Entire home

Family-Friendly Retreat Close to Town w/ Heated Pool & Hot Tub on 3 Acres

Family-friendly holiday home with outdoor pool and Hot tub

Sitting area off of kitchen with wood stove (firewood provided!)

Overview
Amenities
Policies
Location

Exceptional

4 bedrooms2 bathroomsSleeps 91800 sq ft

Popular amenities

Fireplace
Dryer
Washer
Kitchen

Place, Woodstock Music Shop
Place, Woodstock Golf Club
Place, Overlook Mountain Trailhead
Airport, Hudson, NY (HCC-Columbia County)

Rooms & beds

4 bedrooms (sleeps 9)

Downstairs Bedroom #1

1 Queen Bed

Downstairs Bedroom #2

1 Queen Bed

Master Bedroom

1 King Bed

Upstairs Bedroom

1 Double Bed and 1 Single Bed

2 bathrooms

Downstairs Bath

Toilet · Shower only

Master Bath

Toilet · Shower only · Jetted bathtub

Spaces

Deck or patio

Kitchen

Outdoor play area

Garden

Dining area

About this property

Family-Friendly Retreat Close to Town w/ Heated Pool & Hot Tub on 3 Acres

Experience Woodstock, NY and the Catskill Mountains while staying at our lovely four-bedroom home. Located on nearly three-acres, Our Woodstock House offers both privacy and convenience. The Woodstock Green is just 2.5 miles away, yet from our home you'll hear the sound of the Sawkill River and the stream that bisects our land. Our Woodstock House can be a great spot for exploring the area -- nearby options include river tubing, hiking, skiing, shopping and wonderful dining, but you can also have a great time just relaxing at our home. You can swim in the pool (in season), soak in the hot tub, cook meals with friends, watch movies, listen to music, explore the outdoors or just enjoy the fresh air, all without leaving the property. Our home is designed to accommodate families -- we've got a stash of toys and games for kids, and you won't have to worry about lugging all the accessories that they require: we have a high chair, gate, pack 'n play and more available.

We bought our home in Woodstock, NY after attending Levon Helm's Midnight Ramble several years in a row and falling in love with the area. Our Woodstock House is not just a vacation rental -- it's our family's retreat and we have set it up to be comfortable for our family and yours. The well-stocked kitchen is a joy to cook in, and the space is perfect for sharing with others. The kitchen table seats 8 adults easily, and we have a folding table and chairs for 6 more if you're hosting a crowd. There are two separate sitting areas, with comfortable couches for relaxing with friends. All beds are comfortable and in good condition and we provide all required linens and towels.

Hot tub is available for guests year-round. Pool is open seasonally from Memorial Day to Labor Day it is heated to 78.

Bedroom Setup:
- Master Bedroom has a king bed
- Second upstairs bedroom has a twin bed and a full-sized bed
- Downstairs bedroom has a queen sized bed
- Second downstairs bedroom has a queen sized bed

Woodstock STR Permit: SUP #23-0678

Add dates for prices

Amenities

Pool

Hot tub

Kitchen

Washing machine

Dryer

Pet-friendly

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Pool
Hot tub
Kitchen
Washer

House Rules

Check in after 4:00 PM

Minimum age to rent: 25

Check out before 11:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

Pets allowed: dogs and cats less than 23 kg per pet (limit 2 pets total)

Keep pets off furniture and out of pool

Smoking

Smoking is not permitted

We allow a 30 minute check-out grace period, but there is a $50/15 minute charge for renters that have not left the property on time.

Cleaning fee covers ordinary cleaning, but if excessive cleaning is required, the monies to cover the cost will be deducted from security deposit.

No smoking or candles inside the home. (Except birthday candles!) If you smoke outside, dispose of butts properly. $100 fee for cigarette clean-up.

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

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 and a deadlock

This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

Property Registration Number 10474

We should mention

A car is recommended for transport to and from this property

About the area

Bearsville

Located in Bearsville, this holiday home is on the waterfront. Hunter Mountain and Kaaterskill Falls are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Catskill Mountains. Consider Byrdcliffe Barn for a night out or Kiwanis Ice Arena if you're travelling with kids. Enjoy the area's slopes with skiing, and don't miss out on the sledging and ice skating.

