Skip to main content

Hilltop

Spectacular Hilltop Vistas with Private Pool in Hillsdale
5 39 reviews
  • Hillsdale
  • House

With 360-degree views of the Catskill and Berkshire Mountains from the highest point in Hillsdale, Hilltop is a contemporary home with complete privacy and everything you need, including a pool, hot tub, fireplaces in the living room, screened porch and guest house.

Hilltop is between the towns of Great Barrington and Hudson, Catamount Ski Resort is within 10 min, and there are many options for hikes, biking and leaf peeping.

8

Guests

4

Bedrooms

3

Bathrooms

Rooms and Beds

Bedroom 1
King beds: 1
1
Bedroom 2
Double beds: 1
2
Bedroom 3
Double beds: 1
3

Features and Amenities

Hot tub
Microwave
Oven
Patio or balcony
Refrigerator
Shampoo
Smoke detector
Stove
TV
Washer
Wireless Internet
Laptop friendly workspace

Rates and Availability

Taxes and fees are additional

Need Help With Flexible Dates or a Longer Term Rental?
Let Us Find You The Perfect Home!

What Guests Are Saying

Great!

5star rating
Great!

We had a fantastic stay at Hilltop, the privacy was

5star rating
We had a fantastic stay at Hilltop, the privacy was just what we needed, and the views of the Berkshires were stunning. The cottage was extremely comfortable for our group of 6. The Red Cottage team was responsive and set a high standard for service and hospitality. Unfortunately, we weren’t able to use the hot tub due to filter issues, which we reported during our stay for attention.

This house was spectacular! The setting was gorgeous and the

5star rating
This house was spectacular! The setting was gorgeous and the design of the building was truly unique. There we amazing views of the mountains in every direction, including from the soaking tub in the upstairs suite. It was the perfect setting and home base for a fun weekend in the southern Berkshires, within easy driving of Great Barrington and numerous hiking trails. We relaxed in the jacuzzi, chatted around fires in the living room, and enjoyed the heated floors. The host was responsive and helpful with our questions while there. Couldn’t recommend it enough!

Beautiful modern space with an abundance of large windows and

5star rating
Beautiful modern space with an abundance of large windows and modern amenities secluded in nature.
Reviews for Hilltop

Great!

5star rating
Great!

We had a fantastic stay at Hilltop, the privacy was

5star rating
We had a fantastic stay at Hilltop, the privacy was just what we needed, and the views of the Berkshires were stunning. The cottage was extremely comfortable for our group of 6. The Red Cottage team was responsive and set a high standard for service and hospitality. Unfortunately, we weren’t able to use the hot tub due to filter issues, which we reported during our stay for attention.

This house was spectacular! The setting was gorgeous and the

5star rating
This house was spectacular! The setting was gorgeous and the design of the building was truly unique. There we amazing views of the mountains in every direction, including from the soaking tub in the upstairs suite. It was the perfect setting and home base for a fun weekend in the southern Berkshires, within easy driving of Great Barrington and numerous hiking trails. We relaxed in the jacuzzi, chatted around fires in the living room, and enjoyed the heated floors. The host was responsive and helpful with our questions while there. Couldn’t recommend it enough!

Beautiful modern space with an abundance of large windows and

5star rating
Beautiful modern space with an abundance of large windows and modern amenities secluded in nature.

Location

House Rules

Check-in after 4:00 PM
Checkout before 11:00 AM
Pets Not Allowed, Smoking Not Allowed, Parties not allowed, Not Suitable for Infants. .,

Additional: VRBO: Guests must sign and return the rental agreement within 24 hours. If arriving tomorrow, complete the check-in form ASAP for instructions.

AGE REQUIREMENT
Primary guest booking must be 25 years or older. The person booking should also not have any negative reviews.

PETS
Sorry, pets are not permitted at this property.

SMOKING
No smoking is permitted inside the house. If you must smoke, please do so outside and dispose of butts properly. Any violation of this policy is subject to a $500 fee.

EXCESSIVE CLEANING FEES
We kindly ask that guests treat the home with care and respect. Should the property require cleaning beyond the standard turnover—due to excessive mess or incidents involving bodily fluids such as blood, vomit, or waste—a $500 fee may apply. Any linens or furnishings damaged beyond repair will also be subject to replacement charges. These situations are considered outside the scope of routine housekeeping and require specialized attention to ensure the safety and well-being of our team.

ACCURATE GUEST COUNT
The number of guests must be accurately disclosed at the time of booking. While we don’t charge extra for additional guests up to the home’s maximum occupancy, this information is essential so we can properly prepare and stock the home. Please note that penalties may apply if guest counts are inaccurate or intentionally misrepresented.

OUTSIDE SERVICE PROVIDERS
Outside staff such as private chefs, massage therapists, or other service providers are welcome, but prior approval is required before they come on-site.

SUPPLEMENTAL AGREEMENTS
Guests may be required to sign a rental agreement. If applicable, it will be sent after the booking is confirmed.

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.

Price Details

When
Member-Only Feature
Extended Availability Booking Request
Member-only feature

Want to plan further ahead? Join our membership program to unlock the ability to request stays beyond our standard booking dates.