Here is the beginning of a Cidiot guide of where to stay. It's a mix of hotels, motels, short-term rentals (STRs), and even farm stays across towns in the Hudson Valley, Catskills, and Berkshires. (Towns are New York, unless otherwise noted)
Also check out this comprehensive directory by real estate company AndNorthand a Catskills-specific listing page at Mountain-Hiking.com. Inside+Out Upstate NY also has a searchable directory, and Forgather has a site of a few special properties in Austerlitz and Hillsdale, especially for groups visiting the Hudson Valley and Berkshires.
Drop a line through the Contact us form if you need ideas for restaurants and things to do. Posts for all of that, and even sample itineraries, coming soon.
Inness: A bit over the top, but a stunning new resort that recently opened about 30 minutes southwest of Kingston and 20 minutes west of New Paltz. (Brian and I plan to shlep out there and try it to see if I can recommend it.)
Hilltop House Bed & Breakfast: A cozy, country inn in this 1788 town on the very eastern edge of Dutchess County near Millerton and close to the Connecticut border.
Troutbeck: Luxurious guest rooms on a manor property with a top-rated restaurant.
The Mae House: An incredible home with a mission. Your stay enables them to offer sliding scale rates to BIPOC guests who cannot afford a full-priced stay as well as maintaining a quarterly residency program for BIPOC. Athens is adorable too, directly across from Hudson (ferry part-time) and north of Catskill.
The Compass House: 3-bedroom, 2 bath short-term rental across 25 acres of a trail system secluded in the woods. Pet-friendly. Available for rent after renovations, Fall 2022.
Piaule: Super modern cabins on stunning property with spa and restaurant.
The Alander: A converted motel into a modern boutique lodge near Hillsdale, Hudson, and the Berkshires. 12 rooms and fire pits.
Central House: Built in 1876, it's been a brother, a speakeasy and various restaurants. Now it's a six-bedroom inn right across the street from one of our favorite gastropubs, Gaskins. Germantown is a great little hamlet north of Tivoli and south of the city of Hudson (closest Amtrak).
Hearty Roots Farm: Stay in the 1820s guest house at one of our favorite farms run by Lindsey and Ben Shute (we've been a member of their CSA). Be sure to pop into their amazing farm store.
GREAT BARRINGTON, MA
The Barrington: An elegant B&B of suites right on Main Street in this terrific small city. Tons to do in Great Barrington, including theatre, restaurants, parks and hiking. No pets, though which Cidiot thinks is uncool. No candles either, which makes me think they're paranoid.
Holiday Inn Express & Suites: Convenient location to Lenox and GB on Stockbridge Road / Route 7. Up the road from the Fairfield Inn.
Marriott Fairfield Inn & Suites: Also convenient on Route 7, just north of main town and just south of Barrington Brewery.
The Windflower Inn: Looks like a comfy inn to stay in and explore Great Barrington as well as surrounding towns. Set on 10 acres with trails and a pond, so you could also just explore there! My sister has stayed there and says good things.
Sylvan Motor Lodge: Renovated motel that's designed to rent out for groups. Looks great on Instagram and its convenient location near Hudson to the west and the Berkshire towns to the east.
The Maker: Hip hotel in the center of town on the main drag, Warren Street, in Hudson. Great little restaurant and bar scene, pool, plus a gym.
The Orchard House: Stay on a working apple orchard in this beautiful 2BR 1874 farmhouse on Blue Hill Road (gorgeous road) outside Hudson.
Rivertown Lodge: We love this updated motel into hotel with it's beautiful lobby and intimate bar restaurant. Towards the eastern end of town also on the main drag, Warren Street.
Wm. Farmer & Sons: Known for its restaurant by the train station, they have a bunch of accommodations for weekend or short-stays, single rooms or even two-room suites.
Scribner's Lodge: You've probably heard of this place and looks amazing and cozy especially during skiing season, though, what do I know: I don't ski.
Roosevelt Inn:This larger inn, practically a hotel, is near the FDR Presidential Library, 10 miles, or 15 minutes, south of Rhinebeck.
Cookhouse: This short-term rental was gorgeously created by Doug and Sloan, two designers we know, to be a heaven and haven for coming away to cook with its amazing kitchen. You can book directly or via Airbnb.
