Best Hillsdale Hotels

When you stay at The Brooks Motel in Hillsdale, you'll be near ski lifts, within a 5-minute drive of Catamount Aerial Adventure Park and Catamount Ski Area. This motel is 2.6 mi (4.2 km) from Taconic State Park and 6.7 mi (10.8 km) from Bash Bish Falls State Park. This motel features snowboarding nearby, downhill skiing nearby, and cross-country skiing nearby. Free self parking is available onsite. Make yourself at home in one of the 16 air-conditioned rooms featuring LED televisions. Your memory foam bed comes with Egyptian cotton sheets. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. Bathrooms feature shower/tub combinations, complimentary toiletries, and hair dryers.

Escape to this beautifully restored 7BR farmhouse nestled in the rolling hills of Hillsdale. Just minutes from Catamount ski area and close to Great Barrington, this spacious retreat features a private pool, 7-person hot tub, arcade game room, fire pit, and chef’s kitchen. Ideal for family reunions, group getaways, team business trips, or peaceful weekends in nature with fast Wi-Fi, Smart TVs, and room for 14+ guests (plus a crib). Thoughtfully designed for connection, relaxation, and memory-making, the layout offers the perfect setting for both large gatherings and cozy weekends with friends.BEDROOMS & SLEEPING ARRANGEMENTS:● Bedroom 1 (Main level): Queen bed + ensuite bathroom, window A/C● Bedroom 2 (Main level): Queen bed, window A/C● Bedroom 3 (Main level): Twin bed, window A/C● Bedroom 4 (Main level): Twin bed, window A/C● Bedroom 5 (Upstairs): Two twin beds, window A/C● Bedroom 6 (Upstairs): King bed + ensuite bathroom, floor A/C fans● Bedroom 7 (Upstairs): Two full beds + crib, window A/C● Bonus: Twin rollaway bed availableAll bedrooms feature cozy linens, charming decor, and plenty of natural light.KITCHEN & DINING● Fully equipped chef’s kitchen with stainless steel appliances● Keurig + drip coffee makers, wine fridge, spices, toddler plates & bowls● Eat-in breakfast nook for 6● Formal dining room with seating for 10—ideal for holiday meals and celebrationsGAME ROOM & ENTERTAINMENT:● Dedicated game room with arcade machine, poker table & board games● Sunroom with ping pong table, mountain views & 55” Smart TV● 5 Smart TVs throughout home● Fast Wi-Fi for streaming or remote workOUTDOOR FEATURES:● Private backyard with breathtaking views of the hills● Brand new hot tub with built-in speakers● 2 fire pits: one propane lounge set, one 10-person wood-burning pit● Weber grill, outdoor dining table (seats 10), string lights for evening ambianceOUTDOOR POOLOur private pool is open from Memorial Day to mid-October (weather permitting).Please note: Pool heating is optional and offered as an add-on amenity and not pre-charged. If you’d like the pool heated during your stay, there is an additional charge of $100 per day which will be charged on the day of check-in. This fee covers the significant energy costs required to maintain a comfortable water temperature.We kindly ask that you let us know 48 hours in advance of your stay if you’d like the pool heated so we can prepare it prior to your arrival.*Pool Heater Disclaimer*The Property is equipped with a pool heater, available as an additional amenity for $100 per day. Use of the heater must be requested by the Guest at least 48 hours prior to check-in, and the fee must be paid at the time of check-in.While the Host will make reasonable efforts to maintain the pool heater in good working condition, equipment failures may occur beyond the Host’s control. The Host does not guarantee the availability, functionality, or performance of the pool heater before or during the Guest’s stay. If the pool heater is unavailable, the Guest shall not be entitled to any credit or refund, except that any fee paid for the pool heater will be refunded in full.GENERALFree WiFi, radiator heat, window A/C, hot tub towels, towels/linens, washer/dryer, hair dryerWASHER/DRYERAn in-unit washer/dryer combo set. Complimentary scent-free detergent is provided for your stay.PARKINGThe driveway accommodates up to 5 vehicles. Parking is allowed only in designated areas. Further parking instructions will be provided at check-in.MAINTENANCEPlease note: routine maintenance such as lawn care or snow plowing may take place during your stay.***IMPORTANT NOTES***SHORT-TERM RENTAL AGREEMENTAll guests are required to sign our Short-Term Rental Agreement upon booking.It includes important details such as check-in/check-out times, house rules, and stay guidelines.PET FRIENDLYWe welcome dogs under 50 lbs (maximum of 2 dogs).-Pet fee: $150 per pet, per stay-No cats allowed at this time.-Please let us know how many pets you’re bringing at the time of booking. Platform will automatically include the first pet fee.For additional pets, we’ll request an extra $150 per pet through the app. All pet fees must be paid prior to check-in.PARTIES & GATHERINGSAbsolutely no parties or large gatherings allowed — no exceptions!HILLSDALE TOWNSHIP NOISE ORDINANCEOur home is in a peaceful rural area, so please respect quiet hours.-Quiet hours: 9 PM to 8 AM-No loud music should be played during these hours. Be mindful of our neighbors and the local ordinance.STAIRS REQUIREDThis charming historic farmhouse features a distinctive layout that enhances its character. Inside, you’ll encounter several small sets of steps, with the kitchen thoughtfully positioned on the opposite side of the living room. Two bedrooms are located on one side of the house on the second level, while a third bedroom is accessible via a separate staircase off the dining room. The home’s cozy, old-world charm is truly captivating, though the layout may be less suited for guests with mobility challenges.FIREPLACE NOTICEThe indoor fireplace is currently not available for guest use.SECURITY AWARENESS4 exterior security cameras are installed facing outward for guest and property safety. No cameras face any interior living spaces. Cameras do not actively record video or sound during guest stays.WILDLIFE AWARENESSLocated in a rural area — you may spot deer, foxes, coyotes, or even bears. Please be cautious and avoid leaving food or trash outdoors.TRAFFIC NOTICEOur home is along State Route 22, so you may hear outdoor traffic noise.Thank you and looking forward to your reservation!About pets:Pets allowed: dogs less than 50 lbs per pet (limit 2 pets total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:No smoking, vaping, or marijuana use, burning incense, sage. Smoking is allowed outdoors only. Evidence of indoor smoking will result in a $500 fine..Do not lock the bottom door under the Schlage keypad lock, doing so will prevent entry from outside. Lock out fees will incur in any case of lock out.,Pets are not allowed on furniture, including sofas, beds, and chairs. Excessive pet odors or damage to furniture may result in a $350 cleaning fee..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.

