Wine Country: Epic Game Room, Lake Views, Fire Pit
Entire home in Naples, New York
- 10 guests
- 5 bedrooms
- 5 beds
- 2.5 baths
Hosted by Jake
- Superhost
- 1 year hosting
Listing highlights
Top 10% of homes
This home is highly ranked based on ratings, reviews, and reliability.
Dedicated game room for the group
A 1,200 sq ft turf-floor game room with skee-ball, ping pong, air hockey, foosball, and more
Jake goes above and beyond
Guests highlight how responsive and helpful Jake is, from booking through checkout
Your Fun Uncle called...he's lending you THE house.
The one where nobody checks the time, kids disappear into the game room for hours, and someone always ends up at the fire pit saying, "five more minutes."
Private 5-acre wooded hilltop with lake views, a 1,200 sq ft turf-floor game room packed with skee-ball, ping pong, air hockey, foosball, cornhole, and more.
First winery is 4 minutes away. Bristol Mountain is 7. Beach is 9.
Designed for 10, dogs welcome, zero boring allowed.
The space
Some houses you stay in. Some houses you remember.
The Hill House has four living spaces, five bedrooms, two decks, a fire pit, five acres of wooded hilltop, and a 1,200 sq ft game room that is technically a garage but has completely forgotten that. There is always somewhere to be and always somewhere to escape to. The group can be together without being on top of each other. That is harder to find than it sounds.
Warm, a little weird, and completely intentional. If that sounds like your kind of place, welcome home.
⭐THE HIGHLIGHTS⭐
🏓 1,200 sq ft turf-floor game room — skee-ball, ping pong, air hockey, foosball, basketball shootout, cornhole. Not a pool table in a corner.
🛏️ 5 bedrooms, 5 real beds — nobody on a pull-out or in a loft
🍽️ Dining table that seats all 10 at the same time
🏠 4 separate living spaces — sunroom, great room, family room with fireplace, basement den
🌊 Canandaigua Lake views from a private 5-acre wooded hilltop
👑 King suite with private ensuite bath and lake-view balcony
🫎 Gerald. He judges nobody. He approves of everything.
🎲 Board game wall: Clue, Pictionary, Finger Lakes-opoly, Scattergories, Monopoly, UNO and more
☀️ Covered front deck with string lights and gas fire table
🌳 Back deck with outdoor dining table for 10
💧 Full water treatment system + reverse osmosis tap — great water, no well water surprises
🍷 4 min to first winery on the Canandaigua Lake Wine Trail
⛷️ 7 min to Bristol Mountain ski resort
🏊 9 min to public beach on Canandaigua Lake
🎵 20 min to CMAC outdoor concert amphitheater
🛋️ THE BASEMENT DEN
You walk in through the basement. Cedar-paneled walls, a leather sofa, vintage cane chairs, a TV, and a green velvet bench from a Knights of Columbus hall. This is where the teenagers set up immediately. It's also where the kids migrate when they need their own world, away from the adults who are trying to have a conversation upstairs. The ski rack in the corner keeps winter gear organized. The door at the end connects directly to the game room, which means by the time anyone has put their bags down, someone has already picked up a paddle.
🏓 THE GAME ROOM
Not a pool table in a corner. Not a dart board on a wall.
A 1,200 sq ft garage finished with turf flooring and loaded for people who take fun seriously: skee-ball, ping pong table, air hockey table, foosball table, basketball shootout arcade, cornhole, and a giant Tetris installation that makes absolutely no apologies for existing. And yes, there is an outdoor playhouse inside the garage. The Fun Uncle does not follow conventional rules about what goes where.
Young kids have the playhouse. Older kids claim ping pong immediately. Adults who said they were just going to watch end up under the umbrella with a drink, calling the shots. Thirty minutes later someone has drawn up a tournament bracket and the evening is no longer what anyone planned. Rain, shine, or apres-ski — nobody is bored.
🌿 THE SUNROOM
Someone always finds this room and decides it belongs to them.
Floor-to-ceiling windows on two sides, cedar-paneled walls, hanging plants, a live-edge dining table, rattan lounge chairs, a papasan that gets claimed within the first hour, and a chess table in the corner. This is where a grandparent sits down with a grandkid and teaches them chess or checkers while the rest of the house does whatever it does. Nobody interrupts that. It opens directly into the great room so everything flows together, but the sunroom has its own quiet gravity. Morning coffee here becomes the ritual by day two. Evening wine was always the plan.
