Holiday rentals in Amenia

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Top-rated holiday rentals in Amenia

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Guest favourite

Home in Amenia

4.89 out of 5 average rating, 108 reviews

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.

1–8 Jul

$528 SGD per night

Guest favourite

Flat in Copake Falls

4.93 out of 5 average rating, 255 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

14–21 Oct

$135 SGD per night

Superhost

Cottage in North East

4.86 out of 5 average rating, 129 reviews

Sunset Cottage: Unplug - Relax - Recharge

Charming country cottage in Millerton, New York with a variety of nearby destinations. Unwind on a quiet country road with bunnies , dairy and beef cows as your closest neighbors. Use as a base to explore the Tri-State area. Perfect for Parent Weekends for the nearby private schools. Get away from the stress: no Six O’clock news, no Wi-Fi, no beeping microwave. Strap the bikes, skis, kayaks, or canoes to the car because you’ll be centrally located for adventures.

22 Feb – 1 Mar

$195 SGD per night

Guest favourite

Cottage in Red Hook

4.98 out of 5 average rating, 596 reviews

bright serene + spacious barn

a bright serene space built by locals on the property we live on. we are in what we think is the most beautiful notch of the Hudson River Valley - surrounded by pastoral beauty and dramatic landscapes. quaint yet cultured towns in all directions. please read the entire description & rules before booking • beyond 2 guests, the rate adds 50$/night/per person • please add dogs (2 max. 50$/per dog) when booking • we look forward to having you here, at gallatin farmstead!

19–26 Sep

$500 SGD per night

Guest favourite

Home in Cornwall

4.92 out of 5 average rating, 225 reviews

Secluded modern forest cabin with private brook

Renovated cozy cabin (orig 1930s) with modern interior. Two bedrooms, new kitchen & bathroom, overlooking a beautiful private brook and forested hill. Minutes drive to the general store & Kent Falls, 10 minutes from fantastic restaurants, Mohawk Ski Resort & summer activities like swimming & kayaking. Great hiking trails and close to the Appalachian Trail. High speed internet, Netflix, and a deck with outdoor seating. Instagram @GunnBrookCabin

20–27 Oct

$316 SGD per night

Guest favourite

Cottage in Sharon

4.9 out of 5 average rating, 123 reviews

Foxfire Hill: A Bit of Luxury in the Countryside

Enjoys luxurious Get away to lovely Sharon, CT, just 2 hours from NYC/3 hours from Boston. Enjoy a chill vibe, garden and mountain views, and fresh organic eggs from our lovely flock of hens. We’ve created a luxurious and spacious modern feel, in a bucolic farmland setting. All newly refurbished with a luxurious modern bath with rain shower and fabulous marble stone work. Coyuchi bedding, soft organic cotton linens, and gourmet kitchen!

19–26 Nov

$290 SGD per night

Guest favourite

Farm stay in Ancram

4.95 out of 5 average rating, 264 reviews

Relaxing secluded stay with loving social animals.

Do you love nature, animals, and spa comforts? Then this is the perfect place for you! This is a fully finished, private area ground-floor walk-out, in the basement of the main house. Right outside your front door is 800 acres of hiking trails. You are surrounded by a mature forest, with loving and social goats, geese, ducks, kitty, and pups. To enhance this private retreat there are a hot tub and sauna steps from your door.

8–15 Dec

$225 SGD per night

Guest favourite

Flat in Stanfordville

4.95 out of 5 average rating, 152 reviews

Country Apartment great for a romantic getaway

Second story apartment above garage with private entrance has everything you need for a comfortable getaway. Located on quiet rural neighborhood road with off street parking. Enjoy nature right out your door walking to the beaver pond in the back woods or on the many nearby hiking and biking trails. Relax in the backyard. An easy drive from the Taconic Parkway or 20 minutes from the Metro-North Wassiac train station.

25 Jun – 2 Jul

$186 SGD per night

Guest favourite

Guest house in Millbrook

4.86 out of 5 average rating, 222 reviews

Quaint Cottage near Millbrook Village

This space is a small cottage on our property located just a mile from the Village of Millbrook. The cottage is very private and removed from the main house. It features a queen-size bed, small bath with shower, and modest kitchenette with coffee/tea maker and refrigerator but no stove. The cottage is good for couples or solo adventurers. Small house-broken dogs are welcome. No cats, please.

19–26 Jul

$210 SGD per night

Guest favourite

Flat in Millbrook

4.93 out of 5 average rating, 205 reviews

Red Tail Ridge

One BR with bath, full kitchen, eating area and living room. Separate entrance and sliding glass door in rear with country views. Located on 12 acre parcel. Close to village of Millbrook (less than 4 miles). We are located in center of Dutchess County. There is great antique shopping, historic sites and some of the finest restaurants and chefs with tastes to suit most everyone. .

6–13 Aug

$174 SGD per night

Guest favourite

Guest suite in Morris

4.99 out of 5 average rating, 340 reviews

Lakeside Private Guest Suite

Feel like you're in your own studio apartment in the spacious, bright lower level of our home! Walk out to your own private lounging/dining area. Separate entrance and parking space. Enjoy the serenity of Camp Columbia state park, as it is our extended backyard. Tip: The sunsets are beautiful! 2 hours from NYC, 30-45 minutes to local skiing and just 10 minutes to Washington Depot.

19–26 Nov

$127 SGD per night

Guest favourite

Flat in Millerton

4.8 out of 5 average rating, 230 reviews

Gardens Galore and Village Whimsy Retreat

My place is close to restaurants and dining, the city center, and parks. My place is good for couples, solo adventurers, business travelers, and families (with kids). It is a steal for the price. nothing is as good around here, a true bargin. The apartment is below the 1850's victorian house. During the day you can hear children's feet pitter patter. After 7 The place is quite.

18–25 Jan

$139 SGD per night