Our 6 Favorite Places To Stay Upstate This Fall

There is nothing quite like fall in upstate, NY. From the arrival of cider donuts at your local farmer’s market, to the chilly breeze that inspires layering, to the bright bursts of red and yellow foliage, traveling upstate allows you to experience the season in a way no other region can offer. Now that the leaves have begun to change and everyone’s attention has turned to warm drinks and apple picking, we thought we would share our 6 favorite autumnal spots to stay upstate. Because fall is a time to get cozy, we decided to focus our guide on rental properties from Airbnb and Red Cottage, offering intimate getaways in unique locations. From an elegant home in Hudson, to an airy Catskills apartment, to a rustic barn in Tivoli, we think there is something for every kind of traveler. So, grab some friends or a loved one and head north where the leaves are bursting and your hot toddy is waiting. Happy travels!

Make sure to tag your best fall photos with #andnorthfall as you travel north. The top twelve images will be featured on our site and one lucky winner will win a getaway to Brushland Eating House and a gorgeous leather backpack from TM1985. Visit our Instagram page for details on how to enter.

Brushland Eating House
Our 6 Favorite places to stay upstate this fall. andnorth.com
Our 6 Favorite places to stay upstate this fall. andnorth.com
  • After miles of driving down country roads past fields of wildflowers, grazing cattle and century-old barns, you’ll arrive at our bucolic dream: Brushland Eating House. This two bedroom apartment, located on Main Street in the tiny hamlet of Bovina, sits above a culinary Catskills gem of the same name. Dinner at Brushland Eating House is a delectable experience that awaits every guest just downstairs and the trail that extends at the back of their property is a perfect spot for stargazing and exploring the scenic landscape.
  • Bovina Center, NY
    155.58 miles from New York City
    Sleeps: 8

    Images by Christian Harder
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Haviland House
Our 6 Favorite places to stay upstate this fall. andnorth.com
Our 6 Favorite places to stay upstate this fall. andnorth.com
  • Haviland House is one of our favorite places to stay for a weekend getaway in Hudson. The landmark home, built in 1825, retains many of its original details like wooden wide plank floors and charming pocket doors. Enjoy a farm-to-table dinner at Fish and Game, located only a short walk to town, or gather fresh provisions from Talbott and Arding to create your own meal in the home’s chef kitchen complete with stunning soapstone countertops. As the evening settles, you can ease into the leather chesterfield sofa and warm up beside one of the home’s two elegant fireplaces.
  • Hudson, NY
    119.94 miles from New York City
    Sleeps: 8

    Images by Emma Tuccillo
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The Barn in Tivoli
Our 6 Favorite places to stay upstate this fall. andnorth.com
Our 6 Favorite places to stay upstate this fall. andnorth.com
  • There’s something especially nostalgic about the feelings that arise when we escape to The Barn in Tivoli, a rustic country hideaway in the Hudson Valley village of Tivoli, NY. As the temperature’s drop, a wood burning stove keeps the loft’s sleeping nooks warm and inviting. Our favorite way to unwind from the day is with a novel from the eclectic collection of books in the library or with a relaxing soak in the antique clawfoot tub.
  • Tivoli, NY
    111.64 miles from New York City
    Sleeps: 8

    Images by Emma Tuccillo
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Saugerties Farm House
Our 6 Favorite places to stay upstate this fall. andnorth.com
Our 6 Favorite places to stay upstate this fall. andnorth.com
  • We love this 200-year-old rambling farmhouse for its picturesque views of the Catskill Mountains and treasure trove interiors that are full of vintage and estate finds, picked and curated from years of yard sales, antiquing and thrift store shopping. Owners David and Lori Brown achieved an artful balance of modern and primitive when they restored this 19th century home over the last five years and we find ourselves continually delighted by the vibrant, cozy presence of their space.
  • Saugerties, NY
    107.94 miles from New York City
    Sleeps: 6

    Images by Emma Tuccillo
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Smokey Belles
Our 6 Favorite places to stay upstate this fall. andnorth.com
Our 6 Favorite places to stay upstate this fall. andnorth.com
  • If you’re looking for a bit of seclusion and an escape from the bustle of the city, we recommend a stay at Smokey Belles, a private homestead and queer-friendly multimedia artists retreat in the creative community of Narrowsburg, NY. The house, with its three private bedrooms and a kid-friendly loft, is ideal for a group of dear friends or a larger family. Sprinkled throughout each of the rooms are delightful curios that have been gathered from nearby antique store – Maison Bergogne.
  • Narrowsburg, NY
    101.63 miles from New York City
    Sleeps: 8

    Images by Katie Lobel
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Windrift Hall
Our 6 Favorite places to stay upstate this fall. andnorth.com
Our 6 Favorite places to stay upstate this fall. andnorth.com
  • It is worth the two and a half hour drive from New York City to stay in this 1790s Federal Style Manor home located at the end of a long country road punctuated by stone walls, meadows, and a private pond. As the leaves turn and reveal their colorful hues, you can relax on chaise lounges to take in the foliage of the mature forest of trees that surrounds the property. If you’re feeling more adventurous, borrow a map and embark on one of the many gorgeous hikes through the Catskills of Greene County.
  • Coxsackie, NY
    134.36 miles from New York City
    Sleeps: 9

    Images by Emma Tuccillo
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3 comments

  1. I completely agree that New York State is a great place to spend the fall. Just last weekend I spent time in four different towns and I managed to find a pear cocktail in each one! I always stay at The Pig Hill in Cold Spring.

  2. This is a beautiful blog. I’m excited to plan a visit to the area and the photography of the interiors are design inspiration. Thank you!

    1. Thanks so much Siobhan. We’re so glad this has inspired you to venture north!

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