☕ THE GREAT ROOM
The heart of the house and where the trip actually happens.
A soaring wood-planked ceiling with skylights runs the length of the open-concept living room, kitchen, and dining area. Two full sofas, original art, two octagon windows — because of course there are. This is where the adult kids cook dinner while grandparents are in the sunroom and the grandkids are somewhere in the basement — voices carrying up through the floor, everyone accounted for, nobody in anyone's way. The kitchen island is command central. Someone claims a barstool and doesn't leave for the rest of the afternoon. Bar seating for three, full electric range with hood vent, subway tile backsplash, stainless appliances, open shelving. Fully stocked and built for a group that actually wants to cook.
The dining table seats all ten — because someone always gets left at the kids' table and that someone is usually an adult and it is not happening here.
The water is worth a mention: full treatment system plus a reverse osmosis tap at the kitchen sink. Clean, clear, actually good. Fill your bottles freely.
🫎 THE FAMILY ROOM
Gerald the moose lives on the wall in here. He takes everything in, judges nothing, approves of everything. He has been the backdrop to more board game arguments than anyone can count and he has never once taken a side.
Cedar walls, electric fireplace, and a floor-to-ceiling board game wall stocked with Clue, Pictionary, Finger Lakes-opoly, Scattergories, Monopoly, UNO, Dominoes, TriBond, Bop It — yes Bop It, the game you didn't think you needed until it gets passed around the circle and suddenly everyone's wrist hurts and nobody wants to stop — and more. This is where the rainy afternoon goes. Where the after-dinner argument about which game to play happens every single time. Where the teenagers who said they were going to bed are still sitting two hours later. Gerald watches. Gerald approves.
🛏️ THE BEDROOMS
Bedroom 1 — King, main level. Private ensuite bath and a private balcony overlooking the lake. The grandparents' room, if this is that kind of trip — they've earned it. If this is a group of friends, may the best bracket win.
Bedroom 2 — King, upper level. Lake views and a cozy sitting area that makes it genuinely hard to leave in the morning. A very gracious second place finish.
Bedroom 3 — Queen, upper level. Crib available for the little ones who have no idea how good they have it.
Bedroom 4 — Queen, main level. Cedar walls, an iron bed frame, and a Bicentennial Chief Justice Windsor Armchair tonce described simply as "the fat man chair." It is large. It is beautiful. It is exactly right for this house.
Bedroom 5 — Queen, main level. Home to Ben Franklin — a hand-carved wooden chair of deeply uncertain origin who plays cello and asks nothing of anyone. Guests photograph him. We don't ask why.
Bedroom 1 has its own ensuite. Bedrooms 2, 3, 4, and 5 share a full bath and a half bath. Both bathrooms have personality. The photos will explain.
☀️ OUTDOOR LIVING
The covered front deck is where the trip exhales. String lights overhead, a gas fire table at the center, lounge chairs and a chaise for people who have nowhere to be. This is where the group ends up after dinner and where nobody actually wants to go inside.
The back deck is for the mornings and the meals. A full outdoor dining table set for ten, backed by a wooded hillside with an exposed shale rock ledge rising behind it. Private, dramatic, exactly the kind of setting that makes a simple breakfast feel like something worth remembering.
The fire pit is where the night goes. Ten black Adirondack chairs — one for each of you, because it was intentional — set against the shale rock face with five acres of woods surrounding it. No road noise. No neighbors. Just the fire, the dark, and whoever is still out there at midnight saying five more minutes. You already know who that is.
📍 THE AREA
Arbor Hill Winery — 4 min. First stop on the Canandaigua Lake Wine Trail, practically in the backyard.
Grimes Glen County Park — 10 min. Waterfall hike through a shale gorge. Best easy hike in the Finger Lakes.
Bristol Mountain — 7 min. Skiing and snowboarding in winter, chairlift rides and zip lines in warmer months.
Canandaigua Lake Onanda Park public beach — 9 min.
Naples Brewing Company — 12 min. Craft beer on Main Street. Try the Grape Pie Sour.
Inspire Moore Winery — 12 min. Local Naples favorite.
Hazlitt’s Red Cat Cellars — 12 min. Historic Widmer Winery in Naples.
Monica’s Pies — 10 min. Grape pie. Open year-round. Non-negotiable.
