We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals in Hillsdale, NY and nearby

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Change Dates
    Price
    per night
    |||
    |||
    $0
    $303 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Don't let other travellers get your favourite Hillsdale area vacation rental. You're so close to securing your perfect getaway. Book today.
    Applied filters:
    Nearby
    Clear All
    1 / 26
    5 of 5 stars (8) Excellent
    Hillsdale
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 11
    5 of 5 stars (2) Excellent
    Hillsdale
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 18
    5 of 5 stars (1) Excellent
    Hillsdale
    3 Bedrooms, 2 Bathrooms, Sleeps 13 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Hillsdale
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This extremely private luxury home is situated on 48-acres at the end of a cul de sac and is located two miles from NY Route 22 in Columbia County just 10 minutes from the Massachusetts boarder and 30 minutes from the Vermont border. Recently renovated, this contemporary home with 5 bedrooms... View all property information
    Location Information
    Hillsdale, New York 12529

    The following rentals are within 10 kilometres of Hillsdale, New York.

    1 / 26
    5 of 5 stars (2) Excellent
    Copake
    3 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Parking
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Mountain Views
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Elegant and tranquil 2 level lakefront retreat, the perfect escape for any season. 3 bedrooms, 2 bath plus a powder room, gourmet kitchen with island counter, cathedral ceilings, large deck facing lake and spectacular Taconic mountain range + small screened porch. Breathtaking lake and mountain... View all property information
    Location Information
    Copake, New York 12516
    5 of 5 stars Reviewed 29 May 2016
    Fantastic place to unwind and reconnect with nature: huge oak trees frame the view of the lake & mountains in the distance. Birds, wind, and occasional fish splashing in the...
    5 of 5 stars Reviewed 31 October 2015
    We were delighted to find this attractive cottage on Robinson Pond. We enjoyed watching the ducks and geese out the expansive windows and were so pleased to see no other humans...
    See all reviews
    1 / 14
    5 of 5 stars (1) Excellent
    Copake
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Grill
    • Outdoor Dining Area
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beautifully restored 2 bedroom (plus attic loft) home brings contemporary living to this hidden gem just 2 hours from NYC. We gutted the house completely incorporating modern amenities like a brand new stainless steel kitchen with granite countertops, hardwood bamboo flooring and a large deck to... View all property information
    Location Information
    Copake, New York 12516
    5 of 5 stars Reviewed 6 February 2014
    The home fit all 5 of my guests comfortably. It was centrally located to skiing and was a wonderful home and a very cozy experience
    See all reviews
    1 / 52
    5 of 5 stars (8) Excellent
    North Egremont, MA
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Grill
    • Satellite TV
    • Waterfront
    • DVD Player
    • Patio
    • Air Conditioning
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    Located in the Berkshire mountains on more than 5 acres <BR>surrounded by 29 acres of conservation land. Featuring<BR>beautiful views of meadows, mountains and farm land bordering the crystal clear Green River (great trout fishing).Only 10 minutes from Great Barrington's Main Street stores,... View all property information
    Location Information
    North Egremont, Berkshires 01230
    5 of 5 stars Reviewed 1 week ago
    From the moment we turned off the beautiful country road and into River Song's driveway my wife and I sensed we were in for a treat. Barbara and Phillip came out to meet us and...
    5 of 5 stars Reviewed 7 October 2015
    My husband and I were looking for a relaxing getaway for a long weekend. We chose the River Song and were not disappointed. The suite is beautifully and comfortably furnished...
    See all reviews
    1 / 16
    5 of 5 stars (4) Excellent
    Copake
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    About this property
    House, 3 Bedrooms + Loft, 2 Baths (Sleeps 7)<BR><BR>BE SURE TO CLICK ON THE LINK BELOW TO SEE MORE OF OUR BEAUTIFUL PHOTOS.<BR><BR>This three bedroom , two living rooms with flate screen home theater system, 2 Baths, plus sleeping loft(or office) has it all. Our deeded lake access on a clean... View all property information
    Location Information
    Copake, New York 12516
    5 of 5 stars Reviewed 20 October 2014
    We spent seven days at this house in the New York side of the Berkshires. I'd never rented in this way before so I was a little nervous. When we got there, we were really wowed...
    See all reviews
    Craryville
    2 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Mountain Views
    • Grill
    • Hot Tub
    • Private Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    You won't see another property like this. This is no ordinary barn. As you step inside you are greeted by a custom made dining room table that comfortably sits 16-20 people! Sit back and watch the deer/turkey/pheasant go by your window. Experience full upscale luxury in a beautifully restored and... View all property information