Escape to Serenity in the Heart of the Berkshires: A Modern Retreat Surrounded by NatureImmerse yourself in the awe-inspiring tranquility of the Berkshires within this secluded and contemporary home, offering breathtaking mountain and rolling meadow views on 6 acres of stunning countryside. Tucked away at the end of a winding country road, this haven ensures complete privacy, providing the perfect sanctuary from a hectic schedule.Only a 9-minute drive from the Taconic Parkways and strategically located near Catamount Ski, Butternut Ski, and Copake Lake, this residence seamlessly combines country living with modern convenience. A scenic 50-minute drive takes you to Jiminy Peak Mountain Resort Ski and Bousquet Mountain Ski Area for a winter wonderland retreat.This beautiful home, boasting an open floor plan, features 4 bedrooms, 2.5 baths, an inviting kitchen -renovated in 2025- and multiple spacious living areas, including a wood-burning fireplace. Revel in al Fresco dining on the deck, overlooking mountain vistas, or cozy up by the fireplace for intimate moments with loved ones.The upper level hosts 4 bedrooms, including two master suites with luxurious amenities. The main level's expansive living space opens to a deck with multiple seating areas, perfect for gatherings. Downstairs, discover a recreation haven with a ping pong table, a Smart TV lounge, and sliding doors leading to an outdoor deck.Enjoy high-speed fiber optic internet, ensuring seamless remote work or streaming, facilitated by premium WiFi systems. Fully furnished and strategically located 100 miles from NYC and 150 miles from Boston, this rustic yet modern retreat awaits your year-round escape. Keywords: Bash Bish Falls, Catskills, Summer, Weekend, Hudson Valley, Skiing, Hiking, Tanglewood, Winery, Stargazing."About pets:Pets allowed: dogs (limit 2 total).Cats not allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:- Please, keep feminine products or wipes from being disposed in the toilets. -Ashes from the grill and fireplace must be bagged and trashed..Garbage recycling collection is on Mondays so have all the garbage and recycling INSIDE bags, before putting it in the bins by the driveway.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.Can smoke outside 20 feet from house.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.

