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Private Woodstock Retreat • Walk to Town • Hot Tub

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A cozy living room with a brown leather sofa, a coffee table, and a television. There is a staircase with wooden beams and a blue wall.
A spacious hall with a central statue, rows of red cushions, and traditional decor.
A garden with a black fence, a yellow door, and a tree with white flowers.
A black house with a yellow door, a stack of firewood, a welcome mat, and a potted plant.
A backyard with a wooden fence, a yellow umbrella, string lights, a hot tub, and a garden area.

Reviews

9.8 out of 10, Loved by Guests
Top 10% of guest reviews in this area
Set in a village, this cottage accommodates 4 guests with 2 bedrooms and 1 bathroom. It features 1 hot tub and offers games for entertainment. Enjoy outdoor areas like a deck, yard, and balcony, while adventure activities such as fishing, kayaking, and hiking await nearby, along with attractions like SweetHeart Gallery and Woodstock Music Shop. The stay is pet-friendly.

Highlights

  • Bring your furry friends
    Top-rated for creating memorable stays with your pets.
  • Arcade/game room
    A rare find - fun for all ages with on-site arcade/game room.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Near Catskill State Park
2 bedrooms1 bathroomSleeps 4

Popular amenities

  • Hot tub on site
  • Onsite parking available
  • Dog-friendly
  • Kitchen
  • Washer
  • Air conditioning

Explore the area

View in a map
Woodstock, NY
  • Place, Catskill State Park
    ‪1 min walk‬
  • Place, Woodstock Music Shop
    ‪5 min walk‬
  • Place, Colony
    ‪6 min walk‬
  • Airport, Hudson, NY (HCC-Columbia County)
    ‪53 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 • Walk to Town • Hot Tub

The whole house is yours: no host on site and no other guests. This private, quiet 2-bedroom home sits on a hidden lane one block behind Woodstock's main street. Walk to the Village Green, restaurants, shops, galleries and live music, then come back to your own fenced yard, hot tub, fire pit, grill and patio under bistro lights. A working wood stove makes winter cozy. Great for couples, small families, friends and dogs. Weekly and monthly rates available.

Highlights
• Walk to the Village Green, restaurants, shops, coffee spots and live music
• Hot tub, fire pit & BBQ with Weber grill
• Private fenced-in yard with a gate (great for dogs)
• Bistro-lit patio dining area
• Working wood stove, plus heaters in every room for cozy winters

Inside the Home
2 queen bedrooms with A/C, a cozy living room with large Roku TV, and a bright, spacious loft with games, puzzles, movies, yoga mats and light weights, and a second smart TV. Perfect for artists, musicians or writers, and ideal as a home office.

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 the loft for groups over 4.

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

Parking
2 free on-site parking spaces plus additional street parking. For HITS guests, oversized vehicles can fit in the driveway.

Getting Around
The house is a short walk or quick drive to local hiking trails and a two-minute walk to the bus stop. Family-owned restaurants, an organic market, boutiques, thrift and metaphysical shops, and a pharmacy are all within easy reach. Hunter, Windham and Belleayre ski areas are a short drive; NYC and the Adirondacks are about two hours away.

Interaction with Guests
I live just outside of town and usually respond to texts right away. I have full-time maintenance help if I'm not immediately available.

Pet Policy
Dogs welcome, but please check with me first. The yard is fenced, but please be mindful of neighbors: dogs can't be left alone or bark excessively. Many nearby shops and restaurants are dog friendly!

House Notes
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.

