Holiday rentals in Peekskill

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Top-rated holiday rentals in Peekskill

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Guest favourite

Rental unit in Philipstown

4.9 out of 5 average rating, 214 reviews

Foxglove Farm

Peace and tranquility await you at the end of this private road surrounded by forest. My home is a log cabin with a private apartment on the lower level, which includes a patio as well as use of other outdoor spaces. There is a fire pit just past your patio and a short path will put you on the Appalachian Trail. As an herbalist and ethnobotanist, plants are my love and my livelihood. They are an integral part of my life and my home. I welcome you to stroll through the many gardens and paths.

Guest favourite

Cottage in Cortlandt

4.99 out of 5 average rating, 176 reviews

The Little Cottage in the Woods

The Little Cottage in the Woods Nestled among the trees, and in close proximity to our main house, this studio cottage is newly refurbished, very private and is in a great location to access the Hudson Valley. Hiking trails are within minutes of the cottage or right out the front door. Golf courses are also minutes away. Whether you are in the area on business or just looking to escape for the weekend and enjoy the out doors. It is situated on 9 1/2 hikeable acres, all available to our guests

Guest favourite

Guest house in Mahopac

4.93 out of 5 average rating, 165 reviews

Sunny Lakeview Guesthouse

Art and light filled spacious studio with panoramic views overlooking lake Mahopac perched on a steep hill. A short 5 min walk down the hill to swimming/paddleboarding/canoeing. Walkable to an on-the-lake restaurant/ other dining/ takeout options + excellent boba tea shop! Drivable to farm fresh food markets, restaurants and art museums. Endless nearby cute towns and hikes include Fahenstock Park, Pound Ridge, Cold Spring, Beacon, Ridgefield, or walk up the hill to the trails of Volz park!

Superhost

Rental unit in Peekskill

4.81 out of 5 average rating, 149 reviews

Little haven by the woods

This is a walk-out basement with two private entrances, and it’s own private outside area. The patio has comfy furniture with a bbq. The kitchen is small, yet efficient with large windows. The bedroom is cozy and comfy with a large smart tv on the wall. The bedroom has a 3/4 wall dividing it from the rest of the apt, but no actual door. So it could be considered a “studio”. We are steps from the trail heads into Blue Mt park. We’re also walking distance to the metro north & downtown.

Guest favourite

Rental unit in Ossining

4.95 out of 5 average rating, 384 reviews

Hudson River Peaceful Getaway, Explore from here

Self Check-In/Private Entrance. House trained Dogs and declawed Cats are Welcome (No additional pet fee). Driveway Parking for two cars. Peaceful, private flat on the Hudson River. Train to NYC (Scarborough Station) 10 min walk through historic neighborhood. Arcadian Mall (Grocery Store, Starbucks, etc) 7 min walk. Lots to explore in the area. Panoramic Rivers views from inside and out. Two televisions. Coffee/Condiments/Cooking Essentials provided. $25 cleaning with or without pets.

Guest favourite

Guest house in Cold Spring

4.99 out of 5 average rating, 127 reviews

Modern+bright forest escape; near village & train

Modern, efficient, and elegant private flexible garden apt. Guesthouse can be used as a studio apartment, or as a private personal retreat space for art/work/rest/meditation. Hiking trails available right out the door, and just a few minutes walk to Cold Spring's vibrant Main Street and Metro North train station to NYC and beyond. Comfortable bed, all modern amenities. Private patio. Native pollinator gardens and forest surround. Solar orientation brings in natural sunlight.

Superhost

Home in Peekskill

4.9 out of 5 average rating, 172 reviews

The Peekskill RiverView House

The Peekskill RiverView House A fully renovated dream house overlooking the historic Peekskill Bay. This 3 bedroom 3.5 bath designer house is a 5 minute walk to the train station as well as the historic downtown. It’s truly the gateway to the Hudson Valley along with having the walkable access to culture, hiking, biking, culinary, spa, and entertainment activities within City limits. Expansive decks on all 3 floors with spectacular Hudson River views from every room.

Guest favourite

Rental unit in Beacon

4.98 out of 5 average rating, 126 reviews

Beacon Bridge Lounge | Private Guest Suite

Escape to this private lower level oasis with a cozy living room, spacious bedroom, and full private bathroom. Amenities include a dining table, flat screen TV with Apple TV, Fios, and a coffee maker. The bedroom features a queen bed, dresser, clothing rack, mirror, microwave, small fridge, and desk setup. Just a 20-25 minute walk, 10-15 minute bike ride, or 5-7 minute drive to Beacon's main street. Relax and unwind in this comfortable space!