Starlite Model: This revamped motel has gotten so much press you probably already heard of it and it's probably already booked.
Hotel Kinsley: Hip hotel of four different buildings in the very center of the Uptown (Stockade) district of Kingston. Gorgeous bar and great restaurant.
1910 House: A vintage-style bed & breakfast on Green Street in Uptown (Stockage) district of Kingston.
Courtyard Marriott: Well, it's what you expect. At least you'll get points.
Interlaken Inn: This inn is more of a small resort, just south of the Berkshires and right across the border from Millerton. We stayed there for a family retreat there and loved the lake too.
The Ponds at Foxhollow: This looks like a nice resort in Lenox with on-site activities, a library, and some nice grounds. My sister is trying it this summer so will report back.
Buttermilk Falls Inn: This looks so gorgeous, if it weren't so close, I'd want to vacation here. Henry's at the Farm looks like a good restaurant to try.
Willow Vale House: Our friends Stephen and Amy rent out their 1783 historic 2BR short-term rental in the cute town of Pine Plains, just east of Red Hook and Rhinebeck and near Millerton and Amelia.
The Inn at Pine Plains: Haven't stayed here but it looks like a decent place and convenient location to explore various towns up here on both sides of the Taconic State Parkway. A few rooms have kitchenettes.
RED HOOK / TIVOLI
Hotel Tivoli: Small, modern, boutique hotel with great bar and restaurant The Corner, owned by artists Brice and Lori Marden.
The Barn in Tivoli: Short-term rental property with cute little house and bigger barn for small groups.
Grand Dutchess: A cute bed & breakfast along Broadway on the north end of the Village of Red Hook.
Reclaimed Motel: I'm most excited about our friends Kendra and Jared's new motel that they're just re-opened (formerly The Hearthstone Motel) along Route 9, north of Red Hook Village in late 2022. Use code CIDIOT in your reservation for a discount while it lasts. Follow it on Instagram.
Red Hook Country Inn: Right in the center of Village of Red Hook on Broadway south of Market Street.
Baker House: Bed and breakfast on the edge of Rhinebeck Village. Built in 1870, with four bedrooms, each themed around an artist.
Beekman Arms and Delameter Inn: Historic Beekman Arms claims to be the oldest inn in America. Cool tap room.
Gables of Rhinebeck Inn: Charming looking inn on the edge of the town.
Mirabeau Spa and Inn: A luxurious (albeit fake) French chateau-style hotel dropped into the middle of a quaint Hudson Valley village. Positive reviews of the spa.
Rhinebeck Motel: This motel along Route 9 between Red Hook and Rhinebeck was just renovated and, completely unrelated, is next door to our favorite kitchen store.
Whistlewood Farm Bed & Breakfast: Stay on a working farm outside town.
The Graham & Co: A boutique hotel located in the Catskills, owned by (my former colleague) Martin and Joe. As seen on the Discovery+ and Magnolia Network show [re]MOTEL.
Catskill Animal Sanctuary: Animal lovers, you can stay at The Homestead at the sanctuary as well as schedule a tour to meet the rescued animals.
Tonga Cabin: Our friends Mark and Lori rent out this adorable tiny house, perfectly outfitted for staying on a beautiful piece of land just outside Saugerties and near Woodstock. Dog friendly.
Waterfront Cottage: Mark and Lori also recommended this waterside cottage as well by a different owner on AirBnB. Also dog friendly.
High Falls House and Harmony Hills: Two homes rented out by a former colleague and weatherman Dave Edwards. One's a four-bedroom with a pool and hot tub and the other is a 3-bedroom 1840's farmhouse with hot tub.
Kinderhook Farm: This well-known farm for its meats has overnight stays starting in May.
The Hotel Dylan: On Route 28 at the base of Overlook Mountain. Fire pits. Pool. With its peace symbol logo, you get the drill.
A few tourism links:
- The Berkshires
- Columbia County Tourism
- Dutchess County Tourism
- Greene County / Northern Catskills
- Visit Hudson, NY
- Litchfield County Connecticut
- Putnam County Tourism
- Sullivan Catskills
- Ulster County Tourism
Itineraries to the area and more coming soon. Send in suggestions to or comments for this list through the Contact form.