My safest mid-pandemic trip yet: A stay at Winvian Farm in Connecticut

Jan 14, 2021

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This year, the holidays looked a lot different.

Instead of redeeming points for a beach vacation in the Caribbean, my family and I stayed much closer to home. My future in-laws are avoiding flying during the pandemic, so our vacation options were limited to a roughly 200-mile driving radius around New York City.

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We packed our winter clothes and checked in to a four-night stay at Winvian Farm in Morris, Connecticut, located just two hours outside New York.

Turns out, it was my safest mid-pandemic trip to date and one that I’ll even add to my post-pandemic bucket list. Here’s why.

It has unique, freestanding and distanced cottages

Winvian’s 18 cottages are spread out around the 113-acre property, offering plenty of space to maintain distance from others.

Unlike traditional hotels where everyone’s hoping for a suite upgrade, Winvian is unique in that each cottage is designed in a different motif based on its namesake. When you make your reservation, you’ll book directly into your preferred cottage.

Winvian Farm, Connecticut
(Photo by Zach Griff/The Points Guy)

During our stay, my fiancée and I loved our “camping” cottage. With vaulted ceilings, forest murals on the floor-to-ceiling windows and a massive dual-vanity bathroom, we were effectively glamping in the middle of the Connecticut woods.

Despite the cold, the two fireplaces — one indoors and one on the screened-in porch — kept us warm during our stay.

Winvian Farm, Connecticut
(Photo by Zach Griff/The Points Guy)

There was a lot to love about “camping,” but the highlight was easily the bathroom. The oversized walk-in shower turned into a steam room, and the bathtub overlooked miles of untouched forest.

We checked out a few of the other cottages during our stay, including Charter Oak — a single-story barn-like structure built around a massive oak tree in the living room.

Winvian Farm, Connecticut
(Photo by Zach Griff/The Points Guy)

The space was perfect for our family. Between the oversized living room and wet bar, we had plenty of space to drink away 2020.

Winvian Farm, Connecticut
(Photo by Zach Griff/The Points Guy)

Each cottage is unique — and prices vary accordingly — so you’ll want to check out the resort’s website before booking. Rates are steep, starting at around $500 a night, and fluctuate based on the season.

Winvian isn’t part of a larger chain, so redeeming points at the hotel isn’t really an option, unless you book directly with the Chase Ultimate Rewards travel portal with either the Chase Sapphire Preferred or Chase Sapphire Reserve cards.

For aviation enthusiasts, Winvian offers the “helicopter” cottage, and that’s where you’ll find me when I return to the property.

Winvian Farm, Connecticut
(Photo courtesy of Winvian Farm)

Winvian restored a 1968 Sikorsky Sea King chopper and converted it to the ultimate aviation geek cottage. The cockpit is still intact, but the rest of the interior was gutted to make space for a living room, which is decked out with a sofa, flatscreen TV and small bar.

Winvian Farm, Connecticut
(Photo courtesy of Winvian Farm)

The bed and bathroom are located just outside the chopper.

During our stay, we mostly kept to our cottages. There was plenty of space to spread out, and we didn’t once interact with other Winvian guests — about as good as you’ll get for socially distant pandemic-era travel.

There’s an excellent restaurant with COVID-safe room service

As if the cottages weren’t enough to convince you to stay at the property, the resort’s restaurant is a destination unto itself.

Before the pandemic, locals from the surrounding area would flock to Winvian for its farm-to-table fare.

Though the restaurant is currently open under Connecticut state health guidelines, it’s primarily offering indoor dining, which we’re avoiding due to the increased risk.

The restaurant itself is located in the main reception area, which spans two floors.

Winvian Farm, Connecticut
(Photo by Zach Griff/The Points Guy)

The lower level offers a solarium with a fully stocked bar, while the upstairs offers plenty of cozy, tavern-like seating areas.

Winvian Farm, Connecticut
(Photo by Zach Griff/The Points Guy)

Some guests nonetheless opted to eat indoors, but others, like us, stuck to room service during our stay. (I look forward to alfresco dining if I return during the summer.)

Winvian Farm, Connecticut
(Photo by Zach Griff/The Points Guy)

The restaurant offers three meals a day, and each was truly delectable. Breakfast, up to $70, is included with most rates and it’s served until 9:30 a.m., a bit of an early cutoff in my opinion.

