5121 Main St
Millbrook, US
Sleeps 12 · 5 bedrooms · 3 baths
About this place
The graduation is tomorrow. Or the wedding. Or the reunion nobody wanted to miss. Tonight the real reason you came is happening. The kids have claimed their corner. Someone pours another drink. Stories get louder around that ridiculously long table. Nobody disappears down a hotel hallway when the night ends. This 1830s house gives your people something hotels can't: the weekend together. Room to gather. Room to disappear. And enough character to make this trip one you'll talk about long after. This historic 5-bedroom home is built for the moments your group actually came for—long dinners, kids claiming their own space, conversations that stretch late, and plenty of room to spread out between gatherings. ** 5 bedrooms | Sleeps up to 12 ** Bedroom 1: Queen bed + Smart TV + ensuite bathroom ** Bedroom 2: Queen bed + Smart TV ** Bedroom 3: Queen bed + Smart TV ** Bedroom 4: Queen bed + patio access ** Bedroom 5 / Upstairs Play Area: 2 queen air mattresses ** 2.5 bathrooms including primary ensuite ** Huge dining table with seating for 12 — one of the home's standout gathering spaces ** Multiple living/conversation areas so the group doesn't have to crowd into one room ** Upstairs play area with bean bags, play tent, toys, and games ** Fully equipped kitchen with granite countertops and modern appliances ** Dedicated workspace with desk and chair ** Smart TVs for movie nights and downtime ** Covered front porch with swing ** Back patio with outdoor dining for 6 ** Spacious yard with room for kids to play ** Shared pool — seasonal, open May 1 through September (not heated). Shared with guests staying in the other two homes on the property ** Semicircle driveway at the front, with free on-site parking ** High-speed Wi-Fi ** Central air conditioning + heating ** Washer and dryer ** Pet-friendly Important sleeping note: Four bedrooms have permanent queen beds. The fifth sleeping area uses two queen air mattresses. This is an historic home with the character and quirks that come with its age—not a newly built hotel disguised as one. The house is exclusively yours, without interruption during your stay, so relax, unwind, and make yourself at home. Park in the semicircle driveway at the front of the house. There are four to five stairs up to the front door, which has an electronic smart lock deadbolt. Your code is released in your digital guidebook once your rental agreement is signed, your check-in form is complete, and your balance is paid. Other than the already mentioned amenities, our home is also equipped with the following: ✔ High-Speed Wi-Fi ✔ Air Conditioning ✔ Heating ✔ Laundry Room (Washer/Dryer, Iron/Board) ✔ Free Parking ***Please note the pool area is SHARED with guests staying in the other two homes on the property. Full pool safety rules are in the Other Things to Note section and posted at the pool fence — please read them before anyone gets in. Driving or getting an Uber is the best way of experiencing the picturesque area. As you already know, there's plenty of parking available on the property as well. Other Things to Note A few important details to know before booking: POOL: The pool is seasonal — open May 1 through September and closed October through April. Guests staying during the off-season should plan for the pool to be unavailable. 📝 Rental Agreement Every guest is required to sign a short rental agreement after booking This is not optional: our property insurance requires a signed agreement for each stay, and our attorneys have advised the same It covers house rules, check-in and check-out procedures, occupancy limits, and responsibility for damage It takes about two minutes — there is no app to download and no account or password to create We send it after booking along with a brief check-in form, and your access details follow once both are complete 🏊 Pool Safety — please read before anyone gets in A PARENT OR RESPONSIBLE ADULT MUST SUPERVISE CHILDREN AT THE POOL AT ALL TIMES. An older child is not a substitute for a parent Never leave a child unattended near the water, not even for a moment. Drowning is the leading cause of unintentional death for children aged 1 to 4, and it happens quickly and quietly If a child goes missing, check the pool first No lifeguard is on duty. Guests swim at their own risk and assume all liability for pool use The pool is fenced, with a self-closing, self-latching gate. Please keep the gate closed and latched, and NEVER prop it open — a gate that doesn't latch is the single most common way a child reaches the water Life-saving equipment is at the pool: a ring buoy and a rescue hook on a pole. This is emergency equipment, not pool toys. Please make sure children understand they are not to play with it — the pole can puncture the pool liner, and damaged equipment is not there when someone actually needs it. Guests are responsible for damage caused by misuse The pool is 4 feet deep throughout — NO DIVING Keep children away from pool drains, pipes and other openings No pets in the pool No glass near the pool Pool rules are also posted on the fence Know the property address so you can direct emergency services if you ever need to 🏡 Shared Pool — three homes on this property The pool area is SHARED with guests staying in the cottage and the cabin Please approach other guests with courtesy No visitors beyond the guests on your reservation The pool is open seasonally, May 1 through September. It is not heated, so in-season water temperature depends on the weather 🚗 Parking & Getting In Park in the semicircle driveway at the front of the main house Four to five stairs up to the front door The smart lock deadbolt is on the front door The cottage and cabin have their own separate driveway, divided by a white picket fence 🐾 Pets Pet-friendly — bring your furry friends along Please leash pets and clean up after them outdoors, out of courtesy to guests in the other homes Pets are not permitted in the pool 🏛️ Historic Home — please read This house was built in the 1830s and is nearly 200 years old It has central heating and air, but during extreme temperatures indoor conditions may be less even than in a modern build The outdoor walkways use repurposed materials and can be uneven or slick Fireplaces are not for use This is a historic home with the character and quirks that come with its age 🚬 No Smoking Inside Smoking inside the home is strictly prohibited Indoor smoking incurs a $275 fine plus deep cleaning and ozone treatment costs 🎉 No Parties or Events Please treat our home as your own to preserve its condition for future guests Quiet hours after 9:00 PM ⏰ Early Check-In & Late Check-Out With five bedrooms, early check-in and late checkout are NOT offered on same-day turnovers here On other dates every request is manually approved Fee: $20 per hour, with a one-hour minimum Please request as early as possible 🔧 On-Site Team You may see us or our maintenance team on-site periodically for routine tasks such as mowing, pool cleaning, or maintenance 🔑 Minimum Booking Age Because this property is a single-family home, the primary booking guest must be at least 25 years old The primary guest must be present throughout the reservation The primary guest is responsible for their group, visitors, and compliance with house rules Reservations that misrepresent the primary guest's age may be canceled in accordance with the applicable booking terms
Availability
From $175/night (2 nights minimum).
