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Lake Peekskill Holiday Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
50 rentals in Lake Peekskill.
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!, holiday rental in Lake Peekskill
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!, holiday rental in Lake Peekskill
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!, holiday rental in Lake Peekskill

'The Glabin’: Garrison Gem w/ Deck & Fire Pit!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The following properties within 20 miles of Lake Peekskill match all your filters:
Putnam Valley Vacation Rental: Patio & Lake Views!, holiday rental in Lake Peekskill
Putnam Valley Vacation Rental: Patio & Lake Views!, holiday rental in Lake Peekskill
Putnam Valley Vacation Rental: Patio & Lake Views!, holiday rental in Lake Peekskill

Putnam Valley Vacation Rental: Patio & Lake Views!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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DOMIR Yorktown stay, holiday rental in Lake Peekskill
DOMIR Yorktown stay, holiday rental in Lake Peekskill
DOMIR Yorktown stay, holiday rental in Lake Peekskill

DOMIR Yorktown stay

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Rustic Getaway w/ HBO, Porch & Grill Near Lake, holiday rental in Lake Peekskill
Rustic Getaway w/ HBO, Porch & Grill Near Lake, holiday rental in Lake Peekskill
Rustic Getaway w/ HBO, Porch & Grill Near Lake, holiday rental in Lake Peekskill

Rustic Getaway w/ HBO, Porch & Grill Near Lake

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Stay on Main St! ~Walk to EVERYTHING West Point! Mountain Views/private parking, holiday rental in Lake Peekskill
Stay on Main St! ~Walk to EVERYTHING West Point! Mountain Views/private parking, holiday rental in Lake Peekskill
Stay on Main St! ~Walk to EVERYTHING West Point! Mountain Views/private parking, holiday rental in Lake Peekskill

Stay on Main St! ~Walk to EVERYTHING West Point! Mountain Views/private parking

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Modern, Magical Woodsy Escape 1 Hour From NYC, holiday rental in Lake Peekskill
Modern, Magical Woodsy Escape 1 Hour From NYC, holiday rental in Lake Peekskill
Modern, Magical Woodsy Escape 1 Hour From NYC, holiday rental in Lake Peekskill

Modern, Magical Woodsy Escape 1 Hour From NYC

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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*iHeartNYState 5. Hot Tubs Sauna Jacuzzi, holiday rental in Lake Peekskill
*iHeartNYState 5. Hot Tubs Sauna Jacuzzi, holiday rental in Lake Peekskill
*iHeartNYState 5. Hot Tubs Sauna Jacuzzi, holiday rental in Lake Peekskill

*iHeartNYState 5. Hot Tubs Sauna Jacuzzi

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Upstate group-sized home in Putnam Valley, 15 minutes from Cold Spring, NY, holiday rental in Lake Peekskill
Upstate group-sized home in Putnam Valley, 15 minutes from Cold Spring, NY, holiday rental in Lake Peekskill
Upstate group-sized home in Putnam Valley, 15 minutes from Cold Spring, NY, holiday rental in Lake Peekskill

Upstate group-sized home in Putnam Valley, 15 minutes from Cold Spring, NY

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Peekskill Guesthouse- Downtown PrivateRoom EpicViews KingBed Hotel Amenities, holiday rental in Lake Peekskill
Peekskill Guesthouse- Downtown PrivateRoom EpicViews KingBed Hotel Amenities, holiday rental in Lake Peekskill
Peekskill Guesthouse- Downtown PrivateRoom EpicViews KingBed Hotel Amenities, holiday rental in Lake Peekskill

Peekskill Guesthouse- Downtown PrivateRoom EpicViews KingBed Hotel Amenities

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Stay into a private room., holiday rental in Lake Peekskill
Stay into a private room., holiday rental in Lake Peekskill
Stay into a private room., holiday rental in Lake Peekskill

Stay into a private room.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Peekskill Guesthouse- Downtown DoubleBed PrivateRoom EpicView Chill Host!, holiday rental in Lake Peekskill
Peekskill Guesthouse- Downtown DoubleBed PrivateRoom EpicView Chill Host!, holiday rental in Lake Peekskill
Peekskill Guesthouse- Downtown DoubleBed PrivateRoom EpicView Chill Host!, holiday rental in Lake Peekskill

