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.

Guest favorite

Apartment in Mount Kisco

4.93 out of 5 average rating, 147 reviews

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

This cozy apartment is on the lower level of a house, just a 5 minute walk to town and the Harlem Line, Metro North Train stop. A separate entrance to the apt offers complete privacy. This gorgeous space has a fully equipped kitchen, bathroom, comfy twin beds . Located in the adorable town of Mount Kisco, allowing you to take strolls to access restaurants, boutique shops, library, park and bars. It has the feel of a country retreat, a quaint town, and it's an easy commute to White Plains or NYC.

Nov 13 – 20

ﺩ.ﺇ490 per night
Superhost

Home in Ossining

4.84 out of 5 average rating, 124 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.

Jan 7 – 14

ﺩ.ﺇ1,514 per night
Guest favorite

Cottage in Cortlandt

4.99 out of 5 average rating, 158 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

Sep 11 – 18

ﺩ.ﺇ496 per night

Popular amenities for Ossining vacation rentals

Stay near Ossining's top sights

3 Westerly Bar and Grill15 locals recommend
DD's Diner8 locals recommend
Stop & Shop7 locals recommend
The Boathouse23 locals recommend
Los Abuelos Restaurant5 locals recommend
Landmark Diner3 locals recommend

Other great vacation rentals in Ossining

Guest favorite

Guesthouse in Mahopac

4.96 out of 5 average rating, 104 reviews

Sunny Lakeview Guesthouse

Jun 9 – 16

ﺩ.ﺇ498 per night
Guest favorite

Barn in Mount Kisco

4.91 out of 5 average rating, 538 reviews

NY Rustic Cottage Getaway

Jun 9 – 16

ﺩ.ﺇ570 per night
Guest favorite

Guest suite in Stamford

4.93 out of 5 average rating, 110 reviews

Tranquil Retreat in North Stamford

Oct 6 – 13

ﺩ.ﺇ326 per night
Guest favorite

Guesthouse in Suffern

4.91 out of 5 average rating, 110 reviews

Private Studio w/Full Kitchen & Bath

Apr 6 – 13

ﺩ.ﺇ340 per night
Guest favorite

Home in Dobbs Ferry

4.92 out of 5 average rating, 302 reviews

Small cozy room in historic 1828 Dobbs Ferry home.

Dec 3 – 10

ﺩ.ﺇ223 per night
Guest favorite

Cottage in Valhalla

4.97 out of 5 average rating, 218 reviews

Charming private 1BR apt. Easy access to NYC

Jun 6 – 13

ﺩ.ﺇ660 per night
Guest favorite

Bungalow in Hastings-on-Hudson

4.92 out of 5 average rating, 705 reviews

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

Sep 14 – 21

ﺩ.ﺇ590 per night
Guest favorite

Cottage in Cortlandt

5.0 out of 5 average rating, 103 reviews

Cottage at Peekskill Hollow

Jul 7 – 14

ﺩ.ﺇ901 per night
Guest favorite

Cottage in Mohegan Lake

4.93 out of 5 average rating, 167 reviews

The Pearl of Westchester

Sep 4 – 11

ﺩ.ﺇ652 per night
Guest favorite

Guesthouse in Suffern

4.96 out of 5 average rating, 119 reviews

Hiking trails steps from your door!

Sep 6 – 13

ﺩ.ﺇ594 per night
Guest favorite

Guest suite in Tarrytown

4.94 out of 5 average rating, 208 reviews

Brand new private Studio in the heart of Tarrytown

Jun 14 – 21

ﺩ.ﺇ1,180 per night
Guest favorite

Apartment in Brookfield

4.94 out of 5 average rating, 179 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Nov 29 – Dec 6

ﺩ.ﺇ463 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

1.5K 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 20 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.

  • How much does it cost to stay in apartment rentals in Ossining?

    Experience the best of Ossining with our apartment rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • What are the most popular amenities for House Rentals in Ossining?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with wifi, over 10 homes with air conditioning, over 10 homes with a kitchen, over 10 homes with free parking, 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.

Destinations to explore

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