Vacation Rentals By Owner In Hillsdale, NY

Enjoy the quiet beauty of Copake Lake in this summer home only 2+ hours from New York City.brCentral heating and air conditioning brFull kitchen with dishwasher, washer/dryer, pots/pansbrWireless internet access and all utilities (except phone) includedbr2 LCD TVs with Roku for streaming Netflix, Amazon Prime, and many othersbrOutdoor barbecuebrSpacious deckbrLake dock (sandy beach for swimming) and private boat dock on Copake lakebrLocated near tristate boundary and numerous cultural venues including Tanglewood, Jacob's Pillow, Shakespeare and CompanybrGreat recreational opportunities nearby for golf, tennis, hiking, and kayaking

Copake Lake home near cultural attractions Of The Berkshires

Hillsdale, New York, United States

Bed

Bath

Sleeps

Exceptional(12)

$467.17

Summary:brWelcome to the Hudson Valley getaway. Located in the heart of the Hudson Valley in Hillsdale NY, sits our 4 bedroom oasis.brbrThe Space:brCompletely renovated, the space has 2 beautifully decorated open concept living areas with a modern kitchen stocked with amenities, 3 large bedrooms, an office with pullout couch, and 3 bathrooms. brbrWhat sets this villa apart are the floor-to ceiling windows surrounding the home, bringing warm natural light and tranquility to every corner. Additionally, the primary bedroom is truly stunning, boasting a high ceiling with natural wooden beams, a gorgeous en suite bathroom, and access to the wrap-around deck.brbrHigh-speed WiFi is available throughout the property and the office setup is available when inspiration (or those pesky emails) hits.brbrTake in the picturesque landscape and fresh air from the enormous wrap-around deck, furnished with a large outdoor dining table with seating for 13. Serene views and access to the stream provides a total sense of calm and relaxation, perfect for those looking to be in nature, while still enjoying luxury.brbrParking is in the driveway with stone steps leading directly to the entrance.brbrGuest Access:brGuests will receive an entry code 12 hours prior to their arrivalbrbrThe Neighborhood:brExplore the Hudson Valley by starting in Hillsdale, NY. With plenty of things to do within a short drive, you can find everything you'll need to getaway across Upstate New York and the Berkshires:brbrRestaurants/Breweries - All Within 15 minutesbr1) Roe Jan Brewing Cobr2) Barrington Brewery & Restaurantbr3) Chatham Brewingbr4) Four Brothers Pizza Innbr5) Hillsdale Housebr6) Sweet Peas Country Dinerbr7) Little Cat LodgebrbrbrAttractions/Things To Do:br1) Ski Resorts:br- Catamount Mountain Resort - 15 minutesbr- Jiminy Peak Ski Resort - 35 minutesbrbr3) Chatham, NY - 15 minutesbr- Idyllic Hudson Valley town with charming storefronts, restaurants, breweries, and galleriesbrbr4) Great Barrington, MA - 15 minutesbr- Great Barrington is the hub of Southern Berkshire County with a vibrant Main Street and side streets packed with shops, theaters, and restaurants. While tourism is its biggest draw, its hidden open spaces and vistas has made this beautiful southern town ideal for vacation- and second-home owners.brbr5) Hudson, NY - 30 minutesbr- Hudson has a historical richness and contemporary vibrancy far bigger than its size would suggest. Hudson’s compact urban core makes it an eminently walkable city. You'll find history, art galleries, culture, and restaurants, making Hudson an extraordinary city to visit, offering sights, sounds, curiosities and great food around every corner.brbr6) Lenox, MAbrbr7)Tanglewood - 25 minutesbr- A World-Class Outdoor Performing Arts Venue! The famous performing arts venue of Tanglewood is nestled away in the Berkshire Hills of western Massachusetts and sets high standards for musical festivals, especially in the warmer months. Home to the famous Boston Symphony Orchestra, and the site of one of the world’s best-known music festivals, Tanglewood hosts the Festival of Contemporary Music, along with many other events including concerts of various genres from jazz to pop and frequent visits from James Taylor, John Williams, and the Boston Pops.brbr8) Taconic State Parkbr- Bish Bash Falls - 60 foot waterfall and highest waterfall in Massachusetts.br- Copake Iron Works Historic Sitebr- Hiking, Simming, cross-coutry skiing, and snow shoeingbrbr9) Art OMI - 25 minutesbr- Situated on one-hundred and twenty acres in the Hudson Valley, Art Omi presents the works of contemporary artists and architects, and offers a range of large-scale works in nature, plus a 1,500 square foot gallery. The Sculpture & Architecture Park currently offers more than 60 works by artists and architects on view, with pieces added or exchanged each year.brbr10) Mass MoCA - 60 minutesbr- The Massachusetts Museum of Contemporary Art (MASS MoCA) is one of the world’s liveliest centers for making and enjoying today’s most evocative art. With vast galleries and a stunning collection of indoor and outdoor performing arts venues, MASS MoCA is able to embrace all forms of art: music, sculpture, dance, film, painting, photography, theater, and new, boundary-crossing works of art that defy easy classification.

