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PRISCILLA'S HOMESTEAD: Authentic Private Estate with Pool Tennis FirePit

Family-friendly vacation home in Middletown with an outdoor pool

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Interior - PRISCILLA'S HOMESTEAD: Authentic Private Estate with Pool Tennis FirePit (Middletown)
Exterior - PRISCILLA'S HOMESTEAD: Authentic Private Estate with Pool Tennis FirePit (Middletown)
Sport court - PRISCILLA'S HOMESTEAD: Authentic Private Estate with Pool Tennis FirePit (Middletown)
Fridge, microwave, oven, stovetop - PRISCILLA'S HOMESTEAD: Authentic Private Estate with Pool Tennis FirePit (Middletown)
Interior - PRISCILLA'S HOMESTEAD: Authentic Private Estate with Pool Tennis FirePit (Middletown)
Experience the Authentic Hudson Valley estate, a tranquil get-away built in 1917, where friends and families can reconnect. Take advantage of the heated saltwater pool or relax by the fire pit with roasted marshmallows and delicious s’mores.

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms3 bathroomsSleeps 12372 sq m

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi

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.

PRISCILLA'S HOMESTEAD: Authentic Private Estate with Pool Tennis FirePit

Superhosts Susan and Charlie have delivered on providing a tranquil get-away for friends and families to reconnect in the beautiful Hudson Valley, NY. Surrounded by nature this Authentic Hudson Valley estate built in 1917. It is close to LegoLand, hiking, breweries, and wineries (to name just a few), yet feels like a completely private oasis with modern conveniences in a beautifully renovated farmhouse. After a day exploring the area or simply lounging in the heated salt water pool, (in season May-September), take a seat in one of the 12 Adirondack chairs surrounding the fire pit for roasted marshmallows or delicious s’mores; and don't forget to look up, the stars put on a beautiful show.

Property amenities

Beach

  • Beach towels

Pool/Spa

  • Heated pool
  • Massage
  • Outdoor pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Kitchen island
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Chef service
  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 2.5 bathrooms
  • Bathtub
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room
  • Separate dining area

Entertainment

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

Outdoor areas

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

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 2 pets total (up to 50 lbs per pet)

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In a rural location

Things to do

  • Heated pool
  • Tennis

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

General

  • Garden
  • Unit size: 4,000 square feet

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Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 25

Check-out

Check-out before 10:00 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

Rules

No trespassing signs around the property must be honored. It may be tempting to walk into the meadow, or beyond our tennis court, but it’s not ours
Pool use IN SEASON May through September. No children/non-swimmers allowed in the pool without adult who can swim-Fence gate must be kept closed
Please be familiar with locations of Extinguishers: Kitchen, Den, Priscilla's room. Take one out to fire pit when using, and return once fire is out.

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
2 total (up to 50 lbs per pet)

Children and extra beds

Children are welcome
Note from host: There are stairs which do not have any barriers.

Events

No events allowed

Smoking

Smoking is not permitted

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
Onsite parties or group events are strictly prohibited
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 and a first aid kit
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

About the neighborhood

Map
Middletown, NY

What's nearby

  • Highland Lakes State Park - 6 min drive - 3.5 km
  • Galleria at Crystal Run - 11 min drive - 11.3 km
  • Orange Regional Medical Center - 12 min drive - 13.0 km
  • Orange County Fairgrounds - 14 min drive - 11.3 km
  • Orange County Fair Speedway - 15 min drive - 12.0 km

Getting around

  • Stewart Intl. Airport (SWF) - 30 min drive

Restaurants

  • ‪Dunkin' - ‬9 min drive
  • ‪Silverlake Deli - ‬11 min drive
  • ‪Stewart's Shops - ‬12 min drive
  • ‪Mountain View Bar Restaurant & Pizzeria - ‬13 min drive
  • ‪Casa Mia Latin Kitchen - ‬10 min drive

Frequently asked questions

Does PRISCILLA'S HOMESTEAD: Authentic Private Estate with Pool Tennis FirePit have a pool?

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

Is PRISCILLA'S HOMESTEAD: Authentic Private Estate with Pool Tennis FirePit pet-friendly?

Yes, this property allows dogs (limit 2 total) with a maximum weight of up to 50 lbs per pet.

How much is parking?

Onsite parking is available at the property.

What time is check-in at PRISCILLA'S HOMESTEAD: Authentic Private Estate with Pool Tennis FirePit?

Check-in begins at 4:00 PM.

What time is check-out at PRISCILLA'S HOMESTEAD: Authentic Private Estate with Pool Tennis FirePit?

Check-out is at 10:00 AM.

Where is PRISCILLA'S HOMESTEAD: Authentic Private Estate with Pool Tennis FirePit located?

This family-friendly Middletown vacation home is located in a rural location, 2.2 mi (3.5 km) from Highland Lakes State Park, and within 9 mi (15 km) of Orange County Fairgrounds and Galleria at Crystal Run. Mamakating Town Park and Thomas Bull Memorial Park are also within 9 mi (15 km).

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PRISCILLA'S HOMESTEAD: Authentic Private Estate with Pool Tennis FirePit Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travelers 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.
Rating 10 - Excellent. 12 out of 12 reviews
Rating 8 - Good. 0 out of 12 reviews
Rating 6 - Okay. 0 out of 12 reviews
Rating 4 - Poor. 0 out of 12 reviews
Rating 2 - Terrible. 0 out of 12 reviews

10

Cleanliness

9.8

Location

Reviews

10/10 Excellent

Betty G.

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

Pleasant Homestead

Our family gathering at Pricilla’s Estate was amazing. We had a great time in this lovely home. The house was very clean and the beds were all comfortable. The grounds were amazing and the pool was so much fun! Planning to visit again in the future. Thank you so much Susan and Charles!
Stayed 5 nights in Jul 2022

10/10 Excellent

Steven K.

