Hamptons-area boarding is its own market. Demand spikes hard around the same five weeks every year, supply hasn't grown much in a decade, and the best kennels and in-home sitters take repeat clients first. If you only book three weeks out for July 4, your options are usually the spots nobody wants — long drives, basement kennel runs, no webcams, no group play.
The booking calendar
- Memorial Day weekend (last weekend in May): book by mid-March
- July 4 week (June 29 – July 7 typically): book by April
- Labor Day weekend: book by mid-July
- Thanksgiving (Wed-Sun): book by mid-September
- Christmas week (Dec 22 – Jan 2): book by late October
Cage-free vs traditional kennel — what to actually ask
Cage-free Hamptons facilities (think Camp Bow Wow, Pet Au Pair, etc.) book first because they look the best in Instagram photos. But cage-free isn't always right for your dog. Ask: how many dogs share the play space? What's the staff-to-dog ratio? Where do dogs sleep — together, in suites, in crates? How are dog groups separated by size and play style? An anxious or reactive dog often does better in a private suite at a traditional kennel than thrown into a 12-dog play yard.
In-home sitters: the locals' secret
If you've ever called every kennel in East Hampton and gotten 'we're full' five times, in-home sitters are the answer. Rover and Time to Pet both have active East End networks. The premium ones charge $75-120/night, take one client at a time, and become your dog's second family. Book the same sitter three trips in a row and you're basically locked in.
What to bring
- Vaccine records (DHPP, rabies, bordetella required; flu often required)
- Two weeks of medication in original bottles even if you're going for one weekend
- Their normal food, pre-portioned in labeled bags
- One unwashed t-shirt of yours (separation anxiety helper)
- Emergency contact + your regular vet's number
- A photo of your dog on its leash — surprisingly useful if a sitter loses track
What to confirm in writing
Even with kennels you trust, get the exact pickup and drop-off times in writing. Hamptons traffic on a Sunday in August can add two hours to a pickup window, and some facilities charge late fees that escalate fast. Confirm: their emergency vet (it should be 24/7), their playgroup policy if your dog hasn't been there before, and what happens if your flight delays and you can't pick up on time.