Hudson Valley and The Berkshires getaway

Hillsdale, New York, United States

Bed

Bath

Sleeps

Exceptional(66)

$286.08

Charming , newly renovated cottage wIth AC and dock on Copake Lake. Bring your boat to your private dock and boat launch. Enjoy this 2 bedroom (king & 2 twin beds)1 bath nestled in the woods with a short walk to the Lake. Cozy fireplace plus an outdoor fire pit for those chilly nights. Cottage is fully stocked for your convenience. Barbecue grill and picnic table for when you feel like grilling and enjoying your meal outside. Ideal place to be all year round. Lots of activities to be had on Copake Lake. Have cocktails on your dock and watch the beautiful sunsets. If you are a skier, snowboarder, etc we’re convenient to Catamount, Butternut, Windham and Hunter. Minutes away from Copake Country Club for a delicious meal or a round of golf. Take a scenic drive through the Berkshires. This is a place you’ll want to revisit time and time again.

Cottage at Copake Lake

Hillsdale, New York, United States

Bed

Bath

Sleeps

Exceptional(25)

$524.85

Tucked away on private lane and bordering hundreds of acres of preserved land, this tastefully renovated 1840 farmhouse offers a perfect country escape with all the best Columbia County has to offer. This 4-bedroom, 3-bathroom home sleeps up to 6 people (yet works just as well for one or two people), is loaded with character, and features original pine floors and trim, new bathrooms with dinner-plate-sized shower heads and marble floors, and a kitchen featuring Viking/Sub Zero/Bosch appliances, with designer furnishings/decor and high-speed internet. brbrThe interior of the home is modern, understated and unexpectedly luxurious. This is our weekend home and we renovated it to have a quiet escape for ourselves, outfitting it with finishes, furniture and objects that we enjoy. We are opening it up for rent after having shared it with friends and family and hope to find others who love it as much as we do. The kitchen is outfitted with everything you would ever need for a chef to cook a meal, including Jura and Ascaso espresso machines, Calphalon/Staub pots and pans, good wine glasses/dishes/flatware/bar accoutrements, etc. brbrThe ground floor has 9’ ceilings and contains a large Living Room with a decorative fireplace (not for use) and TV, dining room, a 3-season screened-in porch (storm windows for the winter months), a large mudroom with LG washer and dryer, country kitchen and dinette, foyer, one bedroom, a full bathroom, and a 700-square foot bluestone terrace with teak furniture outside. Three additional bedrooms and two recently renovated bathrooms occupy the second floor. brbrWhile well-behaved children and pets are welcome, this is not a party house. It’s the ideal place to escape to the country with a screened in porch, a good bathtub and light-filled rooms with high quality mattresses, too many coffee table books and designer furniture. There are also premium mattresses, high quality linens and towels and every type of pillow option imaginable.brbrLocation:brLocated on a tree-lined, quiet country road, just east of the Taconic, it’s a 20-minute drive to Hudson (Amtrak stop) and 30-minutes to Great Barrington, in the hills of NW Hillsdale, and a five-minute drive to the famed Hawthorne Valley Farm Store. It’s a 2 hour drive to NYC and 2h 15 min drive to Boston. The house is nestled above a small stream with a separate garage space from the main driveway, allowing for tons of natural light, open fields and privacy. We have one neighbor with hundreds of acres of property, so the home is reached at the end of a private road.brbrKitchen: Sub Zero refrigerator, Viking Range, Bosch dishwasher, high quality pans and dishware, along with every cooking device, type of serve ware and