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Private Woodstock Retreat • In Town • Hot Tub • Dog Friendly

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Living area
Living area
Living area
Interior
Living area

Reviews

9.8 out of 10
Exceptional
2 bedrooms1 bathroomSleeps 41600 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

Explore the area

View in a map
Woodstock, NY
  • Place, Catskill State Park
    ‪1 min walk‬
  • Place, Woodstock Music Shop
    ‪5 min walk‬
  • Place, Woodstock Public Library
    ‪7 min walk‬
  • Airport, Hudson, NY (HCC-Columbia County)
    ‪42 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 Woodstock Retreat • In Town • Hot Tub • Dog Friendly


Welcome to The Sled Hill House!

A private retreat in the heart of Woodstock, NY—just a short walk to town and the Village Green.

Enjoy the entire home and fenced-in yard surrounded by gardens and Catskills foliage. Relax in the new hot tub, gather around the fire pit, or dine outside on the patio.

Perfect for couples, small families, friends, and longer stays looking for a relaxing getaway—with restaurants, shops, galleries, live music, and hiking just steps away.

Dogs are welcome, but please check with me first.

Monthly and seasonal stays available at a discounted rate.

Update: The hot tub has been replaced and is working great. The wood-stove has been decommissioned. All rooms have heaters to ensure the house is comfortably heated throughout the winter months.

The Space:
Located on a private, hidden road one block from the center of town. Enjoy complete privacy—the entire house and yard are yours alone.

Highlights
• Hot tub, fire pit & BBQ with new Weber Grill
• Private fenced-in yard
• Bistro lighting and secluded patio dining area
• Short walk to the Village Green where you’ll find a mix of restaurants, shops, coffee spots, and live music

Inside the Home
Features 2 queen bedrooms with A/C, a cozy living room with large Roku TV, and a bright, spacious loft with games, puzzles, movies, and an additional smart TV—perfect for artists, musicians, or writers, and also ideal as a home office or workout space.
The fully equipped kitchen includes new appliances, dishwasher, microwave, coffee maker, and laundry. You'll also find cookware, utensils, coffee, tea, and a full selection of spices and oils for easy meals at home. Queen air mattress and futon in loft for groups over 4.

Outdoor Living
Relax in the new hot tub, gather around the fire pit, or cook on the Weber Grill and dine outside under bistro lights on the secluded patio.

Parking
2 on-site parking spaces plus additional street parking available.

Guest access:
You’ll have full access to the entire home during your stay—it’s all yours. The property features a fully fenced in yard and private parking for two vehicles. For HITS guests, oversized vehicles can fit in the driveway, and additional street parking is available if needed.

Interaction with Guests:
I live just outside of town and I usually respond to texts immediately. I have full time maintenance help if I am not readily available.

Other Details to Note:
The house is just a short walk or quick drive to local hiking trails, sits one block behind Woodstock’s main street, and is a two minute walk to the bus stop. You’ll find a variety of family-owned restaurants, an organic market, boutiques, thrift and metaphysical shops, and a pharmacy all within easy reach.

I hope you enjoy my home and our town as much as I do, and treat both with care. The house includes a deck and porch areas for relaxing outdoors, but please no smoking inside. As part of the Woodstock Artists community, guests are asked to be respectful of neighbors and the peaceful nature of the area.

Pet Policy: Dogs welcome, but please check with me first. While the yard is fenced, we ask that guests be mindful of neighbors: dogs cannot be left alone or bark excessively. Many of the nearby shops and restaurants are dog friendly!

Day Trips: The home is a short drive to Hunter, Windham, and Belleayre ski areas. Vermont is about 1.5 hours away, and both NYC and the Adirondacks are roughly two hours away—perfect for a day trip while still making it back in time for dinner at one of the great local restaurants nearby.

Please message with any questions—we’re here to help make your Woodstock stay great.

Sled Hill House | Town of Woodstock Permit #20N-063
Our prices include all fees. No hidden fees.