CMAC — 20 min. The Finger Lakes’ premier outdoor concert amphitheater. Dave Matthews, Kenny Chesney, The Killers, Hozier. If there’s a show on your weekend, this is the move.
Hollerhorn Distilling — 15min. Maple spirits, gin, whiskey. Worth a stop.
Engine 14 Brewery — 13min. Fire house-themed craft brewery.
Old School Cafe — 12 min. Creative brunch in a renovated 1870s schoolhouse.
Naples Grape Festival — 12 min. Late September. A regional institution.
Guest access
A couple of utility areas are reserved for maintenance access, but otherwise you have the run of the place. Self check-in via smart lock — your code will be sent before arrival.
Other things to note
GOOD TO KNOW
Check-in: 4:00 PM / Check-out: 10:00 AM
Maximum 10 guests / Maximum 6 vehicles — park in designated areas only, no blocking driveways or access roads
A rental agreement is required prior to check-in per Town of South Bristol requirements.
Dogs welcome — $75 per dog, declare at booking. No pets on furniture. Pets may not be left unattended inside. Owners are responsible for cleaning up after them.
No smoking anywhere on the property, indoors or out.
Quiet hours: 10 PM to 7 AM Sunday through Thursday, 11 PM to 7 AM Friday and Saturday.
The Hill House is in a residential area in the Town of South Bristol — please be respectful of neighbors and their privacy at all times. Stay on the property; neighboring lands are private.
Fire pit: use at your own risk. Fires must be fully extinguished after use. No glass near the fire pit.
The property sits on a hill with some areas that have significant drop-offs. Young children and pets should not be left unattended outdoors.
Deck can be wet and slippery after rain.
No direct lake access — public beach is 9 min away.
Private hilltop gravel road — 4WD/AWD strongly recommended in winter.
Hosting a gathering or celebration? Reach out before booking, we're happy to chat.
The one where nobody checks the time, kids disappear into the game room for hours, and someone always ends up at the fire pit saying, "five more minutes."
Private 5-acre wooded hilltop with lake views, a 1,200 sq ft turf-floor game room packed with skee-ball, ping pong, air hockey, foosball, cornhole, and more.
First winery is 4 minutes away. Bristol Mountain is 7. Beach is 9.
Designed for 10, dogs welcome, zero boring allowed.
The space
Some houses you stay in. Some houses you remember.
The Hill House has four living spaces, five bedrooms, two decks, a fire pit, five acres of wooded hilltop, and a 1,200 sq ft game room that is technically a garage but has completely forgotten that. There is always somewhere to be and always somewhere to escape to. The group can be together without being on top of each other. That is harder to find than it sounds.
Warm, a little weird, and completely intentional. If that sounds like your kind of place, welcome home.
⭐THE HIGHLIGHTS⭐
🏓 1,200 sq ft turf-floor game room — skee-ball, ping pong, air hockey, foosball, basketball shootout, cornhole. Not a pool table in a corner.
🛏️ 5 bedrooms, 5 real beds — nobody on a pull-out or in a loft
🍽️ Dining table that seats all 10 at the same time
🏠 4 separate living spaces — sunroom, great room, family room with fireplace, basement den
🌊 Canandaigua Lake views from a private 5-acre wooded hilltop
👑 King suite with private ensuite bath and lake-view balcony
🫎 Gerald. He judges nobody. He approves of everything.
🎲 Board game wall: Clue, Pictionary, Finger Lakes-opoly, Scattergories, Monopoly, UNO and more
☀️ Covered front deck with string lights and gas fire table
🌳 Back deck with outdoor dining table for 10
💧 Full water treatment system + reverse osmosis tap — great water, no well water surprises
🍷 4 min to first winery on the Canandaigua Lake Wine Trail
⛷️ 7 min to Bristol Mountain ski resort
🏊 9 min to public beach on Canandaigua Lake
🎵 20 min to CMAC outdoor concert amphitheater
🛋️ THE BASEMENT DEN
You walk in through the basement. Cedar-paneled walls, a leather sofa, vintage cane chairs, a TV, and a green velvet bench from a Knights of Columbus hall. This is where the teenagers set up immediately. It's also where the kids migrate when they need their own world, away from the adults who are trying to have a conversation upstairs. The ski rack in the corner keeps winter gear organized. The door at the end connects directly to the game room, which means by the time anyone has put their bags down, someone has already picked up a paddle.