appliance you could imagine, i.e. a citrus juicer, blenders, Dualit toaster, custom pizza stone for the oven, etc. For example, we are coffee fanatics, so we have a Chemix pour over, a French press, an Ascaso espresso machine, a Jura coffee/espresso machine, a Japanese kettle and iced coffee maker -- we like options! It’s these details that make staying at the home an enjoyable experience.brbrMudroom: slate floors with an LG Washer and Dryer, sink and a great space to store everything, along with anything you could want for the property: snow shoes, candles, bug spray, board games, Rowenta iron, raclette machine, air fryer, etc. brbrTerrace: Recently built a 700 square foot blue stone terrace with Barlow Tyrie teak furniture (table and living space) and gas Weber grill. We also have a great charcoal grill if you prefer to cook with that. We just added a Yukon SoloStove fire place for the terrace that's really easy to use and does not leave you smelling of smoke. During the spring and summer, we spend most of our time on the screened-in porch that has three sun exposures and is fully weather protected (it’s enclosed with storm windows for Fall/Winter).brbr4 Bedrooms:br1. Primary Bedroom: King-size bed with master bathroom (2 people) – upstairs. br Incredible mattress, good linens and lots of pillow options. br2. Guest Bedroom 1: queen-size bed (2 people) – upstairs. Same mattress as primary bedroom.br3. Guest Bedroom 2: XL Twin Donald Judd-style bed (1 person) – upstairs. Great mattress, Parachute linensbr4. Guest Bedroom/Office 3: currently used as an office with a CB2 daybed (ideal 1 person, but turns into a queen bed that can sleep 2 people comfortably with the featherbed, if need be, sleeping up to 7 people for the home, but we really prefer 6 people max, and do not recommend a couple sleeping in that room; it’s not as nice an experience as the others) - ground floorbrbr3 Bathrooms:br1. Master Bathroom: freestanding soaking tub; huge shower with dinner plate-sized rainfall shower head, standard shower head and jets for the wall; marble floors, shiplap walls, glass dividers, heat lamp and freestanding sink, Restoration Hardware fittings.br2. 2nd Floor Hall guest bath. Recently renovated, huge shower with dinner plate-sized rainfall shower and standard shower heads, vintage sink and nice chrome RH hardware.br3. Ground floor full bathroom is more standard, but the shower gets excellent water pressure (Speakman showerhead).brbrTechnology: brWe have high speed fiber optic internet (500 Mbps) and a cell phone extender, which allows us to watch Netflix, make cellular phone calls and take Zoom/video conference calls for work purposes with ease. 55” LG LED TV, Bose Bluetooth speaker, charging stations, etc., are on site. brbrMiscellaneous:br• We have an incredible caretaker who cleans the home and manages anything associated with it, should you need anything during the stay, including snow removal and lawn care.br• We have individual a/c units for the main rooms and bedrooms for the summer months.br• The fireplace finicky and easily back drafts into the living room, which can easily fill with smoke, so we are not allowing it for use during the stay; we are rebuilding that in the spring. If you would like a fire, we have a SoloStove on the terrace that works perfectly for outdoor fires.br• We ask you to be mindful of water usage. brbrWe have only recently started renting the space, since we will not be able to spend as much time there as we would like. Please message me if you have any questions or would like to see additional photos. This is a really special home and is perfectly located with great attractions in every direction. br

Beautifully Restored, Secluded Farmhouse

Hillsdale, New York, United States

Bed

Bath

Sleeps

Exceptional(21)

