A rural road flanked by dense greenery and power lines under a cloudy sky.

Holiday Homes in Amenia

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Amenia holiday homes

A living room with a television, a cabinet, a glass coffee table, and a framed picture on the wall.

1. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is AU$967
includes taxes & fees
14 Oct - 15 Oct
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

2. Chic Barn Style * Fireplace * Near Stissing House

Chic Barn Style * Fireplace * Near Stissing House
Pine Plains
10.0 out of 10, Exceptional, (3 reviews)
"We loved the property and everything was so welcoming! Having a pool there would be the best addition for this place!"
United States
Estefany G.
The price is AU$1,157
includes taxes & fees
13 Oct - 14 Oct
Chic Barn Style * Fireplace * Near Stissing House
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

3. Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Kingston
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful house to stay in, convenient to numerous restaurants and hikes. Our host was very communicative and had great recommendations for the area!"
United States
Brendan B.
The price is AU$371
includes taxes & fees
27 Oct - 28 Oct
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

4. Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Millbrook
10.0 out of 10, Exceptional, (6 reviews)
"This is a charming, historic, well-maintained home on a beautifully landscaped lot. The updates in the home balance a respect for tradition while also providing modernization. The village of Millbrook is a quintessential twee New England village. The house felt very comfortable and homey and the caretaker was attentive and accommodating. We enjoyed our stay!"
United States
Beth E.
The price is AU$1,181
includes taxes & fees
11 Oct - 12 Oct
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

5. Cozy private room in a shared home with a Full-size bed and private bathroom.

Cozy private room in a shared home with a Full-size bed and private bathroom.
New Milford
10.0 out of 10, Exceptional, (1 review)
"Clean and close to activitys"
United States
randall
The price is AU$234
includes taxes & fees
13 Oct - 14 Oct
Cozy private room in a shared home with a Full-size bed and private bathroom.
A wooden cabin interior with a bench, a rug, and a hanging plant.

6. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
10.0 out of 10, Exceptional, (2 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is AU$351
includes taxes & fees
1 Nov - 2 Nov
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

7. Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (33 reviews)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
The price is AU$413
includes taxes & fees
12 Oct - 13 Oct
Campfire Cottage: Fireplace, fire pit & no chores!
A large wooden dining table surrounded by chairs, with a stone fireplace and large windows in the background.

8. The George is an elegant restored home in the Hudson Valley

The George is an elegant restored home in the Hudson Valley
Stanfordville
9.6 out of 10, Exceptional, (10 reviews)
"Clean, comfortable, private, and plenty of room. Hosts went above and beyond to make our stay easy and memorable."
United States
Polly J.
The price is AU$1,568
includes taxes & fees
12 Oct - 13 Oct
The George is an elegant restored home in the Hudson Valley
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

9. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (45 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AU$622
includes taxes & fees
12 Oct - 13 Oct
Cheerful 3-bedroom cottage with woodstove
A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

10. Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful property with ample space for parking. Host was super nice and met all of our needs!"
United States
Nicole Y.
The price is AU$617
includes taxes & fees
4 Oct - 5 Oct
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A spacious living area with a dining table, sofa, and large windows offering a view of the outdoors.

11. 3BR Modern Home in Kingston - Sleeps 6 -Fire Pit -Game Room -Pet Friendly

3BR Modern Home in Kingston - Sleeps 6 -Fire Pit -Game Room -Pet Friendly
Kingston
10.0 out of 10, Exceptional, (3 reviews)
"great host and property! recommended and would go back."
United States
Themis H.
The price is AU$824
includes taxes & fees
5 Oct - 6 Oct
3BR Modern Home in Kingston - Sleeps 6 -Fire Pit -Game Room -Pet Friendly
A modern living room with a sofa, a coffee table, and a dining table. There are two doors, one black and one white, and a window with blinds.

12. Hot Tub - Hammock- Games - Grill - Large Colonial

Hot Tub - Hammock- Games - Grill - Large Colonial
Kingston
10.0 out of 10, Exceptional, (12 reviews)
"We had a great stay! Great location and was clean and comfortable for all of our friends."
United States
Amanda R.
The price is AU$779
includes taxes & fees
8 Oct - 9 Oct
Hot Tub - Hammock- Games - Grill - Large Colonial
A neatly made bed with white bedding and a few colorful pillows, a wooden headboard, and a wall-mounted light fixture.

13. Retro Retreat: renovated 2BR, desk, no chore list!

Retro Retreat: renovated 2BR, desk, no chore list!
Kingston
9.6 out of 10, Exceptional, (15 reviews)
"Great, easy, full of everything you’d need. Stayed with 2 others for a work trip and it was perfect! "
United States
Kelley Marie
The price is AU$486
includes taxes & fees
1 Nov - 2 Nov
Retro Retreat: renovated 2BR, desk, no chore list!
A modern kitchen with white cabinets, a large island, and a skylight.

14. A Country Lodge Straight Out of the Pages of a Great Novel

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
10.0 out of 10, Exceptional, (15 reviews)
"We loved the house and it really added to our upstate experience!!"
United States
stephen r.
The price is AU$1,858
includes taxes & fees
16 Oct - 17 Oct
A Country Lodge Straight Out of the Pages of a Great Novel
A room with a built-in bench along a wall with large windows, a door, and a tiled floor.

15. The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining

The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
New Milford
The price is AU$1,143
includes taxes & fees
7 Oct - 8 Oct
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
A hot tub in a backyard with a house, trees, and a clear sky.

16. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is AU$5,018
includes taxes & fees
7 Oct - 8 Oct
Las Flores Villa
A building with a large arched window and a garden with tables and chairs.

17. Church Des Artistes a Hudson Valley retreat

Church Des Artistes a Hudson Valley retreat
Rondout
9.8 out of 10, Exceptional, (10 reviews)
"Beautiful, unique stay! Julie was really kind walking us through the ins and outs of the property during check-in. So much care and attention put into every room. And the book collection is amazing."
United States
Molly M.
The price is AU$3,615
includes taxes & fees
8 Oct - 9 Oct
Church Des Artistes a Hudson Valley retreat
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Amenia Hotel Reviews

The Abner Hotel

The Abner Hotel

10/10 Excellent
"We loved our stay- the room was so well presented/had everything we could need, and we felt so well looked after by all staff. We enjoyed the breakfast, and drinks on the rooftop bar were definitely a highlight! We had dinner one out of the two nights we were staying, which was also lovely. Highly recommend if you’re in the Litchfield area!"
Jessica 2-night trip
Posted 2 hours ago
The Abner Hotel

Find out more about Amenia

Amenia Holiday Homes information

Number of reviews
163
Accommodation
263 Holiday Homes
Lowest Price
AU$234
Highest Price
AU$5,018