Holiday rentals in Red Rock

4.91 out of 5 average rating, 130 reviews

Cabin in Chatham

Rustic Secluded Cabin near Berkshires. *wood stove

The Red House is surrounded by acres of forest and is close to conservation areas with hiking trails. Minutes to antiquing, Kripalu, Norman Rockwell Museum, The Mount, Tanglewood, Skiing, Shakespeare & Co. You’ll love my place because of the peace, quiet and seclusion. Located up an old dirt country road. Relax by the wood stove (bring wood), in the sun room or explore nearby Spencertown, Chatham or West Stockbridge. Many ski slopes nearby & a small lake! If visiting in winter, 4wd recommended.

4.99 out of 5 average rating, 269 reviews

Cabin in Ghent

Cozy chalet w/ fireplace near Hudson & hiking

3-bedroom (5-beds), 2-bathroom home on 4 acres on a quiet street in charming Ghent, NY. Renovated in late 2021, this lovely chalet features an open floor plan, luxury bathrooms, new, high-end appliances and cookware, a wood-burning fireplace, outdoor deck, and fire pits. The home is surrounded by nature—trees, trails, streams, and farms—all close by. Hike, bike, kayak, or go to a brewery. Discover the nearby Hudson Valley farms, ski in the Berkshires, or visit the trendy town of Hudson, NY.

4.99 out of 5 average rating, 253 reviews

Cabin in Canaan

Rustic Barn Studio Apartment

Built from a saved, moved, & reconstructed 1850s- era barn from a former local dairy farm, this upstairs studio space features views of the Berkshire Mountains and walking paths on the 5 acre grounds. 20 mins from Jiminy Peak. 20 mins from Tanglewood Music Center. The space has a queen bed, sofa, kitchen area with fridge, sink, oven, stove, microwave, Keurig and coffee, toaster, and cooking essentials. **EV Charging Station coming sometime summer of 2023. We'll update when available.

4.95 out of 5 average rating, 193 reviews

Cottage in New Lebanon

The Writer's Cottage

The Writer's Cottage is a tiny white house on a country road; vintage, complete, and inspiring. Built in the nineteenth century, it's perfect for a solo traveler or a pair of travelers exploring the Berkshires and the Hudson Valley. If you like rustic buildings, you'll be a fan of the cottage; it's an incredibly cozy time warp. Queen bed and living quarters downstairs; airy loft up a narrow set of enclosed stairs. There's an orchard and lawn with grill, hammock and table.

4.89 out of 5 average rating, 187 reviews

Chatham Villg Walk to Main. 100% Smoke/Animal Free

WELCOME ALL. Pedestrian/Bike friendly Village home sits 200' to Main St pubs/pizza/movies/fine dining shopping 12mi Hudson Amtrak (taxi, Uber avail). Town park w/swim pond & tennis courts half-mile. Tanglewood 24mi. Keyless entry. Host on premises always available. 100% smoke/pet-free property. Check-in 4pm/-out 11a. 55" Sony TV. Free high-speed WiFi. Fully stocked home. Private outdoor dining w/propane bbq. 2 guests max for ultimate comfort. Park @ door. See more details within

4.89 out of 5 average rating, 171 reviews

Country house on Indian Creek

Tucked away in a beautiful valley, this house is surrounded by farm hills and creeks. Located on 5 acres of grassland and 10 acres of woodland. Close to 3 ski mountains, 2 lakes, and tons of hiking and mountain biking trails. Very peaceful and spacious place to unwind. Just 5 minutes away from town center but feels miles away from everything. If you open my profile picture you will find my guidebook, which gives you a idea of some places to eat and attractions around the area.

5 out of 5 average rating, 115 reviews

Flat in Coxsackie

Hudson River Beach House

Explore all the activities the Hudson Valley has to offer and then relax in a room full of windows overlooking the Hudson River. Make a meal in the full kitchen or hang out by the beach, build a fire, play lawn games, read a book or float in the river. For you early risers, the sunrises are spectacular. This 1860 river house is 1/2 mile from the charming Village of Coxsackie NY and a central location to many great destinations such as Hudson, Woodstock, Athens, and Catskill.

4.99 out of 5 average rating, 244 reviews

Tiny home in Chatham

Tiny House, Big Adventure on 70 acres

Welcome to "The Tiny" at The Hemptons in the Hudson Valley. The not-so-tiny house is 400sf with plenty of space to stretch out. Each of the two bedroom lofts have a comfy queen bed on a low profile frame. The kitchen is equipped for basic cooking (read: Not good for Thanksgiving, but perfectly suited for standard cooking endeavors). Regretfully, we are unable to accommodate service animals due to the health risk it poses it the owners.

