NY 1129 The Highland Villa Woodridge-Upstate, NY


Inquire for Booking Details

  • Drone footage - The Highland Villas and beautiful surrounding Catskill mountains and Fall foliage as seen from the air
  • The Villa and Beautiful Surroundings
  • The Villa and Beautiful Surroundings

NY 1129 The Highland Villa Woodridge-Upstate, NY






360 View

Sleeps 10
Bathrooms 4


Every booking includes mandatory insurance, and cleaning fees in addition to the nightly rent. Please request a quote using the form for exact fees and total.

Park your car in front of the two-story Highland Villa and you will feel as though you just arrived “back home.” Beautiful landscaping escorts you up the path to the entry porch, where two chairs and a small table await. Take a seat and relax awhile before you open the front door and let the warmth of the sun welcome you to Woodridge.

Upon stepping inside you are met with a beautiful dark wood-tone and granite kitchen. The large island seats six for casual dining and surrounds the milchig prep area and sink. The main counter has a fleishig sink as well as plenty of drawers and cabinets. There is also an electric plata, hot water urn, and crock pot for Shabbos. Stainless steel appliances complete the look of this modern, functional kitchen.

Just a few steps away and you enter a huge living and dining area painted a relaxing seafoam green, with high vaulted ceilings that provide a dramatic effect and open up the space even more. The dining room table coordinates in style with the kitchen motif and seats eight with ease. There is a sideboard that contains all of your Shabbos needs, such as challah board and knife, bentchers, candles, etc. plus seforim and siddurim, obviating the need to shlep them from home. Impromptu gatherings with friends are easy and fun with the large bbq grill and zero gravity lawn chairs that are located outside on the deck, directly off the dining room.

The living room is outfitted with comfortable seating on the leather crème color couch and two recliners, and boasts an electric fireplace for making wintry nights cozy ones. The view from the oversized windows is magnificent, as it features the enormous beautiful back yard area of the property.

Three bedrooms and three full baths are located on this main floor. There is a master bedroom with two twin beds that offers an en suite with bathtub. Two other bedrooms each have two twin beds, and one bathroom has a tub while the other is outfitted with a shower stall.

Off the dining area are steps leading you downstairs. Your kids will gasp in delight at the enormity of the carpeted den. With the combined ping pong and pool table, L-shaped wraparound couch, and huge open space to play twister and build lego towers, calling them upstairs for the Shabbos Seudah will be wasted effort on your part. Perfect for the married children who are bringing their own kids, on this floor you will also find two additional bedrooms plus a “jack and jill” full bathroom with tub.

Sliding glass doors lead out from the den to the expansive fenced in backyard where the choice will be a difficult one when deciding what to enjoy first. The property backs up to the famed “Rails to Trails” biking and hiking path that takes you through the town on your own personal tour. If you prefer to stay “closer to home,” you can hang out on the hammock, dine al fresco on the picnic table, or shoot some hoops on the basketball court. The young ones can entertain themselves for hours on the swing set and playground equipment and enjoy endless rounds of relay races and tag. And when everyone is ready for some cooling off, the 36×16 foot covered in-ground swimming pool completes this magical “backyard package.” Built with the frum vacationer in mind, it offers privacy from the neighbors with its huge dome covering while still providing plenty of sunlight under the tinted plexiglass. Heated in the wintertime, you can go swimming every day of the cold months, even if the snow is piled up high on the ground.

Woodridge is the only town in the mountains that has offered a daily minyan three times a day for the past 100 years. And with the year-round kosher supermarket steps from your villa and the shul a five minute walk from your front door, vacationing at The Highland Villa is something you can put on your wish-list for every day of the year.


Additional cleaning and damage waiver fees apply to every booking.

