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Tower Hill - Hilltop Country Retreat with Panoramic Views

Family-friendly holiday home in Millbrook with an outdoor pool

Photo gallery for Tower Hill - Hilltop Country Retreat with Panoramic Views

Property grounds
Aerial view
Living area
Dining
Aerial view

Reviews

10 out of 10, Loved by Guests
4 bedrooms3+ bathroomsSleeps 6

Popular amenities

  • Parking available
  • Kitchen
  • Pet-friendly
  • Fireplace
  • Dryer

Explore the area

View in a map
Millbrook, NY
  • Place, Orvis Sandanona Shooting Grounds
    ‪12 min drive‬
  • Place, Wing's Castle
    ‪16 min drive‬
  • Place, Millbrook Vineyards and Winery
    ‪17 min drive‬
  • Airport, Danbury, CT (DXR-Danbury Municipal)
    ‪56 min drive‬

Rooms & beds

4 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

2 Single Bunk Beds

Bedroom 3

2 Single Beds

Bedroom 4

1 King Bed

3 bathrooms, 1 half bathroom

Bathroom 1

Bathtub · Toilet · Shower only

Bathroom 2

Bathtub · Toilet · Shower only

Bathroom 3

Toilet

Bathroom 4

Bathtub · Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Separate dining area
Outdoor play area
Garden
Dining area

About this property

Tower Hill - Hilltop Country Retreat with Panoramic Views

Up a winding country road, lies Cloud Walk. Twelve private acres of peace and quiet across from a world class horse farm. Large eat-in kitchen (La Cornue stove) opens up into Dining Room, Living Room, Study and Sun room. 3 bedrooms upstairs with 2 bathrooms as well as an additional bedroom suite downstairs with bathroom.
Beautiful gardens surround the property with a large swimming pool.
High-speed wi-fi
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi

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House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 2:00 PM
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Children

Children allowed: ages 0–17
Playroom, kids library & toys galore.
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Events

No events allowed
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Pets

Pets allowed: dogs (limit 2 total)
Dogs are allowed with approval.
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Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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

About the area

Millbrook

Located in Millbrook, this holiday home is in a rural area. Macedonia Brook State Park and Buttercup Farm Audubon Sanctuary reflect the area's natural beauty and area attractions include Trevor Zoo and Innisfree Garden.
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Map
Millbrook, NY

What's nearby

  • Orvis Sandanona Shooting Grounds - 12 min drive - 12.2 km
  • Trevor Zoo - 13 min drive - 10.2 km
  • Amenia Town Hall - 14 min drive - 13.8 km
  • Wing's Castle - 16 min drive - 12.4 km
  • Millbrook Vineyards and Winery - 17 min drive - 13.1 km

Getting around

  • Appalachian Trail - 26 min drive
  • Danbury, CT (DXR-Danbury Municipal) - 63 min drive

Restaurants

  • ‪McDonald's - ‬13 min drive
  • ‪Dunkin' - ‬13 min drive
  • ‪Cumberland Farms - ‬11 min drive
  • ‪Isabela - ‬16 min drive
  • ‪Nooch's - ‬13 min drive

Frequently asked questions

Does Tower Hill - Hilltop Country Retreat with Panoramic Views have a pool?

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

Is Tower Hill - Hilltop Country Retreat with Panoramic Views pet-friendly?

Yes, this property allows dogs (limit 2 total). Some restrictions may apply, so please contact the property for more details.

How much is parking at Tower Hill - Hilltop Country Retreat with Panoramic Views ?

On-site parking is available at the property.

What time is check-in at Tower Hill - Hilltop Country Retreat with Panoramic Views ?

Check-in begins at 3:00 PM.

What time is check-out at Tower Hill - Hilltop Country Retreat with Panoramic Views ?

Checkout is at 2:00 PM.

Where is Tower Hill - Hilltop Country Retreat with Panoramic Views located?

