In the village of Tivoli, NY, two rental properties sit sid-by-side on the outskirts of Main Street. Together, they’re Homestead 33: a barn and a house that share 4.5 acres of land, including forest, a pond, a creek, and multiple firepits. Separately, they’re the The Barn in Tivoli and the Modern-Bohemian Escape. And they’re both wonderful.

We first stayed at the The Barn in Tivoli last summer, which is a three-story, beautifully converted barn. Every design detail is thoughtfully placed and curated—from the antique rugs on its gorgeous original floors, to the big exposed barn beams throughout. Upstairs, three sleeping spaces accommodate up to six guests. The open format spaces are loft-like and communal, so guests should be acquainted with one another—or they will be by the time they leave. (As one visitor wrote in the guestbook, “it felt like a giant sleepover!” We couldn’t have said it more eloquently.) Downstairs, the kitchen and a second bathroom are totally up-to-date with luxury amenities, including a huge rain shower head and a fully stocked kitchen. A big wood stove, reading nook, and dining room table complete the picture.

The barn is a perfect spot for a small gathering, whether its a creative retreat, elopement celebration (!!!) or just get-together/escape with friends. We recently had our own little party at the Barn in Tivoli to celebrate the arrival of autumn and harvest season. Each guest brought some contributions for the evening. For their part, Sarah and Nick of Gaskins in nearby Germantown cooked up our main courses: a carrot, butternut squash, turmeric and coconut milk soup; and a ground pork, heirloom bean soup with kale and parmigiano broth. Sawkill Farms‘ Kallie and Michael brought chorizo and bratwurst straight from their farm, which raises wholesome meats just fifteen minutes down the road. To drink, Tracy and Jamie of Brunette Wine Bar in Kingston kept our wine glasses full… And Tivoli’s own Jesse and Jake from Murray’s provided some sweet treats for dessert. Together, we turned the back patio of the barn into a little garden party, with a bonfire in the yard as our backdrop.

Across the driveway, we also stopped in to check out the new addition to Homestead 33, the Modern-Bohemian Escape. The two-bedroom house is super cozy, decorated with modern-bohemian decor with items collected from travels around the world, in flea markets, and in nature. Other items were personally designed and handcrafted by the owners, Bruna and Andrew. Upstairs, two bedrooms and a bathroom overlook the larger downstairs, with a huge living room, kitchen, and dining space. The bathroom is incredibly cool, designed by owner Andrew, who’s a designer/builder and sustainability consultant. Low-hanging skylights open right above the front of the shower space, so guests can look straight out into the forest and straight up into the sky. All said and done, you can’t go wrong renting either property—but the barn is better for larger social groups, while the Bohemian Escape is better for families or couples.

What to Do Around Tivoli, NY: Relax in Your Own Private Swimming Hole, Take a Mini-Daytrip Through the Hudson Valley

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Exploring the property at The Barn in Tivoli is an adventure in itself. Just beyond the firepit in the back yard leads a path to a pond, a swimming hole, a creekside yoga platform, and two more firepits. We enjoyed morning coffees by the creek, and beers by the bonfire at night. And though we definitely spent the majority of our time at the barn during our stay, when we did need something in town, it’s just a five minute walk away.

If you’re looking to spend the day outdoors, check out Tivoli Bays. Be sure to bring wellies if you plan to hike here—it’s quite swampy, but the views are worth it. There are multiple entries to the bay; the one we visited is about 20 minutes from the barn, taking down 9G for a bit then a right on Cruger Lane. Follow the gravel road until you reach the parking lot. From here, you can get out and hike to Cruger Island for a magnificent overlook. (This is the hike you’ll need wellies for!) For an easier overlook, sans boots, you can continue in your car past the parking lot, turning right, until it dead ends. From this spot, there’s a short path that leads to an overlook with no mushy hike. We also visited the North Bay canoe launch, which was a lovely overlook, but lacks any buildup that a hike might provide; you literally leave your car, walk down some stairs, and walk to end end of the dock to take in the view.

Art lovers should check out Olana, the home and studio of Frederic Church. He was one of the founding members of the Hudson River School of painting, the first American artistic movement. The painting style combined landscapes with romanticism, and delved into the themes of discovery, exploration, and settlement. The ornate and fascinating Victorian-style property is available for tours by reservation, or simply walk the grounds to feel inspired.