Season NamePeriod NameStartEndDaily rate
Post Pesach 2022Post Pesach 202204/26/202206/01/2022from $695.00
Shavuos Weekend 2022Shavuos Weekend 202206/02/202206/06/2022from $695.00
Late Spring 2022Late Spring 202206/07/202206/29/2022from $695.00
July 4th WeekendJuly 4th Weekend 202206/30/202207/04/2022from $695.00
Early Summer 2022Early Summer 202207/05/202208/07/2022from $695.00
Post Tisha B'av 2022Post Tisha B'av 202208/08/202209/05/2022from $695.00
Early Fall 2022Early Fall 202209/06/202210/05/2022from $695.00
Succos 2022Succos 202210/06/202210/18/2022from $795.00
Late Fall 2022Late Fall10/19/202212/17/2022from $695.00
Winter 2022-2023Winter 2022-202312/18/202203/08/2023from $695.00


Indoor Amenities

  • Central Air Conditioning and Heating
  • Linens and Towels
  • Shabbos Pkg. - Tablecloth, Tea Lights, Havdala Set, Becher, Etc.
  • Pack & Play / Crib
  • Hair Dryer
  • Seforim and Siddurim
  • Dedicated Internet Access
  • No TV
  • Washer/Dryer
  • Iron/Board
  • Billiards or Game Room
  • Ground Floor Rental

Outdoor Amenities

  • Year-Round Enclosed Outdoor Pool
  • Deck or Patio
  • Gas BBQ Grill
  • Swing Set / Playground Set
  • Private Parking

Area Amenities

  • Eiruv
  • Frum Neighborhood
  • Quick Walk to Shuls and/or Kollel
  • Fitness Trail: Walking / Running / Jogging - Waterfront Path
  • Playground / Park within Walking Distance
  • Golf Courses Nearby
  • Boating and Biking Facilities Nearby
  • Kosher Restaurants & Eateries Nearby
  • Groceries & Shopping Nearby

Kitchen Amenities

  • Kosher Kitchen (Chezkas Kashrus)
  • Eat-In Kitchen
  • Shabbos Hot Water Urn
  • Shabbos Hot Plate (Electric Plata)
  • Shabbos Crock Pot
  • Full Size Refrigerator / Freezer
  • Full Size Oven / Stove
  • Microwave
  • Dishwasher


  • No Smoking anywhere on property
  • No Pets Allowed
  • No Motzei Shabbos Check-outs
  • 2 Night Minimum - No Exceptions!


5 Star+ stay at Highland Villa in Woodridge

The Highland villa was spectacular! It had everything you'd want when on vacation, the grounds were beautiful, the place was spacious and comfortable, a lot of living space and of course the pool is outstanding. The staff at Florida kosher villas were helpful and Mr Rosenberg was very accommodating to our needs. We had a blast staying there for the weekend and look forward coming back again soon iyh. Thanks

Amazing stay at The Highland in Woodridge

The heated Pool is amazing! Hosts were very responsive. House is well-kept and clean. Would definitely rent again.

winter vacation rental in Woodridge NY

House was clean and comfortable. Everything was as advertised, Owner was pleasantly responsive to all our questions. The pool was wonderful- large, clean, and warm despite the subzero temperature outside. Bottom line- everyone had a great time!

A wonderful vacation rental in Woodridge, NY

We had a wonderful time staying at the Highland Villa Woodridge. The house was clean and conveniently located near shuls, stores with kosher take out, a kosher bakery and a kosher supermarket. The pool was amazing. Having the opportunity to have a private winter family swim was exciting for both kids and adults alike. We would definitely recommend the house to others and hope to rebook the house in the future

Great service and very house. We were happy

The house was amazing and exceeded expectations. The pool was heated to a very comfortable temperature which is unusual especially in the fall. House is clean private yet close to all. We highly recommend this house.

Beautiful Place - Excellent Service

We really had a great time here. The owner thought of everything from the big things to the small. Beautifully maintained, clean, comfortable, spacious. We loved the pool.

We had a great stay for our special needs group

Thank you, we had a very nice time. Very clean, organized and management is very friendly and helpful toward special needs groups and families. 

A Peaceful Pesach stay in the Country!

We were 9 adults & 3 children in the Highland Villa. The accommodations were very good for our family and we had a fantastic yomtov. Thanks you so much 

Great Shabbos getaway in Woodridge

The villa was clean comfortable spacious and very nicely set up to accommodate guests from arriving till leaving all details included so many things to do and a well-maintained pool minyan and grocery close-by kids had a blast of a shabbos including the adults.

