Briarcliff Manor Vacation Rentals

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Briarcliff Manor vacation homes

An outdoor dining area with tables set for a formal event, featuring candles, glassware, and floral centerpieces.

1. Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
8.8 out of 10, Excellent, (10 reviews)
"It's an elegant older house with lots of room for company. Family friendly. The pool was great. My family enjoyed it."
United States
Karen O.
The price is CA $510
CA $1,115 total
includes taxes & fees
Nov 16 - Nov 17
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

2. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is CA $736
CA $1,489 total
includes taxes & fees
Nov 16 - Nov 17
Summer Pool Oasis Custom Bar Arcade Pool Table
A spacious living area with a black leather sofa, a coffee table, a ceiling fan, and a blue cabinet.

3. Spacious 4-bedroom house in northern Westchester with sweeping views

Spacious 4-bedroom house in northern Westchester with sweeping views
Montrose
The price is CA $699
CA $869 total
includes taxes & fees
Nov 16 - Nov 17
Spacious 4-bedroom house in northern Westchester with sweeping views
A bedroom with a large bed, a black sofa, a mirror, and a chandelier.

4. Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Southeast Yonkers
8.0 out of 10, Very good, (20 reviews)
"Great location"
United States
Jordan S.
The price is CA $133
CA $177 total
includes taxes & fees
Nov 16 - Nov 17
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
A dock with kayaks and a canoe, surrounded by trees and a calm lake.

5. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (46 reviews)
"Nice stay"
United States
Christopher J.
The price is CA $248
CA $477 total
includes taxes & fees
Nov 16 - Nov 17
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
An outdoor patio with a fire pit, green chairs, and a table.

6. Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
New Rochelle
10.0 out of 10, Exceptional, (14 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
The price is CA $180
CA $410 total
includes taxes & fees
Nov 16 - Nov 17
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
A blue house with a white porch, a welcome sign, and a mailbox.

7. 3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.4 out of 10, Very good, (7 reviews)
"Space was excellent, the multiple bedrooms with the extra bathroom was great. Kitchen was stocked with utensils, bathrooms were clean, living space was comfortable and cozy."
United States
Christine T.
The price is CA $170
CA $632 total
includes taxes & fees
Nov 12 - Nov 13
3BR West Point Retreat-3min to Back Gate+ King Bed
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

8. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (43 reviews)
"We’ve actually stayed here twice so that should tell you we enjoy the space and the host is lovely."
United States
Heather M.
The price is CA $318
CA $565 total
includes taxes & fees
Nov 16 - Nov 17
Contemporary Cozy Cottage
A room with a wooden floor, a white door with a number, and a window with blinds.

9. Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
The price is CA $282
CA $508 total
includes taxes & fees
Dec 8 - Dec 9
Lovely 3BR Home with parking-Walk to WP Gate!
An outdoor seating area with a round table, a chair, and a hanging light fixture.

10. Gem by the water+ firepit and all fenced backyard

Gem by the water+ firepit and all fenced backyard
Waterside
10.0 out of 10, Exceptional, (22 reviews)
"Property was exactly what we needed for our stay"
United States
Christopher E.
The price is CA $317
CA $628 total
includes taxes & fees
Nov 22 - Nov 23
Gem by the water+ firepit and all fenced backyard
A patio with a wooden fence, a table with chairs, and raised planters.

11. Private Single Fam, walk 2 train/ Theater- Dogs OK

Private Single Fam, walk 2 train/ Theater- Dogs OK
Greenwich
The price is CA $350
CA $1,125 total
includes taxes & fees
Dec 6 - Dec 7
Private Single Fam, walk 2 train/ Theater- Dogs OK
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

12. Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (12 reviews)
"House was exactly as described. Would stay again."
United States
Beth M.
The price is CA $299
CA $517 total
includes taxes & fees
Dec 8 - Dec 9
Fabulous 3bdrm Home w/parking!
A wooden deck with a table and chairs, overlooking a lake with cherry blossoms and autumn foliage.

13. Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms

Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Lake Peekskill
8.0 out of 10, Very good, (3 reviews)
"This home was just as advertised and perfect for a girls weekend getaway. It was clean, cozy and a picture-perfect fall view. Would highly recommend."
United States
Karen W.
The price is CA $468
CA $883 total
includes taxes & fees
Nov 16 - Nov 17
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
A living room with a wooden floor, a black sofa, a coffee table, and a ceiling fan.

14. Perfect 2BR with Free Parking! Walk to West Point!

Perfect 2BR with Free Parking! Walk to West Point!
Highland Falls
The price is CA $283
CA $455 total
includes taxes & fees
Nov 16 - Nov 17
Perfect 2BR with Free Parking! Walk to West Point!
A square fire pit with flames, surrounded by a wooden deck, set against a backdrop of a lake and trees under a clear sky.

15. Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views

Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views
Greenwich
10.0 out of 10, Exceptional, (2 reviews)
"Great location on the lake which the kids loved. The hosts were very friendly and easy to communicate with. The addition of the outdoor grill was a big plus and we enjoyed many afternoons out on the deck. We would stay again."
United States
Nathan R.
The price is CA $1,983
CA $3,125 total
includes taxes & fees
Nov 17 - Nov 18
Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views
A modern living room with a white sofa, a glass coffee table, and a piano.

16. Spacious 3BR Townhome | Garage + Near Downtown

Spacious 3BR Townhome | Garage + Near Downtown
West Side
9.2 out of 10, Wonderful, (9 reviews)
"Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again."
United States
Dave J.
The price is CA $377
CA $734 total
includes taxes & fees
Nov 15 - Nov 16
Spacious 3BR Townhome | Garage + Near Downtown
A living room with a sofa, armchair, ottoman, and coffee table.

17. Stamford Home | Family, Work and Plenty of Parking

Stamford Home | Family, Work and Plenty of Parking
Cove - East Side - Shippan
8.6 out of 10, Excellent, (9 reviews)
"the home was nice clean if in the area I would stay here again"
United States
james w.
The price is CA $288
CA $632 total
includes taxes & fees
Nov 16 - Nov 17
Stamford Home | Family, Work and Plenty of Parking
A wooden staircase with a chandelier, leading to an upper floor. A stone wall and a flower arrangement are visible on the left.

18. 6 BR, 4 BA Mansion Close to the City

6 BR, 4 BA Mansion Close to the City
Getty Square
8.0 out of 10, Very good, (7 reviews)
"So much space to hang out with our friends!"
United States
Tamara H.
The price is CA $565
CA $1,174 total
includes taxes & fees
Nov 16 - Nov 17
6 BR, 4 BA Mansion Close to the City
A modern outdoor patio with a seating area, a central table, and a large umbrella.

19. Mansion in Greenwich with private lake and river

Mansion in Greenwich with private lake and river
Greenwich
9.8 out of 10, Exceptional, (6 reviews)
"Beautiful home. Exquisite decor and our kids enjoyed fishing right out back. Thoroughly enjoyed. "
United States
J.J. O.
The price is CA $5,604
CA $7,331 total
includes taxes & fees
Nov 14 - Nov 15
Mansion in Greenwich with private lake and river
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

20. Hudson Valley/West Point Retreat w/ parking!

Hudson Valley/West Point Retreat w/ parking!
Highland Falls
The price is CA $413
CA $680 total
includes taxes & fees
Dec 8 - Dec 9
Hudson Valley/West Point Retreat w/ parking!
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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Learn more about Briarcliff Manor

Explore the scenic trails of Rockefeller State Park Preserve, where wooded paths lead to tranquil Swan Lake and stone bridges. History buffs can visit the 1850s Gothic Revival Beechwood mansion or enjoy riverside picnics at Scarborough Park with views of the Hudson.

See all hotels in Briarcliff Manor
A stone bridge over a stream surrounded by autumn foliage.

Top reviews in Briarcliff Manor

A modern reception area with a wooden reception desk, a blue accent wall, and a large glass door leading to an outdoor seating area.
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
Hawthorne

10/10 Excellent

Room and all around the hotel was cleaned and kept clean throughout my stay. Staff were VERY welcoming and helpful and the free breakfast was a bonus & I can’t forget about their 24hr coffee machine, it is definitely worth the entire stay.
Canada
Kiarra
Reviewed August 6, 2026
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

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