Peekskill, NY Vacation Homes from $279

Peekskill Vacation Homes
New York
United States of America
Vacation Homes
Expedia.com

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A calm lake with a forested island in the distance, a picnic area, and a rocky shoreline.

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Our top choices for Peekskill vacation homes

A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

A living room with a large artificial tree, several potted plants, and a dining area with chairs and a table.

A room with a white wall, a wooden staircase, a clear plastic chair, a small wooden table with a plant, and a metal rack with a pumpkin.

A modern living room with a flat-screen TV mounted above a fireplace, two grey sofas with cushions, a glass coffee table with decorative items, and a potted plant.

1. Contemporary Cozy Cottage

Contemporary Cozy Cottage

Lake Peekskill

9.8 out of 10, Exceptional, (40 reviews)

9.8/10

Exceptional

(40 reviews)

"Our stay was very nice and described as listed! We recommend anyone who is interested to stay! "

Aj L.

$395 nightly

The price is $452

$452 total

Sep 30 - Oct 1

Total with taxes and fees

Contemporary Cozy Cottage

A room with a wooden floor, a white door with a number, and a window with blinds.

A bed with white bedding and three pillows with different patterns.

A wooden staircase with a handrail, leading upwards.

A wooden deck with white railings, leading to a white building with a brown roof.

2. 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)

10/10

Exceptional

(7 reviews)

"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "

Briana T.

$417 nightly

The price is $479

$479 total

Sep 29 - Sep 30

Total with taxes and fees

Lovely 3BR Home with parking-Walk to WP Gate!

A wooden deck with a table and chairs, overlooking a lake with cherry blossoms and autumn foliage.

A cozy room with a large window overlooking a snowy landscape, a bookshelf filled with books and a model car, and a plush beige blanket on the bed.

A kitchen with white cabinets, a black faucet, and a window with a view of bare trees.

A dining room with a dark wooden table, two chairs on each side, and a vase of flowers in the center.

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

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

Lake Peekskill

$557 nightly

The price is $615

$615 total

Sep 8 - Sep 9

Total with taxes and fees

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

A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

A two-story house with a porch, a flag, and a fenced yard.

A staircase with carpeted steps and wooden handrails, leading to a door with glass panels.

A bed with a quilted headboard and a stack of folded towels.

4. House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!

Highland Falls

10.0 out of 10, Exceptional, (11 reviews)

10/10

Exceptional

(11 reviews)

"Good stay, awesome place"

Scott G.

$378 nightly

The price is $400

$400 total

Sep 8 - Sep 9

Total with taxes and fees

House on the Babbling Brook- Quiet 2BR + King Bed!

A blue house with a white porch, a welcome sign, and a mailbox.

A cozy living room with a grey sectional sofa, a wooden coffee table, and a stone fireplace.

A blue house with a white porch, a welcome sign, and a covered window.

A kitchen with wooden cabinets, a granite countertop, a stove, and a window with a plant.

5. 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)

8.4/10

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."

Christine T.

$447 nightly

The price is $506

$506 total

Sep 8 - Sep 9

Total with taxes and fees

3BR West Point Retreat-3min to Back Gate+ King Bed

A bedroom with a bed, a ceiling fan, a nightstand, a window with curtains, and a wall with framed pictures.

A modern kitchen with a wooden table and chairs, a stainless steel refrigerator, and a white cabinet.

A walk-in closet with open shelves, hanging space, and a bench.

A deck with a fire pit, outdoor furniture, and a grill.

6. Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Highland Falls

9.4 out of 10, Exceptional, (8 reviews)

9.4/10

Exceptional

(8 reviews)

"Great location and super host. "

James U.

$438 nightly

The price is $445

$445 total

Sep 7 - Sep 8

Total with taxes and fees

Sleek Escape: Modern 3 BR- 4 Min from West Point !

A house with a white front door, a small porch with a white railing, and a window with a green curtain.

A kitchen with dark cabinets, a white tiled backsplash, a blue microwave, a stainless steel faucet, and a coffee maker.

A house with a wooden deck, a white railing, and a front door.

A wooden staircase with a white handrail, leading upwards.

7. Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!

Highland Falls

9.4 out of 10, Exceptional, (12 reviews)

9.4/10

Exceptional

(12 reviews)

"House was exactly as described. Would stay again."

Beth M.

$413 nightly

The price is $460

$460 total

Sep 29 - Sep 30

Total with taxes and fees

Fabulous 3bdrm Home w/parking!

A deck with Adirondack chairs, a fire pit, and a grill.

A modern kitchen with white cabinets, a dishwasher, a stove, and a window overlooking a wooded area.

A bedroom with a bed, a dresser, a lamp, and a window.

A dining area with a white table and four chairs, a brick wall, and a door leading outside.

8. 3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

Cornwall

10.0 out of 10, Exceptional, (13 reviews)

10/10

Exceptional

(13 reviews)

"Everything you could ask for!!"

