Vacation 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, 268 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.

4.96 out of 5 average rating, 124 reviews

Guesthouse in Housatonic

Sweet Victorian in Housatonic

Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newly renovated Victorian house in Housatonic. Tasteful clean furniture, organic new sheets, pillows and duvets. Lovely clean kitchen that is fully equipped to host dinners. Situated up on a hill in Housatonic this three bedroom is conveniently located to to Great Barrington, Lake Mansfield, Stockbridge, Butternut, Catamount, Tanglewood, Kripalu and Monument Mountain.

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.

4.98 out of 5 average rating, 83 reviews

Barn in East Chatham

Luxury Barn Retreat — All-Season Escape Awaits!

An exceptionally private getaway on 8 beautiful acres near Chatham, NY, this historic barn has been meticulously renovated, including a full chef’s kitchen. It’s one of the area’s most stunning accommodations, ideally located between some of the most picturesque destinations— including the Berkshires, Great Barrington, Taconic State Park, Beebe State Forest, Ooms Conservation Area, Queechy Lake, Tanglewood, Hudson, Kinderhook, and so much more!

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, 237 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, 131 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, 414 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.

4.99 out of 5 average rating, 68 reviews

Home in East Chatham

Relaxing Retreat-Enjoy Hudson Valley & Berkshires

Welcome to our cottage in the woods! We hope to cultivate a relaxing space for a getaway with friends or family. Our home is your home for a weekend, a week, or even several months. Use it as your personal retreat or home base for exploring the Hudson Valley and the Berkshires.

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Other great vacation rentals in Red Rock

5 out of 5 average rating, 12 reviews

Chalet in Canaan

SRC-Hudson Valley/Berkshires Cultural Corridor

CariRating, 5 stars5 months ago

If you're thinking about booking Kristen's Chalet - do not hesitate! Book it - you won't be disappointed. The house has ample room to spread out with your family. We enjoyed our Christmas dinner at the dining table and afterwards, we were able to watch a movie together. The location was perfect for us to go out every day and explore - Red Lion Inn, The Mount and several other towns. We had to make plans to stay in so we could enjoy the beautiful Chalet for an evening. We can not wait to return and enjoy this beautiful home. ♡

Home in East Chatham

4.79 out of 5 average rating, 189 reviews

Hot Tub under the STARS 3 Queen 2 Bath! Windswept!

PatriciaRating, 5 stars3 weeks ago

This was a really comfortable and private retreat. The mattresses were AMAZING and we all slept like stones. The house is larger than I had imagined, giving members of my family more privacy than we'd anticipated -- great layout. The pellet stove heats a small and cozy sitting room that has a small library of books and a cabinet of games for those days when rain invited you indoors. The hot tub was a lovely amenity, as were the cows and horses next door. The instructions to get there and to get in were easy to follow. Lots of walking in the area, lots to do, and a very gracious host.

4.95 out of 5 average rating, 225 reviews

Farm stay in New Lebanon

Barn Stay at Shadowbrook Farm

JenniferRating, 5 stars1 month ago

The space was beautiful, clean, and exactly as pictured! We enjoyed a weekend away and appreciated the local recommendations shared in the guide. We spent time exploring the farm, the surrounding area, and also were able to kick back and relax in the amazing property.

4.65 out of 5 average rating, 85 reviews

Secluded Post-and-Beam Chalet w/Breathtaking Views

MaggieRating, 5 stars3 weeks ago

Was a great stay and exactly what we were looking for, for a weekend away! The house is located close to nearby attractions but secluded enough to feel very nature vibes. Perfect for a group trip.

4.96 out of 5 average rating, 23 reviews

Cottage in Malden Bridge

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

BonnieRating, 5 stars12 months ago

Martha was a great host! The cabin was perfect and exactly as described. The fenced in yard was perfect for our pup! She took time to make a list of local things to do. I hope to come back and stay here again soon!

5 out of 5 average rating, 16 reviews

Cabin in Canaan

The Hideaway

RogierRating, 5 stars2 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

5 out of 5 average rating, 16 reviews

Home in East Chatham

Charming house in historic hamlet

JimRating, 5 stars10 months ago

this is our second time staying at Anne's place. it's really a magical place. the house and area makes you feel like we went back in time. the house is amazing, and the nature around the house is beautiful. we were here to visit Tanglewood which is not too far. if you are looking for someplace quiet and peaceful to get a way this is perfect.