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Private Home ~ All Yours ~ In town ~ fenced in yard ~ Pets welcome!

Family-friendly cottage with fitness centre and Hot tub

Photo gallery for Private Home ~ All Yours ~ In town ~ fenced in yard ~ Pets welcome!

Living area
Living area
Living area
Exterior detail
private fenced in hot tub area in back yard with bistro lighting

Reviews

9.8 out of 10
Exceptional
2 bedrooms1 bathroomSleeps 41600 sq ft

Popular amenities

  • Gym
  • Dryer
  • Washer

Explore the area

View in a map
Woodstock, NY
  • Place, Woodstock Music Shop
    ‪5 min walk‬
  • Place, Woodstock Golf Club
    ‪6 min walk‬
  • Place, Overlook Mountain Trailhead
    ‪7 min drive‬
  • Airport, Hudson, NY (HCC-Columbia County)
    ‪55 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

1 bathroom

Bathroom 1

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

Spaces

Deck or patio
Porch or lanai
Kitchen
Office
Outdoor play area
Garden
Dining area

About this property

Private Home ~ All Yours ~ In town ~ fenced in yard ~ Pets welcome!

Monthly and seasonal rentals encouraged starting in 2026. Please message me with questions. While weekends are super popular I offer larger discounts for monthly and seasonal rentals. Please message me if you have questions about pricing.
*Hot tub is not working at the moment*
The Sled Hill House is in the center of town yet secluded, private and off the beaten path. The bungalow is surrounded by a privacy-fenced yard with outdoor seating and beautiful foliage. The house and property are completely yours. There is a sunny and bright loft area which works well as a home office, workout area, game room for the kids with a large screen Roku tv and comfortable seating.. Two bedrooms with comfortable queen beds share a full bath on the first floor. A well appointed eat-in kitchen and a comfortable living room with large screen Roku tv finish the first floor layout. Outside you'll find a hot tub, new Weber Grill for cookouts and patio dining. A short walk to Woodstock village filled with restaurants, coffee shops, shopping and people watching.
The Sled Hill House is a charming family cottage in town
*Entire house and yard is yours. Private and secluded. You are not sharing the property with anyone else.
*High Speed Wi-Fi
*Located on a quiet, hidden road one block from the center of town
*No parties. Sound ordinance 11pm.
*One block walk to everything in town. you son't find anything closer
- restaurants
- movie theater
- farmers market
- nightlife
- pharmacy
- health food store
- golf course
- hiking
- the Mill Stream

The House:
• Completely private - entire house and yard is yours alone
• BBQ and Outdoor Weber Grill, Fire pit and outdoor bistro lighting in back yard
• private, secluded, shady outdoor dining area and patio
• Large upstairs loft area, equipped with games, puzzles, and movies
• Air conditioning in bedrooms and loft for the warmer seasons
• Fenced in yard
• beautiful gardens and walking paths
• 2 master bedrooms with queen sized beds, closets and AC
• 1 full bathroom
• Large screen smart TVs in the living room and upstairs loft
• Kitchen with all new appliances, coffee maker, laundry, dishwasher, microwave
• Pots, Pans, utensils, coffee, tea, complete pantry of spices and oils, for cooking
• Wood stove in living room for the colder seasons
* Close to all ski areas
• Two parking spaces on site and additional parking on the street

- House is secure. Many of the nearby shops and restaurants are within a three minute walk

Guest access:
You have full access to the house, fenced in yard and private parking spots for two vehicles. (for HITS guests, oversized vehicles can fit in driveway and there is additional parking on the street.

Interaction with guests:
I live just outside of town and I respond to texts immediately. I have full time maintenance help if I am not readily available. I am usually around but give you your space.

Other things to note:
No car needed. We are a two minute walk to the bus stop and to all the wonderful restaurants and shopping and all that town has to offer.

House is also just down the street from the mill stream and a short walk or drive to local hiking trails. Our hidden road is right behind Tinker Street which includes all sorts of family owned restaurants, an organic supermarket, boutiques, thrift and metaphysical stores, and a pharmacy.

Day Trips. We are a short drive to Hunter, Windham, and Belleayre Ski areas. We're just 1.5 hours from Vermont, 2 hours from NYC, 2 hours from the Adirondacks so you can take a day trip to explore and still make it back in time to have dinner at the organic restaurant up the street.

I hope you enjoy my home and our town as much as I do, and respect it. There is a deck and porch areas for hanging out and dining but please no smoking inside. You are a part of the Woodstock Artists Community and must be respectful of our neighbors.