View more Holiday homes in Bearsville

Woodstock, NY

What's nearby

Woodstock Music Shop - 4 min drive - 3.3 km
Woodstock Golf Club - 4 min drive - 4.0 km
Overlook Mountain Trailhead - 10 min drive - 6.4 km
Karma Triyana Dharmachakra Monastery - 10 min drive - 6.4 km
Ashokan Rail Trail- Woodstock Dike Trailhead - 11 min drive - 10.6 km

Getting around

Rhinecliff Station - 31 min drive
Hudson, NY (HCC-Columbia County) - 51 min drive

Restaurants

‪Good Night - ‬4 min drive
‪Bread Alone Bakery - ‬4 min drive
‪Colony - ‬4 min drive
‪Caffe Woodstock - ‬5 min drive
‪Silvia - ‬4 min drive

Frequently asked questions

Does Family-Friendly Retreat Close to Town w/ Heated Pool & Hot Tub on 3 Acres have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

Is Family-Friendly Retreat Close to Town w/ Heated Pool & Hot Tub on 3 Acres pet-friendly?

Yes, this property allows cats and dogs (limit 2 total) with a maximum weight of up to 23 kg per pet. Some restrictions may apply, so please contact the property for more details.

What time is check-in at Family-Friendly Retreat Close to Town w/ Heated Pool & Hot Tub on 3 Acres?

Check-in begins at 4:00 PM.

What time is check-out at Family-Friendly Retreat Close to Town w/ Heated Pool & Hot Tub on 3 Acres?

Checkout is at 11:00 AM.

Where is Family-Friendly Retreat Close to Town w/ Heated Pool & Hot Tub on 3 Acres located?

This family-friendly Bearsville holiday home is located on the waterfront, within a 10-minute walk of Catskill State Park and Woodstock Dog Park. Woodstock Music Shop and Woodstock Public Library are also within 3 miles (5 km).

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

10/10 Excellent

Greg S.

24 Aug, 2025

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

Heather was fantastic to communicate with. She immediately responded to any & all questions or concerns that we had. The pool was a huge hit with everybody (we had a nice, hot week for our stay). Favorites: Pool, Sunroom, & availability of A/C. Needs a wee bit o' work: The 1st floor shower (could use an upgrade). Overall: A great stay for our group.

Stayed 7 nights in Aug 2025

10/10 Excellent

Elizabeth S.

2 Feb, 2025

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

Just perfect!

We had a wonderful time at this home. The privacy is perfect yet so close to everything. Great open floor plan! Loved the sunroom & jacuzzi! We hope to book this summer so we can enjoy the pool & outdoor space.Thank you! Elizabeth

Stayed 3 nights in Jan 2025

10/10 Excellent

Mia M.

15 Apr, 2024

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

Great place to stay

This house is lovely and conveniently located. It has all you need to cook in the kitchen and basics like spices are provided. We were very happy with our weekend.

Stayed 3 nights in Feb 2024

10/10 Excellent

Julia B.

3 Oct, 2019

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

We had the most relaxing weekend celebrating my Grandfathers 90th birthday.

House was perfect and my kids had a wonderful time in the pool. Heather responded to all concerns quickly and house was well stocked.

Stayed 2 nights in Sep 2019

8/10 Good

Melanie Z.

1 Sept, 2024

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

Our 2024 trip

Had a great time, the pool was awesome and the hot tub was even better. Loved the fully stocked kitchen it really helped us with our meals for the week. Host was quick to answer and understanding during one issue, which was corrected fast and efficient. Wont lie the septic smell was unpleasant outside but we managed. Other than updating some pictures i would say id recommend anyone to stay and enjoy a week! Thank you for allowing us to stay!

Stayed 7 nights in Aug 2024

This review was submitted before 2018 and has not been verified.

10/10 Excellent

Roman K.

17 May, 2014

Family friendly home in Woodstock

We stayed at Our Woodstock Home last weekend. It is a beautiful home, and it is kid friendly. It is in a peaceful wooded setting, and comes with all the amenities. The kids had a great time there and had plenty to do: walk by the creek, play on the swings, walk through the woods. Thanks Heather for letting us spend Mother's day weekend as a family in your lovely home..

8/10 Good

Nick N., Chicago, Illinois

16 Oct, 2019

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

Nice time in the country.

Property was nice, we didn't get to try out the pool. Maintenance of the premises could be better.

Stayed 2 nights in Oct 2019

This review was submitted before 2018 and has not been verified.

8/10 Good

Lynne C.

28 Aug, 2016

Lovely family home, clean, wonderful for kids

Heather was a great hostess and really went out of her way to make our stay comfortable. Positives were the toys for the kids, the hot tub, the location, the quick response to complaints that the pool needed to be cleaned, great seating by the pool. Things to improve: it is very very dark in the sunroom at night, the refrigerator needs to be updated, it hums constantly and has no ice maker. The septic tank backed up if we ran multiple loads of laundry and that created a smell.