Peekskill Guesthouse- Downtown DoubleBed PrivateRoom EpicView Chill Host!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Peekskill Guesthouse- PrivateRoom Downtown KingBed Hotel Amenities EpicViews, holiday rental in Lake Peekskill
Peekskill Guesthouse- PrivateRoom Downtown KingBed Hotel Amenities EpicViews, holiday rental in Lake Peekskill
Peekskill Guesthouse- PrivateRoom Downtown KingBed Hotel Amenities EpicViews, holiday rental in Lake Peekskill

Peekskill Guesthouse- PrivateRoom Downtown KingBed Hotel Amenities EpicViews

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Peekskill Carriage House Downtown Studio, holiday rental in Lake Peekskill
Peekskill Carriage House Downtown Studio, holiday rental in Lake Peekskill
Peekskill Carriage House Downtown Studio, holiday rental in Lake Peekskill

Peekskill Carriage House Downtown Studio

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Adorable Cottage NY minutes from train to city, holiday rental in Lake Peekskill
Adorable Cottage NY minutes from train to city, holiday rental in Lake Peekskill
Adorable Cottage NY minutes from train to city, holiday rental in Lake Peekskill

Adorable Cottage NY minutes from train to city

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Peekskill Guesthouse-Private GuestSuite w/Privatebath Downtown KingBed EpicView, holiday rental in Lake Peekskill
Peekskill Guesthouse-Private GuestSuite w/Privatebath Downtown KingBed EpicView, holiday rental in Lake Peekskill
Peekskill Guesthouse-Private GuestSuite w/Privatebath Downtown KingBed EpicView, holiday rental in Lake Peekskill

Peekskill Guesthouse-Private GuestSuite w/Privatebath Downtown KingBed EpicView

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Private lake escape, holiday rental in Lake Peekskill
Private lake escape, holiday rental in Lake Peekskill
Private lake escape, holiday rental in Lake Peekskill

Private lake escape

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Mountain lake lodge., holiday rental in Lake Peekskill
Mountain lake lodge., holiday rental in Lake Peekskill
Mountain lake lodge., holiday rental in Lake Peekskill

Mountain lake lodge.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Cold spring mtn house, holiday rental in Lake Peekskill
Cold spring mtn house, holiday rental in Lake Peekskill
Cold spring mtn house, holiday rental in Lake Peekskill

Cold spring mtn house

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Secluded Lakefront Cottage near Hudson Valley, holiday rental in Lake Peekskill
Secluded Lakefront Cottage near Hudson Valley, holiday rental in Lake Peekskill
Secluded Lakefront Cottage near Hudson Valley, holiday rental in Lake Peekskill

Secluded Lakefront Cottage near Hudson Valley

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Log Cabin on Quiet 20 Acres, holiday rental in Lake Peekskill
Log Cabin on Quiet 20 Acres, holiday rental in Lake Peekskill
Log Cabin on Quiet 20 Acres, holiday rental in Lake Peekskill

Log Cabin on Quiet 20 Acres

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails., holiday rental in Lake Peekskill
Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails., holiday rental in Lake Peekskill
Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails., holiday rental in Lake Peekskill

Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy range close to FDR park convent location, holiday rental in Lake Peekskill
Cozy range close to FDR park convent location, holiday rental in Lake Peekskill
Cozy range close to FDR park convent location, holiday rental in Lake Peekskill

Cozy range close to FDR park convent location

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Westchester feel Hudson valley view, holiday rental in Lake Peekskill
Westchester feel Hudson valley view, holiday rental in Lake Peekskill
Westchester feel Hudson valley view, holiday rental in Lake Peekskill

Westchester feel Hudson valley view

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Stay in the HEART of West Point~Walk to academy!, holiday rental in Lake Peekskill
Stay in the HEART of West Point~Walk to academy!, holiday rental in Lake Peekskill
Stay in the HEART of West Point~Walk to academy!, holiday rental in Lake Peekskill

Stay in the HEART of West Point~Walk to academy!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy Modern Home in the Hudson Valley, holiday rental in Lake Peekskill
Cozy Modern Home in the Hudson Valley, holiday rental in Lake Peekskill
Cozy Modern Home in the Hudson Valley, holiday rental in Lake Peekskill

Cozy Modern Home in the Hudson Valley

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Modern Home in the Hudson Valley, holiday rental in Lake Peekskill
Cozy Modern Home in the Hudson Valley, holiday rental in Lake Peekskill
Cozy Modern Home in the Hudson Valley, holiday rental in Lake Peekskill

Cozy Modern Home in the Hudson Valley

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stone Fireplace,  one hour from new york . . ., holiday rental in Lake Peekskill
Stone Fireplace,  one hour from new york . . ., holiday rental in Lake Peekskill
Stone Fireplace,  one hour from new york . . ., holiday rental in Lake Peekskill

Stone Fireplace, one hour from new york . . .

