Hilltop
Spectacular Hilltop Vistas with Private Pool in Hillsdale
5 • 30 reviews
Rooms and Beds
Bedroom 1
Bedroom 2
1
Bedroom 3
2
Guest House
3
Features and Amenities
Rates and Availability
Save 15% on weekly and 20% on monthly stays!
Taxes and fees are additional
House Rules
ARRIVAL
Check-in is at 4pm unless otherwise agreed to in writing.
DEPARTURE
Check-out is by 11am unless otherwise stated in writing. The cleaner will be arriving shortly after to begin preparing for the next renters.
AGE REQUIREMENT
Primary guest booking must be 25 years or older. The person booking should also not have any negative reviews.
PETS
This property does not permit pets.
SMOKING
No smoking is permitted inside the house. If you must smoke, please do so outside and dispose of butts properly.
SEPTIC
Please be mindful of the septic system and do not flush anything down the toilets or drains other than toilet paper. This includes any and all personal hygiene products, baby wipes, bleaches and strong chemical cleaners.
BUGS
To avoid unwanted bugs and critters, please do not leave food out or doors open. As well, lyme, a tick-born disease, is a concern in the Hudson Valley and Catskills regions. Please be mindful by wearing long pants and sleeves while hiking or playing outdoors, and remember to check yourself, kids, and pets daily for ticks.
WINTER WEATHER:
In the winter, we recommend a car with four-wheel drive that can handle the snow and slippery roads. While we have someone that plows and salts the roads, weather in the area can be unpredictable so please check and plan accordingly.
Massachusetts Department of Revenue Certificate C0351261930
Check-in is at 4pm unless otherwise agreed to in writing.
DEPARTURE
Check-out is by 11am unless otherwise stated in writing. The cleaner will be arriving shortly after to begin preparing for the next renters.
AGE REQUIREMENT
Primary guest booking must be 25 years or older. The person booking should also not have any negative reviews.
PETS
This property does not permit pets.
SMOKING
No smoking is permitted inside the house. If you must smoke, please do so outside and dispose of butts properly.
SEPTIC
Please be mindful of the septic system and do not flush anything down the toilets or drains other than toilet paper. This includes any and all personal hygiene products, baby wipes, bleaches and strong chemical cleaners.
BUGS
To avoid unwanted bugs and critters, please do not leave food out or doors open. As well, lyme, a tick-born disease, is a concern in the Hudson Valley and Catskills regions. Please be mindful by wearing long pants and sleeves while hiking or playing outdoors, and remember to check yourself, kids, and pets daily for ticks.
WINTER WEATHER:
In the winter, we recommend a car with four-wheel drive that can handle the snow and slippery roads. While we have someone that plows and salts the roads, weather in the area can be unpredictable so please check and plan accordingly.
Massachusetts Department of Revenue Certificate C0351261930
Location
Reviews
6/26/2025
My wife and I had a magical time in this secluded beautiful hilltop sanctuary. We enjoyed morning coffee listening to the birds and trees and watching the sun come up over the mountains. The pool and hot tub provided a playful afternoon and relaxing evening! We didn’t want to leave! Hope to return soon.
6/3/2025
We had a wonderful stay! The place was clean and beautiful and we really enjoyed the hot tub and pool. Communication excellent throughout
5/28/2025
My fiancé and I celebrated our engagement at the Hilltop and it was a perfect place for the occasion. The open-concept design of the house makes it feel very spacious and airy. The island in the middle of the kitchen can seat 2-3 people and has ample counter space. It quickly became our favorite place to sit and have a glass of champagne. There are large windows everywhere that offer plenty of natural light. The design of the master bedroom is also very unique—sliding doors connect the bedroom to the bathroom and walk-in closet, allowing one to leave the space open or close the doors for extra privacy. The view from the bathtub is totally spectacular. The outdoor pool and hot tub were also highlights of our stay. The pool is long enough to swim laps and the hot tub jets have great pressure for those seeking a nice massage! The views of the sunset from the lawn (also where the bathtub faces) are stunning (picture pink skies framed by beautiful trees). We will definitely be back!
2/24/2025
Our stay at Hilltop was lovely – the house was comfortable and well-appointed and the property was beautiful. The Red Cottage team was very responsive in dealing with some initial issues related to an extreme ice storm, and we were happy with the resolution as well. Recommended!