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 2 total)
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Smoking

Smoking allowed: in designated areas
Smoking on outdoor patio only

Important information

You need to know

Property # 1071071
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
Onsite parties or group events are strictly prohibited
Long-term renters welcome
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

About the neighborhood

Woodstock

Woodstock is home to this cottage. Catskill State Park and Thorn Preserve - Catskill Center reflect the area's natural beauty and area attractions include Kiwanis Ice Arena and Ulster Performing Arts Center. Looking to enjoy an event or a game while in town? See what's happening at Dietz Stadium or HITS-on-the-Hudson. Take in the nearby slopes with cross-country skiing and snowboarding, or check out other outdoor activities such as sledding and ice skating.
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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 - 8 min walk - 0.7 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
  • ‪Cumberland Farms - ‬3 min walk
  • ‪Bread Alone Bakery - ‬3 min walk
  • ‪Tinker Street Tavern - ‬4 min drive

Frequently asked questions

Is Private Woodstock Retreat • Walk to Town • Hot Tub pet-friendly?

Yes, this property allows dogs (limit 2 total).

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

As of Oct 1, 2026, prices found for a 1-night stay for 2 adults at Private Woodstock Retreat • Walk to Town • Hot Tub on Nov 30, 2026 start from $347, 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?

Onsite parking is available at the property.

What time is check-in at Private Woodstock Retreat • Walk to Town • Hot Tub?

Check-in begins at 3:00 PM.

What time is check-out at Private Woodstock Retreat • Walk to Town • Hot Tub?

Check-out is at 11:00 AM.

Where is Private Woodstock Retreat • Walk to Town • Hot Tub located?

Situated in Woodstock, this cottage is within a 5-minute walk of Catskill State Park, Woodstock Music Shop, and Woodstock Artists Association and Museum. SweetHeart Gallery and Woodstock Playhouse are also within 10 minutes.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 127 out of 146 reviews
Rating 8 - Good. 17 out of 146 reviews
Rating 6 - Okay. 2 out of 146 reviews
Rating 4 - Poor. 0 out of 146 reviews
Rating 2 - Terrible. 0 out of 146 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 review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Rental was just as described. Beds were comfortable, kitchen is well equipped. House was clean and comfortable. Walk into town was short, restaurants right around the corner! Hot tub was terrific. In short, we had a delightful time! Highly recommended!!!
Stayed 3 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was great, we really enjoyed the upstairs area for relaxing and watching TV. The outdoor area was fun as we enjoyed the fire pit and s'mores in the evening. The location was fantastic... Once we arrived, the car was not used at all to explore Woodstock. Everything was within walking distance. Definitely, would recommend staying at this location. Our family of 4 found it to be a perfect spot .
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent
Stayed 6 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great stay! The location was perfect—an easy walk into town, which made everything super convenient. The house was clean, comfortable, and well cared for. The beds were especially comfortable, and the kitchen had everything we needed. We would definitely stay here again!
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
I stayed three nights with my partner and enjoyed the location, the hot tub, the upstairs TV room, and the woodburning stove. It's close to everything!
Stayed 3 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great time at Dave's house. It was a very comfortable and clean home. The location could not have been better. Right in the heart of town on a quiet street. Walkable to all the restaurants and shopping. Can't wait to come back!
Stayed 5 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing place and great location
Stayed 2 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house beautiful home and host was super welcoming!
Stayed 2 nights in Feb 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great experience - love the dog door
Stayed 2 nights in Mar 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We always enjoy staying at "Dave's" in Woodstock. This house is the perfect location.And we love that are dogs are so comfortable there.
Stayed 4 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great weekend here. We’ll be back!
Stayed 3 nights in Mar 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

8/10 Good

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

Great location

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

8/10 Good

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 review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a nice stay in this cozy home. We particularly enjoyed lounging on the spacious sectional when we weren’t sleeping on the comfortable bed or exploring all that the Hudson Valley has to offer. Dave’s messages were friendly and timely. We didn’t need to ask for anything because the house was well equipped with everything we needed. We accidentally left something behind and even before we noticed it was gone, the cleaner messaged with a plan to mail it to us. We will definitely consider staying here again for another visit.
Stayed 3 nights in Apr 2026
Verified review

8/10 Good

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 review

10/10 Excellent

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

10/10 Excellent

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 review

10/10 Excellent

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

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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