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

Experience the best of Ossining with our apartment rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

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.

Do apartment rentals in Ossining have wifi?

Absolutely! We offer over 10 apartment rentals with wifi 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.

Places to stay in Ossining

Book unique places to stay, houses, and more on Airbnb

Top-rated places to stay in Ossining

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

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Superhost

A welcoming entrance is framed by lush green plants and flowers. A decorative gate stands slightly ajar, leading to a stone pathway that guides toward a colorful house with a distinctive entrance. The overall ambiance is inviting and friendly.

Home in Poughkeepsie

4.8 out of 5 average rating, 108 reviews

Garden Retreat Theme

KristinRating, 5 stars2 months ago

Everything about this place was wonderful. It was centrally located to Poughkeepsie and was with 15 minutes of everything we hoped to do. The apartment was very clean, well stocked, and private with lots of homey touches that made it extra comfortable. We particularly loved the robes that were provided and the comfortable king sized bed. Delia was extremely responsive and proactive in communicating with us prior to and during our stay. We highly recommend this place for a cozy getaway in the Hudson Valley.

Guest favorite

A welcoming porch features a ceiling light fixture, two comfortable black seating chairs, and vibrant flower arrangements with red and white blooms. The entrance door presents a decorative glass panel, contributing to the inviting atmosphere of the home.

Home in Port Jervis

4.93 out of 5 average rating, 237 reviews

Victorian At Orange Square Entire Home

CynthiaRating, 5 stars1 month ago

This is the 2nd year we stayed here in March for a bike event in town. The location is perfect, you can walk to town, plenty of room for our bikes in the garage and the hot tub is great amenity. The kitchen was stocked with everything we needed to have meals at the house. Bruce is a great host, very helpful and always responsive. We look forward to staying again next year!

Top guest favorite

A private outdoor deck featuring a wooden floor and a shaded area. Several seating options include four light-colored lounge chairs and a dining table surrounded by additional chairs, providing ample space for relaxation and dining while enjoying the ocean views.

Apartment in Long Beach

4.99 out of 5 average rating, 174 reviews

Incredible Long Beach Private Rental

AllanRating, 5 stars3 months ago

Absolutely superb hosts and such a great location. Steven couldn’t have been a better host, our kids and us loved his place and would highly recommend. Thoughtful touches everywhere and very clean. Hope we can stay again sometime.

Guest favorite

A serene outdoor space features wooden benches surrounding a fire pit, with a stone patio extending towards a stunning view of the Hudson River. Lush trees provide natural shade, and the horizon showcases gentle hills under a soft blue sky.

Guest suite in Ossining

4.71 out of 5 average rating, 58 reviews

House on the hudson is a 3bed 2bath private kit/LR

JoshuaRating, 5 stars6 months ago

Perfect for festive fall getaway! Jeni's place was great for our group of 5. We enjoyed sitting by the Firepit in the evening and taking in the amazing view from the deck during the day. Location is very close to Sleepy Hollow and other fall attractions. Great visit, Thanks!

Guest favorite

A panoramic view of the Manhattan skyline illuminated at night, showcasing iconic buildings such as the Empire State Building and One World Trade Center. The reflection of the skyline glimmers on the water in the foreground, highlighting the vibrant city lights.

Loft in Weehawken Township

4.91 out of 5 average rating, 106 reviews

Exquisite Studio and Perfect location

ManuRating, 5 stars4 months ago

Our stay at Checha's was just perfect. The apartment is as described, very well-equipped and very clean! The neighborhood is great, quiet with shops nearby (Lidl is a 5-minute walk) and above all an incredible view of New York! The bus stop is right next to the house, allowing you to reach Manhattan in 15-20 minutes. Checha is a very friendly host, attentive and very accommodating! The quality of the accommodation and Checha's kindness helped make this trip an exceptional one! I recommend it 100%.