Located in a rural location, this family-friendly holiday home is within 9 mi (15 km) of Dover Plains Stone Church, Trevor Zoo and Macedonia Brook State Park. Orvis Sandanona Shooting Grounds and Wing's Castle are also within 9 miles (15 km).

Reviews

10

Exceptional

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy
Rating 10 - Excellent. 15 out of 15 reviews
Rating 8 - Good. 0 out of 15 reviews
Rating 6 - Okay. 0 out of 15 reviews
Rating 4 - Poor. 0 out of 15 reviews
Rating 2 - Terrible. 0 out of 15 reviews

Reviews

10/10 Excellent

Victoria G.

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

Great Stay, Great Host

Host was easy to communicate with and the property was beautiful and in a remote area. Our guests who came for our work event enjoyed their stay.
Stayed 1 night in Nov 2023

10/10 Excellent

Fabiola S., Brooklyn

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

Beautiful house

We had a wonderful time at the house. Plenty of room and beautifully furnished. Great views of the Hudson Valley and lots of property to relax and do sports.
Stayed 1 night in Oct 2023

10/10 Excellent

Maeve O.

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

Lovely!

Gracious and lovely house in a beautiful spot. This was our second stay, and we hope to be back! The owners could not be nicer, very helpful and responsive.
Stayed 3 nights in Jan 2021

10/10 Excellent

Mirel S.

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

Lovely house, pool and beautiful grounds

The house is beautiful, the pool is fantastic, and the grounds absolutely huge and stunning. We had a lovely stay with 2 adult couples and 4 children. The house was perfectly equipped, with plenty of towels, extra linens, coffee pods and everything we could have hoped for. Would absolutely gladly return for future visits.
Stayed 2 nights in Sep 2023

10/10 Excellent

Letitia P.

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

Graduation weekend.

It was a wonderful property beautiful. The house was very well appropriated. The owners were very accommodating and easy to coordinate with. We were so lucky to have found it so that we could enjoy time together as a family as our daughter graduated from school.
Stayed 3 nights in May 2024

10/10 Excellent

elizabeth P.

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

Wonderful country house for family!

My family (grandparents, parents and a toddler and baby) had the most magical stay. Chani was beyond helpful and accommodating. The house and grounds are a delight for parents and children. The pool is wonderful too. The house is beautifully appointed, super clean, stocked with toys and other kid-necessary stuff. Wonderful area for a visit and Chani is the best guide. We all look forward to our next visit. Thank you again, Chani, for everything.
Stayed 4 nights in May 2023

10/10 Excellent

Barbara G.

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

Lovely stay

and perfect for a family
Stayed 14 nights in Aug 2022

10/10 Excellent

NATAN S.

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

Amazing Upstate vacation in a magical setting

If you could will into existence the perfect upstate getaway, what would it look like? Beautiful hilltop views, expansive grounds with lovely wild and tended landscaping?Total privacy and peace with plentiful birdsong? A perfect pool and loungers for sunning? A charming character-infused old home with the very best of updates, and with plenty of nooks and overstuffed chairs for reading plus an amazing book collection? A well-stocked and perfectly equipped kitchen, with lovely dining areas indoors and out for family gatherings? This describes the property where we spent a blissful ten days, and to which we hope to return in seasons hence.
Stayed 8 nights in Jun 2022

10/10 Excellent

Jonathan P.

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

To the Owner Only

Great property. Interesting history of the Churchill family. Here are some things that we suggest to improve things: 1) Fix freezer. Never worked quite right. Ice cream always in a semi-melted shape. 2) Put blinds up in Master Bathroom. This is a MUST. 3) Instructions for gas grill 4) Get at least one more set of twin sheets for bedroom upstairs with twin beds. There was only a single set. 5) Recommendations for local dining. 6) Provide pool skimming net. 7) Provide a standard coffee maker, not an expresso one. These are all pretty important. Otherwise it was a wonderful weekend.
Stayed 3 nights in May 2022

10/10 Excellent

Philip E.

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

Wonderful property!