10/10 Excellent

Susana H., Hoboken

15 Jul, 2020

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

Perfect Home for a NY Getaway

We just returned from a week at this charming home in Woodstock and it exceeded our expectations. The home was exceptionally clean and organized, and offered many amenities that are often missing in rental homes (nice bedding, plush bath and pool towels, great pool toys). The home was also fully stocked (seasonings, coffee, hot chocolate, etc.) and while we did not use any of these (we brought our own), it was nice to see them offered. It's evident that the homeowners are not pinching pennies in their rental and want you to feel at home. The grounds are simply amazing - from the pool, to the hot tub, to the creek, and playground - the kids and adults had an absolute blast. If I had to point to any "cons," I would say that the air conditioner in the kids room is a bit noisy (we couldn't have it on during the evening), and the check-in time (4pm) is too late, especially given the check-out time (11am). Essentially, we lost two days of our week vacation and given it rained 80% of the time, we could've used them (especially the last day since it was the second of two sunny days we had the whole week). I did not ask for a late check-out because our request to check-in early was denied on the basis of the cleaning crew needing the time to clean thoroughly, but given the size of the home, I don't think 5 hours are necessary for cleaning, especially if there are 2-3 people cleaning. However, Heather was absolutely wonderful to deal with overall, and always responded promptly and in a friendly manner, which I really appreciated. (And the home and grounds were spotless.) Overall, I would definitely rent this home again.

Stayed 7 nights in Jun 2020

6/10 Okay

Stephanie K., Washington, DC

14 Oct, 2019

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

Pleasant but Disappointing

Our family of five enjoyed our stay at this property. The layout of the ground floor was excellent, with lots of comfy seating and areas for adults and children to be together. It was wonderful to be able to be in a dog-friendly environment that was surrounded by lovely woods and a lovely play area/pool area/hot tub and grilling sections. However, there were some drawbacks that did diminish our enjoyment of the weekend home. The downstairs bedrooms have little room and few amenities, such as bedside tables. The master bedroom does not have two bedside tables. No rooms have ideal situations for plugging in electronics--way too few outlets for the number of people allowed and no extension cords. The televisions are a mystery to the common person, including a young man in the tech field who was part of our group. More info on the televisions' operation and how to access special channels is needed. The upstairs shower water has a low pressure and probably needs a new shower head. The house is barely clean enough but certainly does not sparkle. Paper products were in short supply in the kitchen--one roll of paper towels, no napkins that we could identify, and few plastic bags. This is difficult because there is no garbage disposal. The dishwasher turns itself on from time to time! Heather was very pleasant to deal with. The only problem on that front was house instructions--we received someone else's in August and did not get ours until the day of arrival after several requests. She was saintly in answering our questions and requests both in advance of and during our stay. All in all, we believe this house is justifiably priced on the high side because of the pool, the play area, the pet allowance, and the setting. We think that the condition of the home and the absences of sparkle and shine in its upkeep and comfort amenities makes the price too high.

Stayed 3 nights in Oct 2019

10/10 Excellent

Linda S.

12 Aug, 2025

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

This place was amazing, it has everything you could possibly need . We loved the deck it was so spacious and the whole pool area was great with plenty of loungers to relax and the kids loved the slide . It is so close to everything and we all had a wonderful time . Thank you

Stayed 7 nights in Aug 2025

10/10 Excellent

Mariana P.

1 Jul, 2025

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

It’s just what we needed

We had a very relaxing time! My 3 and 4 yr old were so happy with the toys and their bedroom. It’s a very beautiful and cozy home with everything we needed. Thank you!!

Stayed 5 nights in Jun 2025

10/10 Excellent

Amanda Eyrich D.

23 Apr, 2025

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

Amazing Catskill Getaway

We've been staying in rental homes in the Catskills for nearly 20 years. This home was one of our all-time favorites! Close to the center of town in Woodstock and also tucked away in the woods with amazing views of the river. Heather was a gracious, responsive host. Can't wait to return again soon!

Stayed 3 nights in Apr 2025

10/10 Excellent

Stephen W.

12 Aug, 2024

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

Great Location

We had a wonderful vacation. The house served it's purpose, mostly just for cooking and sleeping. The location was great for local and short distance activities. We saw deer, a bear and a snake eating a frog. Everyone had a good time.

Stayed 7 nights in Jul 2024

10/10 Excellent

Victoria R.

16 Jul, 2024

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

Great stay for families

A great home for our group, including 2 small children (1 & 3 years old). Loved having the pool!

Stayed 7 nights in Jul 2024

10/10 Excellent

Rachel F.

4 Jul, 2024

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

Relaxing Getaway

We truly enjoyed our relaxing respite. Peace, quiet, and nature from the pool to the hot tub. Thank you for our wonderful vacation!

