The maples on Robert Frost Mountain are turning right now. Below them, seven timber-frame cabins sit scattered across 112 private acres, a campfire waiting in the meadow and a hot tub pointed at the ridge. It is our first Vermont estate, and it sleeps 40. It sets the tone for this issue. A wildflower homestead on Alaska’s Kenai Peninsula, our first there. A lakefront mansion outside Cleveland. A cabin above Skaneateles Lake. And a Milwaukee brew house with its own turret. Five northern ways to rent the whole place, from $6,100+. | | Featured Estate |  | Ripton, Vermont | Guests 100 • Sleeps 40 • From $10,100+ |
Seven cabins, each built from white pine and black cherry cut in the estate’s own meadow, tucked into the eastern slope of Robert Frost Mountain beside the Green Mountain National Forest. Vows happen outdoors with the ridge behind you, the reception goes under a tent in the meadow, and the night ends at the communal fire with s’mores before everyone walks back to their own porch. Up to 100 guests, 40 of them sleeping on the mountain, about an hour from Burlington. |
| Also Up North | Alaska, Ohio, the Finger Lakes, and Milwaukee |  | Anchor Point, Alaska Event Guests 125 | Sleeps 29 | From $10,500+ |
Our first Alaska estate. Fourteen acres of spruce and wildflowers on the Kenai Peninsula, a short drive from Homer, with Cook Inlet spread out below the meadow. The ceremony sits under an open-air pavilion built from heavy timber, driftwood and stone, and four handcrafted log cabins keep 29 guests on the homestead. Bear viewing and flightseeing can go on the itinerary. |
 | Medina, Ohio Event Guests 180 | Sleeps 24 | From $15,500+ |
A fountain in the pond, a pickleball court by the water, and 12,000 square feet of house behind it, twenty minutes from the Cleveland airport. Eight bedrooms sleep 24, the game room and theater absorb the cousins, and the lawn takes 180 for the ceremony and dinner. |
 | Skaneateles, New York Event Guests 100 | Sleeps 6 | From $8,000+ |
Ten wooded acres a few minutes above Skaneateles Lake, with a deck strung in lights, a seasonal pool, a barrel sauna that runs all year, and a firepit for after. Room for a tented celebration of 100 on the land, and a three-bedroom cabin that keeps the two of you and four more close. |
 | Milwaukee, Wisconsin Event Guests 24 | Sleeps 12 | From $6,100+ |
Our first Wisconsin listing, and the wedding-party house you actually want. A former Schlitz tied house in Bay View with a castle turret, two full floors that each run as their own residence with a kitchen and entrance, and neighborhood bars and restaurants a block away. Getting ready, rehearsal dinner for 24, and the morning after, all under one historic roof. |
| Dreaming of a specific corner of the world? We add estates every month.Tell us where you want to celebrate. Run the numbers with our budget planner orbrowse every estate. | | From The Journal |  | The Medina estate below gets the full walkthrough here: how 180 guests fit across the indoor and outdoor spaces, what the 18 acres and private pond look like at golden hour, and why a Midwest mansion weekend costs less than most couples expect. Read it before you compare it to a ballroom. Read The Guide → |
| | Partner Picks | Tools Worth Having | A short list of planning partners we trust, starting with the one that ends the seating chart scramble. | Transparency, always: these are affiliate links. Book through one and WedStay may earn a small commission at no extra cost to you. Nothing makes this list unless we’d recommend it anyway. | Featured Partner • Seating Please Find Your SeatThe seating chart, handled. Guests type their name into an elegant digital display at the entrance and their table appears in seconds. No easel, no alphabetizing place cards at midnight, no line at the door. It fits estate weddings especially well, where the party moves between lawn, terrace, and villa. |
| Event Insurance Event HelperOne-day event liability coverage in about ten minutes, from the provider we point WedStay couples to first. Most private estates require it, so cross it off the list early. Get A Quote → |
| Legal Hello PrenupYou’ll spend thousands on the venue. Spend $599 on peace of mind. A modern prenup the two of you complete online together, with attorney review built in. Start Together → |
| Floral Preservation Everlasting Bloom Co.Your bouquet survived the wedding. It deserves to last a lifetime. The preservation studio couples across the country trust with the flowers that mattered most. Preserve Your Bouquet → |
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