Town of Woodstock Listing #20N-063

Add dates for prices

Amenities

Hot tub
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi

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House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed: dogs (limit 1 total)
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Smoking

Smoking allowed: in designated areas
Smoking on outdoor patio only

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Long-term renters welcome
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

We should mention

This property does not have any lifts
A car is required for transport to and from this property

About the area

Woodstock

Woodstock is home to this cottage. Catskill Mountains and Catskill State Park reflect the area's natural beauty and area attractions include Kiwanis Ice Arena and Hudson River Maritime Museum. Travelling with kids? Consider Trolley Museum of New York and Empire State Railway Museum. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Woodstock, NY

What's nearby

  • Woodstock Music Shop - 5 min walk - 0.4 km
  • Colony - 6 min walk - 0.6 km
  • Woodstock Golf Club - 6 min walk - 0.6 km
  • Overlook Mountain Trailhead - 7 min drive - 4.2 km
  • Karma Triyana Dharmachakra Monastery - 7 min drive - 4.2 km

Getting around

  • Rhinecliff Station - 27 min drive
  • Hudson, NY (HCC-Columbia County) - 47 min drive

Restaurants

  • ‪Good Night - ‬6 min walk
  • ‪Colony - ‬6 min walk
  • ‪Bread Alone Bakery - ‬3 min walk
  • ‪Cumberland Farms - ‬3 min walk
  • ‪Tinker Street Tavern - ‬4 min drive

Frequently asked questions

Is Private Home ~ All Yours ~ In town ~ fenced in yard ~ Pets welcome! pet-friendly?

Yes, this property allows dogs (limit 1 total).

What time is check-in at Private Home ~ All Yours ~ In town ~ fenced in yard ~ Pets welcome!?

Check-in begins at 3:00 PM.

What time is check-out at Private Home ~ All Yours ~ In town ~ fenced in yard ~ Pets welcome!?

Checkout is at 11:00 AM.

Where is Private Home ~ All Yours ~ In town ~ fenced in yard ~ Pets welcome! located?

This family-friendly Woodstock cottage is within a 5-minute walk of Catskill State Park, Woodstock Music Shop and Woodstock Artists Association and Museum. The Comeau Property and Woodstock Golf Club are also within 10 minutes.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 102 out of 120 reviews
Rating 8 - Good. 16 out of 120 reviews
Rating 6 - Okay. 2 out of 120 reviews
Rating 4 - Poor. 0 out of 120 reviews
Rating 2 - Terrible. 0 out of 120 reviews

9.2/10

Cleanliness

10/10

Staff & service

6.0/10

Amenities

6.0/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Michael D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very clean and great location. Easy checkin
Stayed 2 nights in Jul 2025

10/10 Excellent

bob t.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We did not have a pet, and we did not use the hot tub.
Stayed 4 nights in Sep 2025

10/10 Excellent

Laura M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property was perfect for my husband & I to enjoy for an extended weekend! The house is clean, comfortable & very well appointed. The beds are comfortable with quality linens. The kitchen has great cookware & knives (which is rare, in many past experiences). The yard is a lovely space to hang out & so is the hot tub!! Easy walk to town and the market. We hardly drove at all, in fact. Most importantly, Dave, the owner, was very accommodating, responsive to us, and sincerely interested in knowing how he could enhance the place for the best experience possible. Overall, 10/10! We will be back!!!
Stayed 3 nights in Sep 2025

8/10 Good

Colleen G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

Great location and responsive host.
Stayed 2 nights in Feb 2025

10/10 Excellent

Kristin I.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Comfy home, perfect location

The home was very comfortable, we loved hanging out in the fenced in yard at night that was safe for our dog to play and explore. House is just steps away from shops and restaurants, great neighborhood with friendly people. Would definitely return!
Stayed 6 nights in Jun 2025

8/10 Good

Monika G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great weekend getaway!

The location was exceptional, close to restaurants and shops, quiet neighborhood, comfortable bed and the house was well stocked with everything you’d need.
Stayed 2 nights in Mar 2025

10/10 Excellent

Cara S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great as always

You had a wonderful time. The kitchen, the dining space and entertainment areas perfect and very close to the center of town. Always fun.
Stayed 2 nights in Apr 2025

10/10 Excellent

Megan S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Comfortable home in convenient location

Just steps from everything, yet the property feels tucked away and private. We loved being able to walk everywhere and then have the cozy house to come back to - the wood burning stove made it extra cozy during our late March trip to Woodstock. Very communicative and friendly host.
Stayed 2 nights in Mar 2025

10/10 Excellent

miles o., New York City, USA

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

Great location, amenities, and super cozy!
Stayed 3 nights in Oct 2022

8/10 Good

Jenna B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location!

Can’t beat location and great outdoor space
Stayed 3 nights in Jun 2023

10/10 Excellent

Mary D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Woodstock Getaway

Best spot to stay in town. Hot tub is lots of fun too. Fresh and clean.
Stayed 3 nights in Feb 2024

10/10 Excellent

Rhonda B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Airshow weekend

Stayed to attend the Old Rhinebeck Airshow. Good location. Right near all in Woodstock, although we didn't have time to enjoy the local businesses. Cute house, love the upstairs to relax and watch TV.
Stayed 3 nights in Sep 2024

10/10 Excellent

Jillian B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Location

This property was in a perfect location and walking distance to the main road with all restaurants and shops. Listing owner was extremely communicative and made sure we were comfortable and happy with our stay. Would definitely stay again!
Stayed 2 nights in Sep 2023

10/10 Excellent

Kevin K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfection!

