Vacation rentals in Ossining

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Ossining

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Apartment in Mount Kisco

4.93 out of 5 average rating, 149 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.

Aug 24 – 31

G$27,718 GYD per night

Superhost

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.

May 6 – 13

G$69,159 GYD per night

Guest favorite

Cottage in Cortlandt

4.99 out of 5 average rating, 159 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

Aug 3 – 10

G$30,165 GYD per night

Guest favorite

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

Nov 22 – 29

G$54,032 GYD per night

Guest favorite

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!

Aug 13 – 20

G$56,926 GYD per night

Guest favorite

Apartment in Ossining

4.94 out of 5 average rating, 302 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 28 – Oct 5

G$58,661 GYD per night

Guest favorite

Barn in Mount Kisco

4.91 out of 5 average rating, 539 reviews

NY Rustic Cottage Getaway

minimum of 3 nights during Covid-19 in order to keep things safe for guests... Prices are slightly elevated winter due to the cost of oil Just 50 min North of NYC (Metro North 5 min away) great for artists, writers, yogi's and creative types or people just wanting to get away from the hustle and bustle, city amenities near by. (Photo Shoots, Seminars, Workshops welcome-Call For different Rates) Tag & Follow Nina’s Cottage on Insta! @ninas_airbnb

Mar 17 – 24

G$32,371 GYD per night

Superhost

Earthen home in Ossining

4.87 out of 5 average rating, 144 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

Aug 22 – 29

G$26,766 GYD per night

Guest favorite

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:)

Jan 12 – 19

G$17,621 GYD per night

Guest favorite

Apartment in Croton-on-Hudson

4.98 out of 5 average rating, 268 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 12 – 19

G$50,150 GYD per night

Guest favorite

Guesthouse in Mahopac

4.96 out of 5 average rating, 110 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

Jan 4 – 11

G$27,611 GYD per night

Guest favorite

Guesthouse in Suffern

4.91 out of 5 average rating, 112 reviews

Private Studio w/Full Kitchen & Bath

Our place is a private, stand-alone building separate from our house, and is cleaned thoroughly between guests including disinfecting all hard surfaces. Private cottage with full kitchen and bath in Suffern, NY. Quick walk to train & bus to NYC. Right off I-87, I-287 (NY & NJ), & NJ Rt. 17. Close to shopping & local restaurants. Off-Street parking & outdoor picnic area. NO CLEANING FEE!

May 18 – 25

G$22,144 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Ossining vacation rentals

Kitchen

Wifi

Pool

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 favorite

Apartment in Peekskill

4.84 out of 5 average rating, 115 reviews

Little haven by the woods

Mar 28 – Apr 4

G$26,972 GYD per night

Guest favorite

Bungalow in Hastings-on-Hudson

4.92 out of 5 average rating, 718 reviews

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

Jul 1 – 8

G$33,469 GYD per night

Guest favorite

Home in Stamford

4.98 out of 5 average rating, 131 reviews

STAMFORD STUDIO CLOSE TO DOWNTOWN AND SHOPPING

Sep 12 – 19

G$20,317 GYD per night

Guest favorite

Cottage in Cortlandt

5.0 out of 5 average rating, 104 reviews

Cottage at Peekskill Hollow

Jan 6 – 13

G$51,450 GYD per night

Guest favorite

Guest suite in White Plains

4.87 out of 5 average rating, 164 reviews

1BR close to White Plains train station

Oct 14 – 21

G$31,372 GYD per night

Guest favorite

Guest suite in Stamford

4.93 out of 5 average rating, 111 reviews

Charming Retreat in North Stamford

Apr 7 – 14

G$18,482 GYD per night

Superhost

Cottage in Mohegan Lake

4.92 out of 5 average rating, 169 reviews

The Pearl of Westchester

Oct 13 – 20

G$33,969 GYD per night

Guest favorite

Tiny home in New Paltz

4.99 out of 5 average rating, 742 reviews

Hudson Valley Tiny House

Jul 13 – 20

G$22,914 GYD per night

Show all

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 a kitchen, over 10 homes with free parking, over 10 homes with air conditioning, 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!

Vacation rentals in Ossining

Top-rated vacation rentals in Ossining

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Ossining vacation rentals

Stay near Ossining's top sights

Other great vacation rentals in Ossining

Apartment in Peekskill

Bungalow in Hastings-on-Hudson

Home in Stamford

Cottage in Cortlandt

Guest suite in White Plains

Guest suite in Stamford

Cottage in Mohegan Lake

Tiny home in New Paltz

Quick stats about vacation rentals in Ossining

Total rentals

Wifi availability

Rentals with dedicated workspaces

Rentals with a pool

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Do house rentals in Ossining have air conditioning?

Are there family-friendly vacation rentals in Ossining?

Do house rentals in Ossining have a kitchen?

Do house rentals in Ossining have wifi?

Do house rentals in Ossining have free parking?

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

Are there vacation rentals with a dedicated workspace in Ossining?

Are there Ossining vacation rentals on Airbnb with pools?

Destinations to explore