Menus were delivered via email before every meal, and it took just a reply to confirm our order. Click here to view a sample breakfast menu and dinner menu.

Winvian Farm, Connecticut
(Photo by Zach Griff/The Points Guy)

When it was time to eat, every dish was delivered individually wrapped in a cast-iron skillet to keep it warm.

Winvian Farm, Connecticut
(Photo by Zach Griff/The Points Guy)

The food itself was spectacular. The resort prides itself on its “seed-to-table” philosophy, and everything was high quality.

Winvian Farm, Connecticut
(Photo by Zach Griff/The Points Guy)

Though the menus weren’t extensive, there was always a vegetarian and vegan option — my favorite was the rotating selection of vegetable soups offered each evening.

The resort also offered to accommodate allergies or dietary restrictions with advance notice.

The spa and pool would be great during the summer

Though we kept to ourselves during our winter escape, Winvian offers both an outdoor pool and spa for those looking for some pampering.

The spa occupies its own 5,000-square-foot cottage, decked out with a lounge, sauna and treatment rooms. During the summer, the resort offers outdoor massages as well.

Winvian Farm, Connecticut
(Photo by Zach Griff/The Points Guy)

Due to the pandemic, the spa is only open for in-house guests, with 50-minute massages starting at $165.

Winvian’s 40-foot swimming pool is nestled among the gardens. Of course, it was closed during our December visit, but I’ve heard that it’s a great place to relax during the warmer months.

Winvian Farm, Connecticut
(Photo by Zach Griff/The Points Guy)

The resort’s gym is attached to the main reception building. It was completely empty during our visit, and the front door could be left wide open for added ventilation.

Winvian Farm, Connecticut
(Photo by Zach Griff/The Points Guy)

The gym was well equipped for an 18-room hotel, but it didn’t offer the most modern or specialized equipment.

Winvian Farm, Connecticut
(Photo by Zach Griff/The Points Guy)

Five-star service

What set our Winvian experience apart from other luxury resorts was the personalized service.

From the moment we checked in, it was clear that the employees genuinely cared about our experience on the property.

Winvian Farm, Connecticut
Welcome amenity (Photo by Zach Griff/The Points Guy)

The restaurant staff quickly learned our dietary preferences. After ordering two soups the first night, they proactively delivered a significantly larger pot of broth on subsequent nights.

When it came time to clear our meal, the staff came back to the cottage, always smiling and offering to do more, whether it was to refill our waters or set up the fireplace.

Winvian Farm, Connecticut
(Photo by Zach Griff/The Points Guy)

With varying levels of COVID precautions among the family, the resort happily catered to our preferences — some rooms wanted housekeeping, others didn’t. Some were okay using the gym, others weren’t.

Every time we picked up the phone, the front-desk staff answered with the utmost professionalism, as if they always wore a smile.

The surrounding area is packed with charming towns

The thought of spending four nights confined to our cottage wasn’t necessarily how I anticipated spending the holidays.  Nonetheless, we quickly got into a routine and thoroughly enjoyed cozying up with a book in front of the fireplace.

While you could theoretically spend your entire time at the resort — and I look forward to doing that during a long summer weekend — we ended up venturing out to some nearby towns for an afternoon.

Winvian Farm, Connecticut
There’s plenty of hiking near the resort

We enjoyed walking around Morris and Litchfield, and we even passed through Great Barrington, Massachusetts during our afternoon adventure.

The hotel is also just a ten-minute drive from Arethusa Farm, offering some of the best ice cream in Connecticut. Plus, Arethusa’s sister restaurant, Arethusa al tavolo, offers an open-air heated patio for quaint (and delectable) outdoor dining.

Bottom line

If you’re looking for one of the most luxurious, socially distant vacations in the Northeast, look no further than Winvian Farm.

Located just two hours from New York City and Boston, Winvian’s 18 cottages offer a respite from the hustle and bustle of the major metropolitan areas.

Winvian Farm, Connecticut

The food is great, the service is spectacular and the grounds are stunning. The only thing not to love is the price, but if you’ve saved the vacation budget for some big 2021 trips, you won’t go wrong spending it at Winvian.

All images by Zach Griff/The Points Guy, unless otherwise noted.

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