Holiday Homes in Bedford Hills

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Find holiday rentals that suit your style

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Apartments
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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Bedford Hills holiday homes

A room with large windows overlooking a lake and greenery.

1. 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 AU$468
includes taxes & fees
12 Nov - 13 Nov
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

2. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (42 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 AU$571
includes taxes & fees
8 Nov - 9 Nov
Contemporary Cozy Cottage
A residential area with a wooden cabin, a white house, and a metal gate.

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

Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Lake Peekskill
10.0 out of 10, Exceptional, (1 review)
"We had an amazing stay at the lake house. The home is beautiful inside and out, and there is every amenity you could think of, from cooking and cleaning supplies to extra towels and blankets. The view of the lake is stunning and we enjoyed the peace and quiet of the little community. Linh is an excellent host and helped answer all of our questions. We will definitely be back!"
United States
Angel R.
The price is AU$902
includes taxes & fees
9 Nov - 10 Nov
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
A modern living room with a large window, a sofa with patterned cushions, a wooden coffee table, and a painting on the wall.

4. 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 AU$1,110
includes taxes & fees
9 Nov - 10 Nov
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.

5. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is AU$1,473
includes taxes & fees
9 Nov - 10 Nov
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.

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

Spacious 4-bedroom house in northern Westchester with sweeping views
Montrose
The price is AU$866
includes taxes & fees
18 Nov - 19 Nov
Spacious 4-bedroom house in northern Westchester with sweeping views
A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

7. Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is AU$477
includes taxes & fees
10 Nov - 11 Nov
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
A living room with a wooden floor, a black sofa, a coffee table, and a ceiling fan.

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

Perfect 2BR with Free Parking! Walk to West Point!
Highland Falls
The price is AU$380
includes taxes & fees
9 Nov - 10 Nov
Perfect 2BR with Free Parking! Walk to West Point!
A blue house with a white porch, a welcome sign, and a mailbox.

9. 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 AU$640
includes taxes & fees
10 Nov - 11 Nov
3BR West Point Retreat-3min to Back Gate+ King Bed
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

10. 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 AU$416
includes taxes & fees
8 Nov - 9 Nov
Fabulous 3bdrm Home w/parking!
A room with a wooden floor, a white door with a number, and a window with blinds.

11. 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 AU$427
includes taxes & fees
8 Nov - 9 Nov
Lovely 3BR Home with parking-Walk to WP Gate!
An outdoor seating area with a round table, a chair, and a hanging light fixture.

12. 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, (21 reviews)
"Property was exactly what we needed for our stay"
United States
Christopher E.
The price is AU$635
includes taxes & fees
9 Nov - 10 Nov
Gem by the water+ firepit and all fenced backyard
A modern living room with a white sofa, a glass coffee table, and a piano.

13. 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 AU$800
includes taxes & fees
11 Nov - 12 Nov
Spacious 3BR Townhome | Garage + Near Downtown
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

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

Hudson Valley/West Point Retreat w/ parking!
Highland Falls
The price is AU$476
includes taxes & fees
11 Nov - 12 Nov
Hudson Valley/West Point Retreat w/ parking!
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 AU$3,065
includes taxes & fees
9 Nov - 10 Nov
Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views
A modern kitchen with white cabinets, a marble island, and black bar stools.

16. Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
9.4 out of 10, Exceptional, (3 reviews)
"We had a wonderful stay."
United States
Linda S.
The price is AU$989
includes taxes & fees
10 Nov - 11 Nov
Spacious Retreat with Game Room and Fire Pit
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 AU$633
includes taxes & fees
9 Nov - 10 Nov
Stamford Home | Family, Work and Plenty of Parking
A modern kitchen with a central island, pendant lights, and a view of the outdoors.

18. Renovated Retreat with Heated Pool

Renovated Retreat with Heated Pool
Redding
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful house, very clean, spacious and a great host!!!"
United States
Alejandro A.
The price is AU$1,006
includes taxes & fees
12 Nov - 13 Nov
Renovated Retreat with Heated Pool
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

19. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.4 out of 10, Exceptional, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
The price is AU$382
includes taxes & fees
8 Nov - 9 Nov
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a central island with stools.

20. 5BR Beach Home | Walk to Cove Beach + Private Yard

5BR Beach Home | Walk to Cove Beach + Private Yard
Cove - East Side - Shippan
9.6 out of 10, Exceptional, (27 reviews)
"The house was perfect! Plenty of bedding and the kitchen was well appointed. We were there for my fathers memorial and the living room provided a great space for us to connect and talk together. "
United States
Maury A.
The price is AU$1,933
includes taxes & fees
27 Nov - 28 Nov
5BR Beach Home | Walk to Cove Beach + Private Yard
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 Bedford Hills

Tucked into Westchester County, Bedford Hills offers peaceful walks through the Ward Pound Ridge Reservation and charming local shops along Bedford Road. Families enjoy the Bedford Hills Memorial Park's playgrounds, while history buffs can explore nearby Katonah Museum of Art in neighbouring Katonah.

See all hotels in Bedford Hills
A stone bridge with a waterfall beneath it, surrounded by trees and a clear sky.

Top reviews in Bedford Hills

A reception area with two counters, a clock on the wall, and a flower arrangement.
Comfort Inn Brewster

Comfort Inn Brewster

Comfort Inn Brewster
Brewster

10/10 Excellent

The hotel was lovely and the staff were very friendly and helpful.
Australia
Martin
Reviewed November 9, 2023
Comfort Inn Brewster