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Vacation rentals in Ossining

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Top-rated vacation rentals in Ossining

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Home in Ossining

4.84 out of 5 average rating, 125 reviews

Lower Hudson Valley Idyllic Retreat

Located 2 minutes from Teatown Nature Reserve (35 mins from NYC) on 1+ acre in the Lower Hudson Valley, this updated 2,600sf oasis is the perfect forest setting for your family or business retreat. It features an oversized gourmet chef's kitchen with adjoining dining room. There are 4 bedrooms, including a nursery/crib, additional sleeping spots, and stunning views from a perfectly perched solarium. The great room features a spectacular working fire place and floor to cathedral ceiling windows.

Oct. 6 – 13

$608 CAD per night

Guest favourite

Apartment in Ossining

4.95 out of 5 average rating, 100 reviews

Gorgeous 1 BR w/High End Finishes, Heated BA Floor

Unwind at this peaceful retreat a short walk from downtown Ossining and Hudson River front parks. Designed with end to end comfort, beautifully decorated, and featuring a gorgeous open kitchen and entertaining room, in this space you can relax and step away from it all. Highlights include: 2nd floor walk-up High End Appliances and all Finishes Heated bathroom floors Contactless entry Off-street parking 1/2 block from multiple parks Weekly discount available Come stay here! You’ll love it

Sep. 27 – Oct. 4

$352 CAD per night

Apartment in Peekskill

4.84 out of 5 average rating, 115 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.

Mar. 22 – 29

$203 CAD per night

Guest favourite

Home in Ossining

4.9 out of 5 average rating, 133 reviews

Hudson River town comfy & cozy getaway home!!

Cozy home in the charming Historic Village of Ossining, perched atop the Hudson River, features an eclectic assemblage of homes, industrial spaces, coffee shops, wonderful restaurants, bars, parks, hiking trails and mom-and-pop stores. Relax and unwind in sought out Indian Village bordering Briarcliff Manor. Walking distance to grocery store, liquor store, food choices, CVS, Carvel, and SPA. Crowned one of the “Best Places to Live” in Westchester Magazine!! COME CHECK IT OUT FOR YOURSELF!

Jul. 8 – 15

$406 CAD per night

Guest suite in Piermont

4.85 out of 5 average rating, 381 reviews

Cozy private apartment with Hudson River views

This cozy apartment just one block from the Hudson River, is on the ground level of a house, with a separate entrance offering complete privacy. This modern space has a fully equipped kitchen, beautiful bathroom, comfy queen bed, reading chair, books galore, and a desk. Located in the adorable town of Piermont, it has the feel of a country retreat, a waterfront town, and it's an easy commute to Manhattan. As of Nov. 2022, the WIFI has been upgraded and it is now RELIABLE & HIGH-SPEED.

Guest favourite

Apartment in Ossining

4.94 out of 5 average rating, 298 reviews

Hudson River Peaceful Getaway

Self check-in and private entrance. Parking for two cars. Peaceful apartment on the Hudson River. Train to NYC (Scarborough Station) is an 8 minute walk through historic neighborhood. Arcadian Mall (Grocery store, Starbucks, etc) 5 minute walk. Rivers views from inside and from three patios (1 on entrance side, 2 on River side). We only allow declawed cats because they can scratch and damage our expensive furniture and carpets. Most house trained dogs are welcome :)

Sep. 15 – 22

$411 CAD per night

Guest favourite

Earth homes in Ossining

4.87 out of 5 average rating, 143 reviews

The Babbling Brook

Unique 2 room and 3rd room ( full bath) with backyard and babbling brook with 5 minute ride to train into NYC and 45 minute car ride to midtown Manhattan (with no traffic, lol) Totally renovated with gorgeous large bedroom overlooking backyard and brook. Private entrance with patio. Private driveway with parking spot. For 1 night only guests add $15.00 cleaning fee. Here is a 2 minute Video of "THE BABBLING BROOK" https://www.youtube.com/watch?v=CRUac3qSOm0

May 8 – 15

$181 CAD per night

Guest favourite

Guest suite in Haverstraw

4.95 out of 5 average rating, 293 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:)