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming 2bdrm on Main St-WALK to everything West Point!, holiday rental in Lake Peekskill
Charming 2bdrm on Main St-WALK to everything West Point!, holiday rental in Lake Peekskill
Charming 2bdrm on Main St-WALK to everything West Point!, holiday rental in Lake Peekskill

Charming 2bdrm on Main St-WALK to everything West Point!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Luxury Lake House Retreat 1 Hour From NYC Near West Point & Bear Mountain, holiday rental in Lake Peekskill
Luxury Lake House Retreat 1 Hour From NYC Near West Point & Bear Mountain, holiday rental in Lake Peekskill
Luxury Lake House Retreat 1 Hour From NYC Near West Point & Bear Mountain, holiday rental in Lake Peekskill

Luxury Lake House Retreat 1 Hour From NYC Near West Point & Bear Mountain

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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DOMIR Yorktown, holiday rental in Lake Peekskill
DOMIR Yorktown, holiday rental in Lake Peekskill
DOMIR Yorktown, holiday rental in Lake Peekskill

DOMIR Yorktown

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Historic home at West Point on Main Street. 1 mile from Thayer Gate!, holiday rental in Lake Peekskill
Historic home at West Point on Main Street. 1 mile from Thayer Gate!, holiday rental in Lake Peekskill
Historic home at West Point on Main Street. 1 mile from Thayer Gate!, holiday rental in Lake Peekskill

Historic home at West Point on Main Street. 1 mile from Thayer Gate!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Bright Charming 3B/3B Secluded Garrison Retreat, holiday rental in Lake Peekskill
Bright Charming 3B/3B Secluded Garrison Retreat, holiday rental in Lake Peekskill
Bright Charming 3B/3B Secluded Garrison Retreat, holiday rental in Lake Peekskill

Bright Charming 3B/3B Secluded Garrison Retreat

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Castle by the Lake, holiday rental in Lake Peekskill
Castle by the Lake, holiday rental in Lake Peekskill
Castle by the Lake, holiday rental in Lake Peekskill

Castle by the Lake

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Sunrise lake house, holiday rental in Lake Peekskill
Sunrise lake house, holiday rental in Lake Peekskill
Sunrise lake house, holiday rental in Lake Peekskill

Sunrise lake house

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Our Rockbound Highland Home * 2 Blocks to West Point * 1/2 Block to Main St, holiday rental in Lake Peekskill
Our Rockbound Highland Home * 2 Blocks to West Point * 1/2 Block to Main St, holiday rental in Lake Peekskill
Our Rockbound Highland Home * 2 Blocks to West Point * 1/2 Block to Main St, holiday rental in Lake Peekskill

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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West Point Graduation 2024 - Great Spot for Family & Friends to Celebrate, holiday rental in Lake Peekskill
West Point Graduation 2024 - Great Spot for Family & Friends to Celebrate, holiday rental in Lake Peekskill
West Point Graduation 2024 - Great Spot for Family & Friends to Celebrate, holiday rental in Lake Peekskill

West Point Graduation 2024 - Great Spot for Family & Friends to Celebrate

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Bear Mountain House., holiday rental in Lake Peekskill
Bear Mountain House., holiday rental in Lake Peekskill
Bear Mountain House., holiday rental in Lake Peekskill

Bear Mountain House.