Mr. Rosenberg is a great host and the Lakewood Hosts team handled the booking. 

We were very happy and would recommend it to other families. 

Loved our stay at The Highland in Woodridge, NY

Great house great service, as usual, thank you for providing us with a great vacation we loved it. 

Everything worked well and was as advertised

A very comfortable home with a lot of space, perfect for a weekend getaway, and really close to a few shuls, plus a large heated pool in the back, and a nice game room with a pool table/hockey table. The ownership were very pleasant to deal with as well, and we would certainly visit again!

Excellent house all around for a frum family

We had a phenomenal weekend at the highland villa. It is next to a shul and year round kosher supermarket. It’s a 5 min drive from year round kosher pizza and ice cream. The house itself was exactly what we expected. It looks exactly like the posted pictures. We immensely enjoyed the extra space this home has to offer. It has a year round heated pool! There is swing set and basketball court as well! We really enjoyed every aspect this house had to offer!

Review of Woodridge New York property

We had a great time here. Mr. Rosenberg the manager was very attentive to our needs. The house is very nice and clean and we loved the heated pool. 

Recommended !!

Very Satisfied. with The Highland Villa We had a great stay !

House was clean and comfortable. Easy to deal with thermostat, pool etc..

Near shul . Near Kosher Supermarket. Very good customer services and in general it is a very nice property well kept and a highly desirable area 

Great Experience with Shaya and The FKV Team !

We B'H had a very good experience and we really enjoyed it. great service and clean house and pool. 

Shabbos in Woodridge, NY

דער הערליכער "היילענד ווילא", אין הארץ פון די אידישע קעסטקיל בערג אין אפסטעיט ניו יארק.

אין דעם מאיעסטעטישן ווילא -- צוגעשטעלט און אויסגערישט דורך די באקאנטע משפחת וויינבערגער, אייגנארטיג בארימט מיט זייערע הערליכע ווילאס אין פלארידא, זייערע זעלטן באקוועמע האוסטס אין לעיקוואד -- ערווארט אייך נישט קיין האר ווינציגער ווי א לוקסוריעזע וואקאציע היים.

Woodridge House Simply Fantastic

We were a family of 10 and did not feel squishy at all. Plenty of space. Great outdoor area and pool was warm and yummy. We were wre able to swim on Friday afternoon before Shabbos, motzei Shabbos and Sunday morning. A + Service from management. 

Nice house on Highland Ave in Woodridge

Just wanted to say a quick thank you, we had an awesome time at our recent stay at your house on highland ave the villa was spacious, clean and very tastefully appointed with nice decor, and it was thoughtfully supplied with all the amenities for a wonderful and relaxing stay Great location and the shul is a few minutes away


Shabbos in Woodridge NY at The Highland Villa

Thanks for a great mini vacation spot ! We were a few couples and it’s our second time back and we really enjoyed it . The rooms and amenities are nice and the big playroom and heated pool makes it a full package. Very close to Shul. Highly recomneded to all hemishe families. 

Could not have been happier with The Woodridge House

Truly great service , very nice house, very close to sheel , heated pool  Fabulous 

The service we got is highly recommended, will definitely reach out again. Thank you.

Roomy House on Highland Ave Woodridge Heated Pool

Nice open areas for eating and playing.  bedrooms were nice. The owner was very strict and didn't allow us to bring more than 10 people . Great house , great pool ., near rabbi lebovitz shul.  very nice family getaway weekend

Nice for a family getaway in the country.

Overall very satisfied with this vacation spot. Was local but far enough to consider it a family getaway. The house was conducive for 4 couples/ a baby plus some singles with space to spread out and not feel on top of each other. Pleasantly surprised to find two pack and plays plus a booster seat. The upstairs is definitely a 5 but the basement accommodations are a little smaller (rooms are significantly smaller and beds are very narrow). We had a pool table but it was a little slanted to be able to play properly, however both floors had nice open areas for family time over shabbos. Some toiletries were available and others weren't’t so it’s best to bring most of your own stuff minus linens towels and toilet paper. Swimming pool was amazing!! For day and night time swim. Huge bonus.