🏓 THE GAME ROOM
Not a pool table in a corner. Not a dart board on a wall.
A 1,200 sq ft garage finished with turf flooring and loaded for people who take fun seriously: skee-ball, ping pong table, air hockey table, foosball table, basketball shootout arcade, cornhole, and a giant Tetris installation that makes absolutely no apologies for existing. And yes, there is an outdoor playhouse inside the garage. The Fun Uncle does not follow conventional rules about what goes where.
Young kids have the playhouse. Older kids claim ping pong immediately. Adults who said they were just going to watch end up under the umbrella with a drink, calling the shots. Thirty minutes later someone has drawn up a tournament bracket and the evening is no longer what anyone planned. Rain, shine, or apres-ski — nobody is bored.
🌿 THE SUNROOM
Someone always finds this room and decides it belongs to them.
Floor-to-ceiling windows on two sides, cedar-paneled walls, hanging plants, a live-edge dining table, rattan lounge chairs, a papasan that gets claimed within the first hour, and a chess table in the corner. This is where a grandparent sits down with a grandkid and teaches them chess or checkers while the rest of the house does whatever it does. Nobody interrupts that. It opens directly into the great room so everything flows together, but the sunroom has its own quiet gravity. Morning coffee here becomes the ritual by day two. Evening wine was always the plan.
☕ THE GREAT ROOM
The heart of the house and where the trip actually happens.
A soaring wood-planked ceiling with skylights runs the length of the open-concept living room, kitchen, and dining area. Two full sofas, original art, two octagon windows — because of course there are. This is where the adult kids cook dinner while grandparents are in the sunroom and the grandkids are somewhere in the basement — voices carrying up through the floor, everyone accounted for, nobody in anyone's way. The kitchen island is command central. Someone claims a barstool and doesn't leave for the rest of the afternoon. Bar seating for three, full electric range with hood vent, subway tile backsplash, stainless appliances, open shelving. Fully stocked and built for a group that actually wants to cook.
The dining table seats all ten — because someone always gets left at the kids' table and that someone is usually an adult and it is not happening here.
The water is worth a mention: full treatment system plus a reverse osmosis tap at the kitchen sink. Clean, clear, actually good. Fill your bottles freely.
🫎 THE FAMILY ROOM
Gerald the moose lives on the wall in here. He takes everything in, judges nothing, approves of everything. He has been the backdrop to more board game arguments than anyone can count and he has never once taken a side.
Cedar walls, electric fireplace, and a floor-to-ceiling board game wall stocked with Clue, Pictionary, Finger Lakes-opoly, Scattergories, Monopoly, UNO, Dominoes, TriBond, Bop It — yes Bop It, the game you didn't think you needed until it gets passed around the circle and suddenly everyone's wrist hurts and nobody wants to stop — and more. This is where the rainy afternoon goes. Where the after-dinner argument about which game to play happens every single time. Where the teenagers who said they were going to bed are still sitting two hours later. Gerald watches. Gerald approves.
🛏️ THE BEDROOMS
Bedroom 1 — King, main level. Private ensuite bath and a private balcony overlooking the lake. The grandparents' room, if this is that kind of trip — they've earned it. If this is a group of friends, may the best bracket win.
Bedroom 2 — King, upper level. Lake views and a cozy sitting area that makes it genuinely hard to leave in the morning. A very gracious second place finish.
Bedroom 3 — Queen, upper level. Crib available for the little ones who have no idea how good they have it.
Bedroom 4 — Queen, main level. Cedar walls, an iron bed frame, and a Bicentennial Chief Justice Windsor Armchair tonce described simply as "the fat man chair." It is large. It is beautiful. It is exactly right for this house.
Bedroom 5 — Queen, main level. Home to Ben Franklin — a hand-carved wooden chair of deeply uncertain origin who plays cello and asks nothing of anyone. Guests photograph him. We don't ask why.
Bedroom 1 has its own ensuite. Bedrooms 2, 3, 4, and 5 share a full bath and a half bath. Both bathrooms have personality. The photos will explain.
☀️ OUTDOOR LIVING
The covered front deck is where the trip exhales. String lights overhead, a gas fire table at the center, lounge chairs and a chaise for people who have nowhere to be. This is where the group ends up after dinner and where nobody actually wants to go inside.