Oct. 17 – 24

$119 CAD per night

Guest favourite

Apartment in Croton-on-Hudson

4.98 out of 5 average rating, 267 reviews

Luxury 2bd⭐Comfort+Style⭐

45 min train to Grand Central. Apt is 1.9mi to train, supermarket. Free PARKING. Two 4K TVs, 4K Blu-ray library, NFLX/AMZN/HBO/Apple TV. XBOX 1X. Fast WIFI. SS APPL, stocked kitchen. Bd1: adjustable queen, 50" 4K TV. Bd2: adj queen. Office area (desk, fast wifi), private porch. Sidewalks. 7 min walk to cafes, a bar, and restaurants. Car rental is 16 min walk. Hiking, kayaking. I LIVE NEARBY IN ANOTHER APT | $75 PET FEE |

Aug. 1 – 8

$360 CAD per night

Guest favourite

Guesthouse in Mahopac

4.96 out of 5 average rating, 107 reviews

Sunny Lakeview Guesthouse

Art and light filled spacious studio with panoramic views overlooking lake Mahopac. Walkable to swimming/paddleboarding; skating/ice fishing. Many fine restaurants or casual takeout options, and boasting an excellent coffee shop. Train ride from Grand Central to Croton Falls, then a 12 minute drive or shuttle ride. Close to Fahenstock Park, Cold Springs, Beacon, Ridgefield,or walk up the hill to the trails of Volz park

Sep. 6 – 13

$185 CAD per night

Guest favourite

Guesthouse in Peekskill

4.94 out of 5 average rating, 206 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

Oct. 28 – Nov. 4

$198 CAD per night

Guest favourite

Home in Dobbs Ferry

4.92 out of 5 average rating, 306 reviews

Small cozy room in historic 1828 Dobbs Ferry home.

This is a sweet warm room with twin bed chest of drawers, desk and hanging closet with shelves. I have a 2nd larger room with two twin beds in it, listed separately, and also a very small bedroom with a slightly narrower bed with a curtain across the doorway. Please note: I have one cat. So if you are allergic, maybe not a good choice for you.

Jan. 10 – 17

$90 CAD per night

Vacation rentals for every style

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Hotels

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Popular amenities for Ossining vacation rentals

Free parking on premises

Air conditioning

Stay near Ossining's top sights

The Boathouse23 locals recommend

3 Westerly Bar and Grill15 locals recommend

DD's Diner8 locals recommend

Stop & Shop7 locals recommend

Los Abuelos Restaurant5 locals recommend

Landmark Diner3 locals recommend

Other great vacation rentals in Ossining

Guest favourite

Apartment in Mount Kisco

4.93 out of 5 average rating, 148 reviews

Cozy 1 Bdrm Apt; Privt Entry; 5 min walk to train

Aug. 20 – 27

$193 CAD per night

Guest favourite

Guest suite in Stamford

4.93 out of 5 average rating, 111 reviews

Tranquil Retreat in North Stamford

Dec. 2 – 9

$149 CAD per night

Guest suite in White Plains

4.87 out of 5 average rating, 164 reviews

1BR close to White Plains train station

Oct. 7 – 14

$210 CAD per night

Guest favourite

Cottage in Cortlandt

4.99 out of 5 average rating, 159 reviews

The Little Cottage in the Woods

Jul. 15 – 22

$210 CAD per night

Guest favourite

Barn in Mount Kisco

4.91 out of 5 average rating, 538 reviews

NY Rustic Cottage Getaway

Feb. 21 – 28

$232 CAD per night

Guest favourite

Bungalow in Hastings-on-Hudson

4.91 out of 5 average rating, 716 reviews

★Tiny House Cottage 35 min to NYC on Hudson River★

Nov. 8 – 15

$233 CAD per night

Guest favourite

Guesthouse in Suffern

4.91 out of 5 average rating, 112 reviews

Private Studio w/Full Kitchen & Bath

May 13 – 20

$145 CAD per night

Guest favourite

Cottage in Valhalla

4.96 out of 5 average rating, 222 reviews

Charming private 1BR apt. Easy access to NYC

Jun. 8 – 15

$303 CAD per night

Quick stats about vacation rentals in Ossining

Total rentals
30 properties
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
1.4K reviews

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