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Vacation rentals in Ossining

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Top-rated vacation rentals in Ossining

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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

G$86,129 GYD per night

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

G$48,450 GYD 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

G$27,025 GYD per night

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

G$57,037 GYD 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.

G$19,189 GYD per night

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

G$59,811 GYD per night

Earthen home 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

G$26,818 GYD per night

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

G$17,656 GYD per night

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

G$50,248 GYD per night

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

G$26,304 GYD per night

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

G$27,454 GYD per night

Home in Dobbs Ferry

4.93 out of 5 average rating, 307 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

G$13,228 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

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Unique stays

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Homes

Comfortable places with all the essentials

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

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

G$27,680 GYD per night

Guest suite in Stamford

4.93 out of 5 average rating, 111 reviews

Tranquil Retreat in North Stamford

Dec 2 – 9

G$18,518 GYD 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

G$28,944 GYD per night

Cottage in Cortlandt

4.99 out of 5 average rating, 159 reviews

The Little Cottage in the Woods

Jul 15 – 22

G$30,132 GYD per night

Barn in Mount Kisco

4.91 out of 5 average rating, 538 reviews

NY Rustic Cottage Getaway

Feb 21 – 28

G$32,434 GYD per night

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

G$33,534 GYD per night

Guesthouse in Suffern

4.91 out of 5 average rating, 112 reviews

Private Studio w/Full Kitchen & Bath

May 13 – 20

G$21,984 GYD per night

Cottage in Valhalla

4.96 out of 5 average rating, 222 reviews

Charming private 1BR apt. Easy access to NYC

Jun 8 – 15

G$41,026 GYD 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

Frequently Asked Questions

Do house rentals in Ossining have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Ossining. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Ossining?
Ossining has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Ossining have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Ossining. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Ossining have wifi?
Absolutely! We offer over 10 house rentals with wifi in Ossining. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Ossining have free parking?
Absolutely! We offer over 10 house rentals with free parking in Ossining. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Ossining?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with free parking, over 10 homes with a kitchen, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there vacation rentals with a dedicated workspace in Ossining?
Yes! Work meets play with ease at over 10 vacation rentals in Ossining featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Ossining vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Ossining, available on Airbnb. Make a splash and soak up the sun in style!

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