Great house . Wonderful amenities. Good location.

Great house . Wonderful amenities. Good location. It was nice having the pool . Kids loved it Kosher restaurants near by shuls too . All you need and more

The house and the property is an ideal vacation home for family and kids

Hi, The house and the property is an ideal vacation home for family and kids. The pool is safe when locked and the property is gated all around making it safe for little kids to play outside. All in all we had a great time. Thanks

Great place to stay

We brought our 3 married children, spouses and our grandchildren. We stayed from Friday until Monday. The house was beautifully done, clean and new. Our beds were comfortable and the A/C was excellent, allowing us to choose the temperature. There was plenty of space to sprawl out so that we weren't on top of each other and the children had lots of room to run around inside and out. The covered pool was a bonus and well kept. The neighbor across the street was very sweet and let us know that if we needed anything, to just ask. If we want to go back to the Catskills, I would love to stay here again. There were 3 shuls in walking distance and plenty of stores (for the last minute items you forgot) and restaurants. There's a plata, urn, crockpot, challah cover, a few tea lights, 6 or 7 bentchers, havdallah candle and b'samim. There are dishes and silverware but not a complete set of 8. I brought my own pots/pans and paper/plastic goods. There are no serving dishes so we left everything in foil on the counter and served buffet style. Whatever you need at home, bring with you.(dishwashing detergent, extra shampoo, etc.) The owner is very easy to work with and very accommodating. It was worth the money to have a nice place to stay with a kosher kitchen and frum environment.

Great house right near the shul in Woodridge

We really enjoyed our vacation and had the very best time in this Villa. I would recommend it for everyone, the pool was amazing! Just 1 little minus, I had to buy myself coffee & sugar.. otherwise nothing was missing was from the house. We really had a very nice Shabbos and would suggest every family that can afford it should get away at least once every few years.

The perfect Pesach Family Getaway

Our family of 7 loved being in this house for Pesach. The owner was extremely accommodating and everything was exactly as advertised. The indoor pool was enjoyed by us all. We would recommend this house and this company to any frum family. 

Amazing weekend in The Highland Villa, Woodridge, NY

This house is very beautiful. We were 4 couples 4 kids the space was perfect. The kids loved it and so did the adults. I would definitely recommend this house to anyone.

Great experience at The Woodridge Villa

We really had a great experience. We stayed in one of your other properties and when we saw this on the website we knew we had to try it. Recommended for any mishpucha for a Shabbos away from the city. Heimishe sheel a few min away and a heated pool what more can you ask for ? Also Mr Rosenberg the manager is very helpful and available and responds quickly. to any calls or texts. 

The perfect place for a "?????? ??? ????'???" vacation in The Highland Villa

The house is beautiful and spacious. We had a great time.

Reviewed: 07/30/2017 for a stay in July 2017

From the minute we arrived until we left every second was worth it

The Highland villa was so nice CLEAN and luxury, furnished with everything a Yiddish house needs to have to enjoy a beautiful vacation in the heart of Woodridge with access to all heimish kosher stores and a sheel a few minutes away...

Our children really enjoyed the pool which was so much fun!! I recommend this to all my friends and for anybody looking to enjoy a vacation you will enjoy .

Call FKV and you can rest assured you will get what was promised to you. 

The H Family Brooklyn , NY 

5 Stars on everything across the board!

We rented a house from Florida Kosher Villas in Woodridge NY and it was our very best vacation ever. We had a kosher kitchen and our own private pool. We loved it. Everything was perfect, The living room, playroom, 5 bedrooms, 4 full bathrooms, the pool, the kitchen, everything.This house has all the small details that makes it a pleasure to stay there, Plus right near Shuls and Minyanim,This was our very best kosher vacation ever. It was a pleasure to deal with Mr. Rosenberg and Florida Kosher Villas. We hope to return there very soon.