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What guests are saying

Guest Suite in Stylish Townhouse, 2bds w/ensuites

4.97 out of 5 average rating, 63 reviews1 month ago

This stay was perfect for us - older couple visiting from Texas. The apartment afforded us the flexibility of being together when we wanted to, and work on our own in privacy when we needed or wanted to. It is located in a real neighborhood, so that the staff of the bodega around the corner gave us a friendly hello when we shopped for groceries, and after a week one of the neighbors gave us a friendly wave. To my mind, it is much better than a Manhattan midtown hotel. The apartment was spotless, the kitchen had everything we needed for a home cooked meal. We used the laundry room, which was as spotless as the rest of the place, and the washer/dryer combo seemed brand new and was easy to use. We stayed a week, but could have stayed longer. Sebastian responded quickly and helpfully the one time we needed help with a random issue. We did not get to meet him, but communication was seamless. We would gladly stay at this apartment again.

Guest suite in Bedford-Stuyvesant

What guests are saying

1 bedroom bed with breakfast

4.97 out of 5 average rating, 32 reviews5 months ago

Susan and her home are an AirBnB treasure. It is such a warm, inviting, and fantastic comfort to stay in her cozy home, surrounded by nature outside and a beautiful artistic home and community inside. Susan is a terrific community-builder, and a gracious, kind, and generous host. It was wonderful and actually fun to stay at her home. I agree with the many positive statements that others wrote about staying at Susan’s; it is my favorite AirBnb, and a place that I am happy to return to while traveling.

Private room in Poughkeepsie

What guests are saying

Serenity in the Glen- with hot tub!

5 out of 5 average rating, 4 reviews1 month ago

Serenity at Glen Spey was just that, serene. A quiet escape from the city with beautiful scenery, and absolute quiet. Plenty of space for kids to run around, enjoy a camp fire, and a lovely fireplace. There's also a really great park near by that has shuffle board, For everyone else, a great hot tub, an amazing bath in the upstairs bedroom and great showers in the lower bedrooms. Renee was incredibly accommodating and attentive. 10/10 would stay again

Home in Glen Spey

What guests are saying

Greenwich/ Hotel Alternative / Boutique Living

4.9 out of 5 average rating, 29 reviews3 months ago

Sherri's home offered a great location and a pleasant accommodation for a family. The space accommodated us very well, and the fact that the home is walking distance to downtown Greenwich is a major positive. We found Sherri to also be very responsive on any questions we had during the visit.

Home in Greenwich

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Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Ossining places to stay

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Ossining's top sights

The Boathouse23 locals recommend

Rockland Lake State Park20 locals recommend

3 Westerly Bar and Grill15 locals recommend

The Great Jack O’Lantern Blaze14 locals recommend

First Village Coffee14 locals recommend

Baked by Susan9 locals recommend

Other great vacation rentals in Ossining

Guest favorite

A serene lake view is presented, showcasing calm waters bordered by lush greenery and residential homes on the opposite shore. A private dock is visible in the foreground, accompanied by a shaded gazebo. The bright blue sky reflects on the lake's surface.

Home in Hopatcong

4.92 out of 5 average rating, 139 reviews

Lakefront Hopatcong w/dock kayaks fishing near NYC

MichelRating, 5 stars2 weeks ago

This was by far the best Airbnb experience we have had. Super clean and comfortable, quiet neighborhood and beautiful view of the lake. Shiying was a very accommodating and friendly host. We absolutely loved our stay and would definitely love to return. Thank you!

Top guest favorite

An outdoor deck area is shown featuring several light-colored Adirondack chairs arranged around a stone fire pit. A neatly stacked pile of firewood is positioned against a backdrop of trees, creating a natural setting for relaxation and gatherings.

Home in Millerton

4.97 out of 5 average rating, 181 reviews

Vacation Home In Millerton

SarahRating, 5 stars1 week ago

We had a wonderful week at Corina's house while out for a family event! The house was spotless and the kitchen was stocked with everything we could need. The outside space was just as amazing. We had a great campfire one night, enjoyed using the grill, and our dog loved being able to run around the large yard. I'm sure we'll be back next year!

Top guest favorite

Cottage in Livingston Manor

4.99 out of 5 average rating, 144 reviews

Cozy mountain top home - views, 5acres & a gym.

