Highland Falls Rentals

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39 Houses

22

Built in 2018 3BR Luxury House near West Point

New York / Highland Falls

Highland Falls house

3 12 min stay varies

  • 3 bedrooms
  • sleeps 12
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$146

Price per night from

$146

Great rentals within 20 miles that match your search

Distance approx 3.37 km from Highland Falls Show on Map

(4) Excellent 

24

Beautiful 4 br in historic Cold Spring!

New York / Cold Spring

Cold Spring house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$460

Price per night from

$460

Distance approx 2.63 km from Highland Falls Show on Map

14

1 Bedroom Getaway West Point & Bear Mountain area

New York / Fort Montgomery

Fort Montgomery apartment

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Private garden

Price per night from

$212

Price per night from

$212

Distance approx 16.32 km from Highland Falls

32

Lake House with Indoor Spa, 1 hour from Manhattan

New York / Carmel

Carmel house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly

Price per night from

$229

Price per night from

$229

Distance approx 12.92 km from Highland Falls

20

"THE HILLTOP"-40Mins From NYC- Private Estate

New York / Pomona

Pomona house

4 12 2 nights min

  • 4 bedrooms
  • sleeps 12
  • 2 nights min
  • Child Friendly

Price per night from

$859

Price per night from

$859

Distance approx 3.95 km from Highland Falls Show on Map

10

Country Chic Cabin~spacious~ private setting~hot tub~pool~ views~75 minutes/NYC

New York / Garrison

Garrison house

3 12 2 nights min

  • 3 bedrooms
  • sleeps 12
  • 2 nights min
  • Child Friendly

Price per night from

$1,265

Price per night from

$1,265

Distance approx 3.77 km from Highland Falls Show on Map

(5) Excellent 

Certificate of Excellence

15

Castle By The Lake

New York / Putnam Valley

Putnam Valley house

4 12 3 nights min

  • 4 bedrooms
  • sleeps 12
  • 3 nights min
  • Air conditioning
  • Private garden

Certificate of Excellence

Price per night from

$287

Responds fast!
avg. 1 hour 9 minutes

Price per night from

$287

Distance approx 17.33 km from Highland Falls

12

Stone Croft Cottage

Westchester County / Chappaqua

Chappaqua cottage

1 4 4 nights min

  • 1 bedroom
  • sleeps 4
  • 4 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$149

Price per night from

$149

Distance approx 6.19 km from Highland Falls Show on Map

10

Spectacular Lake House

New York / Putnam Valley

Putnam Valley house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$418

Price per night from

$418

Distance approx 12.25 km from Highland Falls

(1) Excellent 

5

Caren House Bed and Breafast

New York / Monroe

Monroe b and b

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Child Friendly
  • Air conditioning

Price per night from

$401

Price per night from

$401

Distance approx 17.97 km from Highland Falls

(1) Excellent 

27

Colonial Style ‘Warwick Retreat’ - 1 Hour to NYC!

New York / Greenwood Lake

Greenwood Lake house

4 12 3 nights min

  • 4 bedrooms
  • sleeps 12
  • 3 nights min
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$344

Responds fast!
avg. 22 minutes

Price per night from

$344

Distance approx 8.54 km from Highland Falls

14

PineTop

New York / Cold Spring

Cold Spring house

5 9 2 nights min

  • 5 bedrooms
  • sleeps 9
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$862

Price per night from

$862

Distance approx 11.77 km from Highland Falls

15

An Oasis in the Hudson Valley

Westchester County / Croton on Hudson

Croton on Hudson apartment

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 32 mi
  • Swimming pool
  • Suitable for children age 5+

Price per night from

$189

Price per night from

$189

Distance approx 1.4 km from Highland Falls Show on Map

38

Country Retreat Hot Tub+ Pool+Sauna + more relaxation guaranteed

New York / Garrison

Garrison house

5 15 2 nights min

  • 5 bedrooms
  • sleeps 15
  • 2 nights min
  • Child Friendly

Price per night from

$1,718

Price per night from

$1,718

Distance approx 12.26 km from Highland Falls

(2) Excellent 

11

Westchester Hudson Valley Estate - Private, less than 1 hour from NYC

Westchester County / Croton on Hudson

Croton on Hudson villa

8 24 2 nights min

  • 8 bedrooms
  • sleeps 24
  • 2 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$2,519

Price per night from

$2,519

Distance approx 18.38 km from Highland Falls

48

Large Home, Pool, Hot Tub on Several Acres

Westchester County / Mount Kisco

Mount Kisco house

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$859

Responds fast!
avg. 2 hours 22 minutes

Price per night from

$859

Distance approx 5.88 km from Highland Falls Show on Map

(4) Excellent 

19

50 Mins from Manhattan River view

Cornwall / Cornwall on Hudson

Cornwall on Hudson house

5 17 min stay varies

  • 5 bedrooms
  • sleeps 17
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Spectacular view” We loved this house. It has probably the best view of the Hudson River. The house was very comfortable and had everything we needed. Susan was very helpful with information about the sights and restaurants. We will definitely be
…see more

