Cape Cod Late Summer

My adult kids (2 couples), one 2 year old, and I are looking into spending a few days on Cape Cod in late summer. We are looking at early September.

We are currently negotiating and it’s challenging. As I am paying for it, I don’t wish to be expected to take the smallest bedroom because I am solo. I also feel that the couple with the child deserves a decent bedroom or two.

Five to seven days. An area that’s good with a toddler. Beach or pond.

I think I’ve been on the Cape three times previously but the last time was only a few days and we stayed in a hotel. This time we are looking at renting a house via AirBnB or VRBO.

All recommendations welcome!

What are you negotiating? I gotta be honest- I like my kids to be happy and comfortable. That also makes them enjoy time with us, and all that makes me happy. Many times DH and I have given them the master suite (sometimes b/c they had a pack’n play and needed the extra space in the room, and sometimes they even needed the big closet to put the pack n play in if they needed quiet/ darkness for a sleeping baby’s or toddler) and sometimes b/c the grandkids liked the spa tub that was sometimes in the master. We always pay (well except for the time they took us for my big birthday). Find a place with great amenities (on/near the beach, near shops and a playground) so you can all have fun together. Who cares who is footing the bill?

When I went to the cape, we stayed in Hyannis, Hyannisport or Dennisport. We loved catching crabs on the beach, having lobster, going to candle shops and going to the drive in movie theater! And I believe they still have them on the cape! Enjoy!

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What’s the budget? That’s going to be the limiting factor in this search. Plenty of amazing houses for rent with amazing space for your size group (and no one gets a terrible room) at $1k+/nt.

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That sounds like the perfect trip. Are you negotiating houses or with the kids over rooms?

Regarding $$, late summer is still a popular time in the cape. You would think September would get less expensive, but usually not until late in the month or October. Sometimes there are houses that make deals at that time, but your early planning will not benefit your negotiating.

The budget drives a lot dictating whether on the beach, walk to the beach or neither. Expensive, but not the most expensive, would be New Seabury - Community of houses, walk to beach, even has some amenities for the kids and 2-year old. Ocean Edge in Brewster would be similar. Of course there are houses in 20+ towns that you might consider. One town is truly not better than the other for the most part. Will you be driving from Logan? It can be an hour or 4 hours. From my experience, the beach drives most everything so you pay for that.

If money is more of a factor, consided “cape-ish” towns that are before the bridge. While not cheap, assume 25-40% less and just as nice in some cases - South Dartmouth, Westport, Marian, Mattapoisett. It is the same ocean! This area is now called the Southcoast. Good luck!

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With children…if you plan to go to the beach, I would suggest the bay side beaches…so places like Dennis, Brewster, Orleans, Eastham. The waves are much less so at the bay beaches. You are still close enough to go to the National Seashore beaches if you want to. And there is a lot to do on those areas, and good restaurants.

We vacationed in Brewster for about 10 years, but during the summer (a friend owned a house there…lucky us). Nice location and central to a lot of things.

I think you need to look quickly. It’s only six months away and even in September, folks book sometimes a year in advance.

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I live in Michigan, not Massachusetts so take this with a grain of salt.

September is the best kept secret. Nice but the summer crowds have left. It’s still busy but not as much.

As far as pricing, we find that the only difference is that we are able to rent for a weekend instead of a week block. Still expensive and we found that the good places are booked way ahead of time. Or that’s when the owners go.

We found a place but it was less than optimal. It was fine but we had to make compromises as far as bedroom sizes and older.

You may well have good reasons for choosing the Cape - I mean, it’s popular for a reason and admittedly it’s a trip I’ve wanted to take for years! Will you have to drive or fly to get there??

I do just have to add a +1 to Deb’s Michigan suggestion. The Lake Michigan shoreline is often compared to Cape Cod. Beach town after beach town - not cheap by any means, but I bet cheaper than CC. And September in Michigan is WONDERFUL. Weather can’t be promised anywhere but we did 4 days in the Saugatuck area mid September last year and went swimming easily in the lake, went sailing, ate ice cream galore and truly had a “summer vacation”

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This is true of Maine as well. Seems everyone is trying to get that last bit of summer before the kids go back to school. It would be very hard to find a place in our area during that time. Even after Labor Day, as someone mentioned upthread, owners and others descend thinking it will be quieter once all the families have left, so you really do have to plan early.