Reviews for Hilltop
6/26/2025
My wife and I had a magical time in this secluded beautiful hilltop sanctuary. We enjoyed morning coffee listening to the birds and trees and watching the sun come up over the mountains. The pool and hot tub provided a playful afternoon and relaxing evening! We didn’t want to leave! Hope to return soon.
6/3/2025
We had a wonderful stay! The place was clean and beautiful and we really enjoyed the hot tub and pool. Communication excellent throughout
5/28/2025
My fiancé and I celebrated our engagement at the Hilltop and it was a perfect place for the occasion. The open-concept design of the house makes it feel very spacious and airy. The island in the middle of the kitchen can seat 2-3 people and has ample counter space. It quickly became our favorite place to sit and have a glass of champagne. There are large windows everywhere that offer plenty of natural light. The design of the master bedroom is also very unique—sliding doors connect the bedroom to the bathroom and walk-in closet, allowing one to leave the space open or close the doors for extra privacy. The view from the bathtub is totally spectacular. The outdoor pool and hot tub were also highlights of our stay. The pool is long enough to swim laps and the hot tub jets have great pressure for those seeking a nice massage! The views of the sunset from the lawn (also where the bathtub faces) are stunning (picture pink skies framed by beautiful trees). We will definitely be back!
2/24/2025
Our stay at Hilltop was lovely – the house was comfortable and well-appointed and the property was beautiful. The Red Cottage team was very responsive in dealing with some initial issues related to an extreme ice storm, and we were happy with the resolution as well. Recommended!
2/16/2025
Architecturally stunning home. Great space for our group to spend a chilly weekend. Great living room space with a high ceiling, fireplace, and Eames chair. Hot tub was lovely.
11/29/2024
We had the most wonderful stay. Having traveled from Rhode Island for an escape from the holidays we had actually rented a hotel in Germantown initially. Without going into too much detail the hotel was not up to our standards. After one night there we began looking into alternatives. we found Hilltop and it looked perfect. Quickly, we were able to secure a booking for the remainder of our trip. Very responsive interaction throughout booking. It proved to be a peaceful oasis for the remainder of our trip and was a very memorable experience. The modern aesthetic was fantastic and we appreciated the architectural thoughtfulness which went into the design. It even snowed during our stay at the higher elevation the property is situated on. We were already planning a return visit to experience the surroundings in the summer. Thank you for sharing your place with us!
10/19/2024
Beautiful home and views. Clean. Very responsive.
8/10/2024
Beautiful home, very responsive and communicative host. The views were immaculate, and the pool was perfect for a hot summer weekend. House was very clean and spacious. Would definitely recommend.
8/8/2024
Wonderful 2 weeks. Situated between Great Barrington and Hudson so easy access to both. Heated pool and hot tub were terrific, and hosts were responsive and helpful. Private and secluded as advertised. Great way to relax and have alone time with your loved ones.
7/20/2024
My group had an amazing stay with Red Cottage! We cannot say enough good things about the property and this rental company. Everything looked just liked the pictures and we really enjoyed being immersed in nature on such a private plot of land. I look forward to booking this property again hopefully soon.
7/6/2024
We love this place. Beautiful pool, gorgeous property. It’s a pleasure every time.
6/15/2024
Beautiful panoramic private getaway recommended for a beautiful peaceful relaxation with unbelievable nature. The sunrises and sunsets are breathtaking.
3/2/2024
Unique stay, awesome house, very well equipped, would gladly visit again
2/18/2024
The views were stunning! We had a great stay at this beautiful property.
1/21/2024
We had a lovely, relaxing stay at Hilltop. The home is beautiful from an architecture and design standpoint. The setting is completely private, and the views from every room do not disappoint. Waking up to a gorgeous sunrise each morning really sets the tone of the entire day! We stayed in nearly the entire stay due to the frigid temperatures, but this was no hardship with a roaring fire and the giant soaking tub! But we can imagine what the experience would be like in the warmer weather with use of the pool, and the entire property. Really stunning, highly recommend.
1/18/2024
Fantastic property, location, and host for a getaway! As my solo trip was during the winter season with snow, Posto Property and the house provided everything I could possibly need to make my stay very comfortable, safe, and enjoyable. They were also very responsive to any questions I had.