Price per night from

$1,512

Responds fast!
avg. 2 hours 47 minutes

Price per night from

$1,512

Distance approx 9.76 km from Highland Falls

(2) Very Good 

12

Keith's Classic Film Retreat

New York / Newburgh

Newburgh b and b

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$114

Price per night from

$114

Distance approx 17.86 km from Highland Falls

20

Storms Retreat Guest House - 50mins from NYC, Lower Hudson Valley, NY

New York / Nyack

Nyack house

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$229

Price per night from

$229

Distance approx 16.29 km from Highland Falls

(5) Very Good 

11

Earth Berm House at Terra Casa Retreat Center

New York / Plattekill

Plattekill house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly

Price per night from

$327

Price per night from

$327

Distance approx 5.82 km from Highland Falls Show on Map

28

independent room with office and kitchen

Cortlandt / Cortlandt Manor

Cortlandt Manor b and b

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Nearest beach 8 mi
  • Child Friendly
  • Air conditioning

Price per night from

$58

Responds fast!
avg. 1 hour 48 minutes

Price per night from

$58

Distance approx 18.66 km from Highland Falls

5

Private Highlands

New York / Nyack

Nyack house

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Pet Friendly

Price per night from

$134

Responds fast!
avg. 2 hours 27 minutes

Price per night from

$134

Distance approx 11.06 km from Highland Falls

(4) Excellent 

56

Orchard Hill Estate: Retreat, Reunions, Near West Point,Close to NYC, Hot tub,

New York / Monroe

Monroe house

7 25 2 nights min

  • 7 bedrooms
  • sleeps 25
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,088

Responds fast!
avg. 19 minutes

Price per night from

$1,088

Distance approx 11.37 km from Highland Falls

27

NEW! Monroe Family Home w/ Deck & Spacious Yard!

New York / Monroe

Monroe house

4 14 min stay varies

  • 4 bedrooms
  • sleeps 14
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$327

Responds fast!
avg. 22 minutes

Price per night from

$327

Distance approx 9.94 km from Highland Falls

(6) Excellent 

33

Beacon Nook, escape from the big city

New York / Beacon

Beacon house

3 7 3 nights min

  • 3 bedrooms
  • sleeps 7
  • 3 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$287

Price per night from

$287

Distance approx 8.89 km from Highland Falls

1

Base Camp - Dutch Colonial Estate

New York / Beacon

Beacon apartment

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Air conditioning

Price per night from

$258

Price per night from

$258

Distance approx 0.1 km from Highland Falls Show on Map

(4) Excellent 

12

Our Rockbound Highland Home * 2 Blocks to West Point * 1/2 Block to Main St

New York / West Point

West Point house

3 11 min stay varies

  • 3 bedrooms
  • sleeps 11
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$338

Responds fast!
avg. 40 minutes

Price per night from

$338

Distance approx 17.23 km from Highland Falls

14

House on Top of the Hill

New York / Marlboro

Marlboro house

3 5 7 nights min

  • 3 bedrooms
  • sleeps 5
  • 7 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$115

Responds fast!
avg. 2 hours 32 minutes

Price per night from

$115

Distance approx 8.7 km from Highland Falls

7

Perfectly Located Suite

New York / Central Valley

Central Valley room

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min

Price per night from

$86

Price per night from

$86

Distance approx 19.75 km from Highland Falls

12

The Cottage at Millpond Falls - Warwick NY B&B

New York / Warwick

Warwick cottage

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Air conditioning
  • Private garden

Price per night from

$229

Price per night from

$229

Distance approx 11.83 km from Highland Falls

50

Croton Lodge: Luxury 2bd⭐Comfort+Style⭐45min to NYC,Great Food

Westchester County / Croton on Hudson

Croton on Hudson apartment

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Nearest beach 2 mi
  • Child Friendly
  • Air conditioning

Price per night from

$79

Price per night from

$79

Distance approx 11.73 km from Highland Falls

25

Secluded Contemporary Home on 6-Acre Property!

New York / Blooming Grove

Blooming Grove house

4 16 1 night min

  • 4 bedrooms
  • sleeps 16
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$315

Price per night from

$315

Distance approx 1.74 km from Highland Falls Show on Map

30

COZY RETREAT: HOT TUB, POOL, SAUNA, AND MORE...

New York / Garrison

Garrison house

5 15 min stay varies

  • 5 bedrooms
  • sleeps 15
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,432

Price per night from

$1,432

Distance approx 15.48 km from Highland Falls

7

M1 Couch Bed

New York / New City

New City house

1 1 1 night min

  • 1 bedroom
  • sleeps 1
  • 1 night min
  • Air conditioning
  • Private garden

Price per night from

$58

Responds fast!
avg. 3 hours 34 minutes

Price per night from

$58

Distance approx 2.17 km from Highland Falls Show on Map

9

2 bedroom cottage

New York / Garrison

Garrison house

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$69

Responds fast!
avg. 1 hour 50 minutes

Price per night from

$69

Distance approx 9.6 km from Highland Falls

24

Lakefront 3BR New Windsor House in Hudson Valley!

New York / Salisbury Mills

Salisbury Mills house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$172

Responds fast!
avg. 21 minutes

Price per night from

$172

Distance approx 9.82 km from Highland Falls

19

ROMANTIC GETAWAY COTTAGE ON WATER

New York / Beacon

Beacon cottage

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$258

Responds fast!
avg. 2 hours 2 minutes

Price per night from

$258

Distance approx 12.49 km from Highland Falls

20

LAKEFRONT COTTAGE ON PRISTINE LAKE

New York / Carmel

Carmel cottage

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Ask about children
  • Air conditioning

Price per night from

$226

Price per night from

$226