    Location Information
    Craryville, New York 12529
    1 / 15
    5 of 5 stars (8) Excellent
    Copake
    3 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Porch
    • Grill
    • Washer
    • Satellite TV
    • Parking
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Rustic 3 Bedrooms vacation home 1500 sq ft sleeps 9+ There are 6 beds (1 queen bed, 3 single beds (two beds have a trundle bed underneath) and 1 double sofa-bed, a pack & play and high chair for the little one! Full kitchen, 2 baths and large living and dining space. Wrap around deck, BBQ grill,... View all property information
    Location Information
    Copake, New York 12516
    4 of 5 stars Reviewed 10 August 2015
    Comfortable, well equipped house that's ideal for a family or group of friends outing. Roomy with yard, deck and BBQ. Close to Copake, the local lake and the sights of the area...
    5 of 5 stars Reviewed 5 September 2014
    a great location tucked away yet close to all activities. The house is super comfortable and clean. Includes everything you might want, wifi internet is free and easy to access
    See all reviews
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1 / 19
    5 of 5 stars (1) Excellent
    North Egremont, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Patio
    • Grill
    • Balcony
    • Parking
    • DVD Player
    • Air Conditioning
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    Enjoy beautiful Prospect Lake while staying at our comfortable home. Full kitchen with almost anything you can think of. Farm table seats 8 and is perfect for family meal. Cozy living spaces with enough seating for all to gather. Sunny bright deck in private rear yard . Covered porch is perfect... View all property information
    Location Information
    North Egremont, Berkshires 01230
    5 of 5 stars Reviewed 12 October 2015
    It's my first time booking through flipkey. Zoe, the hostess, helped me a lot during the process. She is warm, kind, and patient. Her email was in details and we checked in...
    See all reviews
    1 / 9
    Copake
    4 Bedrooms, 3 Bathrooms, Sleeps 17 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Balcony
    • Grill
    • DVD Player
    • Central Heating
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Completely furnished kitchen, bedrooms and bathrooms. Master bedroom has full bath, large window overlooking lake, secondary bedroom has 1/2 bath. Downstairs area, has two curtained rooms with king beds, two bunk beds and a 1/2 bath. Dock on property gives access to lake within 30 feet of house,... View all property information
    Location Information
    Copake, New York 12516
    Copake
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Terrace
    • Washer
    • Balcony
    • Central Heating
    • Patio
    • Grill
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    A single storey house with a large basement less than 100 yards from the boat launch to the lake. Swimming, fishing, boating, walking, climbing, cycling and skiing all within 20 minutes ride from the house. A perfect location for all of these activities, plus a quiet location if you just want to... View all property information
    Location Information
    Copake, New York 12516
    Copake Falls
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Washer
    • Central Heating
    • Porch
    • Outdoor Dining Area
    • Grill
    • Wi-Fi
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Ski the Berkshires at Catamount 10 minutes away and Butternut 30 minutes away. Beautifully renovated cottage in walking distance to Taconic State Park. Enjoy farm to table dining nearby. Hike to Birkshires' Bash Bish Falls, bike on the Harlem Valley Bike Trail, and swim in the spring fed iron ore... View all property information
    Location Information
    Copake Falls, New York 12517
    1 / 6
    Copake
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Parking
    • DVD Player
    • Air Conditioning
    • Washer
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Well appointed comfortable 4 season home short walk to lake beach and dock. Large deck with lake views. TV with VCR/DVD Washer/dryer/dishwasher Beds: 1 Queen Bed, 4 Twin Beds View all property information
    Location Information
    Copake, New York 12529
    1 / 4
    4 of 5 stars (1) Very good
    Copake
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Porch
    • DVD Player
    • Washer
    • Grill
    • Central Heating
    • Satellite TV
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This cottage with a view of Copake Lake has 3 bedrooms and a loft. The master bedroom contains a queen bed, a second bedroom contains a double bed, and the third bedroom contains two bunk beds. The recently-renovated bathroom has a washer/dryer and a whirlpool tub. There is also a sunroom and the... View all property information
    Location Information
    Copake, New York 12529
    Copake
    3 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Grill
    • Skiing: Property Is...
    • DVD Player
    • Parking
    • Patio
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This house had extensive renovations in 2014 and has free wifi throughout. The kitchen and living room were combined for a large open family area. The kitchen was completely renovated with high end cabinets, granite countertops, a huge center island that seats five, and a beautiful large mission... View all property information
    Location Information
    Copake, New York 12521