The back deck is for the mornings and the meals. A full outdoor dining table set for ten, backed by a wooded hillside with an exposed shale rock ledge rising behind it. Private, dramatic, exactly the kind of setting that makes a simple breakfast feel like something worth remembering.
The fire pit is where the night goes. Ten black Adirondack chairs — one for each of you, because it was intentional — set against the shale rock face with five acres of woods surrounding it. No road noise. No neighbors. Just the fire, the dark, and whoever is still out there at midnight saying five more minutes. You already know who that is.
📍 THE AREA
Arbor Hill Winery — 4 min. First stop on the Canandaigua Lake Wine Trail, practically in the backyard.
Grimes Glen County Park — 10 min. Waterfall hike through a shale gorge. Best easy hike in the Finger Lakes.
Bristol Mountain — 7 min. Skiing and snowboarding in winter, chairlift rides and zip lines in warmer months.
Canandaigua Lake Onanda Park public beach — 9 min.
Naples Brewing Company — 12 min. Craft beer on Main Street. Try the Grape Pie Sour.
Inspire Moore Winery — 12 min. Local Naples favorite.
Hazlitt’s Red Cat Cellars — 12 min. Historic Widmer Winery in Naples.
Monica’s Pies — 10 min. Grape pie. Open year-round. Non-negotiable.
CMAC — 20 min. The Finger Lakes’ premier outdoor concert amphitheater. Dave Matthews, Kenny Chesney, The Killers, Hozier. If there’s a show on your weekend, this is the move.
Hollerhorn Distilling — 15min. Maple spirits, gin, whiskey. Worth a stop.
Engine 14 Brewery — 13min. Fire house-themed craft brewery.
Old School Cafe — 12 min. Creative brunch in a renovated 1870s schoolhouse.
Naples Grape Festival — 12 min. Late September. A regional institution.
Guest access
A couple of utility areas are reserved for maintenance access, but otherwise you have the run of the place. Self check-in via smart lock — your code will be sent before arrival.
Other things to note
GOOD TO KNOW
Check-in: 4:00 PM / Check-out: 10:00 AM
Maximum 10 guests / Maximum 6 vehicles — park in designated areas only, no blocking driveways or access roads
A rental agreement is required prior to check-in per Town of South Bristol requirements.
Dogs welcome — $75 per dog, declare at booking. No pets on furniture. Pets may not be left unattended inside. Owners are responsible for cleaning up after them.
No smoking anywhere on the property, indoors or out.
Quiet hours: 10 PM to 7 AM Sunday through Thursday, 11 PM to 7 AM Friday and Saturday.
The Hill House is in a residential area in the Town of South Bristol — please be respectful of neighbors and their privacy at all times. Stay on the property; neighboring lands are private.
Fire pit: use at your own risk. Fires must be fully extinguished after use. No glass near the fire pit.
The property sits on a hill with some areas that have significant drop-offs. Young children and pets should not be left unattended outdoors.
Deck can be wet and slippery after rain.
No direct lake access — public beach is 9 min away.
Private hilltop gravel road — 4WD/AWD strongly recommended in winter.
Hosting a gathering or celebration? Reach out before booking, we're happy to chat.
Where you’ll sleep
1 of 3 pages
What this place offers
Lake view
Mountain view
Kitchen
Wifi
Dedicated workspace
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Rated 5.0 out of 5 from 13 reviews.
Guest favorite
This home is in the top 10% of eligible listings based on ratings, reviews, and reliability
Overall rating
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Rated 5.0 out of 5 stars for cleanliness
Rated 5.0 out of 5 stars for accuracy
Rated 5.0 out of 5 stars for check-in
Rated 5.0 out of 5 stars for communication
Rated 4.8 out of 5 stars for location
Rated 4.9 out of 5 stars for value
Guests mention
Where you’ll be
Naples, New York, United States
This listing's location is verified and the exact location will be provided after booking.
Meet your host
Born in the 80s
Where I went to school: St. Olaf College
Hi, we’re Jake and Elise! With our two kids, Desmond and Vivienne, we create vacation homes where families and friends can relax, reconnect, and make memories. As a small, family-owned business, we focus on thoughtful design, cozy details, and personal touches to make every stay feel special. We love welcoming guests, sharing our favorite local spots, and helping every stay feel unforgettable and truly magical. We’d love to host you!
Jake is a Superhost
Host details
Response rate: 100%
Responds within an hour
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