Elisabeth

$339 nightly

The price is $400

$400 total

Sep 9 - Sep 10

Total with taxes and fees

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

A wooden cabin with large windows, a wooden bench, and a view of the forest.

A rustic cabin with a wooden deck, surrounded by tall trees and a gravel path.

A wooden trail signpost with directions to various campsites and trails in a forested area.

A large dining hall with wooden tables and chairs, a buffet setup, and large windows allowing natural light.

9. Harriman Outdoor Center - Cranberry Cabin

Harriman Outdoor Center - Cranberry Cabin

Haverstraw

$279 nightly

The price is $283

$283 total

Sep 7 - Sep 8

Total with taxes and fees

Harriman Outdoor Center - Cranberry Cabin

An outdoor patio area with a covered seating area, a pool, and potted plants.

A cozy living room with a large screen, comfortable seating, and a fireplace.

A dimly lit interior with a large TV screen displaying a video, a small table with a chair, and a fireplace.

A compact kitchen with a dining area, featuring a stove, pots, and a sink.

10. Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Fishkill

9.2 out of 10, Wonderful, (74 reviews)

9.2/10

Wonderful

(74 reviews)

"Great spot! Very unique, has lots of charm!"

Brian

$294 nightly

The price is $340

$340 total

Sep 7 - Sep 8

Total with taxes and fees

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

A rustic cabin with a stone pathway leading to a red chair outside.

A cemetery with stone headstones and a stone wall, surrounded by trees with autumn leaves.

A cozy room with wicker furniture, a bench, and a window with a view of greenery.

11. 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)

9.4/10

Exceptional

(13 reviews)

"Lovely space and situation, unique. Close to the AT, as well."

Peter W.

$247 nightly

The price is $279

$279 total

Sep 7 - Sep 8

Total with taxes and fees

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

A bedroom with a large bed, two bedside tables, a window with curtains, and a view of greenery outside.

A park with a large tree, a flower bush, and a view of a lake.

A table with a vase of flowers and a view of a lake through large windows.

12. 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

9.8 out of 10, Exceptional, (20 reviews)

9.8/10

Exceptional

(20 reviews)

"Beautiful house. Great location and awesome hosts!"

Robert T.

$417 nightly

The price is $452

$452 total

Sep 21 - Sep 22

Total with taxes and fees

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

An outdoor dining area with tables set for a formal event, featuring candles, glassware, and floral centerpieces.

A Tudor-style house with a brick facade, a steeply pitched roof, and a large front yard with a paved patio and a stone wall.

A spacious living room with a large window, a grey sofa with patterned cushions, and a wooden coffee table.

An outdoor dining area with string lights, candles, and floral centerpieces.

13. 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)

8.8/10

Excellent

(10 reviews)

"Super fun location! Host was very helpful. The house is very comfortable for large groups "

natalie l.

$966 nightly

The price is $993

$993 total

Sep 8 - Sep 9

Total with taxes and fees

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.

A swimming pool with lounge chairs and a wooden deck, surrounded by trees and a building with a sloped roof.

A traditional Tudor-style house with a spacious front yard, a stone wall, and a well-maintained garden.

A modern living room with a sectional sofa, a coffee table, and large windows offering a view of trees.

14. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table

2.0 star property

Ossining

$1,107 nightly

The price is $1,233

$1,233 total

Sep 8 - Sep 9

Total with taxes and fees

Summer Pool Oasis Custom Bar Arcade Pool Table

15. Luxury Hudson Valley Retreat near West Point, Storm King & Beacon

Luxury Hudson Valley Retreat near West Point, Storm King & Beacon

Cornwall

9.0 out of 10, Wonderful, (2 reviews)

9.0/10

Wonderful

(2 reviews)

"Great House, less than 15 mins to front gate at West Point, convenient location for visiting and enjoying activities at West Point, e.g. football games, cadet events for family members, etc. Hope to be able to stay there again on another visit to the "Rockbound Highland Home"!!! "

Jeff M.

$886 nightly

The price is $1,047

$1,047 total

Sep 7 - Sep 8

Total with taxes and fees

Luxury Hudson Valley Retreat near West Point, Storm King & Beacon

A modern kitchen with grey cabinets, a central island, bar stools, and a stainless steel range hood.

A dining area with a wooden table and chairs, a brick wall, and a ceiling fan.

A compact living space with a bed, a sofa, a coffee table, and a patterned rug.

A bedroom with two beds, a ceiling fan, a rug, and a window with blinds.

16. Perfect and Spacious Hudson Valley Escape!

Perfect and Spacious Hudson Valley Escape!

Cornwall

8.0 out of 10, Very Good, (2 reviews)

8.0/10

Very Good

(2 reviews)

"Great host, very responsive and accommodating. The house was very clean and comfortable."

Joseph S.

$697 nightly

The price is $823

$823 total

Sep 7 - Sep 8

Total with taxes and fees

Perfect and Spacious Hudson Valley Escape!

A room with a bed, a couch, a desk with a computer, and various wall decorations.

