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Vacation rentals in Ossining

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Top-rated vacation rentals in Ossining

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Rental unit in Mount Kisco

4.92 out of 5 average rating, 172 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.

Home in Ossining

4.85 out of 5 average rating, 137 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.

Rental unit in Ossining

4.95 out of 5 average rating, 125 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

Rental unit in Peekskill

4.81 out of 5 average rating, 150 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.

Guesthouse in Hastings-on-Hudson

4.91 out of 5 average rating, 792 reviews

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

Please read the entire listing to set expectations. Super charming, slightly quirky, private Shangri-La w/backyard chickens in the artistic & quaint Rivertowns, 35 min. from NYC. The Tiny House escape is reminiscent of sleep away camp (rustic), yet tastefully curated w/eclectic art & furnishings. Sleeping loft nest w/8 step ladder or pull out sofa bed. Electric fireplace inside. NO outdoor grilling or fire pits. Fenced in yard. FREE private driveway. Close to the Hudson River. Read on..

Rental unit in Ossining

4.95 out of 5 average rating, 385 reviews

Hudson River Peaceful Getaway, Explore from here

Self Check-In/Private Entrance. House trained Dogs and declawed Cats are Welcome (No additional pet fee). Driveway Parking for two cars. Peaceful, private flat on the Hudson River. Train to NYC (Scarborough Station) 10 min walk through historic neighborhood. Arcadian Mall (Grocery Store, Starbucks, etc) 7 min walk. Lots to explore in the area. Panoramic Rivers views from inside and out. Two televisions. Coffee/Condiments/Cooking Essentials provided. $25 cleaning with or without pets.

Earthen home in Ossining

4.87 out of 5 average rating, 147 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

Guest suite in Haverstraw

4.94 out of 5 average rating, 334 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:)

Rental unit in Croton-on-Hudson

4.97 out of 5 average rating, 317 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 |

Guesthouse in Peekskill

4.93 out of 5 average rating, 247 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

Rental unit in Ardsley

4.89 out of 5 average rating, 411 reviews

Lovely and Well Appointed Suite w/ Indoor Parking

Charming suite with a private entrance, bathroom, indoor parking and dining area with kitchen amenities. Conveniently located in Westchester, and is accessible by the I-87, Henry Hudson, Sprain and Saw Mill Parkways; only a thirty minute drive to NYC. Near a deli, grocery, bakery, Carvel, CVS and a selection of restaurants.

Barn in Mount Kisco

4.91 out of 5 average rating, 563 reviews

NY Rustic Cottage Getaway

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

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Popular amenities for Ossining vacation rentals

Free parking on premises

Air conditioning

Stay near Ossining's top sights

Croton Point Park23 locals recommend

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

Other great vacation rentals in Ossining

Home in Ossining

4.91 out of 5 average rating, 56 reviews

Camped Inn at Sundial Farm -- Tiny House

Home in Ossining

5 out of 5 average rating, 14 reviews

Pool/HotTub - Close to NYC

Rental unit in Croton-on-Hudson

4.82 out of 5 average rating, 66 reviews

Haven On The Hudson

Rental unit in Harrison

4.96 out of 5 average rating, 273 reviews

Luxury Private Apartment - Walk to Train for NYC!

Guest suite in Haverstraw

4.88 out of 5 average rating, 57 reviews

Unique comfortable guest suite

Rental unit in Pleasantville

4.82 out of 5 average rating, 57 reviews

Beautiful Studio Apartment in Perfect Location

Home in Ossining

4.85 out of 5 average rating, 20 reviews

Hudson Valley Escape

Tiny home in Bardonia

4.88 out of 5 average rating, 17 reviews

The Shed - Tiny Home Living

Quick stats about vacation rentals in Ossining

Total rentals
30 properties
Nightly prices starting at
$40 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
30 properties include access to wifi

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.
How much does it cost to stay in house rentals in Ossining?
Experience the best of Ossining with our house rentals, starting at about $40 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 10 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.

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