The Hudson Valley is full of tiny little towns like similar Tivoli, and it’s fun to explore the area for mini-daytrips. We’d recommend stops in Red Hook, Kingston, and Germantown while you’re in Tivoli; they’re all under 20 minute rides by car. Best for an afternoon visit is Red Hook, where you can start at Montgomery Place Orchards, a family run farm (and farmstand) since the 1700’s. These days, it’s owned by Bard College, and is open mid-June through Thanksgiving, depending on the pace of the changing seasons and the availability of the food they grow. Nonetheless, the farm stand is really cute and a great place to stock up on groceries for your time in Tivoli. After that, head into town to Tivoli Mercantile, where curator Jill stocks her store with quality clothing, home goods and children’s accessories. Then check out Hoffman’s Antique Barn for an afternoon of digging through treasures.

Twenty minutes from Red Hook and ten minutes from Tivoli is Germantown, best for a mid-afternoon or evening visit. Head to the corner of Church Ave. and Main St., where the impossibly cute Otto’s Market feels like a step back in time. Opened by an ex-VP at Whole Foods, the throwback gourmet grocery store is committed to American-made and local products. Just down the road, recently-opened Luddite Antiques is a great antique shop who has a special knack for finding amazing lighting. The shop is compact, filled to the brim with amazing antiques that we’d consider to be one of the best collections in NY state. The couple that owns it, Luke and Rebecca just recently relocated from Greenpoint to Germantown to open the store. Set aside an hour to peruse the store and be prepared to dig a little. Across the street from that, this corner is also home to the best new restaurant in the Hudson Valley, Gaskins. More on that below!

Where to Eat and Drink around Tivoli, NY: Breakfast in a Church, Lunch at a Burrito Stand, Dinner at Gaskins

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Tivoli is tiny, but thanks to its proximity to Bard, it’s grown a lot over the last few years and has some great dining options. For breakfast, our favorite spot is Murray’s, a coffee shop and café housed in an old church. The food is fantastic, and brunch is served until 5. For baked goods, check out Tivoli Bread and Baking, next door from Murray’s in a renovated house. Get a sticky bun for breakfast, a lemon square for a snack, or a baguette to serve with dinner!

For an easy grab-and-go lunch, head to Tivoli General for fresh sandwiches. There’s limited seating both inside and outside in this really cute deli and sandwich shop—it’s also the best place to grab a six pack in town. For a more traditional sit-down option in town, The Corner at Hotel Tivoli serves up Mediterranean fare, prepared using local ingredients whenever possible. A bit further out, and well worth the (15 minute) trek, Bubby’s Burritos is a groovy little roadside burrito stand housed in a vintage 1970’s trailer. If you miss burrito season, check out their brick and mortar in Red Hook, Bubby’s Takeaway Kitchen.

Dinner in the area has many great options as well. While there are many cute options in Tivoli, our number one recommendation is just a fifteen minute drive away to Germantown to Gaskins. Now in their second year, Gaskins is the best meal for miles. Serving up fresh, local food using ingredients sourced from nearby farms, owners Sarah and Nick Saurez opened their first business together just last year, after stints at Marlow & Sons, Diner, Roman’s, Franny’s and Gramercy Tavern. Don’t pass up the chance to try Nick’s brother Dan’s brewery, Saurez Family Brewery. After working for Vermont beer kings Hill Farmstead—currently rated #1 in the world—Dan Saurez decided to open his own brewery. The beers are phenomenal. Check out the brewery if you can, but if you don’t make it, definitely grab a pint at Gaskins.

A bit further away, a twenty minute drive will take you to the heart of Kingston, where there’s a huge renaissance in boutiques, restaurants, and cafes. Our favorite spot in town is Outdated Cafe is part-cafe, part-antique shop—combining two of our favorite things! It’s great for lunch or breakfast. Before or after, stop into Clove & CreekHops Petunia and Kingston Wine Co. to do a little shopping. Speaking of wine, don’t miss Brunette Wine Bar, where you’ll feel like instantly transported to a Wes Anderson film. The wine bar’s beautiful marble counters, use of the color pink, and seahorse/pineapple wallpaper are a perfect combination, creating a super cute haven in Kingston’s historic Rondout district.

Back in town, as far as the bar scene goes in Tivoli, there isn’t much of one… The only real “tavern” option is Traghaven, though it’s a good one. The night we visited, it was packed with Bard students, many of whom seemed to be there to watch their friends’ jazz performance. And though it was packed with students, it didn’t feel like a loud, obnoxious college atmosphere; it was quite the opposite. Last, we didn’t make it to either Panzur or Santa Fe, both both get great ratings, have bars, and are also restaurants. But there’s always next time.