Open dates in the next 60 days:
- 2026-10-22 to 2026-10-22 (1 night)
- 2026-10-25 to 2026-11-28 (35 nights)
- 2026-12-05 to 2026-12-09 (5 nights)
- 2026-12-14 to 2026-12-17 (4 nights)
- 2026-12-20 to 2026-12-21 (2 nights)
Good to know
- Check-in: 16:00
- Check-out: 11:00
Amenities
- Board games
- First aid kit
- Towels
- Crockery and cutlery
- Oven
- Laptop-friendly workspace
- Fire pit
- Barbecue utensils
- Air conditioning
- Cleaning products
- High-touch surfaces cleaned with disinfectants
- Outdoor seating
- Contactless check-in
- Laundromat nearby
- Freezer
- Extra pillows and blankets
- Private entrance
- Cooking basics
- Outdoor lighting
- Body soap
- Pool
- Conditioner
- Smart TV
- Fenced pool
- Room-darkening shades
- Desk chair
- Carbon monoxide detector
- Essentials
- Travel cot
- Iron
- Blender
- Bathtub
- Single-level home
- Garden
- Hangers
- Dryer
- Seasonal pool
- Washer
- Wardrobe
- Fenced yard
- Cleaning with disinfectants
- Lock on bedroom door
- Bed linens
- Shampoo
- Baking sheet
- Free parking
- Communal pool
- TV
- Ceiling fan
- Hot water
- Enhanced cleaning
- WiFi (250+ Mbps)
- Refrigerator
- Microwave
- Wine glasses
- Office
- Emergency exit
- Barbecue
- WiFi
- Smoke detector
- Kitchen
- Toaster
- Coffee maker
- Coffee
- Deadbolt lock
- Dishwasher
- High chair
- Stove
- Heating
- Security cameras on property
- Check in option
- Dining table
- Deck or patio
- Fire extinguisher
- Hair dryer
- Pots and pans
- Ventilation fan
Reviews
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★★★★☆
Overall a great stay. Lovely old home with lots of character and charm. Enough space for everyone to spread out if they wanted too. One member of our group requires an electric wheelchair and he was able to access most of the house and the grounds. The pool area was somewhat unkept but we still enjoyed a brief swim. We had originally planned for 12 guest but ended up with only 9 coming. There are four beds and a couple of couches available for sleeping. Blow up mattress tucked away in a couple of closets but we did not get them out. There was no extra bedding available for those sleeping on the couch or for the blowup mattress. We did have to wash towels a couple of times each day because there were only 6 or 7 towels, a few wash cloths, and one hand towel provided for the whole group.
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★★★★☆
We enjoyed the home and had a comfortable stay. However, communication with the host was disappointing. He promptly charged us when we added guests, but when our guest count decreased, we had to ask twice before the charge was adjusted. We also requested an iron that was missing from the home, but it was not delivered until two days later, after we no longer needed it. The home was nice, but the host’s responsiveness and customer service left room for improvement.
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★★★★★
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★★★★★
Great spacious
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★★★★★
Home was beautiful and full of charm. Yard and pool areas were well kept and perfect for the kids to run and play!
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★★★★☆
Beautiful old house with lots of space. The kids thoroughly enjoyed the pool and yard. Lots of bedrooms and huge dining space.
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★★★★★
Beautiful historic home! Very well maintained and had everything we needed. We were new to the area and appreciated the guidebooks Josh provided for the area. Josh was extremely responsive to the couple questions I had and also reached out multiple to see if we needed anything and enjoying our stay. Of all the places we’ve stayed, Josh was the best host we’ve ever had!
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★★★★★
We had a wonderful stay. Loved the charm & character of this historical home. Josh was quick to respond and was very helpful to any questions that came up. The house was perfect for our girls getaway!
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★★★★★
Josh and the other hosts were easy to communicate with, always responded quickly, and the house was perfect for our family.
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★★★☆☆
The area was nice. Pool was great
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