The Cape is one of our favorite places. We have friends in Hyannisport, always a good time, but the traffic on the way down can be brutal.

Keep in mind Dennis Port is on the Nantucket Sound side of the Cape.

I’m a fan of Eastham, Wellfleet, or Truro. All have great beaches. If you don’t want to go that far out on the Cape, Osyterville is really nice. Rental prices will be less expensive later in September.

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I didn’t suggest Dennisport. I suggested Dennis…which is a nice quiet town on the 6A side.

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My daughter’s best friend (and my son’s best friend) parents have a house in Dennis and they usually swim on the bay side. They all love CC (the parents probably spend equal time there as they do in NJ, I don’t know how they deal with the traffic, but they do!).

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So many good ideas here.

The “negotiations” are to make sure everyone gets enough of what they want. (The house with the sauna is no longer available)!

Budget is not firm — and that’s OK. I’d rather have a good, happy house. I’m seeing $4k - $8k for a week for us (likely 9/2-9/9). To me, there are a surprising number of houses available. Labor Day is late this year — September 7th.

Travel: one D wants her family to fly into Hyannis. I will also look at Boston and Providence.

My in-laws spent years in Dennis going to the bay for the beach. My choice would be Welfleet, but I’m not seeing anything for us there right now. There is a pretty good property in Hyannis that I have just suggested to them.

With the suggestion of Michigan, it was considered! I also have a trip with a friend for the Chicago to Mackinaw race in mid-July, so I will get to experience it. We have friends in the Spring Lake area too.

Thanks for all the good ideas and context!

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We spent many happy years renting on the Cape, usually in Orleans, which has town beaches on both the bay and the ocean. Orleans is more of a year-round community with supermarkets and at least one CVS, IIRC. This was very convenient when our DC was little.

You may already know this, but IME most Cape rentals do not include bedding or towels. There are linen rental services, but we brought our own since we were driving up. If you are all flying in, you may want to rent through a realtor who can make these sorts of arrangements for you.

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After renting large homes at the Jersey shore for a week (up to 8 bedroom) with my sister’s family (11 in all, plus kids’ friends and SO’s), I finally said that linens and towels not being included was a deal breaker (she lives a flight away). We rented a home for Easter and I was very careful about making sure they were included. My almost 25 year old is hosting her birthday party at a VRBO with 25+ friends and was deciding between 2. I pointed out that only one came with linens and that made the decision.

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This is most definitely during the summer season on Cape Cod. If you were able to go a couple of weeks later, you would likely find more availability and costs might be a tad less. Is that possible? The traffic Labor Day weekend will be absolutely awful.

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I’m glad someone mentioned linens. We stayed in a large home in Dennis for a wedding and linens were included but I was told this is not always the case. Have also stayed in Truro- both lovely areas. I look forward to going back soon.

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I would not stay in Hyannis. Honestly, its probably the worst town on the Cape. Our favorite towns are Truro and Wellfleet with the most beautiful beaches. Chatham if you want more to do. Brewster, Dennis, Yarmouthport and Harwich are all also very nice. Most kids in MA go back to school on September 2nd so it will be a bit quieter than the summer months esp during the week.

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We go to Cataumet every summer, but only because the family shares a tiny place there right on the water. It’s one of the first towns after the Bourne Bridge. We really like the Cape after Labor Day, but it’s really late this year. Labor Day weekend is the worst for traffic. Anyway because of our location we end up a lot in Falmouth which I think is a nice town with good bookstores, some art galleries and a great library where anyone can get a library card and check out board games. I think the various towns in the elbow are ideal. Lots of good places to walk and bike if you get tired of the beach. Agree with young kids bay side may be preferable.

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We made a selection this afternoon. Found a house the right size, near beaches and a playground. Walking distance to some shops. Good for our bikers, too. And it comes with linens.

Happy to be done with this part!

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