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Holiday houses in Amenia

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Top-rated holiday rentals in Amenia

Guests agree: these stays are highly rated for location, cleanliness and more.

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Home in Amenia

4.87 out of 5 average rating, 119 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.

Guest favourite

Home in Amenia

4.97 out of 5 average rating, 103 reviews

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

Guest favourite

Guest suite in Millerton

4.93 out of 5 average rating, 335 reviews

Romantic Sunset-50 mile view!

ROMANTIC LUXURY! Spring/Summer is beginning now. Flowers are starting to bloom and the nights are crisp and cool. Fresh mountain air. Clear starry nights. Your own private suite, entrance, kitchen, bathroom, outdoor dining facilities, bar b q grill. Located atop a mountain with magnificent SUNSET view 50 miles overlooking the Hudson River Valley. Completely steam cleaned, disinfected and sterilized before each guest. HEPA Air filters installed. High speed WIFI, 500mbps! 55” 4K HD TV;

Guest favourite

Rental unit in Pine Plains

4.98 out of 5 average rating, 126 reviews

Newly renovated cutie

Newly renovated apartment in private home. Pets may be allowed on a case by case basis. Please contact me to discuss. Ample parking off road. Quiet location. Centrally located. Hudson to the north (20 mins). Millerton (10 mins) to the East. Rhinebeck (20 mins)to the west. Poughkeepsie to the south. Summertime polo matches only 5 mins from the house. Town beach a couple mins away. Many dining options within minutes. The Stissing Center offering musical and theater options also within minutes.

Guest favourite

Guesthouse in Stanfordville

4.93 out of 5 average rating, 177 reviews

Eco Cottage in the Woods

The cottage is light and airy, surrounded by forest. You may see birds and deer from the bedroom or living room. The queen bed is divided from the living room by a bookcase wall. There is a sofa bed in the living room which faces a patio overlooking the woods. We have a 16x36 unheated gunite pool, professionally maintained. The cottage works well for a couple or a couple with children. 2 night minimum required. Pets welcome. Pet owners passing through may stay 1 night.

Guest favourite

Cottage in North East

4.87 out of 5 average rating, 143 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.

Guest favourite

Cottage in Pine Plains

4.98 out of 5 average rating, 127 reviews

Pine Plains Cottage

Located just 2 hours north of NYC, our country cottage in bucolic Pine Plains is newly renovated and furnished in a modern yet cozy style, welcoming you to a relaxing retreat! It is located in the heart of Pine Plains, a short walk to the town center. Perfect for 2-4 people. We currently have a 2 night min. stay and 3 night min. for holiday weekends. Contact us directly for week/month/shorter stays and to inquire if we can accommodate your pet or a shorter stay!

Guest favourite

Farm stay in Ancram

4.96 out of 5 average rating, 284 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. Just Added mini split AC!

Guest favourite

Rental unit in Salt Point

4.83 out of 5 average rating, 152 reviews

Arcady - Modern, 1br cottage

Renovated 600 sq ft 1br/1ba cottage! Welcome to Arcady - an ideal rustic paradise. Our recently renovated barn cottage situated on 6 acres of land with private creek and within easy drive of Rhinebeck, Millbrook, Omega Institute, Poughkeepsie and thousands of Hudson Valley Attractions. 10 min drive from Omega, 1 min drive from a town beach - enjoy everything area has to offer including hikes, mansions, farm visits, wineries and much more.

Guest favourite

Cottage in Sharon

4.91 out of 5 average rating, 146 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!

Guest favourite

Rental unit in Stanfordville

4.95 out of 5 average rating, 169 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.

Guesthouse in Millbrook

4.85 out of 5 average rating, 234 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.

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Popular amenities for Amenia holiday rentals

Free parking on premises

Air conditioning

Stay near Amenia's top sights

Four Brothers Pizza Inn78 locals recommend

Serevan39 locals recommend

Freshtown of Amenia13 locals recommend

Back In the Kitchen7 locals recommend

Amenia Steakhouse6 locals recommend

Monte's Local Kitchen & Tap Room6 locals recommend

Other great holiday rentals in Amenia

Guest favourite

Home in Cornwall

5 out of 5 average rating, 51 reviews

The Farmhouse

Guest favourite

Home in Cornwall

4.99 out of 5 average rating, 77 reviews

The Brookside Barn

Guest favourite

Campervan/RV in Wassaic

4.97 out of 5 average rating, 31 reviews

Surrounded by Nature - Pet Friendly Glamping

Guest favourite

Cabin in Millerton

5 out of 5 average rating, 20 reviews

Luxe Cabin Oasis: 40 acres with stream-ideal for 2

Home in Sharon

4.91 out of 5 average rating, 33 reviews

Beautiful sun filled cottage in the woods

Guest favourite

Home in Millerton

5 out of 5 average rating, 16 reviews

Gorgeous Modern New Ranch near Rail Trail!

Guest favourite

Cabin in Wassaic

4.96 out of 5 average rating, 49 reviews

Cozy Hudson Valley House

Guest favourite

Home in Amenia

4.97 out of 5 average rating, 29 reviews

Treemendous View Cottage

Quick stats about holiday rentals in Amenia

Total rentals
10 properties
Nightly prices starting at
$128 NZD before taxes and fees
Total number of reviews
330 reviews
Family-friendly rentals
10 properties are a good fit for families
Wi-Fi availability
10 properties include access to Wi-Fi
Popular amenities
Kitchen, Wi-Fi and Pool

Destinations to explore