4.9 out of 5 average rating, 239 reviews

Pet-friendly. Private. Host leans left. F Trump.

This is a recently renovated 120-year-old house. There are no neighbors in sight. The backyard is a wooded area. There is a stream, fire pit, table, and chairs. The garage has been converted into a game room with ping pong, pool, couches and a bar. Across the road is farmland. It's less than one mile off the Taconic State Parkway exit, and about a half hour to both Catamount and Jimminy Peak (ski resorts). Twenty minutes from Hudson.

4.97 out of 5 average rating, 132 reviews

Cabin in Chatham

The Upstate Cabin: A secluded getaway in the woods

Cozy cabin tucked away in the woods, 2.5 hours north of NYC and 2.5 hours west of Boston - where the Catskills meet the Berkshires. There's hiking in the summer, skiing in the winter, and total peace & quiet year-round. This entire cabin has been hand-lovingly restored and we can't wait to share the space with you. Follow us on Insta at @theupstatecabin to follow our upstate adventures and cabin transformation.

4.99 out of 5 average rating, 415 reviews

Tiny home in Chatham

Sugar Shack | Romantic Tiny Home + Hot Tub

Sugar Shack | Romantic Tiny Home + Hot Tub. Escape to this 300 sq ft tiny home with private hot tub and she-shed. A peaceful, romantic getaway in the heart of Chatham—just steps from shops, dining, and theater. Only 2.5 hrs from NYC & Boston. Hike, explore, soak under the stars, or cozy up by the firepit. Thoughtfully designed for privacy, comfort, and indulgence. A blissful upstate NY retreat at @artparkhomes.

4.92 out of 5 average rating, 206 reviews

Cottage in East Chatham

Beautifully Nestled Berkshires Home

Beautifully nestled 19th century colonial house situated on 60 acres of land. Very quiet and peaceful. Great Skiing in the area which include Jiminy Peak and Butternut just 30 minute from the house. 20 minutes from Tanglewood and the Kripalu Center for Yoga and Health. 15 minutes from the charming town of Chatham. 30 minutes from Hudson.

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Other great holiday rentals in Red Rock

Superhost

5 out of 5 average rating, 3 reviews

Chatham Farmhouse Hudson Valley

NazariyRating, 5 stars5 months ago

We had an amazing weekend stay at Micah’s place! The home was absolutely stunning—super clean, beautifully furnished, and stocked with everything you could possibly need. The kitchen was fully equipped with all the appliances, making it easy to cook and enjoy meals. The highlight was the TV room, which had incredible sound quality and made for a perfect spot to relax. The home was also very child-friendly, which made our stay even more enjoyable. Overall, a fantastic experience! Highly recommend this place.

Campervan/Motorhome in East Nassau

5 out of 5 average rating, 31 reviews

The Hawk's Nest

ArsalanRating, 5 stars6 days ago

We had best time there! awesome host ! She was really kind in entire trip, we were there with our baby and she gave him toys & books ❤️ Everything was perfect and safe , Thanks to her

4.96 out of 5 average rating, 25 reviews

Cottage in Malden Bridge

Cozy, charming cottage by the creek w/2 queen beds

TanyaRating, 5 stars1 week ago

Martha made our stay very welcoming. We had sold our home and wanted to stay in the area to be with our son and family for a week longer before heading out of state to our new home. The cottage was a ver quiet and peaceful time. Much needed after all the packing and moving we had done. Weather was not the best for being outside much but nights we could we enjoyed the fire pit . Thank you again for the cookies and the warm invite you gave us while there .

5 out of 5 average rating, 38 reviews

Cabin in Saugerties

Luxury A-Frame Cabin w/ Hot Tub

BingRating, 5 stars1 week ago

We absolutely loved our stay at Fil & Ellie’s place, it made it the highlight of our trip. From the minute we walked in, it felt so calm. The place is beautiful with all the amenities. We enjoyed the hot tub, grill, fireplace. We’ve been to the Catskills countless times and this is the best experience due to the wonderful stay. Thank you!

5 out of 5 average rating, 16 reviews

Cabin in Canaan

The Hideaway

RogierRating, 5 stars3 weeks ago

We (2 people and dog) stayed 4 nights at Julie's place. It is a true hideaway, quiet, serene, comfortable. It was a perfect base for us to venture out and discover all the beauty of Columbia County. Thank you, Rogier & Jo

Guest house in Old Chatham

4.94 out of 5 average rating, 17 reviews

Mountain View Retreat in Hudson Valley

JulianRating, 5 stars1 week ago

Yasmin was an amazing host. She was very communicative and helpful. She even brought us fresh muffins which were delicious. Her cottage was well appointed and perfect for our stay. Highly recommend!