Vacation rentals in Amenia

The Wheelhaus—Restored Home in Hamlet of Amenia

Open a bottle of wine and stretch out on the blue sectional sofa in the sunny living room. The fun and stylish decor is a modern interpretation of the area’s agricultural roots, with wood floors and exposed-brick accents in the loft bedroom. Two laptop friendly work spaces available and high speed WiFi. Reach out with any special requests! Check out our other properties nearby! Hitchbrook in Sharon, CT Thimble House in Millbrook, NY Social: @amenia.union Guests will have access to the entire home and yard. Happy to help enhance your experience and address any concerns if they arise! Walk to restaurants and cafes in the center of town, and catch a new release at the drive-in movie theater. Explore the vineyards and go hiking and biking in the local area. Explore further afield from Metro North train station, only minutes away. Parking available at the house. Close (3 miles) to Metro North Railroad. Easy access (.25 miles) to the Harlem Valley Rail trail, a walking and bike path. Walking distance to restaurants in the town of Amenia.

Amenia Main St Cozy Studio

Cozy studio in well maintained house from 1900. 150 sq ft with full size bed. Unit is comfortable for one, tight for two. Right in small town of Amenia. Front porch with seats/table. Walking to food, shops, drive-in movie theatre, and rail trail. Trail is 1/4 mile from house, paved and only allows walking/biking. On trail: Arts village Wassaic (3 miles south) Millerton (8 miles north). Train to NYC is 2.5m south. Tons in area: wineries, distillery, lakes, hiking, theatre & quaint towns.

The Red Country Cottage

Perfect getaway in this countryside cottage nestled in nature but walking distance to town center. Spend some relaxing time watching the creak run by, walk or bike (provided/bring own) on the 26mi flat scenic Harlem Valley Rail Trail from the cottage. Enjoy the evening sitting by the fire/comfortable patio. Visit the 60’s themed movie theater and restaurant walking distance, near by brewery/winery/cafe/restaurants, wedding venues, Lime Rock Racing, skiing. Direct train to Wassaic from MetroNorth

Boulder Tree House

Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

Hilltop Home on 10 acres, hot tub, firepit + solar

Welcome to our retreat in the Smithfield Valley, between the charming towns of Amenia, Millerton and Millbrook, and near the ski slopes of Catamount, Mohawk and Butternut. Our house overlooks the Elk Ravine farm, surrounded by scenic woods on a 10+ acre estate. Our home has 3 bedrooms, 3 full bathrooms, sleeps 9, a spiral staircase into a kids loft, a media room with fold-out bed, hot tub, BBQ grill, firepit, large lawn, parking for up to 4 cars, a high-grade HEPA air purifier, and more.

Cozy Hudson Valley House

Recently renovated A-Frame in beautiful Hudson Valley. Floor to ceiling windows bring in tons of natural light. The house sits up a hill with beautiful views of surrounding area. The village of Wassaic which has the super cool restaurant/bar The Lantern and the incredible community and arts space the Wassaic Project, is just a mile away. Sweet HV towns like Millbrook, Millerton, Kent and Lakeville 20 mins away. Skiing at Catamount 40 mins away. Tons of excellent hiking all around.

Woodland A-Frame

Our A-frame home stands out for the way it invites the outdoors in. With skylights and soaring windows, you can experience the natural beauty of the forest from every room—whether you're sipping coffee while watching deer or wild turkeys wander through the yard, enjoying the gentle drift of autumn leaves, or cozying up during a summer storm. Even on chilly days, the house feels connected to nature in a peaceful, grounding way. Guests have access to our local swimming hole, Mudge Pond.

The Cottage on Babbling Brook

A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

The Farmhouse

Enjoy staying at our charming Farmhouse in the heart of our working dairy farm. Our farm sits on some of the most beautiful hills in Cornwall with the famous Gateway to Cornwall view where you can see our dairy cows grazing in the grandeur of nature. Come say hello to the cows in the barn during milking or watch the herd cross the road evoking sites you might expect to see in small European farming villages. You'll likely see us on our tractors bringing hay and water to our cows!

The Studio

Millerton, NY is a weekender's dream! Enjoy a peaceful stay in our newly renovated studio, fully furnished with a queen bed and private entrance. You're just a short walk from everything the village has to offer—from breakfast at Oakhurst Diner and coffee at Irving Farm to shopping at Westerlind, browsing Oblong Books, or catching a film at The Moviehouse. We also offer simple, transparent pricing with no cleaning fee. Perfect for a relaxing Hudson Valley getaway.

Gorgeous Modern New Ranch near Rail Trail!

Brand new top to bottom high end renovation on a stylish home just a mile from the quaint town of Millerton on 3 acres with tremendous views of the rolling hills of the Hudson Valley. Immaculate home boasts all the comforts and amenities to fully relax and absorb the landscapes. The Harlem Valley Rail Trail is a few hundred yards away. Walk or bike into town. Walk up the hillside 50 yards to capture unbelievable views. A truly stunning home and area.

Charming 2nd floor studio(w/ Seasonal Heated Pool)

Consider this studio your home away from home while you visit Amenia. This welcoming space features a nice living room with a queen bed, perfect for a cozy stay. With amenities like AC, WiFi, and a washing machine, guests can relax and unwind after exploring the area. The bathroom with a shower adds convenience to your stay. Fall in love with Amenia and enjoy the magic it has to offer. Pool open May 15th-October 15th Resort-style amenities!