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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Amenia holiday homes

A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

1. 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, (3 reviews)
"I really enjoyed my four night stay here."
United States
Jim B.
The price is €132
includes taxes & fees
3 Nov - 4 Nov
Cozy private room in a shared home with a Full-size bed and private bathroom.
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

2. 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, (7 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 €748
includes taxes & fees
3 Nov - 4 Nov
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A living room with a television, a cabinet, a glass coffee table, and a framed picture on the wall.

3. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is €627
includes taxes & fees
25 Oct - 26 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.

4. 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 €704
includes taxes & fees
16 Nov - 17 Nov
Chic Barn Style * Fireplace * Near Stissing House
A large wooden dining table surrounded by chairs, with a stone fireplace and large windows in the background.

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

The George is an elegant restored home in the Hudson Valley
Stanfordville
9.8 out of 10, Exceptional, (12 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 €1,136
includes taxes & fees
3 Nov - 4 Nov
The George is an elegant restored home in the Hudson Valley
A modern kitchen with white cabinets, a large island, and a skylight.

6. 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 €1,296
includes taxes & fees
3 Nov - 4 Nov
A Country Lodge Straight Out of the Pages of a Great Novel
A wooden cabin interior with a bench, a rug, and a hanging plant.

7. 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, (4 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is €181
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.

8. 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 €232
includes taxes & fees
3 Nov - 4 Nov
Campfire Cottage: Fireplace, fire pit & no chores!
A bedroom with a bed, a chair, a lamp, and a wall with a speckled pattern.

9. 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, (7 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 €221
includes taxes & fees
27 Oct - 28 Oct
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
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
9.8 out of 10, Exceptional, (6 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 €386
includes taxes & fees
25 Oct - 26 Oct
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A neatly made bed with white bedding and a few colorful pillows, a wooden headboard, and a wall-mounted light fixture.

11. 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 €280
includes taxes & fees
2 Nov - 3 Nov
Retro Retreat: renovated 2BR, desk, no chore list!
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

12. 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 €390
includes taxes & fees
2 Nov - 3 Nov
Cheerful 3-bedroom cottage with woodstove
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.

13. 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 €480
includes taxes & fees
28 Oct - 29 Oct
Hot Tub - Hammock- Games - Grill - Large Colonial
A bedroom with a bed, a dresser, and a window with curtains.

14. 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
10.0 out of 10, Exceptional, (1 review)
"Perfect!!"
United States
Jeni O.
The price is €773
includes taxes & fees
28 Oct - 29 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.

15. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is €3,121
includes taxes & fees
4 Nov - 5 Nov
Las Flores Villa
Exterior

16. Serene 2-bedroom house with Master Suite, fenced in yard in charming Kingston

Serene 2-bedroom house with Master Suite, fenced in yard in charming Kingston
Kingston
The price is €371
includes taxes & fees
27 Oct - 28 Oct
Serene 2-bedroom house with Master Suite, fenced in yard in charming Kingston
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 €2,222
includes taxes & fees
29 Oct - 30 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

DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

10/10 Excellent
"Friendly accommodating staff. Very clean beautiful river-view room. Free parking. Convenient to everything."
Barbara 2-night trip
Posted 9 hours ago
DoubleTree by Hilton Poughkeepsie Convention Center

Find out more about Amenia

Amenia Holiday Homes information

Number of reviews
158
Accommodation
258 Holiday Homes
Lowest Price
€132
Highest Price
€3,121