Late Checkout: Experience Off-Season Hamptons at Topping Rose House

‘Off-season’ is my new favorite word. It means great deals, fewer crowds, and a totally different experience from peak. I'm not a Hamptons person (I’d only been once for a day trip to the Wölffer Estate for a friend's birthday), but when I saw an influencer’s post about an unbelievable “WFH in the Hamptons” promotion at the Topping Rose House, I decided to plan a winter getaway in Bridgehampton. I loved the idea of a WFH-style vacation during the stressful holiday season because it doesn't come with the pressure of a full-fledged vacation that burdens you to maximize every single moment and make those PTO days count. I didn’t know if off-season meant nearly everything would be closed, but I was confident the hotel’s Jean-Georges restaurant (and bar) could keep my boyfriend and me occupied for a few days of our working vacation. Luckily, ‘off-season’ translated to about 50% capacity (of stores and restaurants open) and we took the opportunity to explore neighboring towns.

The Deal

The marketed promotion was an astonishing $100/night for five-night stays Monday-Friday (you can’t finagle Sunday-Friday). Beyond the stipulated weekdays, there was no catch. I found several weeks where I could get this exact deal by booking a House King room (five nights translated to a base rate of $500 plus taxes and fees). For comparison, the same room in July is $2,595 per night. The House rooms (as the name suggests) are in the beautiful historic house on the second floor and above (the restaurant occupies most of the first floor).

There was more availability for other slightly more expensive rooms, so I went with the $200/night Cottage King room, which goes for $3,495/night in July. For anyone keeping track, this is a 94% discount. I cannot overstate what a ridiculously good deal this was because it also included breakfast every day for both of us. I booked three nights during the third week of December for a grand total of $669.75 (I didn’t need to book five nights to get the promotional rate).

Accommodations

The Cottage rooms and suites are set apart from the main house in a modern-looking building with conveniently located parking. The room was spacious as promised and we had our own private yard. The first thing I did was unpack my luggage, which I managed to restrain to my Horizn Studios H6 ($495) check-in size suitcase and my go-everywhere Lo & Sons Catalina Deluxe-Large ($225) weekender (the pass-through sleeve is the best invention of the decade).

These two pieces in combination allow me to overpack to my heart’s content without encumbering me: I can easily wheel both with one hand and carry an additional bag if necessary. The suitcase can take a beating despite its light weight (I’ve traveled internationally with just a few scuffs) and the separate shoe compartment in the Catalina bag is something I cannot live without.  

You can always judge a hotel’s quality by the calibre of its bathrooms and I was immediately impressed by enormous floor-to-ceiling, frosted windows that enclosed us. Our room had everything you’d expect for a $3,000+ per night rate: Matouk towels, Frette linens, SFERRA bathrobes, and a minibar stocked with Tate’s and Acqua Panna. I was feeling a little gross from traveling so before changing for dinner, I turned to Glo Skin Beauty’s Brighten + Glow Travel Set ($65) to rejuvenate my tired-looking skin. The Hydra-Bright AHA Cleanser is my secret vacation weapon to combat dullness and when paired with the Hydra-Bright Alpha Arbutin Drops, you’ll look as relaxed as you feel.

I’m torn over whether to judge my stay based on the rate I paid or the peak season rate — so take all of my criticisms with the caveat that they are not complaints but my attempt to soberly assess the hotel (and not be blinded by the absurdly low rate). Now that that’s out of the way…

WFH Setup  

While this promotion was billed as a WFH deal, when I called ahead to ask where else (besides my room) I could work, the response was somewhat lackluster. I was told that the restaurant is laptop-friendly and that the small library could accommodate a couple of people, but the expectation was that I would work in my room. Understood.

Luckily, I can work from pretty much anywhere thanks to the 1.7 lb Sidetrak dual-screen laptop attachment ($300). It clamps onto my laptop to provide a secondary screen, which is extremely helpful because I almost always need to reference several windows simultaneously. When I’m not using it, the Sidetrak screen stows away discreetly and adds minimal bulk. It’s a great solution for traveling compactly without giving up the convenience of a traditional multi-screen desktop setup.

A ‘working vacation’ is almost an oxymoron — it’s not like I anticipated getting loads of work done, so the lack of co-working spaces wasn’t a deterrent. Plus, TRH is a boutique hotel, which doesn’t jibe with conference rooms or business centers. Just know, if you need to take a call, it will definitely be in your room. I did manage to find a perfect work spot that wasn’t mentioned by the staff: near the event space and overlooking the pool is a large room with long tables and plenty of light.

The gym was well-equipped and empty when I peeked in (I did not actually use it, but good to know it’s there!). The same staff member who mentioned the W in WFH is meant to be done in your room said that there are usually fitness classes available (at no cost to guests) on the weekends, but for now they aren’t available during weekdays (though they are working on adding some to the calendar).

Bar and Restaurant

Breakfast was the time to get a feel for how full the hotel was. There were roughly six other parties that I counted, and it never felt crowded or noisy. There was a mix of couples and singles, and people kept to themselves. We spent close to $70 on the comped breakfast (tax and tip not included) each morning — it’s easy to do when avocado toast is $20.

The food and service were of the quality you’d expect from a Jean-Georges restaurant. As great as it was, since we spent every breakfast at the hotel, we preferred to have dinner off-premises (dining recommendations at the bottom). We had a car so it was easy to explore Sag Harbor, Montauk, and Amagansett on our own, but the hotel site mentions a complimentary BMW shuttle for rides under 5 miles.

The bar was crowded every night with non-hotel guests, which made for a cheerful, buzzy atmosphere. The bartender was kind enough to let us order off-menu Hot Toddies, which we brought outside for my absolute favorite part of the entire trip: the fire pit!

Off-Season Service

The rate for a hotel of this caliber was truly unbeatable, but staying off-season is more of a ‘what you make of it’ experience. The onus is on you to research and request service. For example, the staff doesn’t mention that the fire pits or shuttle are available (I’m now wishing I had asked if it was possible to heat the hot tub), but if you ask, they are perfectly willing to accommodate you.

I think the overall approach is summed up in the piping hot welcome cider that greets you right after check-in: it’s such a lovely gesture and it’s accompanied by a message that says if you’d like a shot of whiskey to go with the cider, please call the front desk and someone will deliver it to your room. It’s a nice idea, but why not just leave a nip? It feels like they know I’m not going to make that call to the front desk when I’ve just come from the front desk. Basically, it’s still a luxury hotel, but they’re cutting a few corners for off-season guests.

The WFH promotion was a great way to experience off-season Hamptons and as I write this, I see there is a $150/night rate for the Cottage King that I absolutely recommend seizing on.

If you stay here, make sure to…

EAT at Sag Pizza (which is reminiscent of now closed Pizza Beach RIP) for amazing hot honey pies, and Tutto Il Giorno (which used to have a Tribeca location if the name sounds familiar) for great Italian.

BROWSE the amazing collection of rare first editions and contemporary must-reads at Sag Harbor Books.  

PITSTOP at Tanger Outlets Deer Park on your way home for deals at Le Creuset, Roller Rabbit, and more.