Holiday houses 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.

Family · Value · Nearby

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

Value · Family · Check-in

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.

Family · Location · View

Charming Mountain House

Tastefully updated 1860's farmhouse on 5 rewilded acres, less than 2 hours from New York City. Quiet and private with great energy. Nestled in a mountain hollow near world class food, bike paths, swimming, skiing, horse farms, the Appalachian Trail, this home is ideally located for exploring the Hudson Vally, from the Catskills to the Berkshires. Artesian spring water, on-demand hot water, fast Wi-FI, solar power, birds and nature all around. Lots of nature. Accessible via Metro North (Wassaic).

Family · Location · Getting around

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.

Family · Location · Nearby

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.

Family · Location · Wi-Fi

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!

Location · Value · Accuracy

Romantic Sunset view, Peace n Quiet, 10 Mn to Silo

Luxurious private suite with stunning 60 mile Hudson River Valley sunset views! Horse country, ideal for horse and nature lovers and 200+bird species. Private entrance, kitchen, bathroom, HEPA filters, 500Mbps WiFi, 55” 4K TV. During the Fall, Winter and Spring seasons it is cold , snowy , icy, frozen ground. You agree that you are on the property at your own risk. Stargaze & delight in fireflies! Relax on the deck with crisp mountain air. Near picturesque towns.

Family · Value · Decor

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.

Family · Value · Amenities

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.

Family · Location · Backyard

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!

Value · Location · Hospitality

Three Corner Farm

Our lovely 1810 cottage with views of fields and protected wetlands is on a quiet country road, with cows and sheep as our neighbors. With two bedrooms, a kitchenette, living room, & separate study, there is plenty of room to read, rest, create, reflect! Our barn has a private gym, as well--steps from the cottage. We are 3 miles from the village of Millerton and 1/2 mile from the rail trail. We welcome dogs and children.

Location · Family · Quiet