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

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Entire home

Lounge at the heated, salt water built-in Pool.

Bright spacious living room with fireplace

Tennis, Pickleball court, with Basketball hoop.

Overview
Amenities
Policies
Location
Host

Exceptional

5 bedrooms2+ bathroomsSleeps 12371.6 sq m

Popular amenities

Dryer
Washer
Pet-friendly
Fireplace
Kitchen

Explore the area

Middletown, NY

Orange County Fairgrounds
‪13 min drive‬
Galleria at Crystal Run
‪14 min drive‬
Orange County Fair Speedway
‪14 min drive‬
Montgomery, NY (MGJ-Orange County)
‪18 min drive‬

Rooms & beds

5 bedrooms (sleeps 12)

Holly

2 Single Beds

Hudson

1 Single Bunk Bed

Magnolia

1 Queen Bed

Meadow

1 King Bed

Priscilla’s Suite

1 King Bed

2 bathrooms, 1 half bathroom

Bathroom 1

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo · Hair dryer

Bathroom 2

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

Bathroom 3

Toilet

Spaces

Deck or patio

Porch or lanai

Kitchen

Separate dining area

Outdoor play area

Garden

About this property

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.

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Amenities

Pool

Kitchen

Washer

Dryer

Pet-friendly

Free WiFi

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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 10:00 AM

Children

Children allowed: ages 0–17

There are stairs which do not have any barriers.

Events

No events allowed

Pets

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

Smoking

Smoking is not permitted

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.

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 first aid kit

About the area

Middletown

Located in Middletown, this holiday home is in a rural area. Paramount Theatre and Orange County Farmers Museum are cultural highlights, and some of the area's activities can be experienced at City Winery Hudson Valley and Brimstone Hill Winery. Travelling with kids? Consider LEGOLAND® New York and Orange County Fairgrounds.

Middletown, NY

What's nearby

Orange County Fairgrounds - 13 min drive - 12.3 km
Galleria at Crystal Run - 14 min drive - 9.6 km
Paramount Theatre - 14 min drive - 12.3 km
Orange County Fair Speedway - 14 min drive - 12.4 km
LEGOLAND® New York - 18 min drive - 22.1 km

Getting around

Newburgh, NY (SWF-Stewart Intl.) - 30 min drive

Restaurants

‪McDonald's - ‬12 min drive
‪Taco Bell - ‬12 min drive
‪Silverlake Deli - ‬11 min drive
‪KFC - ‬13 min drive
‪Buffalo Wild Wings - ‬12 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 23 kg per pet.

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?

Checkout is at 10:00 AM.

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

This family-friendly Middletown holiday 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 miles (15 km).

Exceptional

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

Learn more

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

10/10 Excellent

Betty G.

2 Aug 2022

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

Ginny D.

23 Jan 2023

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

Lourdes L.

19 July 2024

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

Katie D.

22 May 2023

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

Tala

12 June 2024

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.

30 Aug 2022

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.

8 Aug 2022

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.

31 Oct 2022

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.

7 Dec 2022

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.

27 Nov 2022

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

About the host

Your host

What makes this property unique

Priscilla’s was named after the matriarch of Charlie’s family, and this is where he grew up. We are completely hands on as hosts, and pride ourselves in providing the experience we believe is the most desired by groups of families and friends. We take to heart that our guests entrust us with their precious time away, and work hard to deliver an unforgettable, stress-free getaway.

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

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Reviews

Popular amenities

Explore the area

Rooms & beds

5 bedrooms (sleeps 12)

Holly

Hudson

Magnolia

Meadow

Priscilla’s Suite

2 bathrooms, 1 half bathroom

Bathroom 1

Bathroom 2

Bathroom 3

Spaces

About this property