Magical Woodstock Getaway
Hosted by Jesse
Jesse is the host.
10 guests
4 bedrooms
6 beds
2 baths
10 guests
4 bedrooms
6 beds
2 baths
You won’t be charged yet

This quirky place is 2 miles from the town of Woodstock and great for cozy winter nights or as a base for summer hiking. 4 bedrooms set around an octagonal tower and plenty of couches make it great for gatherings of friends or family. NOTE: Brand NEW HOT TUB has been installed. Ready for your enjoyment!

The space

This house centers around an enormous open main floor with open ceilings, making it perfect for gatherings of friends and family in a lodge-like space. In addition to a main fireplace, there are 3 wood burning stoves (including one in the master bedroom) making it great for cold winter nights. It's off the grid (just a landline - no cable, wi-fi or cell service) but that is the beauty of getting out of the city!

The 4 bedrooms (2 twin, 1 full and 1 queen) are on the second floor around an octagonal balcony. The master bedroom includes a ladder up to the tower, perfect for (URL HIDDEN) a really quirky, unique space with a ton of character.

A screened-in porch and huge wraparound deck are perfect for relaxing during the summer or having a bbq.

The property sits on 25 acres of undeveloped woodlands so you have plenty of quiet and privacy.

There's a hot tub on the deck as well!

Guest access

You will have access to the entire house and property. The only areas off limits is the basement.

Interaction with guests

This is a 2nd home for me. I use it as much as I can but will never be there when you are.

Other things to note

Cell Service is basically non-existent. And there is no cable or wi-fi so plan on shutting off for a bit! There is a landline though so you will have that to reach people or give to others to contact you during your stay. It's an easy to drive to town to get wi-fi however. Also note there is no air conditioning. However, there are fans and the house stays relatively cool in the summer.

Indoor fireplace

Extra people No Charge
Cleaning Fee $148 NZD
Security Deposit $740 NZD
Weekly Discount: 22%
Weekend Price $666 NZD / night
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Sleeping arrangements
Bedroom 1
1 queen bed
Bedroom 2
1 double bed
Bedroom 3
2 single beds
Bedroom 4
2 single beds
Common spaces
1 sofa bed, 2 sofas

House Rules
No smoking
No parties or events
Check in time is 10AM - 12AM (midnight)
Check out by 2PM
Self check-in with lockbox

I am ok with well behaved pets as long as my guests pay for any damage they cause. There is a big porch to smoke on...don't smoke inside.

Overall, I want my guests to have a great time here. Party if you want, make some noise (the neighbors are pretty far away but don't go totally crazy!), but just be respectful that this is a home I use too. I just bought the place and am planning to upgrade a few areas in it and get some nicer furniture (don't worry, what's there is fine) so just treat it as you would your own home. If you make a big mess, do the right thing and clean up what you can before leaving. Thanks!


Safety features
First aid kit
Fire extinguisher

2 nights minimum stay

93 Reviews

Check In
Ryan User Profile
October 2017
The weekend we spent in Jesse's home was absolutely wonderful. The house is massive and one of the most unique places any of us have ever stayed. It definitely made our trip to Woodstock all the more exciting. The hot tub and fire pit were an amazing addition. Looking forward to visiting Woodstock again in the near future and hope we will have the opportunity to stay here again.

George User Profile
September 2017
This place is huge and secluded. The property is tucked away and very private which is exactly what we were looking for. The main space is gigantic with lots of places to sit and relax. The hot tub was nice to have and the center of attention. When we arrived it was crystal clear, hot and fresh.

Norisuke User Profile
September 2017
Jesse's house is simply amazing. The house has so much characters, huge space for living room and plenty of private space. Hot tub is great point but what I really like was no wifi, no signal around that area. simply we don't use phone and not checking email or social media which is so important for our life. I dft would like to go back one day. Thank you so much!

Danielle User Profile
August 2017
I very much appreciated the size of the home, location, and easy and flexible check in and out. The bedrooms and bathroom were clean, spacious and comfortable for our group of 7. Some of the common areas (living rooms, sunroom, kitchen) could have been cleaner. Because the home is massive, I would recommend charging a higher cleaner fee so all groups can enjoy this magical Woodstock getaway. Other than that, I would definitely stay here again and recommend it to others.

Tom User Profile
August 2017
Wonderous, wacky castle hidden away in the woods. Super great place to get away from the world with some your friends. This is our second year in a row coming here and we plan to do it again!

Joey User Profile
June 2017
The house is gorgeous, enormous, and maintained very well. There's tons of space to run and play outdoors, too. Can't wait to go back.

Mackenzey User Profile
June 2017
This place is totally rocks I would definitely recommend it to everyone. This place isn't like anything you've ever seen before, it is truly magical. Very dog friendly. The little town of Woodstock is only a five minute drive close to restaurants and cute shops. The Jacuzzi is absolutely amazing. I have gone in the fall and I've gone in the summer and they both are equally great times to go during the year

New York, New York, United StatesJoined in October 2013
Jesse User Profile

I grew up in Nashville, Tennessee but have been a New Yorker for close to 10 years now. I'm into food (constantly struggling between the urge to be healthy and my love for fried chicken), exploring the 5 boroughs through running, singing karaoke and watching bad action movies.

I work at an awesome company called Tough Mudder ( that puts on extreme obstacle course races built on the philosophy that teamwork is more important than personal time. I was an early joiner and have seen the company grow from 5 to 150 employees around the world. We will have 800,000 participants at our events in 2014 alone. I lead the People team, focusing on building an amazing company culture that puts values and employees first.

I am not a big talker but a good listener. When I travel, I get bored of monuments quickly and like looking at maps.

For those of you looking at my Woodstock home, this is a place that I really love and enjoy myself. I need to rent it out to cover costs and will do everything in my power to make your experience there a good one. I can't promise it will always be perfect, but I'll go out of my way to fix any problems and do right by you.

Response rate: 90%
Response time: within a day

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