AngelaRating, 5 stars1 month ago

It’s was close to all but private and peaceful… picture were accurate however seeing the sunrise peek through the windows were just breathtaking! Love it my family/friends enjoy it too! And as the sunset, beautiful lights came on on the porch and Christmas tree lights. It was just lovely. It was a nice touch and a nice surprise.

Guest favorite

An open living area is presented with a spiral staircase leading to an upper level. A dining table with dark placemats and a vase of fresh flowers is centrally located. Cozy seating options include a textured sofa and an accent chair, while a television is mounted on the wall.

Condo in Vernon Township

4.96 out of 5 average rating, 73 reviews

Peaceful Mountain Retreat

Adam Rating, 5 stars1 week ago

Perfect stay. Felt at home from the moment I arrived and Adam was really easy to communicate with and very accommodating. The condo was clean and cozy. For sure will be back.

Superhost

The entrance of Minerals Resort and Spa is showcased, featuring a prominent sign surrounded by vibrant autumn foliage and colorful flower beds. The building's stone accents and unique architecture complement the natural scenery of the lush mountains in the background.

Condo in Vernon Township

4.73 out of 5 average rating, 111 reviews

200 yds Minerals - great for hotel weddings

SaraRating, 5 stars5 months ago

We had a great time! The unit is an easy walk to Minerals, and the layout was perfect for our needs. Joann was a fantastic host and we can’t wait to stay again!

Guest favorite

Condo in Vernon

4.96 out of 5 average rating, 56 reviews

New Luxury Ski Condo-2 Full Bathrooms

ChasityRating, 5 stars4 months ago

An overall outstanding experience. Pristinely clean, comfortable furniture, cozy bed & bedding - can’t say enough great things about this place and the hosts. We will definitely be back!

Superhost

A designated outdoor seating area features four wooden Adirondack chairs arranged around a stone fire pit. Lush green trees and shrubs create a natural backdrop, while a paver stone pathway invites relaxation and conversation in a serene setting.

Condo in Vernon Township

4.92 out of 5 average rating, 119 reviews

Perfect Retreat! Ski in/out, hot tub, bike races.

BruceRating, 5 stars1 month ago

A great weekend ski retreat. Easy access to the unit and close to the elevator. Great little kitchen, with toaster and k-cups. Very large bathroom. Host gave clear instructions with codes for all amenities. The heated pool and outdoor sauna were a big hit. Host allows late check out for a fee which was very convenient for us.

Top guest favorite

Home in Greenwood Lake

5 out of 5 average rating, 119 reviews

Escape to the lake!LAKEFRONT/Hot-tub/1 hour to NYC

TatyanaRating, 5 stars1 month ago

We had a staycation here and it was absolutely lovely. We enjoyed the space, especially the view. The hot tub was great in the chilly nights, played in the game room a bit, cooked in the kitchen and enjoyed some meals in the dining room. Easy to find, but felt very private. Thank you for sharing the lovely place.

Show all

Quick stats about vacation rentals in Ossining

Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ147 before taxes and fees
Total number of reviews
1.7K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi

Frequently Asked Questions

How much does it cost to stay in apartment rentals in Ossining?
Experience the best of Ossining with our apartment rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
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.
Do apartment rentals in Ossining have wifi?
Absolutely! We offer over 10 apartment rentals with wifi 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.

Places to stay in Ossining

Top-rated places to stay in Ossining

Nice place to stay

Staycation Haven 1 In Newark

Modern Elegance Studio

Guest Suite in Stylish Townhouse, 2bds w/ensuites

Top Side

Beacon Creek House

1 bedroom bed with breakfast

Home Sweet Home NY-LI

Romance Vacation Sweet Home

Serenity in the Glen- with hot tub!

Greenwich/ Hotel Alternative / Boutique Living

Quaint spacious unit, A+ location

Vacation rentals for every style

Popular amenities for Ossining places to stay

Stay near Ossining's top sights

Other great vacation rentals in Ossining

Quick stats about vacation rentals in Ossining

Total rentals

Nightly prices starting at

Total number of reviews

Family-friendly rentals

Rentals with dedicated workspaces

Wifi availability

Frequently Asked Questions

Destinations to explore