The Woodridge/Highland Avenue House is GREAT

We recently spent Shabbos in Woodridge in this house managed by Mr Rosenberg and Mr Weinberger. Very impressed and way better than we expected. The family loved the kids had a blast and the heated pool in middle of the winter was an experience we cant wait to do again next year. We felt like we didn't waste our money and it was well worth the expense.

??????? ????? ???????? ?????

לכבוד ר' ישעי' וויינבערגער מיר קענען זיך נאך אלס נישט איבערקומען אויף דעם געוואלדיגן געשמאקן וואקאציע וואס מיר האבן געהאט ביים איינשטיין אינעם "היילענד ווילא" אין וואודרידש. אין יעדן פרט איז דער וואקאציע געווען אויסנאם, מיר ווייסט ממש נישט וואו אנצוהייבן. דאס הויז - רחבות'דיג, פריש, געשמאק, ברייט, לופטיג, און וואס נישט? די גארטן - גרויס, מיט שיינע גראז און פארברענגען פאר די קינדער, און א פלאץ געאייגענט ממש פאר מנוחת הנפש די סווימינג פול - געווארעמט און זויבער, פריוואט און אהער געשטעלט אויף א געשמאקן שטייגער. די לאקאציע - נאנט צו שוהלן, מקוה, גראסערי, און היימישע געשעפטן, ממש א נחת און אין די זעלבע צייט איז עס פריוואט, נישט אינמיטן די רוישיגע גאסן. ס'איז די חלום פון א דירה! גענוי דאס ריכטיגע ארט פאר איינעם וואס זוכט א געשמאקע זומער וואקאציע. ר' ישעי' וויינבערגער פון  האט א סטאנדארד! און ווען מ'נעמט א דירה ביי אים ווייסט מען פונקטליך וואס מ'נעמט! די סטאנדארטן זענען הויך און ווערן נישט געבראכן. נאכאמאל א דאנק און מיר קענען קוים ווארטן פאר די קומענדיגע וואקאציע מיט  משפחת ראזענבערג, מאנסי

Outstanding First Class Property in Woodridge , NY

Our family recently stayed at The Highland Villa for a long Shabbos Weekend stay. We had previously stayed in one of FKV's Villa in Florida and knew that if they are listing this house it has to be special. We truly were not disappointed at all. A really well appointed upscale house in great condition and plenty of room for our family of 10. The Heated pool was the highlight of our trip and where else can you get a completley kosher house with a heated pool in the winter ? Enough Said. Levy Family Brooklyn, NY

A Great Shabbos Getaway. Woodridge NY Right Near Shul and Stores

The house is absolutely beautiful! ! We enjoyed our stay immensely! ! So clean and fresh and well taken care of! !! The pool is heated and we were able to enjoy it even though it wasn't the perfect pool weather. Thank you so much for making our vacation so enjoyable and pleasant!

This is a really beautiful house and pool! We had an awesome stay in August

This is a really beautiful house and pool! We had an awesome stay in August this year. Both the house and the pool are spacious, well appointed and perfectly clean. The owner of the house is very helpful and very nice to deal with. For sleeping space, in addition to the bedrooms, there is a playroom with a sleeper sofa and air mattress. The playroom also has an air hockey/pool table. That and the swimming pool were such a hit - there was no need to find any other activities for the grandkids, b"H. There is a beautiful kosher kitchen and a working kosher BBQ grill. The pool has a dome over it and is heated - which allows for swimming no matter what the weather. Food is easy - there are a number of pizza shops, restaurant/takeout places and a large grocery - all less than a 5 minutes drive from the house. I recommend this rental highly - it should be a great place to stay even in the Fall or Spring

Thank you for a great Vacation

We rented this house for a Shabbos and we loved every minute of it. The house is beautiful, state of the art equipment. The pool is gorgeous! Totally private, warm immaculate! And the best part is if it rains you can swim anyways! Beautiful linens and towels, house was spotless, we'll stocked. Owner a pleasure to deal with. We have rented many homes but this was something special, would definitely want to go back again. Thank you .