Vacation rentals in Highland Falls, NY

Best Vacation rentals and Airbnb offers in Highland Falls, NY

Lovely 1-bedroom studio located in the basement. Private entrance

Apartment, Highland Falls

Lovely 1-bedroom studio located in the basement. Private entrance is a apartment in Highland Falls, with pet-friendly space and room for a group. This stay gives travelers a comfortable…

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About Lovely 1-bedroom studio located in the basement. Private entrance

Lovely 1-bedroom studio located in the basement. Private entrance is a apartment in Highland Falls, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $809.

From$81/night

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Cozy Cottage Get Away

Cottage, Highland Falls

Cozy Cottage Get Away is a cottage in Highland Falls, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Cozy Cottage Get Away

Cozy Cottage Get Away is a cottage in Highland Falls, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $872.

From$85/night

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🤣🏡 \"Welcome to our basement suite, where humor and professionalism coexist!

Holiday Home, Highland Falls

🤣🏡 \"Welcome to our basement suite, where humor and professionalism coexist! is a holiday home in Highland Falls, with parking. This stay gives travelers a comfortable base for exploring…

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About 🤣🏡 \"Welcome to our basement suite, where humor and professionalism coexist!

🤣🏡 \"Welcome to our basement suite, where humor and professionalism coexist! is a holiday home in Highland Falls, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, gym, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,055.

From$113/night

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Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Apartment, Highland Falls

Quiet Apt with Coffee Bar, 1/2 Mile to West Point! is a apartment in Highland Falls, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point! is a apartment in Highland Falls, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,244.

From$135/night

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Browse Vacation Rentals with a Pool in Highland Falls, NY

Add a pool to the search when you want an easy place to cool off between outings.

Private lake escape

Holiday Home, Highland Falls

Private lake escape is a holiday home in Highland Falls, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Private lake escape

Private lake escape is a holiday home in Highland Falls, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,456.

From$375/night

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Cold Spring Village Maisonette with Pool

Holiday Home, Highland Falls

Cold Spring Village Maisonette with Pool is a holiday home in Highland Falls, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Cold Spring Village Maisonette with Pool

Cold Spring Village Maisonette with Pool is a holiday home in Highland Falls, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,993.

From$423/night

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Secluded Getaway: Bear Mt, Cold Spring, Beacon, West Point!

Holiday Home, Highland Falls

Secluded Getaway: Bear Mt, Cold Spring, Beacon, West Point! is a holiday home in Highland Falls, with pool access. This stay gives travelers a comfortable base for exploring the area,…

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About Secluded Getaway: Bear Mt, Cold Spring, Beacon, West Point!

Secluded Getaway: Bear Mt, Cold Spring, Beacon, West Point! is a holiday home in Highland Falls, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $8,826.

From$1,052/night

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Garrison Getaway | Pool, Sauna & Gym

Holiday Home, Highland Falls

Garrison Getaway · Pool, Sauna & Gym is a holiday home in Highland Falls, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Garrison Getaway | Pool, Sauna & Gym

Garrison Getaway · Pool, Sauna & Gym is a holiday home in Highland Falls, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $11,068.

From$1,235/night

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Best Highland Falls, NY vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Cozy studio with WiFi and AC in charming New Windsor

Apartment, Highland Falls

Cozy studio with WiFi and AC in charming New Windsor is a apartment in Highland Falls, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Cozy studio with WiFi and AC in charming New Windsor

Cozy studio with WiFi and AC in charming New Windsor is a apartment in Highland Falls, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, parking, free parking, and tv.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $898.

From$99/night

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Modern and Bright with office+ walk to nearby Waterfront, 1st FL.

Apartment, Highland Falls

Modern and Bright with office+ walk to nearby Waterfront, 1st FL. is a apartment in Highland Falls, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Modern and Bright with office+ walk to nearby Waterfront, 1st FL.

Modern and Bright with office+ walk to nearby Waterfront, 1st FL. is a apartment in Highland Falls, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,139.

From$113/night

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Modern Modest Design Newburgh, Beacon, Westpoint 2nd. FL Apt.

Apartment, Highland Falls

Modern Modest Design Newburgh, Beacon, Westpoint 2nd. FL Apt. is a apartment in Highland Falls, with parking and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Modern Modest Design Newburgh, Beacon, Westpoint 2nd. FL Apt.

Modern Modest Design Newburgh, Beacon, Westpoint 2nd. FL Apt. is a apartment in Highland Falls, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,139.