This rental could not have been more perfect. Everything was so comfortable and relaxing, it was hard to leave. The location was amazing, steps to Bread Alone for coffee and breakfast treats, next to the Flea Market but still super private and felt like we were in a secluded cabin in the woods. We will definitely be booking again, thank you!
Stayed 2 nights in Oct 2024

10/10 Excellent

Kathe P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quiet but in town

Lovely house in town but very private and quiet. Pretty fenced yard/garden space. Well appointed kitchen. Comfy bed, big tv. My husband, our corgi and I had everything we needed for the perfect Woodstock getaway. We hope to stay again next year.
Stayed 5 nights in Oct 2024

10/10 Excellent

Craig K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect location, awesome host!

This house couldn’t be closer to town - literally steps from our favorite restaurant. Perfect for our family of three (plus our dog) but would also work well for two couples (with a loft area that could sleep a kid or two on the couch or an air mattress). Great communication with our host who was super responsive and accommodating. All the amenities we needed and the hot tub was a great bonus. We’d stay again in a heartbeat!
Stayed 3 nights in Nov 2024

10/10 Excellent

Robin H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

If you want Woodstock this is the place to stay.

1/2 block to downtown Woodstock, everything you need for a comfortable stay. Best part is the Host Dave, cool guy!
Stayed 2 nights in Nov 2023

8/10 Good

J V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect house to be in the center of everything

Loved the location. Walked to tinker st every day, it was so easy getting around. House was great and perfect for our dog (a lab). Yard is fenced so loved that. Shower was a little weak on the pressure and heat but thats the only complaint I could make
Stayed 3 nights in Sep 2024

10/10 Excellent

Steve K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

Amazing location with a quick walk to everything in Woodstock. House is cozy and well appointed. Dave is a great host and made sure that we had everything we needed for a wonderful stay. Can’t wait to come again!
Stayed 4 nights in Nov 2022

10/10 Excellent

Cara S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great time

Wished we could have stayed longer. Beautiful property…perfect for just being in town and not having to drive anywhere. Thanks, Dave!
Stayed 2 nights in Apr 2024

10/10 Excellent

Michael M.

Liked: Check-in, communication, location, listing accuracy

Great location

The location enhanced our overall experience - it was nice to be able to walk around. The grounds are very pretty and well thought out. The stove was great.
Stayed 3 nights in Oct 2023

10/10 Excellent

Olivia R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

An awesome stay in Woodstock

Dave’s place was exactly as advertised if not better! Everything in town was a quick walk away yet his property still felt intimate and private. We loved the chess board and other games/fun little things provided in the house!
Stayed 2 nights in Apr 2024

10/10 Excellent

Evelyn Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Our stay

The home was cozy, well stocked and so close to stores, restaurants, etc. The booking process and communication with the property manager all went smoothly. Silivia’s to celebrate; wonderful evening.
Stayed 2 nights in Oct 2023

8/10 Good

Verified traveller

Liked: Check-in, communication, location, listing accuracy

Cozy spot right in town!

The house was very cozy and warm—easy and fast to heat woodstove, and comfy skylight lit upstairs loft! We loved the outdoor are with firepit—perfect to sit with our dog. The location can’t be beat, right in downtown and even walking distance to grocery store. Loved spending Christmas there with my husband and son!
Stayed 3 nights in Dec 2023

10/10 Excellent

Jill R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Ski House Getaway

This adorable house is in the heart of Woodstock, walking distance to all the restaurants and shops. And about 30 minutes to local ski areas. We love the hot tub and the loft and all the games-perfect for our family with teens!
Stayed 3 nights in Dec 2023

About the host

Hosted by Dave Leonard

Host profile image
I have lived in the area since 1989 and the house was built in the early 90's. I lived there with my children during their formative years and have since moved to the outskirts of town with my two teenage daughters Eva and Luci and my two dogs Jasper and Juno. I am a hands-on Dad during the week and I DJ weddings locally on most weekends. I also have my own weekly radio show recorded locally and syndicated nationally. I like to bike, play softball and enjoy landscaping and working on the yard in the warmer seasons.

Why they chose this property

The house is airy and bright, in a private, shady setting all yours and yet so close to town. The house was built in the mid 90s and is in great shape. Stays cool in the summer and warm in the winter. The upstairs loft is a gem and one of my favorite parts of the house and is what sets it apart from others. I know the architect and builder personally and I love how well built it is. I raised my kids here until just a few years ago.

What makes this property unique

Location, location, location. No vehicle needed as it's one block to town. Unique design, bright and open, large cathedral ceilings yet cozy and extremely private. I've spent a lot of time gardening and landscaping. New construction in the mid 90s by one of the best builders in town, it is solid and spacious, clean and cozy, shady and private yet close to everything.

Languages:

English

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