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.


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$ 295

per night

Year-round, 4 Bedrooms + Detached Loft, 2.5 Baths, (Sleeps 8+ depending on loft use)

My family and I l...

$ 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...

$ 273

per night

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

Coming Soon ...

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happy traveler

Wendi D.

When we walked through the door, we were so thrilled with how meticulously clean it was! Because this is our second summer renting Evelyn and Dave's lovely Chatham home, we felt right at home! The bedrooms are so ...

Jennifer R.

We had a GREAT time in Chatham and this property was great for our big family. We loved the fenced in yard with children and a grand dog! The house was really clean and well appointed. The backyard was a great place t...

Brian S.

We had a great stay at David and Evelyn's home. This really felt like a home away from home. Great property. Very clean, comfortable and a great yard. Awesome location to. Minutes to Chatham Bars Inn, Chatham fish...

David S.

Worked out great. Well stocked and maintained.

John K.

We were in town for a weekend wedding and were happy with our decision to stay here. We piled in 2 grandparents, 2 kids and 4 adults and had plenty of room and distractions to pass the time we weren't being weddin...

julia s.

The house didn't disappoint. The garage was great to have, keeping our bikes covered and for loading/unloading. Well- equipped kitchen and comfortable furnishings. The house was clean and well maintained, with nic...

Wendi D.

Our family, which now includes 3 young adult children and 2 dogs, have been vacationing on the Cape for 23 years. This was by far one of our most favorite houses to rent. The space was perfect for us and had all the a...

Kate J.

Our family, which includes three young children and a small dog, enjoyed this home for a week in July 2016. Although we have been vacationing in Chatham for years, we found this location in North Chatham to be ideal i...

ellen c.

Your house was immaculate, cozy with a spacious private yard. We had a family wedding so children and grandchildren stayed with us. Close to everything especially the Lazy Lobster right across the street. We called in...

Aaron A.

Wonderful house with loads of charm. Meticulous detail in every room from comfortable beds to well stocked kitchen. Owners are very responsive and quick to return email or phone calls. Coffee shop and wine shop 5 minu...

Blanca S.

We had a great time and enjoyed Chatham very much. The house was lovely, warm, and inviting! Very close to beaches, restaurants, and shops in town of Chatham. Our children had a great time as well and felt right at ho...

Melina Y.

We loved everything about this home. It was conveniently located close to the center of town and the house had such a cozy feeling it made you feel right at home.

Evelyn and David also made it super easy to ...

Lisa L.

Adorable house, great location. Very relaxing weekend. We had a great time!

Sonya B.

We were a party of 6 women enjoying a trip to New England. Your property was clean, comfortable, and cozy, a home away from home. Thank you for a lovely place to stay.

Erin C.

This is the second time that we stayed at this home for a girls weekend in October ... it is a lovely home and in a perfect location so close to town that we could walk. Plenty of bedrooms and outdoor space, but a sma...

Donna D.

Nothing not to like. Beautifully decorated and very spacious. It was wonderful to be able to walk to the Market and CVS.

Nancy D.

Your home is spacious and attractively appointed, ideally located close to Town and Oyster Pond (for the little ones) and not far from adventures at Nauset and elsewhere for the rest of us - 3 generations. Thank you!

Dawn M.

Kitchen was well equipped, beds were comfortable we walked almost every where we went. My family all agreed we would do this again. Even the weather was beautiful. David and Evelyn have a comfortable and beautiful hom...

Carol T.

3 special couples in this special house !

The location was perfect for us ..we could walk to town ...we didn't cook a thing ( despite the fully equipped kitchen ) because there were too many great restau...

Deborah L.

We rented the house with our adult children and a dog. The house is everything described and more. The yard is completely fenced in and we found that comforting. We were so impressed with how clean the house was insid...

Claire H.

Our son just got married on the Cape. We rented this property for us and some family members. It was perfect! Very clean. Very nicely appointed. Fantastic yard. David and Evelyn were so easy to work with. Very respons...

Nancy R.

We had a very comfortable stay at this home because it had all the amenities we needed for the two weeks. I highly recommend it.

Kathleen O.

My family and I had a wonderful time at your vacation home! It is very family friendly! We loved playing outdoor games in your spacious backyard! Your home was well stocked with everything a family would need on vacat...

Gary H.

The place was great, love the set up and seemed roomy even with 8 adults staying there. The deck really brings the place together and the outdoor ping pong table is a plus.

Everyone enjoyed the stay.

Joe L.

We couldn't have asked for a better weekend getaway spot. Great location... a short drive to the beach, restaurants and bars. The house itself was comfortable and roomy and the back yard and porch was the ideal sp...

David & Evelyn G.

My wife and our three kids chose to spend our Christmas this year in this gorgeous condo right near downtown Chatham off of main street. We can't say enough about our hosts and the property as from the moment we chec...