to my daughters wedding venue. We had an enchanting, magical wedding!!! BR

Kelly B.

Recently, my husband brought our three kids (15, 14, and 4 years old) to Dave and a Evelyn’s house for a quick getaway before our sons’ youth sports schedules start back up. Initially, I was a little hesitant to h...

Rebecca H.

We had a great stay with our whole family over the Christmas holiday. The house was a great size with a well equipped kitchen. Location is fantastic - just a mile or so from the beaches and shops Chatham has to offer....

Chris S.

Perfect location! We attended a wedding at the Chatham Bars Inn. This house trumps the Inn!

Bernadette Bonnie K.

Clean, neat, comfortable and owners were very accommodating!

Kim W.

Our party of 9 was quiet comfortable in this clean and well equipped home. The location is a short drive to the lighthouse, downtown and several beaches. It is also walkable but we were there in November when temps we...

christopher t.

This is a great place to stay. The pictures do not do it justice. It's a great spot in a great location


We were visiting Chatham to attend a Family Wedding and we wanted to spend some quality time together as a family unit and rented the apartment so we could have that luxury. Everything about the apartment was perfect!...

Melina Y.

This place was a gem. Perfect location, the place was impecable. Super close Main Street Chatham and Chatham Bars Inn. The condo was the perfect size, it’s actually quite deceiving and much more spacious than you ca...

Vincent P.

What a beautiful property for our weekend away for a family wedding! As soon as we opened the door, we were pleasantly surprised - the space is even more beautiful than the photos.

Extremely clean, and a per...

Kris J.

We needed a place to rent for a wedding. The condo has been set up in a way that makes you feel at home.