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

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Smart TV, fireplace, books, stereo - Private Woodstock Retreat • In Town • Hot Tub • Dog Friendly (Woodstock)
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Banquet hall - Private Woodstock Retreat • In Town • Hot Tub • Dog Friendly (Woodstock)
Exterior detail - Private Woodstock Retreat • In Town • Hot Tub • Dog Friendly (Woodstock)
Property grounds - Private Woodstock Retreat • In Town • Hot Tub • Dog Friendly (Woodstock)
Experience the charm of Sled Hill House, a secluded bungalow in the heart of Woodstock village. Enjoy private outdoor seating surrounded by beautiful foliage, a sunny loft area perfect for work or play, and comfortable living spaces with large screen Roku TVs. With high-speed Wi-Fi and modern appliances in the kitchen, this family cottage offers relaxation and convenience.

Reviews

9.8 out of 10
Exceptional

Entire home

2 bedrooms1 bathroomSleeps 4149 sq m

Popular amenities

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

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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. Walking distance to music venues.

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

Property amenities

Ski

  • Cross-country skiing nearby
  • Snowboarding nearby

Pool/Spa

  • Hot tub

Internet

  • Available in the cottage: Free WiFi

Parking and transport

  • Car required
  • Limited on-site parking (max 2 spaces)

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Ice maker
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room
  • Wood stove

Entertainment

  • Books
  • Games
  • Smart TV with cable/satellite channels
  • Stereo

Outdoor areas

  • Barbecue grill
  • Fenced yard
  • Firepit
  • Garden
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Computer monitor
  • Desk
  • Desk chair
  • Office

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • One pet total

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Area rugs in public areas
  • Hardwood flooring in public areas
  • No lift
  • Stair-free path to entrance
  • Well-lit path to entrance
  • Designated smoking areas
  • Note from host: Smoking on outdoor patio only

Services and conveniences

  • Iron/ironing board
  • Limited housekeeping

Location highlights

  • In a village
  • Near a health/beauty spa

Things to do

  • Arcade/game room
  • Golf
  • Gym
  • Snow sports gear
  • Basketball nearby
  • Birdwatching nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Ice skating nearby
  • Kayaking nearby
  • Mountain biking nearby
  • Mountain climbing nearby
  • Rafting nearby
  • Rock climbing nearby
  • Sledding nearby
  • Swimming nearby
  • Water tubing nearby
  • Wildlife walks nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Garden
  • Unit size: 1,600 square feet

Similar properties

Policies

Check-in

Check-in time starts at 3:00 PM
Minimum check-in age - 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
1 total pets

Children and extra beds

Children are welcome

Events

No events allowed

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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

We should mention

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

Property is also known as

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About the area

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. Visit our Woodstock travel guide
View more Cottages in Woodstock
Map
Woodstock, NY

What's nearby

  • Catskill State Park
    Catskill State Park
    1 min walk - 0.0 km
  • Manufacture of guitars of the brand Woodstock.
    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 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.

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

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 118 out of 136 reviews
Rating 8 - Good. 16 out of 136 reviews
Rating 6 - Okay. 2 out of 136 reviews
Rating 4 - Poor. 0 out of 136 reviews
Rating 2 - Terrible. 0 out of 136 reviews

9.4

Cleanliness

10

Location

10

Staff & service

6.0

Property conditions & facilities

Reviews

Verified

10/10 Excellent

Christina

Liked: Cleanliness, check-in, communication, listing accuracy
From the very start, communication with Dave was excellent. He was incredibly helpful and responsive. The place was even nicer in person than the photos. It was spotless, thoughtfully prepared, and had everything we needed for a comfortable weekend stay. Although it was quite cold outside, the home was cozy and warm, clearly well insulated, and the wood-burning stove was such a treat. We also braved the cold to enjoy the hot tub, which was absolutely delightful. The location truly can’t be beat. We were able to walk to everything we needed in Woodstock, and for the one outing that took us just outside of town to Bearsville Theater, Dave recommended a car service that was outstanding. We can’t say enough good things about our experience and are already looking forward to coming back. Highly recommend!
Stayed 2 nights in Feb 2026
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

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

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

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

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
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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

8/10 Good

Chris K.

Liked: Check-in, communication, location, listing accuracy
Disliked: Cleanliness
The house was in an excellent location and very comfortable. The neighborhood was quiet and perfect for walking our dog. Both the front and back yards were fully fenced, and the owner was very responsive.The home had everything we needed for traveling with a dog, and the small outdoor sitting area was a favorite spot. We enjoyed morning coffee there before walking to nearby restaurants and bars. The surrounding area was also great for short drives and exploring.That said, the house could use a bit more attention to cleanliness. The air conditioners were somewhat musty, and the bedding had an odor that required extra washing. The washer and dryer also had a lingering smell, and the hot tub’s chemical scent was a bit strong, so we chose not to use it.Overall, a very comfortable and well-located home that’s ideal for travelers with dogs, with just a few areas where housekeeping and maintenance could be improved.
Stayed 8 nights in Sep 2025
Verified

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
Verified

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
Verified

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
Verified

8/10 Good

Rich D.

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

Relaxing Family Retreat in Woodstock Village

The house was in a great location; within walking distance of the village, a CVS, and food store. We had a great time walking into town to shop, have meals, dessert, and loads of adventure with our toddler and family black lab. The fenced in yard was perfect for the dog and our on-the-go toddler. We had a great family stay. Upon arrival at the scheduled check in tim,e the house wasn’t readily cleaned after the previous guests. It was frustrating after traveling with a car sick toddler. Dave was quick to respond to our inquiry and the cleaning employee showed promptly. We left the house for town for about 2 hours. When we arrived back the floors still seemed untouched as when we first arrived which made us uneasy to let our toddler play freely. We brushed it off and decided to enjoy the evening with a cocktail and relax in the hot tub. Unfortunately the hot tub was not working properly, no jets. Dave again responded promptly to the issue, but it wasn’t able to be fixed for us to fully enjoy the amenities. Dave did offer us an additional night's stay, free of charge, to help accommodate the couple of issues, which was was very generous of him! Besides the few unexpected mishaps, we definitely enjoyed our stay, and hope to return in the future with expectations that the season opening quirks will be worked out.
Stayed 3 nights in Apr 2024
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