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37 Houses

(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

$295

Responds fast!
avg. 40 minutes

Price per night from

$295

Great rentals within 20 miles that match your search

Distance approx 14.76 km from West Point

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

$751

Price per night from

$751

Distance approx 1.56 km from West Point 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

$401

Price per night from

$401

Distance approx 4.45 km from West Point 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

$186

Price per night from

$186

Distance approx 18.53 km from West Point

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

$131

Price per night from

$131

Distance approx 3.06 km from West Point 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

$1,102

Price per night from

$1,102

Distance approx 5.34 km from West Point 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

$366

Price per night from

$366

Distance approx 19.37 km from West Point

(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

$301

Responds fast!
avg. 11 minutes

Price per night from

$301

Distance approx 14.92 km from West Point

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

$200

Price per night from

$200

Distance approx 13.01 km from West Point

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

$166

Price per night from

$166

Distance approx 13.49 km from West Point

(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

$350

Price per night from

$350

Distance approx 4.68 km from West Point 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

$1,322

Responds fast!
avg. 2 hours 38 minutes

Price per night from

$1,322

Distance approx 18.79 km from West Point

(9) Very Good 

20

Lake Bliss the Perfect Getaway

New York / Holmes

Holmes house

3 10 1 night min

  • 3 bedrooms
  • sleeps 10
  • 1 night min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$251

Price per night from

$251

Distance approx 4.57 km from West Point Show on Map

(4) 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

$251

Responds fast!
avg. 1 hour 9 minutes

Price per night from

$251

Distance approx 6.74 km from West Point Show on Map

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

$750

Price per night from

$750

Distance approx 8.31 km from West Point Show on Map

(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

$100

Price per night from

$100

Distance approx 13.58 km from West Point

(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

$2,203

Price per night from

$2,203

Distance approx 14.81 km from West Point

(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

$286

Price per night from

$286

Distance approx 19.14 km from West Point

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

$751

Responds fast!
avg. 2 hours 22 minutes

Price per night from

$751

Distance approx 7 km from West Point 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

$50

Responds fast!
avg. 1 hour 48 minutes

Price per night from

$50

Distance approx 1.07 km from West Point 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

$1,502

Price per night from

$1,502

Distance approx 19.58 km from West Point

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

$201

Price per night from

$201

Distance approx 12.45 km from West Point

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

$286

Responds fast!
avg. 10 minutes

Price per night from

$286

Distance approx 13.84 km from West Point

13

Faces The Hudson + Only An Hour Outside NYC

New York / New York City

New York City villa

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Air conditioning

Price per night from

$425

Responds fast!
avg. 54 minutes

Price per night from

$425

Distance approx 12.38 km from West Point

(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

$952

Responds fast!
avg. 20 minutes

Price per night from

$952

Distance approx 7.1 km from West Point Show on Map

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

$225

Price per night from

$225

Distance approx 8.23 km from West Point Show on Map

(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

$250

Price per night from

$250

Distance approx 15.49 km from West Point

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

$100

Responds fast!
avg. 2 hours 32 minutes

Price per night from

$100

Distance approx 9.92 km from West Point

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

$75

Price per night from

$75

Distance approx 9.16 km from West Point

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

$150

Responds fast!
avg. 10 minutes

Price per night from

$150

Distance approx 12.23 km from West Point

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

$275

Price per night from

$275

Distance approx 1.35 km from West Point 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

$1,252

Price per night from

$1,252

Distance approx 17.3 km from West Point

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

$50

Responds fast!
avg. 3 hours 34 minutes

Price per night from

$50

Distance approx 3.88 km from West Point 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

$60

Responds fast!
avg. 1 hour 50 minutes

Price per night from

$60

Distance approx 13.3 km from West Point

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

$69

Price per night from

$69

Distance approx 8.04 km from West Point Show on Map

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

$225

Responds fast!
avg. 2 hours 2 minutes

Price per night from

$225

Distance approx 11.34 km from West Point

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