We thoroughly enjoyed a winter weekend getaway at Cloud Walk with friends and our young children and dogs. Chani was terrific as a host and we would certainly love to come back!
Stayed 3 nights in Jan 2022

10/10 Excellent

Julia B.

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

Perfect Fall weekend getaway in Millbrook!

Our family (including two teenage boys) enjoyed a lovely weekend at Cloudwalk. The house and grounds are beautiful. Rooms are very comfortable and bathrooms are renovated and well designed Kitchen is well equipped and we made a great family dinner. Highly recommend!
Stayed 2 nights in Oct 2021

10/10 Excellent

Nate E.

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

Lovely Cloudwalk

We spent 10 days at Cloudwalk with 3 kids 10-12 years old, my mother, and our dogs. This place is an absolute delight. What a lovely getaway! It has the perfect blend of luxury feel without being fussy. There are toddler blocks in the formal living room, and animal portraits everywhere. The flower gardens are lush and mature, the pool is large and well maintained. The hosts provide thoughtful things like bug spray, sunscreen, portable speaker, pool towels, and refreshments in the fridge. The towels are plush and plentiful, the bedding is soft and clean. Beds and pillows were comfy, the master bath feels like a spa. The downstairs king bedroom essentially has its own suite, and the bunk bed room has one bunk with double full sized mattresses. The kitchen is well stocked and spacious. The note from the host was delightfully simple and welcoming, no stern warnings or demands, just a list of great places to go and their contact info if you need anything. This is a tranquil country oasis, like being back on my gram’s farm in Vermont hearing horses right down the road. There are TWO playrooms with tons of toys for the small kiddos, every great book you can think of, ROku tv, WiFi, a projector screen (bring your own projector), large yards, croquet, outdoor dining, screened in porch, and a trampoline. There is a winding stream further down tower hill road, and gorgeous horses as your neighbors. We were a bit disappointed to learn the horse farm next door is a breeding farm only, and there is next to no touristy trail-riding for the inexperienced riders in the area. Most horse farms in the area cater to experienced riders doing dressage or fox hunting, however the neighbors at Victory Lane Farm were the loveliest people, and we were able to visit with horses Loretta and Primrose in their paddock by the road each day. We even got to meet their friendly goat, Oreo and ask lots of questions about the farm. We did go in to town for a night at the drive in, and checked out the mini golf. I have honestly never felt so relaxed on a trip with the whole family in tow, and would highly recommend.
Stayed 10 nights in Aug 2021

10/10 Excellent

J B.

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

Great house, great experience

This is an excellent property! The house is more spacious and grand than the pictures indicate. The pool is large, beautiful and private (and completely fenced off, so the kids can't get to it alone). The hosts are very thoughtful and responsive. We were there for a week with our kids (5 and 2). The house was far larger than we actually needed. We could have brought another family with us. My wife is a stickler for the aesthetics and cleanliness of rental houses, and she was very impressed. There are tons of toys for the little ones. Cooking is a breeze with the large range (and grill outside). The yard is large and very private. The hosts were very responsive to any questions, and clearly went out of their way to make our vacation great. They left a few newly purchased supplies tailored to our group. There are more than enough activities within a ~15 mile radius to entertain a 2 and 5 year old for a week, with a relaxed schedule. If your crew is older, horseback riding will be available, opening up far more options. We'll definitely be back, schedule permitting!
Stayed 7 nights in Jun 2021

10/10 Excellent

ANDREW E.

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

Excellent country retreat!

Had a really great week with my wife and two children (ages 6 and 2). Perfect place for families looking to spend some time in the country. The owner was very helpful and pleasant. Definitely considering a return trip.
Stayed 9 nights in Mar 2021

10/10 Excellent

Diana T.

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

Wonderful home, beautiful property

We had two families stay there together and it was perfect! Lovely property with gorgeous views. Very gracious home, comfortable for families with kids and pets. Very well-stocked kitchen. Hosts were a pleasure and made everything easy! We’ll be back!
Stayed 4 nights in Dec 2020

About the host

Hosted by Chani Churchill

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