Peekskill Vacation Rentals from AED 378: Search Short-Term Rentals

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Our top choices for Peekskill vacation rentals

A living room with a grey sofa, a round coffee table, and a ceiling fan.

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

Highland Falls

Andrew L.

AED 1,098 total

includes taxes & fees

9 Nov - 10 Nov

A bedroom with a bed, two bedside tables, a window with blinds, and a ceiling light.

2. Cozy 1-bedroom retreat minutes from West Point!

Highland Falls

Zack C.

AED 708 total

includes taxes & fees

8 Nov - 9 Nov

A single-story house with a red front door, white shutters, and a small porch with two wooden benches.

3. Contemporary Cozy Cottage

Lake Peekskill

Heather M.

AED 1,470 total

includes taxes & fees

11 Nov - 12 Nov

A mountainous landscape with autumn foliage and a river.

4. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery

Jasmine

AED 1,158 total

includes taxes & fees

7 Dec - 8 Dec

A living room with a sectional sofa, a coffee table, a flat-screen TV, and a patterned wall.

5. Local Artist Inspired | Walk to WestPoint + King Bed

Highland Falls

Morgan S.

AED 1,534 total

includes taxes & fees

11 Nov - 12 Nov

A living room with a sofa, a wooden bench, a TV, a fireplace, and a ceiling fan.

6. 3BR West Point Retreat-3min to Back Gate+ King Bed

Highland Falls

Christine T.

AED 1,719 total

includes taxes & fees

10 Nov - 11 Nov

A bedroom with a TV displaying a fireplace, a bed with patterned bedding, and a door leading to another room.

7. Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

CROTON HDSN

Margaret S.

AED 1,299 total

includes taxes & fees

12 Nov - 13 Nov

A living room with a wooden floor, a black sofa, a coffee table, and a ceiling fan.

8. Perfect 2BR with Free Parking! Walk to West Point!

Highland Falls

AED 979 total

includes taxes & fees

9 Nov - 10 Nov

A modern living room with a grey sofa, a wooden side table, a blue and white patterned chair, and a cityscape painting on the wall.

9. Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Highland Falls

Maria L.

AED 907 total

includes taxes & fees

8 Nov - 9 Nov

A living room with a black leather sofa, a grey sofa with red and white cushions, a wooden coffee table, a floor lamp, and a flat-screen TV mounted on the wall.

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

Highland Falls

Briana T.

AED 1,094 total

includes taxes & fees

8 Nov - 9 Nov

A living room with a sofa, a coffee table, a chair, a ceiling fan, and a kitchen in the background.

11. 3BR Near West Point | Coffee Bar | Sleeps 6

Highland Falls

mario b.

AED 1,535 total

includes taxes & fees

11 Nov - 12 Nov

A modern living room with a sofa, a small round wooden table, and a potted plant.

12. Fabulous 3bdrm Home w/parking!

Highland Falls

Beth M.

AED 1,065 total

includes taxes & fees

8 Nov - 9 Nov

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

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

Lake Peekskill

Angel R.

AED 2,598 total

includes taxes & fees

9 Nov - 10 Nov

A stone wall, a blue kayak, a paddleboard, and a table with chairs in a garden area.

14. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

Croton-on-Hudson

Eva C.

AED 1,483 total

includes taxes & fees

9 Nov - 10 Nov

A beige pillow with a bicycle and the text "Enjoy the Journey" on a black leather couch.

15. Walk to WP Gate + Free Parking!

Highland Falls

Daniel C.

AED 987 total

includes taxes & fees

8 Nov - 9 Nov

A modern living room with a stone fireplace, a leather sofa, a yellow armchair, a flat-screen TV, and a bookshelf.

16. 'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

Croton-on-Hudson

Mateo A.

AED 1,603 total

includes taxes & fees

19 Nov - 20 Nov

A living room with a sofa, a chair, a coffee table, a rug, and a ceiling fan.

17. Mountain-View 2BR Steps from Thayer Gate

Highland Falls

AED 906 total

includes taxes & fees

8 Nov - 9 Nov

A bedroom with a bed, two bedside tables, and a ceiling fan.

18. Hudson Valley/West Point Retreat w/ parking!

Highland Falls

AED 1,242 total

includes taxes & fees

9 Nov - 10 Nov

A cozy living room with a brown leather sofa, a wooden coffee table, and a brick fireplace.