Welcome to The Johnson Farmhouse, a delightful retreat steeped in charm and history, located in the heart of the picturesque hamlet of Hillsdale, NY. Location, Location, Location!Nestled just minutes away from an array of restaurants, shops, and grocery stores, you’ll find everything you need right at your fingertips. For outdoor enthusiasts, Catamount Mountain Resort is only 3.2 miles away, offering skiing in the winter and an exhilarating aerial park in the summer. A short 15-minute drive east will take you to the stunning Great Barrington, MA, while a 16.9-mile drive west leads you to the trendy upstate gem of Hudson, NY. Don’t miss exploring charming nearby towns like Millerton and Chatham, each offering its unique character and attractions.Cultural and Outdoor ActivitiesThe Johnson Farmhouse is perfectly situated for those looking to immerse themselves in the rich cultural and outdoor activities of the Hudson Valley and Berkshires. Discover the breathtaking Bash Bish Falls, enjoy a performance at Tanglewood, experience the art of dance at Jacob's Pillow, or explore the stunning installations at Art Omi. Plus, for cycling enthusiasts, the scenic Harlem Valley Rail Trail is less than a mile away—perfect for a leisurely ride through beautiful landscapes!The SpaceYou’ll have private access to half of the farmhouse, including a charming main entry and foyer, a spacious living room that doubles as a dining/game room, a sun-soaked sun porch, and a screened-in porch perfect for relaxing with a book. Choose between a restful King bedroom and a charming Queen bedroom, both designed for comfort, and enjoy the convenience of a private bath.While this rental does not include a full kitchen, we’ve equipped a kitchenette with a microwave, Keurig coffee maker, and apartment-sized refrigerator for your convenience. Enjoy complimentary coffee pods, sugar, and eco-friendly disposable plates, flatware and coffee cups (with lids) during your stay.Experience the perfect blend of historic charm and modern comfort at The Johnson Farmhouse; the perfect base to exploring the natural beauty and cultural richness of the Hudson Valley and Berkshires.About pets:No pets allowed.About checkOut:Check out before 12:00 PM.About children:Adults only.About customRules:Only toilet paper in the toilet..No shoes in the house other than in the foyer.,Quiet hours: 11pm - 7am.About checkIn:Check in after 6:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.

With a stay at Little Cat Lodge in Copake Falls, you'll be near ski lifts, just a 1-minute walk from Catamount Ski Area and 12 minutes by foot from Catamount Aerial Adventure Park. This hotel is 3.1 mi (4.9 km) from Hillsdale Town Hall and 3.2 mi (5.2 km) from Jug End State Reservation. Enjoy recreational amenities such as a sauna and a seasonal outdoor pool. Additional features at this hotel include complimentary wireless internet access, ski storage, and a picnic area. At Little Cat Lodge, enjoy a satisfying meal at the restaurant. Wrap up your day with a drink at the bar/lounge. A complimentary continental breakfast is served daily from 7:30 AM to 9:30 AM. Featured amenities include a business center, express check-in, and express check-out. Free self parking is available onsite. Make yourself at home in one of the 14 air-conditioned rooms featuring MP3 docking stations and minibars. Your memory foam bed comes with Egyptian cotton sheets. 50-inch Smart televisions with digital programming provide entertainment, while complimentary wireless internet access keeps you connected. Bathrooms have deep soaking bathtubs and rainfall showerheads.

Located in Great Barrington, Prospect Berkshires is in the mountains, within a 10-minute drive of W.E.B. Du Bois Boyhood Homesite and Catamount Aerial Adventure Park. This hotel is 3.7 mi (5.9 km) from Catamount Ski Area and 4 mi (6.4 km) from Jug End State Reservation. Be sure to enjoy recreational amenities including an outdoor pool and a sauna. Additional features at this hotel include complimentary wireless internet access, concierge services, and gift shops/newsstands. Satisfy your appetite with local cuisine at The Cliff House, a restaurant which features a bar/lounge. Dining is also available at the coffee shop/cafe. The front desk is staffed during limited hours. Free self parking is available onsite. Treat yourself to a stay in one of the 49 guestrooms, featuring heated floors. Your bed comes with down comforters and Egyptian cotton sheets. Complimentary wireless internet access is available to keep you connected. Conveniences include minibars and free tea bags/instant coffee, and housekeeping is provided once per stay.