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Lakehouse, holiday rental in Lake Peekskill
Beautiful Lakehouse, holiday rental in Lake Peekskill
Beautiful Lakehouse, holiday rental in Lake Peekskill

Beautiful Lakehouse

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Secluded Getaway: Bear Mt, Cold Spring, Beacon, West Point!, holiday rental in Lake Peekskill
Secluded Getaway: Bear Mt, Cold Spring, Beacon, West Point!, holiday rental in Lake Peekskill
Secluded Getaway: Bear Mt, Cold Spring, Beacon, West Point!, holiday rental in Lake Peekskill

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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COZY RETREAT : HOT TUB, SAUNA, POOL + MORE, holiday rental in Lake Peekskill
COZY RETREAT : HOT TUB, SAUNA, POOL + MORE, holiday rental in Lake Peekskill
COZY RETREAT : HOT TUB, SAUNA, POOL + MORE, holiday rental in Lake Peekskill

COZY RETREAT : HOT TUB, SAUNA, POOL + MORE

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Beautiful Cottage in Hudson Valley w/Pool & Views, holiday rental in Lake Peekskill
Beautiful Cottage in Hudson Valley w/Pool & Views, holiday rental in Lake Peekskill
Beautiful Cottage in Hudson Valley w/Pool & Views, holiday rental in Lake Peekskill

Beautiful Cottage in Hudson Valley w/Pool & Views

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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*iHeartNYState, 2.0 Getaway, that's not too far!, holiday rental in Lake Peekskill
*iHeartNYState, 2.0 Getaway, that's not too far!, holiday rental in Lake Peekskill
*iHeartNYState, 2.0 Getaway, that's not too far!, holiday rental in Lake Peekskill

*iHeartNYState, 2.0 Getaway, that's not too far!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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An elegant rustic home/lodge set on 20 acres and 45 miles from NYC, holiday rental in Lake Peekskill
An elegant rustic home/lodge set on 20 acres and 45 miles from NYC, holiday rental in Lake Peekskill
An elegant rustic home/lodge set on 20 acres and 45 miles from NYC, holiday rental in Lake Peekskill

An elegant rustic home/lodge set on 20 acres and 45 miles from NYC

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Garrison Castle Retreat 5B/4B Fireplace Pond Hike, holiday rental in Lake Peekskill
Garrison Castle Retreat 5B/4B Fireplace Pond Hike, holiday rental in Lake Peekskill
Garrison Castle Retreat 5B/4B Fireplace Pond Hike, holiday rental in Lake Peekskill

Garrison Castle Retreat 5B/4B Fireplace Pond Hike

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Sunny house on Lake Oscawana, holiday rental in Lake Peekskill
Sunny house on Lake Oscawana, holiday rental in Lake Peekskill
Sunny house on Lake Oscawana, holiday rental in Lake Peekskill

Sunny house on Lake Oscawana

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Modern Luxurious Country Retreat 1hr from NYC, holiday rental in Lake Peekskill
Modern Luxurious Country Retreat 1hr from NYC, holiday rental in Lake Peekskill
Modern Luxurious Country Retreat 1hr from NYC, holiday rental in Lake Peekskill

Modern Luxurious Country Retreat 1hr from NYC

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Hudson Valley Heaven | a wooded oasis with modern amenities awaits you, holiday rental in Lake Peekskill
Hudson Valley Heaven | a wooded oasis with modern amenities awaits you, holiday rental in Lake Peekskill
Hudson Valley Heaven | a wooded oasis with modern amenities awaits you, holiday rental in Lake Peekskill

Hudson Valley Heaven | a wooded oasis with modern amenities awaits you

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Charming Retreat w/ Fire Pit & Spacious Yard!, holiday rental in Lake Peekskill
Charming Retreat w/ Fire Pit & Spacious Yard!, holiday rental in Lake Peekskill
Charming Retreat w/ Fire Pit & Spacious Yard!, holiday rental in Lake Peekskill

Charming Retreat w/ Fire Pit & Spacious Yard!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Private room in a single family house near Peekskill, holiday rental in Lake Peekskill
Private room in a single family house near Peekskill, holiday rental in Lake Peekskill
Private room in a single family house near Peekskill, holiday rental in Lake Peekskill

Private room in a single family house near Peekskill

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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COZY RETREAT: HOT TUB, POOL, SAUNA, AND MORE..., holiday rental in Lake Peekskill
COZY RETREAT: HOT TUB, POOL, SAUNA, AND MORE..., holiday rental in Lake Peekskill
COZY RETREAT: HOT TUB, POOL, SAUNA, AND MORE..., holiday rental in Lake Peekskill

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

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
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Frequently Asked Questions about Lake Peekskill