$366.4

Summary:brWelcome to your luxury cottage escape. Located in the heart of the Hudson Valley in Hillsdale, NY sits a calm, stylish 1 bedroom cottage; perfect for a couple or a solo vacationer looking for solitude.brbrWe believe you’re here to completely relax, that’s why we have no requirements when checking out, just turn the lights off and lock the door!brbrThe Space:brCompletely renovated, this two-story cottage has a beautifully decorated open concept living area, a kitchen stocked with amenities, a large queen bedroom. On the first floor, you’ll also find a modern art deco bathroom with a soaker tub and a modern, roomy shower. brbrOn the second floor, you’ll find a stunning open space that boasts a grand ceiling with natural wooden beams. The floor contains the full kitchen with bucket-block counter-tops and a comfortable sectional for lounging under the blankets reading a book or watching television. brbrTake in the picturesque landscape and serene views right from the grounds. Access to the stream across the street provides a total sense of calm and relaxation, perfect for those looking to be in nature, while still enjoying luxury.brbrbrHigh-speed WiFi and desk setup is available for when inspiration (or those pesky emails) hits. Parking is across the street with steps leading directly to the entrance of the cottage.brbrGuest Access:brGuests have access to the entire home and outdoor space. There are parking spaces across the street with steps that lead up to the entrance. You will receive an electronic key to access the front and back door.brbrThe Neighborhood:brExplore the Hudson Valley by starting in Hillsdale, NY. With plenty of things to do within a short drive, you can find everything you'll need to getaway across Upstate New York and the Berkshires:brbrRestaurants/Breweries - All Within 15 minutesbr1) Roe Jan Brewing Cobr2) Barrington Brewery & Restaurantbr3) Chatham Brewingbr4) Four Brothers Pizza Innbr5) Hillsdale Housebr6) Sweet Peas Country Dinerbr7) Little Cat LodgebrbrbrAttractions/Things To Do:br1) Ski Resorts:br- Catamount Mountain Resort - 15 minutesbr- Jiminy Peak Ski Resort - 35 minutesbrbr3) Chatham, NY - 15 minutesbr- Idyllic Hudson Valley town with charming storefronts, restaurants, breweries, and galleriesbrbr4) Great Barrington, MA - 15 minutesbr- Great Barrington is the hub of Southern Berkshire County with a vibrant Main Street and side streets packed with shops, theaters, and restaurants. While tourism is its biggest draw, its hidden open spaces and vistas has made this beautiful southern town ideal for vacation- and second-home owners.brbr5) Hudson, NY - 30 minutesbr- Hudson has a historical richness and contemporary vibrancy far bigger than its size would suggest. Hudson’s compact urban core makes it an eminently walkable city. You'll find history, art galleries, culture, and restaurants, making Hudson an extraordinary city to visit, offering sights, sounds, curiosities and great food around every corner.brbr6) Lenox, MAbrbr7)Tanglewood - 25 minutesbr- A World-Class Outdoor Performing Arts Venue! The famous performing arts venue of Tanglewood is nestled away in the Berkshire Hills of western Massachusetts and sets high standards for musical festivals, especially in the warmer months. Home to the famous Boston Symphony Orchestra, and the site of one of the world’s best-known music festivals, Tanglewood hosts the Festival of Contemporary Music, along with many other events including concerts of various genres from jazz to pop and frequent visits from James Taylor, John Williams, and the Boston Pops.brbr8) Taconic State Parkbr- Bish Bash Falls - 60 foot waterfall and highest waterfall in Massachusetts.br- Copake Iron Works Historic Sitebr- Hiking, Simming, cross-coutry skiing, and snow shoeingbrbr9) Art OMI - 25 minutesbr- Situated on one-hundred and twenty acres in the Hudson Valley, Art Omi presents the works of contemporary artists and architects, and offers a range of large-scale works in nature, plus a 1,500 square foot gallery. The Sculpture & Architecture Park currently offers more than 60 works by artists and architects on view, with pieces added or exchanged each year.brbr10) Mass MoCA - 60 minutesbr- The Massachusetts Museum of Contemporary Art (MASS MoCA) is one of the world’s liveliest centers for making and enjoying today’s most evocative art. With vast galleries and a stunning collection of indoor and outdoor performing arts venues, MASS MoCA is able to embrace all forms of art: music, sculpture, dance, film, painting, photography, theater, and new, boundary-crossing works of art that defy easy classification.