Guest favourite

Rental unit in Beacon

4.98 out of 5 average rating, 113 reviews

1 Bedroom with Backyard & Front Porch, Central Air

In heart of Beacon. Large and sunny, on a very quiet block. Private with its own entrance. Back-yard, central air, wifi, TV. Walkable to hiking and Main Street. No need for car. Queen-sized bed. Hosts live upstairs and there is another guest apartment. So you may notice the sounds of others. Therefore we have QUIET HOURS from 10 PM to 8 AM. We only book guests who want quiet hours and who have favorable Airbnb reviews. NO SMOKING please.

Guest favourite

Cottage in Putnam Valley

4.95 out of 5 average rating, 135 reviews

Private Lake House 1 Hour to NYC & Near Westpoint

Escape to this private lake cottage. Just 1h drive from NYC, near lots of skiing & hiking Thunder Ridge (30mi) Mt Peter (30mi) Victor Constant (20mi) Campgaw Mountain (40mi) Enjoy panoramic lake views, 86in TV, ample board games, 5-jet shower, and indoor jetted Jacuzzi tub. Short drive to Bear Mountain & West Point. Legoland is 45 min away Pets are welcome! WiFi is extremely fast and we have free electric car charging

Guest favourite

Guest suite in Haverstraw

4.94 out of 5 average rating, 332 reviews

Haverstraw Hospitality Suite

Quiet & cozy suite, with a comfortable full bed & private bathroom in newly renovated garden (basement) level of a single-family home. WiFi/air conditioning & heat unit/FiOS cable - roku TV. Coffee/tea available. Rollaway available for an extra bed. The neighborhood is quiet, and parking is available in the driveway. Feel free to come and go as you please -- we hope our guests feel like this is their home away from home:)

Guest favourite

Guest house in Peekskill

4.93 out of 5 average rating, 244 reviews

Peekskill Carriage House Downtown Studio

Located close to the center of town, this is the perfect launchpad to experience local restaurants, coffee houses, the Paramount Theater, shopping, etc. and a short drive to stunning hikes, the Hudson Valley and beyond. The apartment is ideal for one or two and features a kitchenette, bathroom, dining island, comfortable queen bed, and couch. peekskillcarriagehouse.com

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Peekskill holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Peekskill's top sights

The Peekskill Brewery37 locals recommend

Birdsall House19 locals recommend

Paramount Hudson Valley Theater16 locals recommend

Taco Dive Bar16 locals recommend

The Peekskill Coffee House15 locals recommend

Peekskill12 locals recommend

Other great holiday rentals in Peekskill

Guest favourite

Cottage in Mohegan Lake

4.92 out of 5 average rating, 189 reviews

The Pearl of Westchester

Guest favourite

Loft in Mountainville

4.97 out of 5 average rating, 108 reviews

Lovely, Quiet and Very Private! Entire Loft!

Guest favourite

Rental unit in Newburgh

4.93 out of 5 average rating, 427 reviews

Riverview Rowhouse, a vintage modern home

Guest favourite

Guest suite in Chester

4.96 out of 5 average rating, 282 reviews

Adorable Guest Apartment in Victorian Mansion

Guest favourite

Rental unit in New Windsor

4.96 out of 5 average rating, 183 reviews

The Loft at 12 Clara Clean Comfy Affordable

Guest favourite

Home in Fort Montgomery

5 out of 5 average rating, 15 reviews

West Point Cottage

Guest favourite

Home in Mohegan Lake

4.98 out of 5 average rating, 42 reviews

A nice place to getaway

Guest favourite

Cottage in Putnam Valley

4.88 out of 5 average rating, 249 reviews

Lakefront Cottage near Hudson Valley

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Quick stats about holiday rentals in Peekskill

Total rentals
20 properties
Total number of reviews
1.5K reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
Local attractions
Stop & Shop, Blue Mountain Park and Paramount Hudson Valley Theater

Holiday rentals in Peekskill

Top-rated holiday rentals in Peekskill

Rental unit in Philipstown

Cottage in Cortlandt

Guest house in Mahopac

Rental unit in Peekskill

Rental unit in Ossining

Guest house in Cold Spring

Home in Peekskill

Rental unit in Beacon

Rental unit in Beacon

Cottage in Putnam Valley

Guest suite in Haverstraw

Guest house in Peekskill

Holiday rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Peekskill holiday rentals

Stay near Peekskill's top sights

Other great holiday rentals in Peekskill

Cottage in Mohegan Lake

Loft in Mountainville

Rental unit in Newburgh

Guest suite in Chester

Rental unit in New Windsor

Home in Fort Montgomery

Home in Mohegan Lake

Cottage in Putnam Valley

Quick stats about holiday rentals in Peekskill

Total rentals

Total number of reviews

Rentals with dedicated workspaces

Wifi availability

Popular amenities

Local attractions

Destinations to explore