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

Legoland Trip

Susan and Charlie were wonderful hosts of Priscilla’s estate. We had a long weekend away visiting Legoland with family and their home was the perfect place to rest.The home is filled with charm and well appointed with too many small details to list. The pool was cleaned daily and they were always responsive if we had any questions. The firepit and hammock were a hit for our young kids as we made smores and listened to music. It was a wonderful getaway and just a quick 20 minute drive to Legoland.If you’re considering a stay look no further.
Stayed 3 nights in Jun 2025

10/10 Excellent

Ginny D.

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

Wonderful Home

We had a great stay at this beautiful home. It had everything we wanted, including lots of firewood, dishes, pots & pans, wine glasses- everything! The rooms were big and bright. We had a fantastic time!
Stayed 3 nights in Dec 2022

10/10 Excellent

Katie D.

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

Great spot for a weekend retreat

I stayed with a group of women on a weekend retreat. Everything at Priscilla’s was as advertised or better - charming property, rambling grounds, thoughtful details and most of all Susan’s constant availability for questions and handling all the little details. We had a great time and some of our group said they’d love to use the house for family reunions or whatever else comes up. Highly recommended!
Stayed 4 nights in May 2023

10/10 Excellent

Lourdes L.

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

Amazing Stay!!!

I booked Priscilla's homestead for my bachelorette party weekend and it was an absolute blast!!! everyone loved the house and the property. We were away from everything yet so close to anything we needed. My family loved our stay and are already talking about booking a family trip next year at Priscilla's. Susan was quick to respond, very nice, and helped us immediately when one of us got locked out of one of the rooms (so Sorry Susan!!) everything from the house, to the firepit, to the pool was AMAZING!!!! We had an amazing time and loved everything, will for sure be back again!!
Stayed 2 nights in Jul 2024

10/10 Excellent

Tala

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

Beautiful place for family gathering.

Me and my family had an amazing time staying here for my sisters birthday. The pool was such a perfect way to kick off the start of summer and we enjoyed being able to sit by the fire into the night. The rooms were comforting and inviting and plenty of towels were provided for all of the pool time we got in. I was worried at first about not having enough indoor things to do if the weekend provided poor weather, but there were some games provided and a great living room for our party of 11 people to gather to play some games! We mostly spent out time outdoors, where we got to play with many outdoor games that were provided by the owner. The owner was super nice and accommodating for our stay as well. I would definitely book here again!
Stayed 2 nights in May 2024

10/10 Excellent

De Anna V.

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

Great Family Space

We were two families of four and a small dog, with kids ages 10-17 and we thoroughly enjoyed our long weekend stay. The inside of the home is very well planned and thoughtfully renovated, and we had a great time in the kitchen and family rooms. The house is spacious and it was wonderful for each family to have its own "wing"- complete with bedrooms and a full bath. Also, the bunkbeds are full-sized, so all 4 of the kids were able to hang out there when they wanted to. The adults enjoyed coffee every morning on the lovely screened porch overlooking the meadow, and we all ate s'mores at the fire pit, swam in the pool, and played tennis and basketball on the courts. All in all, this property was exactly what we were looking for! Susan was extremely responsive, kind and genuinely concerned about making our stay the best it could be.
Stayed 3 nights in Aug 2022

10/10 Excellent

Danielle B.

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

A wonderful property that has it all

When picturing where to celebrate my birthday weekend, this property hit the nail on the head. The pool was wonderful with chairs and toys and a shed near by for our drinks. The view of the fields from the fire pit were lovely during sundown with deer spottings. The house itself was so well decorated with little details to make your stay at ease when looking for items. The den and front room were perfect for game nights and hanging out while the closed in porch was ideal for morning coffee. With a group of 8, this house was made for us to be together in a big group or have smaller group time which was absolutely perfect. And last but not least, the hosts are some of the best I’ve ever experienced. Book a stay and I’m sure you’ll enjoy it just as much. Priscilla’s has a special place in my heart. Thank you for creating such a wonderful home away from home.
Stayed 3 nights in Aug 2022

10/10 Excellent

alexandra r.

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

Best Family Home We’ve rented in New York

First of all, Susan was Very easy to communicate with. Easy check in and lovely property. Gorgeous home and all the details were thought of. Towels, coffee, pans, utensils even snacks and a welcome basket of apple donuts. Played games outside with the lovely view, had tea on the porch watching the leaves fall. Kitchen was perfect for cooking for our party if 12. I love a house that says they fit 12 and actually have the supplies and seating for 12. Games, books supplied. Comfortable beds and bedding. Lots of room for our group to spread out and do puzzles and board games. Quiet location and lovely furnishings. We really enjoyed Docs Room and the outside fire pit area. Susan was a gracious , considerate, and generous host offering us late check out and early check in. We all loved it and would come back for sure. Thanks for the memories.
Stayed 3 nights in Oct 2022

10/10 Excellent

Jeremy B.

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

Perfect Quite Stay

Loved our stay! What a great vintage property with excellent modern touches. Thanks for an excellent week.
Stayed 6 nights in Nov 2022

10/10 Excellent

Sean O.

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

Thanksgiving Family Getaway

We thoroughly enjoyed our stay. We we’re getting away to meet our five (5) adult children and in-laws for a family Thanksgiving celebration. The home exceeded our expectations and made this a memorable holiday! Susan & Charles were the perfect hosts as they ensured the house was ready and allowed for an early check-in. We recommend this property to any family seeking a beautiful home in a farm like setting.
Stayed 3 nights in Nov 2022

10/10 Excellent

Lewis G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Aug 2025