Guest House

Hudson valley and The Berkshires Cottage

Hillsdale, New York, United States

Bed

Bath

Sleeps

$517.03

Summary:brWelcome to this beautiful historical house! We've given this budget-friendly, vintage gem a refresher with 6 comfy bedrooms, 3 full baths, a proper dining room with gas fireplace, & tons of space for your group inside and out. Includes 5 bedroom guest house plus attached in law suite! brbrOnly two mins from Catamount Ski Mountain and close to Downtown Great Barrington & Hudson, NYbrbrThe Space:brWelcome to your affordable home away from home, perfect for making the most of all that the Hudson Valley and Berkshires has to offer - whether you're unwinding or seeking adventure through hiking, skiing, antiquing, and enjoying local cuisine.brbrAs you step inside, a warm entryway welcomes you. To the left, you'll discover the inviting living room, while to the right, you'll find the dining room, sunroom, and fully-equipped kitchen.brbrThe living room boasts a generous 54-inch smart TV equipped for streaming. Feel free to use your own Netflix and other streaming services.brbrThe dining room is designed for entertaining with it’s gas fireplace, boasting an extra-long table with seating for eight, and a china cabinet stocked with plenty of dishes and glassware to host a killer dinner. Adjacent to the dining room, you'll find a bright sunroom, offering additional lounge seating.brbrThe kitchen features a dining table accommodating six, stainless steel appliances (refrigerator, gas stove, microwave, and dishwasher), and it's well-equipped with all your cooking and serving essentials, including cookware, pots, pans, plates, cups, and silverware.brbrAll five bedrooms are located on the second floor of the house. One bedroom boasts two queen beds, while the other four bedrooms each feature one queen bed. The upstairs master bedroom includes a separate office space, ideal for those who need to work remotely.brbrThere are two bathrooms on the second floor - one with a tub/shower combo and the other with a stand-up shower.brbrThe house also comes with an inlaw suite which includes a queen size bed, a 2nd full size kitchen, and bathroom with stand up shower. brbrAnd there's more to look forward to:br-High-quality memory foam mattresses and hotel-grade 100% cotton linens and towels.br-Hardwood floors in the living room and dining room, tiled kitchen, and painted wood floors throughout the rest of the house.br-Window AC units to keep you cool in summer and radiator heating to keep you cozy in winter. Gas fireplace in the dining room.br-Please note that there are around 12 stairs leading to the bedroom and bathroom area, so it may not be ideal for guests with limited mobility.br-Parking is limited to four cars.br- Pet-Friendly Vibes: Furry friends welcome! Bring your buddy along for the journey, no extra fees.br-There is a laundry room off the house that is used by the housekeeping for the motel, they will not access the house at all while you are staying! brbrWe invite you to relax, unwind, and make cherished memories in this welcoming home - your gateway to the best of the Hudson Valley!

Dreamy 6 Bedroom House, Come Enjoy Hillsdale!

Hillsdale, New York, United States

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Bath

Sleeps

Most popular vacation rentals in Hillsdale

$356.76

Saltbox-style residence in the Berkshires

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Bath

Sleeps

$467.17

Hudson Valley and The Berkshires getaway

Hillsdale, New York, United States

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Bath

Sleeps

$448.00

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Hudson valley and The Berkshires Cottage

Hillsdale, New York, United States

Bed

Bath

Sleeps

$272.16

Country House

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Hillsdale, New York, United States

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Bath

Sleeps

$205.96

Country Karma -Quiet Wooded Getaway

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Bed

Bath

Sleeps

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Chalet

Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style

Hillsdale, New York, United States

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Bath

Sleeps

$2184.00