Peekskill Vacation Rentals from $199: Search Short-Term Rentals

A calm river with mountains on either side and a sunset sky.

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Our top choices for Peekskill vacation rentals

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

1. Contemporary Cozy Cottage

Lake Peekskill

Heather M.

$338 nightly

Nov 16 - Nov 17

Total with taxes and fees

A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

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

Highland Falls

Andrew L.

$277 nightly

Nov 16 - Nov 17

Total with taxes and fees

A house with a view of a bridge and mountains.

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

Fort Montgomery

Jasmine

$257 nightly

Nov 16 - Nov 17

Total with taxes and fees

A spacious living area with a black leather sofa, a coffee table, a ceiling fan, and a blue cabinet.

4. Spacious 4-bedroom house in northern Westchester with sweeping views

Montrose

$513 nightly

Nov 15 - Nov 16

Total with taxes and fees

A dining table set with plates, cutlery, and glasses, with a bowl of fruit and a wine glass in the background.

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

CROTON HDSN

Margaret S.

$311 nightly

Nov 18 - Nov 19

Total with taxes and fees

A stone staircase leading to a house with a stone wall and a metal gate.

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

Croton-on-Hudson

Eva C.

$353 nightly

Nov 15 - Nov 16

Total with taxes and fees

Step up to a warm welcome - our charming entryway, complete with a hanging birdhouse, sets the tone for a peaceful stay.

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

Putnam Valley

Lisa

$470 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

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

Croton-on-Hudson

Mateo A.

$355 nightly

Nov 19 - Nov 20

Total with taxes and fees

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

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

Highland Falls

Morgan S.

$405 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

10. Fabulous 3bdrm Home w/parking!

Highland Falls

Beth M.

$324 nightly

Dec 8 - Dec 9

Total with taxes and fees

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

Highland Falls

Zack C.

$182 nightly

Dec 8 - Dec 9

Total with taxes and fees

A hallway with a wooden door, a black table with a sign, and large green plants.

12. 3BR Near West Point | Coffee Bar | Sleeps 6

Highland Falls

mario b.

$397 nightly

Nov 15 - Nov 16

Total with taxes and fees

A modern kitchen with stainless steel appliances, wooden cabinets, and a contemporary light fixture.

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

Highland Falls

Maria L.

$264 nightly

Nov 17 - Nov 18

Total with taxes and fees

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

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

Highland Falls

Briana T.

$310 nightly

Dec 8 - Dec 9

Total with taxes and fees

A wooden coffee table with two decorative planters in a living room.

15. Walk to WP Gate + Free Parking!

Highland Falls

Jerell T.

$298 nightly

Dec 8 - Dec 9

Total with taxes and fees

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

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

Highland Falls

$290 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

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

Lake Peekskill

Karen W.

$562 nightly

Nov 16 - Nov 17

Total with taxes and fees

A dining area with a table, chairs, a vase with flowers, a hanging light fixture, and wall decorations.

18. Mountain-View 2BR Steps from Thayer Gate

Highland Falls

$280 nightly

Nov 15 - Nov 16

Total with taxes and fees

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

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

Highland Falls

$411 nightly

Dec 8 - Dec 9

Total with taxes and fees

A covered area with exercise equipment, chairs, and a view through large windows.

20. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

Ossining

$273 nightly

Nov 15 - Nov 16

Total with taxes and fees

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Find vacation rentals that suit your style

Top Peekskill Hotel Reviews

An outdoor patio area with a stone fire pit, seating, and a Marriott sign in the background.

SpringHill Suites by Marriott Fishkill

Fishkill

10/10 Excellent

MICHELLE

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 modern hotel room with a large bed, a sitting area with a sofa, a small table, a TV, and a bathtub.

The Factory

Beacon

10/10 Excellent

JAYANTI

A hotel entrance with stone pillars, a covered walkway, and a bench.

Sleep Inn & Suites Monroe - Woodbury

Monroe

10/10 Excellent

Lisyani

A buffet with various food items, including omelets and baked goods, served in metal containers.

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

Peekskill

10/10 Excellent

David Allen

A balcony with outdoor seating, a staircase, and a view of the cityscape.

The Dutchess Inn and Spa at Beacon

Beacon

10/10 Excellent

Marjorie

A spacious lobby with a high ceiling, a reception desk, a seating area with blue sofas and armchairs, and a visible Pepsi refrigerator.

Comfort Suites Fishkill near Interstate 84

Fishkill

10/10 Excellent

Laura

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

A hotel room with a large mirror, a white sink, and a small table with toiletries.

Holiday Inn Express Ramsey-Mahwah by IHG

Ramsey

10/10 Excellent

Kelly

A modern lobby with seating areas, a fireplace, and a flat-screen TV mounted on the wall.

Cambria Hotel & Suites - White Plains Downtown

White Plains

10/10 Excellent

Keeping in mind its 3-star classification, this hotel does not disappoint. Front desk staff is outstanding. Metro-North station is in easy walking distance. Of special note: In partnership with the Chazz Palminteri restaurant next door, guests can order a meal, get it delivered and charged to the room. Very nice option when traveling all day. On a lesser note, the slamming doors made a lot of disruption. Soft close, as in other hotels, would improve the guest experience and be worth the...

William

A modern hotel entrance with a glass door, a car parked outside, and a well-lit pathway leading to the entrance.

The Opus Westchester, Autograph Collection

White Plains

10/10 Excellent

Anonymous traveler

Find out more about Peekskill

Everything you need to know about Peekskill vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Peekskill vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Peekskill vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Peekskill vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Peekskill. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Peekskill in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $199 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Peekskill rentals

At Expedia, we put the best Peekskill vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Peekskill rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Peekskill vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Peekskill. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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

Check prices for these dates

Our top choices for Peekskill vacation rentals

1. Contemporary Cozy Cottage

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

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

4. Spacious 4-bedroom house in northern Westchester with sweeping views

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

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

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

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

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

10. Fabulous 3bdrm Home w/parking!

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

12. 3BR Near West Point | Coffee Bar | Sleeps 6

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

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

15. Walk to WP Gate + Free Parking!

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

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

18. Mountain-View 2BR Steps from Thayer Gate

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

20. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

Find vacation rentals that suit your style

Top Peekskill Hotel Reviews

SpringHill Suites by Marriott Fishkill

10/10 Excellent

Find out more about Peekskill

Everything you need to know about Peekskill vacation rentals

Peekskill vacation rentals: An excellent choice for every season

How to find incredible deals on Peekskill rentals

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?

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