1/14/2024
Lovely place in a lovely town! Thank you for a great stay.
12/31/2023
What a beautiful house! We loved staying there!
12/28/2023
Beautiful house! Spotless. Very well managed and maintained. Would love to come back.
9/3/2023
Great house and great location. A little pricey but likely due to holiday weekend. Would visit again!
8/13/2023
Gorgeous property! Exceeded all our expectations. We hope to be back soon.
7/31/2023
One of the best experiences I ever had! Recommended!
7/2/2023
This is a beautiful property and place to relax ! We had a good time together and enjoyed the beautiful surroundings and pool the house offered . We so wished that there were some games /TT or a Pool table in the house . Definitely v private and calm! Would recommend to anyone
3/11/2023
Spent a weekend at Hilltop midwinter and had a wonderful time. Clean, well designed and beautiful inside and out. Snowed while we were there and the (long) driveway was plowed by 930am. Would certainly recommend.
2/19/2023
Beautiful house, love the design and interior of the house with breathtaking view! We had a wonderful ski weekend here, very close to the catamount ski resort and it’s perfect to end the snowboarding day with the hottub! Highly recommended!
1/21/2023
Wow! What a stunner of a property. My husband and I were completely blown away by the house, the views, and the overall relaxation and peace. The nature there is astoundingly beautiful and it truly feels like you’re in a gorgeous open house in the woods with rolling hills and mountains. The hot tub was an amazing way to relax outside during the cold temperatures. The house itself is very modern, sleek and high class while inviting at the same time. The primary bedroom has such a comfortable bed and is a California King size! The bathroom off of the primary bedroom is bigger than a lot of New York City apartments. The shower is an experience in itself and probably the best shower I’ve ever had in my life. I absolutely loved cooking in the kitchen and there were the most amazing grocery stores just 20 minutes away in Great Barrington including Guido’s and the Co-op. I can’t wait to come back in the summer for the scenery and to try the pool which looked huge!
1/15/2023
Beautiful place, views, house, land, decor…. Peaceful, quiet, at the top of the world. Just what we were looking for. Excellent host – very responsive, clear, attentive. Great experience overall. We’ll be back. Thanks!
1/7/2023
My stay at hilltop was a truly incredible experience. The property was completely secluded and offered breathtaking views of the catskill mountains. The hot tub was a great added bonus when it came to taking in the stunning night sky!
Inside, the home was beautifully designed and spacious. We had everything we needed for a comfortable stay – including lavender scented toiletries). the rental service Posto was very responsive and the check in and out process was seamless – One tip I would mention is to not drive there at night as the mountain roads can be tricky! Overall, it was a fantastic stay and I would highly recommend this Airbnb to others looking for a secluded, mountain getaway.
Inside, the home was beautifully designed and spacious. We had everything we needed for a comfortable stay – including lavender scented toiletries). the rental service Posto was very responsive and the check in and out process was seamless – One tip I would mention is to not drive there at night as the mountain roads can be tricky! Overall, it was a fantastic stay and I would highly recommend this Airbnb to others looking for a secluded, mountain getaway.
1/4/2023
Un lugar mágico, una casa rica en arquitectura , cada lugar es especial, cuarto ppal es una suite perfecta, vista 360, la casa tiene una energía unica y te permite disfrutar de cocinar y compartir, la sala con su chimenea es para estar tomando vino y disfrutar, los alrededores son naturaleza pura. Nada te hara falta, y en mi caso la temporada fue invierno y fue maravilloso, pisos climatizados, un sun room con chimenea bello, puedes pasar el día jugando ajedrez y tomando una buena botella de vino blanco, el jacuzi siempre listo ! Volvere x siempre
12/18/2022
A beautiful modern house with very unique design elements and wild open views into the surrounding mountains.
Price Details
When
Save 15% on weekly and 20% on monthly stays!
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Share this property
Beautiful home, very responsive and communicative host. The views were
Beautiful home, very responsive and communicative host. The views were immaculate, and the pool was perfect for a hot summer weekend. House was very clean and spacious. Would definitely recommend.
Gorgeous property! Exceeded all our expectations. We hope to be
Gorgeous property! Exceeded all our expectations. We hope to be back soon.
