Entire home

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

Photo gallery for Private Home ~ All Yours ~ In town ~ fenced in yard ~ Hot Tub ~ 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 4148.6 sq m

Popular amenities

  • Gym
  • Parking available
  • Dryer
  • Washer
  • Fireplace

Explore the area

Map
Woodstock, NY
  • Woodstock Music Shop
    ‪6 min walk‬
  • Woodstock Golf Club
    ‪8 min walk‬
  • Overlook Mountain Trailhead
    ‪8 min drive‬
  • Hudson, NY (HCC-Columbia County)
    ‪47 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 ~ Hot Tub ~ Pets welcome!

Monthly rentals available for summer 2025. Please message me with questions. While weekends are popular I offer larger discounts for weekly, monthly and seasonal rentals. Please message me if you have questions about pricing.

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

Property manager

Dave Leonard
Premier Host

Languages

English

Add dates for prices

Amenities

Hot tub
Kitchen
Washer
Dryer
Pet-friendly
Free WiFi

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

House Rules

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

Children

Children allowed: ages 0–17
default

Events

No events allowed
default

Pets

Pets allowed: dogs (limit 1 total)
default

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 Woodstock Music Shop and Kiwanis Ice Arena. Travelling with kids? Consider Hudson River Maritime Museum and Trolley Museum of New York. 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 - 6 min walk - 0.6 km
  • Woodstock Golf Club - 8 min walk - 0.7 km
  • Woodstock Public Library - 9 min walk - 0.8 km
  • Overlook Mountain Trailhead - 8 min drive - 4.6 km
  • Karma Triyana Dharmachakra Monastery - 8 min drive - 4.7 km

Getting around

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

Restaurants

  • ‪Colony - ‬7 min walk
  • ‪Bread Alone - ‬4 min walk
  • ‪Steve's Pizza & Deli - ‬10 min drive
  • ‪Good Night - ‬6 min walk
  • ‪Tinker Street Tavern - ‬4 min drive

Frequently asked questions

Is Private Home ~ All Yours ~ In town ~ fenced in yard ~ Hot Tub ~ 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 ~ Hot Tub ~ Pets welcome!?

Check-in begins at 3:00 PM.

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

Checkout is at 11:00 AM.

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

This family-friendly Woodstock cottage is within a 10-minute walk of Catskill State Park, Woodstock Music Shop and Woodstock Golf Club. SweetHeart Gallery and Woodstock Public Library 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. 94 out of 111 reviews
Rating 8 - Good. 15 out of 111 reviews
Rating 6 - Okay. 2 out of 111 reviews
Rating 4 - Poor. 0 out of 111 reviews
Rating 2 - Terrible. 0 out of 111 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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

e a.

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

Great stay!

Perfect location and walkable to everything. I'd been concerned about noise since the place is right off the main drag, but this was not a problem at all. Once you're off that road, you're in paradise. Enjoyed the fenced-in yard for our dog and loved hanging out in the loft. Hope to stay again sometime!
Stayed 4 nights in Apr 2023

10/10 Excellent

Mary D.

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

Best location

Great home to rent in the middle of Woodstock. Walk to everything! Great yard with hot tub, campfire pit,and many places to hang out. Love that we could bring our dogs!!!!
Stayed 4 nights in Feb 2023

10/10 Excellent

kerri f.

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

Home Sweet Home

I came back home with my family to visit family and friends during the memorial day holiday. This rental was perfectly situated right in town so all we did was leave and walk around all day.
Stayed 5 nights in May 2023

10/10 Excellent

Nicholas F.

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

Great stay

We stayed for New Years and it was a great time. The house was perfect for our family of 4. We especially enjoyed throwing logs in the wood burning stove and watching movies and playing board games. Neighborhood was great and convenient to town. Would definitely stay again. Dave was easy to work with and made sure we had everything we needed.
Stayed 3 nights in Dec 2022

10/10 Excellent

Tanya L.

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

Awesome!!!!

We stayed here in July, and could not have asked for a more wonderful stay! We brought our dogs, who LOVED running through the wrap-around yard. The space is beautifully landscaped and the neighborhood is super quiet. The jacuzzi was awesome too! Can’t say enough wonderful things about this place—and about Dave’s kindness and hospitality!!!
Stayed 3 nights in Jul 2023

10/10 Excellent

Johanna S.

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

Amazing location, amazing home and property

Dave's home is a wonderful property located in the center of Woodstock. Comfortable, clean with a wonderful fenced in yard that our dog loves. We have stayed here numerous times and continue to enjoy the wonderful feel of this home away from home! Love the wood burning fireplace on chilly and cold evenings. Beautiful yard! Quiet and relaxing! Very comfortable spaces in the home. Dave always responds within a very short period of time and is always helpful. Love the upgrades! We will definetly be back!
Stayed 3 nights in Apr 2024

10/10 Excellent

Stephanie C.

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

Complete Oasis

The home and yard were charming, relaxing, comfortable and well stocked with anything needed, including games, firewood. Great walkable location for the village and many excursions are within 45 minutes drive. Great choice. We came home so refreshed and rested. Thank you for all your thoughtful planning and effort Dave!
Stayed 7 nights in Aug 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

Premier Host

They consistently provide great experiences for their guests