Add dates for prices

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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

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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 Ulster Performing Arts Center. 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.
View more Cottages in WoodstockOpens in a new window
Map
Woodstock, NY

What's nearby

  • Catskill State Park - 1 min walk - 0.0 km
  • 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
  • Woodstock Public Library - 7 min walk - 0.6 km

Getting around

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

Restaurants

  • ‪Stewart's Shops - ‬7 min drive
  • ‪Dunkin - ‬6 min drive
  • ‪Good Night - ‬6 min walk
  • ‪Tinker Street Tavern - ‬4 min drive
  • ‪Bread Alone Bakery - ‬3 min walk

Frequently asked questions

Is Private Woodstock Retreat • In Town • Hot Tub • Dog Friendly pet-friendly?

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

How much does it cost to stay at Private Woodstock Retreat • In Town • Hot Tub • Dog Friendly?

As of 26 Mar 2026, prices found for a 1-night stay for 2 adults at Private Woodstock Retreat • In Town • Hot Tub • Dog Friendly on 11 Jun 2026 start from £195, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Private Woodstock Retreat • In Town • Hot Tub • Dog Friendly?

On-site parking is available at the property.

What time is check-in at Private Woodstock Retreat • In Town • Hot Tub • Dog Friendly?

Check-in begins at 3:00 PM.

What time is check-out at Private Woodstock Retreat • In Town • Hot Tub • Dog Friendly?

Checkout is at 11:00 AM.

Where is Private Woodstock Retreat • In Town • Hot Tub • Dog Friendly located?

This family-friendly Woodstock cottage is within a 5-minute walk of 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. 117 out of 135 reviews
Rating 8 - Good. 16 out of 135 reviews
Rating 6 - Okay. 2 out of 135 reviews
Rating 4 - Poor. 0 out of 135 reviews
Rating 2 - Terrible. 0 out of 135 reviews

9.4/10

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

Verified

10/10 Excellent

Brian H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host was great and the property was amazing. Perfect location and super cozy. Would absolutely return.
Stayed 3 nights in Feb 2026
Verified

10/10 Excellent

Anissa M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful place, the hot tub was clean and fun! Close to stores and restaurants! The owner is very kind and helpful! I’d stay here again!
Stayed 2 nights in Feb 2026
Verified

10/10 Excellent

Tom A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was very cozy. Location was so close to everything. Dave was a great host, and was very attentive and responsive. Perfect getaway for me and my wife. Highly recommend.
Stayed 2 nights in Jan 2026
Verified

10/10 Excellent

andrew m.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic location. Close to everything in townAnd quiet. I loved the second living room in the loft.
Stayed 3 nights in Dec 2025
Verified

10/10 Excellent

Glenn B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great time with the dogs. No place better to get snowed in. 20 inches of snow while we were there, we’ll certainly come back… maybe in a warmer time of year.
Stayed 3 nights in Jan 2026
Verified

10/10 Excellent

David B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect balance of feeling secluded but only a 1 minute walk to the main strip (cafe, CVS, etc.). Fully fenced yard for the dog and close to good hiking. Host was very responsive to any questions in the lead-up. Place was clean with all required amenities. Lovely stay.
Stayed 7 nights in Dec 2025
Verified

10/10 Excellent

Angelina B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property was adorable and host was very attentive. The perfect property for a girls trip!
Stayed 4 nights in Oct 2025
Verified

10/10 Excellent

Kirstan B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed here for my honeymoon and it was perfect! Private and relaxing, cozy spots to hang out, well stocked kitchen, lovely hot tub, and awesome location right in the middle of town. It was great to get to walk to all the restaurants & shops. The host was responsive and went out of his way to make sure the hot tub was in good working order for our stay which we really appreciated. Check in / check out was incredibly easy. We would definitely stay here again!
Stayed 4 nights in Oct 2025
Verified

10/10 Excellent

Julia G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful Thanksgiving break! The house is right in town but tucked on a side street so it is quiet. The house was clean and cozy and just right for our family and our dog. The yard was safely fenced and had enough room for the pup for stretch his legs in the morning. The house is within walking distance of whimsical shoppes, amazing eateries and waterfall laden hiking trails. The host was responsive yet unobtrusive. All in all a magical getaway!
Stayed 7 nights in Nov 2025
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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

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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