Wonderful 2 weeks. Situated between Great Barrington and Hudson so
Wonderful 2 weeks. Situated between Great Barrington and Hudson so easy access to both. Heated pool and hot tub were terrific, and hosts were responsive and helpful. Private and secluded as advertised. Great way to relax and have alone time with your loved ones.
A beautiful modern house with very unique design elements and
A beautiful modern house with very unique design elements and wild open views into the surrounding mountains.
Beautiful house! Spotless. Very well managed and maintained. Would love
Beautiful house! Spotless. Very well managed and maintained. Would love to come back.
What a beautiful house! We loved staying there!
What a beautiful house! We loved staying there!
Architecturally stunning home. Great space for our group to spend
Architecturally stunning home. Great space for our group to spend a chilly weekend. Great living room space with a high ceiling, fireplace, and Eames chair. Hot tub was lovely.
The views were stunning! We had a great stay at
The views were stunning! We had a great stay at this beautiful property.
Beautiful house, love the design and interior of the house
Beautiful house, love the design and interior of the house with breathtaking view! We had a wonderful ski weekend here, very close to the catamount ski resort and it’s perfect to end the snowboarding day with the hottub! Highly recommended!
Our stay at Hilltop was lovely - the house was
Our stay at Hilltop was lovely - the house was comfortable and well-appointed and the property was beautiful. The Red Cottage team was very responsive in dealing with some initial issues related to an extreme ice storm, and we were happy with the resolution as well. Recommended!
Lovely place in a lovely town! Thank you for a
Lovely place in a lovely town! Thank you for a great stay.
Beautiful place, views, house, land, decor…. Peaceful, quiet, at the
Beautiful place, views, house, land, decor…. Peaceful, quiet, at the top of the world. Just what we were looking for. Excellent host - very responsive, clear, attentive. Great experience overall. We’ll be back. Thanks!
Fantastic property, location, and host for a getaway! As my
Fantastic property, location, and host for a getaway! As my solo trip was during the winter season with snow, Posto Property and the house provided everything I could possibly need to make my stay very comfortable, safe, and enjoyable. They were also very responsive to any questions I had.
Wow! What a stunner of a property. My husband and
Wow! What a stunner of a property. My husband and I were completely blown away by the house, the views, and the overall relaxation and peace. The nature there is astoundingly beautiful and it truly feels like you’re in a gorgeous open house in the woods with rolling hills and mountains. The hot tub was an amazing way to relax outside during the cold temperatures. The house itself is very modern, sleek and high class while inviting at the same time. The primary bedroom has such a comfortable bed and is a California King size! The bathroom off of the primary bedroom is bigger than a lot of New York City apartments. The shower is an experience in itself and probably the best shower I’ve ever had in my life. I absolutely loved cooking in the kitchen and there were the most amazing grocery stores just 20 minutes away in Great Barrington including Guido’s and the Co-op. I can’t wait to come back in the summer for the scenery and to try the pool which looked huge!
We had a lovely, relaxing stay at Hilltop. The home
We had a lovely, relaxing stay at Hilltop. The home is beautiful from an architecture and design standpoint. The setting is completely private, and the views from every room do not disappoint. Waking up to a gorgeous sunrise each morning really sets the tone of the entire day! We stayed in nearly the entire stay due to the frigid temperatures, but this was no hardship with a roaring fire and the giant soaking tub! But we can imagine what the experience would be like in the warmer weather with use of the pool, and the entire property. Really stunning, highly recommend.
Un lugar mágico, una casa rica en arquitectura , cada
Un lugar mágico, una casa rica en arquitectura , cada lugar es especial, cuarto ppal es una suite perfecta, vista 360, la casa tiene una energía unica y te permite disfrutar de cocinar y compartir, la sala con su chimenea es para estar tomando vino y disfrutar, los alrededores son naturaleza pura. Nada te hara falta, y en mi caso la temporada fue invierno y fue maravilloso, pisos climatizados, un sun room con chimenea bello, puedes pasar el día jugando ajedrez y tomando una buena botella de vino blanco, el jacuzi siempre listo ! Volvere x siempre
My stay at hilltop was a truly incredible experience. The
My stay at hilltop was a truly incredible experience. The property was completely secluded and offered breathtaking views of the catskill mountains. The hot tub was a great added bonus when it came to taking in the stunning night sky!