Stayed 6 nights in Jun 2024

10/10 Excellent

Peter H.

16 Oct, 2023

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

Beautiful property, great house!

The house was very beautiful and well laid out, everything was as-advertised.

Stayed 4 nights in Oct 2023

10/10 Excellent

Michelle G., New York

17 Sept, 2021

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

Woodstock Family Fun

We had a great week! Our family felt so welcomed and comfortable in this lovely Woodstock home which had just about every single thing we could think of to make our stay perfect. The kitchen is well stocked with kitchen appliances and utensils which was helpful as we stayed in and cooked most meals. We had some rainy days and found the house well stocked with games, books, puzzles, dvds and TV apps so plenty to keep everyone busy. My 3 year old nephew also appreciates all the toys that kept him busy on rainy days. On sunny days we spent all day outdoors by the pool enjoying the pool, hot tub, Tiki bar, BBQ, fire pit, playground and nearby stream. The house is close to town so we also got to enjoy strolling by the shops. There is a nearby field and dog park. We also enjoyed hiking the Ashokan rail trail. Would highly recommend this property for any family gathering.

Stayed 7 nights in Aug 2021

10/10 Excellent

Elizabeth G.

18 Aug, 2021

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

Wonderful stay!

Wonderful stay at this Woodstock house with extended family! Kids enjoyed using the pool and swing set everyday. Parents enjoyed the fire pit and hot tub. Great location, close to downtown Woodstock with many nice restaurants and local hiking spots in the Hudson valley. Would definitely go back!

Stayed 7 nights in Jul 2021

10/10 Excellent

Thomas S.

1 Aug, 2021

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

Excellent

The place was great. Exactly as listed. We stayed in late July which was perfect for the stream and pool. Children ages 4, 7 and 8 loved it.

Stayed 7 nights in Jul 2021

10/10 Excellent

Avital B.

24 Jul, 2021

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

A lovely place

We just returned from a great week. The house is specious and clean. The outdoor is well kept and the pool was wonderful. The beds were comfortable. The owner thought of every detail in making the stay comfortable. Lots of books, games for the kids, pool equipment and more. The town is very laid back and the restaurants are good. We had a great time.

Stayed 7 nights in Jul 2021

10/10 Excellent

ANDREA S.

1 Jul, 2021

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

Wonderful home

This house had everything we needed for a perfect week with a multigenerational family. The beds were comfy, the property is gorgeous, the pool was wonderful and the kitchen had everything we needed. It was the perfect getaway.

Stayed 7 nights in Jun 2021

10/10 Excellent

Liliane M.

27 Jun, 2021

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

Family get together

Given my family is all vaccinated but we still wanted a safe family get together, I was happy to find this property through VRBO. The house was just as described and was very clean, well stocked and very comfortable. My family really enjoyed the pool, the hot tub and hanging out in the family sunroom. Great location to explore rhe surrounding area with lots to see. The hosts gave us a well written info pamphlet prior to arriving so we knew where to go for groceries, places to eat, etc. We had a lovely time!

Stayed 7 nights in Jun 2021

10/10 Excellent

Lisa W.

10 Jun, 2021

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

Perfect Weekend Getaway

This house is so perfectly located close to town and nestled within green scenery. It felt like a private oasis. We booked the house on a weekend that turned out to be 90 degree weather so spent the entire time in the pool while listening to music on the outdoor speakers. And then we crashed hard each night in the comfy beds. It was hard to leave.

Stayed 3 nights in Jun 2021

10/10 Excellent

Claudia S.

1 Apr, 2021

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

Weekend getaway

We had a great time at Heather’s property. We loved driving through the nearby windy roads and seeing pretty views of Catskills. This would be a great place to visit in warm weather when the pool is open as well.

Stayed 3 nights in Mar 2021

About the host

Hosted by Heather Cross

I'm a mom, writer, yogini and travel agent. Woodstock has been a peaceful escape from the concrete jungle we live in and a place that we love to spend time with family and friends. It's truly a joy to be able to share our special place with others who hopefully enjoy it as much as we do.

Why they chose this property

Our Brooklyn family wanted a place to escape the hustle and bustle of city life and we just love Woodstock -- the people, the town, the vibe and the music. And the clean mountain air. When we were visiting potential properties my daughter called this one 'Paradise' and I'm inclined to agree.

Now that we've left the city, we still love spending time at our upstate escape. It always feels like vacation time when we are in Woodstock.

What makes this property unique

We love this house because there is plenty of space for entertaining and enjoying one another, but also privacy with four separate bedrooms. It's close to town, but feels very private. We spend a lot of time ourselves at the house and try to make it the perfect place to stay for ourselves, as well as our guests.