19. Walk-to-Lake Cottage With Grill for Peaceful Fall Days

Putnam Valley

Lisa

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

20. 3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

Cornwall

Elisabeth

AED 1,592 total

includes taxes & fees

9 Nov - 10 Nov

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Find vacation rentals that suit your style

Top Peekskill Hotel Reviews

A large, historic building with a prominent tower, surrounded by well-maintained gardens and a parking area.

The Abbey Inn & Spa

Peekskill

10/10 Excellent

Ralph

A Holiday Inn Express & Suites building with a covered entrance, multiple windows, and a landscaped area with plants and a fire hydrant.

Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

Peekskill

10/10 Excellent

David Allen

A hotel with multiple buildings, a parking lot, and a body of water in the foreground.

SpringHill Suites by Marriott Fishkill

Fishkill

10/10 Excellent

MICHELLE

A neatly made bed with a pink headboard, white pillows, and a matching bench.

The Factory

Beacon

10/10 Excellent

JAYANTI

An outdoor patio area with string lights, seating, and a view of the garden.

Cromwell Manor Inn

Cornwall

10/10 Excellent

Alice

A large, two-story white house with a wrap-around porch and a small front garden.

The Dominion House Bed & Breakfast

Chester

10/10 Excellent

Cindy

A large, historic building with a stone facade, multiple windows, and a prominent entrance.

The Thayer Hotel at West Point

West Point

10/10 Excellent

Amy

A hotel with a covered entrance, multiple floors, and a clear sky.

Comfort Suites Fishkill near Interstate 84

Fishkill

10/10 Excellent

Scott

A hotel indoor pool with lounge chairs, a hot tub, and a warning sign.

Homewood Suites Stewart Airport

New Windsor

10/10 Excellent

Needed a place to stay when moving to the area. This hotel was conveniently located and very affordable - especially considering what you get! The suites were fantastic - spacious, everything we needed, kitchenettes. On top of that they serve a good hot breakfast every morning and a manager's reception (which is essentially a meal) four nights a week. What a deal! Friendly, helpful staff too. I truly don't have anything negative to say about this hotel.

Anonymous traveler

The Dutchess Inn and Spa at Beacon

Beacon

10/10 Excellent

Marjorie

Frequently Asked Questions

Can I find a vacation rental in Peekskill?

Yes, there are vacation rentals in Peekskill close to Paramount Hudson Valley Theater, or you can go with a more remote option if you're looking for extra privacy while you relax. Nature enthusiasts will enjoy the riverfront and mountain landscape in Peekskill. While you're here, grab a bite or have a drink at the restaurants.

What are some of the best vacation rentals that Peekskill has to offer?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This vacation home rental near Peekskill offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with an oven, a microwave, and kitchenware, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Peekskill?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Peekskill stay.

What’s there to see and do in Peekskill?

Enjoy the outdoors at Blue Mountain Reservation and Charles Point Pier Park, or simply take in cultural attractions like Paramount Hudson Valley Theater and Peekskill Museum. Other places in town to visit include Hudson Valley Center for Contemporary Art and Dramatic Hall.

What’s a vacation rental in Peekskill like?

Vacation rentals are privately owned properties you can book for a long or short time in Peekskill. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and busy front desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for family trips or small group gatherings.

Peekskill Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Peekskill vacation rentals

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

2. Cozy 1-bedroom retreat minutes from West Point!

3. Contemporary Cozy Cottage

4. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

5. Local Artist Inspired | Walk to WestPoint + King Bed

6. 3BR West Point Retreat-3min to Back Gate+ King Bed

7. Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

8. Perfect 2BR with Free Parking! Walk to West Point!

9. Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

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

11. 3BR Near West Point | Coffee Bar | Sleeps 6

12. Fabulous 3bdrm Home w/parking!

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

14. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

15. Walk to WP Gate + Free Parking!

16. 'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

17. Mountain-View 2BR Steps from Thayer Gate

18. Hudson Valley/West Point Retreat w/ parking!

19. Walk-to-Lake Cottage With Grill for Peaceful Fall Days

20. 3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

Find vacation rentals that suit your style

Top Peekskill Hotel Reviews

The Abbey Inn & Spa

10/10 Excellent

Frequently Asked Questions

Can I find a vacation rental in Peekskill?

What are some of the best vacation rentals that Peekskill has to offer?

How many vacation rentals are there in Peekskill?

What’s there to see and do in Peekskill?

What’s a vacation rental in Peekskill like?