Inside, the home was beautifully designed and spacious. We had everything we needed for a comfortable stay - including lavender scented toiletries). the rental service Posto was very responsive and the check in and out process was seamless - One tip I would mention is to not drive there at night as the mountain roads can be tricky! Overall, it was a fantastic stay and I would highly recommend this Airbnb to others looking for a secluded, mountain getaway.
Inside, the home was beautifully designed and spacious. We had everything we needed for a comfortable stay - including lavender scented toiletries). the rental service Posto was very responsive and the check in and out process was seamless - One tip I would mention is to not drive there at night as the mountain roads can be tricky! Overall, it was a fantastic stay and I would highly recommend this Airbnb to others looking for a secluded, mountain getaway.
This is a beautiful property and place to relax !
This is a beautiful property and place to relax ! We had a good time together and enjoyed the beautiful surroundings and pool the house offered . We so wished that there were some games /TT or a Pool table in the house . Definitely v private and calm! Would recommend to anyone
My group had an amazing stay with Red Cottage! We
My group had an amazing stay with Red Cottage! We cannot say enough good things about the property and this rental company. Everything looked just liked the pictures and we really enjoyed being immersed in nature on such a private plot of land. I look forward to booking this property again hopefully soon.
One of the best experiences I ever had! Recommended!
One of the best experiences I ever had! Recommended!
We love this place. Beautiful pool, gorgeous property. It’s a
We love this place. Beautiful pool, gorgeous property. It’s a pleasure every time.
Beautiful panoramic private getaway recommended for a beautiful peaceful relaxation
Beautiful panoramic private getaway recommended for a beautiful peaceful relaxation with unbelievable nature. The sunrises and sunsets are breathtaking.
My wife and I had a magical time in this
My wife and I had a magical time in this secluded beautiful hilltop sanctuary. We enjoyed morning coffee listening to the birds and trees and watching the sun come up over the mountains. The pool and hot tub provided a playful afternoon and relaxing evening! We didn’t want to leave! Hope to return soon.
We had a wonderful stay! The place was clean and
We had a wonderful stay! The place was clean and beautiful and we really enjoyed the hot tub and pool. Communication excellent throughout
Spent a weekend at Hilltop midwinter and had a wonderful
Spent a weekend at Hilltop midwinter and had a wonderful time. Clean, well designed and beautiful inside and out. Snowed while we were there and the (long) driveway was plowed by 930am. Would certainly recommend.
Unique stay, awesome house, very well equipped, would gladly visit
Unique stay, awesome house, very well equipped, would gladly visit again
My fiancé and I celebrated our engagement at the Hilltop
My fiancé and I celebrated our engagement at the Hilltop and it was a perfect place for the occasion. The open-concept design of the house makes it feel very spacious and airy. The island in the middle of the kitchen can seat 2-3 people and has ample counter space. It quickly became our favorite place to sit and have a glass of champagne. There are large windows everywhere that offer plenty of natural light. The design of the master bedroom is also very unique—sliding doors connect the bedroom to the bathroom and walk-in closet, allowing one to leave the space open or close the doors for extra privacy. The view from the bathtub is totally spectacular. The outdoor pool and hot tub were also highlights of our stay. The pool is long enough to swim laps and the hot tub jets have great pressure for those seeking a nice massage! The views of the sunset from the lawn (also where the bathtub faces) are stunning (picture pink skies framed by beautiful trees). We will definitely be back!
We had the most wonderful stay. Having traveled from Rhode
We had the most wonderful stay. Having traveled from Rhode Island for an escape from the holidays we had actually rented a hotel in Germantown initially. Without going into too much detail the hotel was not up to our standards. After one night there we began looking into alternatives. we found Hilltop and it looked perfect. Quickly, we were able to secure a booking for the remainder of our trip. Very responsive interaction throughout booking. It proved to be a peaceful oasis for the remainder of our trip and was a very memorable experience. The modern aesthetic was fantastic and we appreciated the architectural thoughtfulness which went into the design. It even snowed during our stay at the higher elevation the property is situated on. We were already planning a return visit to experience the surroundings in the summer. Thank you for sharing your place with us!
Beautiful home and views. Clean. Very responsive.
Beautiful home and views. Clean. Very responsive.
Great house and great location. A little pricey but likely
Great house and great location. A little pricey but likely due to holiday weekend. Would visit again!