A bedroom with a bed, a desk, a chair, a window with blinds, and artwork on the walls.

A bathroom with a window, a toilet, a shower, and a towel rack.

A forested area with trees and fallen leaves.

17. Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

Carmel Hamlet

$272 nightly

The price is $295

$295 total

Oct 5 - Oct 6

Total with taxes and fees

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

A room with a large bay window, two green armchairs, a small round table, a white sofa, and a potted plant.

A room with large windows, a radiator, a chair, and a table.

A bedroom with a large bed, a potted plant, a framed picture, and three windows offering a view of a lake and hills.

A house with large windows, a patio, and a view of a lake.

18. River Views & Hot Tub | Riverview on Washington

River Views & Hot Tub | Riverview on Washington

Newburgh

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"The home has recently been renovated and it is very well presented with luxury furnishings and an excellently stocked kitchen. Views are amazing over the Hudson towards Beacon."

Rachel M.

$686 nightly

The price is $805

$805 total

Sep 8 - Sep 9

Total with taxes and fees

River Views & Hot Tub | Riverview on Washington

A room with two beds, white curtains, a ceiling light, and a window with a view.

A modern kitchen with a dining area, wooden flooring, and large windows.

A modern kitchen with wooden cabinets, a central island with bar stools, and a microwave.

A modern living room with a white sectional sofa, a glass coffee table, and a grey armchair.

19. Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups

Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups

White Plains

$474 nightly

The price is $542

$542 total

Sep 6 - Sep 7

Total with taxes and fees

Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups

A modern kitchen with a central island, bar stools, a round table, and a window with a view.

A modern living room with a beige sofa, a wooden coffee table, and a view of the outdoors through large windows.

A room with a wooden coffee table, a sofa, a decorative lamp, a wine bottle, and a framed artwork.

A house with a front porch, a white door, and large potted plants.

20. Charming 2-bedroom house in Greenwood Lake with Central AC/Heat

Charming 2-bedroom house in Greenwood Lake with Central AC/Heat

Greenwood Lake

10.0 out of 10, Exceptional, (7 reviews)

10/10

Exceptional

(7 reviews)

"Very clean and really cute place. "

Katie C.

$409 nightly

The price is $463

$463 total

Sep 28 - Sep 29

Total with taxes and fees

Charming 2-bedroom house in Greenwood Lake with Central AC/Heat

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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Top Peekskill Hotel Reviews

Baymont by Wyndham White Plains - Elmsford

10/10 Excellent

"Always a very nice experience when I stay at this hotel. Area is quiet - Hotel clean - staff is great Will go back"

Diamaris 2-night trip

Posted 2 hours ago

Baymont by Wyndham White Plains - Elmsford

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

8/10 Good

"Convenient location, Close to stores for food and accessories. Ample parking spot available."

Ulric 1-night trip

Posted 3 hours ago

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Hilton Garden Inn Westchester Dobbs Ferry, NY

10/10 Excellent

"."

Duke 1-night trip

Posted 7 hours ago

Hilton Garden Inn Westchester Dobbs Ferry, NY

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent

"Muy lindo hotel, limpio y con gran desayuno. El hall es impresionante y los jardines muy lindos. El gym chico pero sirve. Le falta a la zona un poco mas de opciones de comida. Pero vale la pena."

Jose roman 2-night trip

Posted 1 day ago

Crowne Plaza Suffern - Mahwah by IHG

Hotel Nyack, a JdV by Hyatt Hotel

10/10 Excellent

"Beds so comfy and love the bathroom layout"

Carolle 1-night trip

Posted 1 day ago

Hotel Nyack, a JdV by Hyatt Hotel

Find out more about Peekskill

Peekskill Vacation Homes information

Number of reviews	193
Accommodation	179 Vacation Homes
Lowest Price	$279
Highest Price	$1,233

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Search Vacation Homes in Peekskill

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Peekskill vacation homes

1. Contemporary Cozy Cottage

2. Lovely 3BR Home with parking-Walk to WP Gate!

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

4. House on the Babbling Brook- Quiet 2BR + King Bed!

5. 3BR West Point Retreat-3min to Back Gate+ King Bed

6. Sleek Escape: Modern 3 BR- 4 Min from West Point !

7. Fabulous 3bdrm Home w/parking!

8. 3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

9. Harriman Outdoor Center - Cranberry Cabin

10. Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

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

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

13. Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

14. Summer Pool Oasis Custom Bar Arcade Pool Table

15. Luxury Hudson Valley Retreat near West Point, Storm King & Beacon

16. Perfect and Spacious Hudson Valley Escape!

17. Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

18. River Views & Hot Tub | Riverview on Washington

19. Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups

20. Charming 2-bedroom house in Greenwood Lake with Central AC/Heat

Find vacation rentals that suit your style

Top Peekskill Hotel Reviews

Baymont by Wyndham White Plains - Elmsford

Find out more about Peekskill

Peekskill Vacation Homes information

Explore a world of travel with Expedia