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

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Amenia vacation homes

A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

1. 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.
Chic Barn Style * Fireplace * Near Stissing House
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 AED 1,286
AED 2,709 total
includes taxes & fees
9 Nov - 10 Nov
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A covered outdoor deck with wicker furniture, a grill, and a view of a lake.

3. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

4. 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 AED 231
AED 479 total
includes taxes & fees
9 Nov - 10 Nov
Cozy private room in a shared home with a Full-size bed and private bathroom.
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, (13 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 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)
"Stayed with a group for Millbrook Horse Trials, we had an amazing weekend at this calm and relaxing home with plenty of beds and amenities! What a treat!"
United States
Marianne R.
The price is AED 3,269
AED 5,144 total
includes taxes & fees
3 Nov - 4 Nov
A Country Lodge Straight Out of the Pages of a Great Novel
A hot tub in a backyard with a house, trees, and a clear sky.

7. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is AED 3,289
AED 5,252 total
includes taxes & fees
2 Nov - 3 Nov
Las Flores Villa
A wooden cabin interior with a bench, a rug, and a hanging plant.

8. 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 AED 380
AED 692 total
includes taxes & fees
8 Nov - 9 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.

9. 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 AED 665
AED 1,370 total
includes taxes & fees
14 Nov - 15 Nov
Campfire Cottage: Fireplace, fire pit & no chores!
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

10. 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 AED 275
AED 893 total
includes taxes & fees
2 Nov - 3 Nov
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
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
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, (46 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AED 651
AED 1,495 total
includes taxes & fees
2 Nov - 3 Nov
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.

13. 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 AED 662
AED 1,597 total
includes taxes & fees
3 Nov - 4 Nov
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A living room with a white sectional sofa, a dining area with a wooden table and chairs, and a staircase leading to an upper level.

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 AED 1,837
AED 3,006 total
includes taxes & fees
1 Dec - 2 Dec
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
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.

15. 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 AED 983
AED 2,035 total
includes taxes & fees
2 Dec - 3 Dec
Hot Tub - Hammock- Games - Grill - Large Colonial
A spacious living area with a dining table, sofa, and large windows offering a view of the outdoors.

16. 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
8.4 out of 10, Very good, (5 reviews)
"Beautiful home, had everything we needed for a great long weekend. Easy to get to town. Highly recommend! Amanda was very clear about the check-in and check out process. Would love to stay again when the weather is warmer."
United States
Mitch B.
3BR Modern Home in Kingston - Sleeps 6 -Fire Pit -Game Room -Pet Friendly
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 AED 5,510
AED 8,931 total
includes taxes & fees
9 Nov - 10 Nov
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

Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

8/10 Good
"Amazing place. Was a little loud at night but then again it was during a Halloween party downstairs"
Enrico 1-night trip
Posted 9 hours ago
Beekman Arms and Delamater Inn