From$113/night

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Hudson River Retreat

Apartment, Highland Falls

Hudson River Retreat is a apartment in Highland Falls, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Hudson River Retreat

Hudson River Retreat is a apartment in Highland Falls, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,515.

From$158/night

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Best Pet-Friendly Vacation Rentals in Highland Falls, NY

Bring your pet along with stays that welcome four-legged travelers.

1 Queen Bed | Non-Smoking, Kitchen

Apartment, Highland Falls

1 Queen Bed · Non-Smoking, Kitchen is a apartment in Highland Falls, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About 1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed · Non-Smoking, Kitchen is a apartment in Highland Falls, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $729.

From$90/night

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Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Apartment, Highland Falls

Cozy Queen Suite, Nsmk Kitchen · Studio 6 Fishkill is a apartment in Highland Falls, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Cozy Queen Suite, Nsmk Kitchen · Studio 6 Fishkill is a apartment in Highland Falls, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $729.

From$90/night

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Studio 6 Fishkill|King bed|Hearing Access|Kitchen

Apartment, Highland Falls

Studio 6 Fishkill · King bed · Hearing Access · Kitchen is a apartment in Highland Falls, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Studio 6 Fishkill|King bed|Hearing Access|Kitchen

Studio 6 Fishkill · King bed · Hearing Access · Kitchen is a apartment in Highland Falls, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $753.

From$93/night

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Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi

Apartment, Highland Falls

Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi is a apartment in Highland Falls, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi

Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi is a apartment in Highland Falls, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,708.

From$474/night

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Best Highland Falls, NY vacation rentals with a kitchen

Compare stays with kitchen access for longer trips and easier meals.

1 Queen Bed | ADA/RI Shower/Smoking/Kitchen

Apartment, Highland Falls

1 Queen Bed · ADA/RI Shower/Smoking/Kitchen is a apartment in Highland Falls, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About 1 Queen Bed | ADA/RI Shower/Smoking/Kitchen

1 Queen Bed · ADA/RI Shower/Smoking/Kitchen is a apartment in Highland Falls, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $792.

From$100/night

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Scenic 1-bedroom rental in Newburgh

Apartment, Highland Falls

Scenic 1-bedroom rental in Newburgh is a apartment in Highland Falls, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Scenic 1-bedroom rental in Newburgh

Scenic 1-bedroom rental in Newburgh is a apartment in Highland Falls, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,223.

From$125/night

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Charming 3-bedroom house.

Holiday Home, Highland Falls

Charming 3-bedroom house. is a holiday home in Highland Falls, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Charming 3-bedroom house.

Charming 3-bedroom house. is a holiday home in Highland Falls, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,004.

From$300/night

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5 BR West Point Family Compound- Sleeps 10!

Holiday Home, Highland Falls

5 BR West Point Family Compound- Sleeps 10! is a holiday home in Highland Falls, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About 5 BR West Point Family Compound- Sleeps 10!

5 BR West Point Family Compound- Sleeps 10! is a holiday home in Highland Falls, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,057.

From$505/night

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Our Favorite Family-Friendly Vacation Rentals in Highland Falls, NY

Plan a trip with stays that give families more room to spread out.

Hudson Valley G.Washington Head Quarter-Largest Historic District

Apartment, Highland Falls

Hudson Valley G.Washington Head Quarter-Largest Historic District is a apartment in Highland Falls, with kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Hudson Valley G.Washington Head Quarter-Largest Historic District

Hudson Valley G.Washington Head Quarter-Largest Historic District is a apartment in Highland Falls, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,718.

From$180/night

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Contemporary Cozy Cottage

Holiday Home, Highland Falls

Contemporary Cozy Cottage is a holiday home in Highland Falls, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Contemporary Cozy Cottage

Contemporary Cozy Cottage is a holiday home in Highland Falls, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,167.

From$225/night

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Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

Cottage, Highland Falls

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days is a cottage in Highland Falls, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable…

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About Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days is a cottage in Highland Falls, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,627.

From$259/night

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Family friendly 4-bedroom home, 2 miles from West Point, loaded with amenities

Holiday Home, Highland Falls

Family friendly 4-bedroom home, 2 miles from West Point, loaded with amenities is a holiday home in Highland Falls, with parking, kitchen access, and room for a group. This stay gives…

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About Family friendly 4-bedroom home, 2 miles from West Point, loaded with amenities

Family friendly 4-bedroom home, 2 miles from West Point, loaded with amenities is a holiday home in Highland Falls, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,077.

From$459/night

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