Waterfront Private Island House in Upstate New YorkN°001
Upstate New York, USA
BeachfrontHot tubWaterfront
From $2,373 per night
Photo by Ryan HiebendahlUpstate New York is the forested, lake-dotted expanse north of New York City, spanning the Adirondacks, Catskills, Hudson Valley and Finger Lakes. Renting a luxury villa or chalet here puts wilderness, vineyards and historic towns at your door, with private pools, lake frontage and Smiling House concierge service.
- Lakeside and mountain villas across the Adirondacks, Catskills and Hudson Valley
- World-class autumn foliage and four distinct seasons
- Finger Lakes vineyards and farm-to-table dining
- Private pools, docks and wood-burning fireplaces
- Concierge service with direct booking, no platform fees
Known forAdirondack and Catskill mountains, Finger Lakes wine country, Hudson Valley estates, autumn foliage and four-season lakeside living
Best time to visitSeptember to October for foliage; June to August for lakes and hiking; December to March for skiing
Nearest airportAlbany International (ALB); Syracuse (SYR) and Buffalo (BUF) serve western regions
Ideal forFamilies, multi-generational gatherings, couples and groups seeking nature, wine and four-season escapes
Waterfront House with Pontoon Boat in Upstate New YorkN°002
Upstate New York, USA
BeachfrontHot tubWaterfront
From $644 per night
Private Pond Cabin in Upstate New YorkN°003
Upstate New York, USA
Sea viewWaterfront
From $450 per night
Beachfront Tiny House in Upstate New YorkN°004
Upstate New York, USA
BeachfrontHot tubWaterfront
From $492 per night
Pet-Friendly Yurt Retreat in Upstate New YorkN°005
Upstate New York, USA
BeachfrontHot tubWaterfront
From $473 per night
5homes available
1–8bedrooms
up to 17guests
Upstate New York in pictures
Events not to miss in Upstate New York
- July to early September
Saratoga Race Course Summer Meet
America's oldest major sporting venue runs forty days of thoroughbred racing in Saratoga Springs, complete with hats, picnics and the Travers Stakes. A gracious summer ritual worth building a stay around.
- Late July
Hall of Fame Induction Weekend, Cooperstown
Baseball's newest legends are enshrined at the National Baseball Hall of Fame as Cooperstown swells with fans. Pair it with Otsego Lake and the Glimmerglass opera season nearby.
- Late August to Labor Day
New York State Fair, Syracuse
One of the country's oldest and largest state fairs brings concerts, agriculture and butter sculpture to Syracuse for nearly two weeks. Pure Americana, ideal for families.
- July
Ironman Lake Placid
One of the longest-running Ironman triathlons in North America loops through the Adirondack High Peaks around the Olympic village of Lake Placid. The town's energy that weekend is infectious.
Upstate New York through the seasons
- Spring (March – May)
Maple syrup and waking waterfalls
Sugarhouses boil sap across the Catskills and Adirondacks while snowmelt sends the gorges of the Finger Lakes thundering. Quiet weeks with early lake light.
- Summer (June – August)
Lake days and porch evenings
Swimming, sailing and kayaking on the Finger Lakes, Lake George and Adirondack waters, with farm stands at every crossroads. A lakefront villa with a dock is the classic upstate holiday.
- Autumn (September – November)
Some of America's finest foliage
The Adirondacks, Catskills and Hudson Valley stage a slow burn of red and gold, with apple orchards and harvest festivals along the way. Book foliage weeks far in advance.
- Winter (December – February)
Snow sports and firelit lodges
Skiing at Whiteface and Hunter, skating on Olympic ice in Lake Placid and snowshoeing through silent forests. Deep-winter cosiness suits a house with a wood-burning fire.
Luxury Villas in Upstate New York
Upstate New York rewards those who rent a private home rather than a hotel room. The region is vast and rural, defined by forested ranges, glacial lakes and rolling farmland between historic river towns. A luxury villa or lakeside chalet gives you space to gather, a dock or pool of your own, and a base from which to explore at your own pace. Smiling House curates a collection of distinctive properties, from Adirondack great camps and Catskills retreats to Hudson Valley estates and Finger Lakes wine-country homes. Each comes with concierge support and the option to book direct, so a multi-generational holiday or a quiet couple's escape feels effortless and genuinely private.
Where to Stay
The choice depends on the experience you want. The **Adirondacks** offer wilderness, vast lakes such as Lake George and Lake Placid, and classic timber-and-stone camps, including remote areas like the Town of Greig and Town of Watson in the western foothills. The **Catskills** are closer to the city, wooded and artistic, popular for weekend escapes. The **Hudson Valley** pairs grand estates with farm-to-table villages like Hudson, Rhinebeck and Kingston. The **Finger Lakes** centre on long glacial lakes and vineyards around Seneca, Cayuga and Keuka. Choose lake frontage for summer, mountain proximity for skiing, or valley estates for culture and dining.
Things to Do
Upstate New York is built for the outdoors. Hike the Adirondack High Peaks, paddle quiet lakes, or cycle the Finger Lakes wine trails. Lake Placid, twice an Olympic host, offers skiing, bobsled runs and skating. The Hudson Valley brings Walkway Over the Hudson, Storm King art park, historic mansions and Hyde Park. Autumn delivers some of North America's finest foliage drives. Families enjoy farm visits, swimming and boating, while couples can tour vineyards and antique towns. In winter, slopes at Gore, Whiteface and Hunter draw skiers, and a villa with a fireplace makes the cold-weather base.
Dining and Local Flavour
The region is a serious food destination. The Hudson Valley pioneered American farm-to-table cooking, with celebrated restaurants, cideries and farm stands across Rhinebeck, Hudson and the Culinary Institute of America in Hyde Park. The Finger Lakes produce acclaimed Riesling and cool-climate wines, with tasting rooms ringing Seneca and Cayuga lakes alongside craft breweries and distilleries. Throughout Upstate you will find maple producers, orchards and cheesemakers. Your villa kitchen, paired with a Smiling House concierge, makes private chefs and provisioning straightforward, so you can dine in overlooking the water or venture out to a vineyard table.
When to Visit
Each season has its character. **Autumn**, especially late September into October, is the signature time, when the Adirondacks and Catskills blaze with colour and the wine harvest peaks. **Summer** is for swimming, boating and lakeside villa living, with warm days and long evenings. **Winter** brings reliable snow and skiing across the mountain regions, ideal for a chalet retreat. **Spring** is quieter and green, good for value and waterfalls. Plan ahead for foliage weekends and holiday periods, when the best lakeside and mountain homes book early.
Getting There
Upstate New York is reached most easily by car, which suits the rural distances and scattered villages. Albany International Airport is central for the Capital Region, Adirondacks and much of the Hudson Valley. Syracuse and Buffalo airports serve the Finger Lakes and western areas, while New York City's airports work for the Catskills and lower Hudson Valley, roughly two hours' drive north. Amtrak's Hudson line links Manhattan with river towns such as Hudson and Rhinecliff. Once settled at your villa, a car is essential for exploring trailheads, wineries and the region's quieter corners.