Compare Ossining Guest House Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Guest Houses in Ossining

The Cottage by the Lake: Hudson Valley Indulgence/1 hr. from NYC/welcome pets!.

The Cottage by the Lake: Hudson Valley Indulgence/1 hr. from NYC/welcome pets!.

Brewster NY
At this guesthouse, guests have access to an outdoor pool, laundry facilities, and barbecue grills. This guesthouse also has a garden.
Pool
Pet friendly
Upscale 3BR NY Home with Free Parking

Upscale 3BR NY Home with Free Parking

2 out of 5
12 Fairview Ave White Plains NY
$330 nightly
The price is $368 total per night
$368 total
Apr 5 - Apr 6
Total with taxes and fees
If you drive, take advantage of free parking.
Pet friendly
Parking included
Peaceful Light-Filled Guesthouse 1 Hour From NYC

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Pound Ridge NY
At this guesthouse, guests have access to an outdoor pool, laundry facilities, and barbecue grills. This family-friendly guesthouse also has a garden.
Pool
Pet friendly
Upscale Modern Luxury 3BR Home

Upscale Modern Luxury 3BR Home

2 out of 5
44 Dekalb Ave White Plains NY
$355 nightly
The price is $396 total per night
$396 total
Apr 6 - Apr 7
Total with taxes and fees
If you drive, take advantage of free parking.
Pet friendly
Parking included
Luxury 3BR NY Home with Free Parking

Luxury 3BR NY Home with Free Parking

2 out of 5
38 Park Ave White Plains NY
$336 nightly
The price is $375 total per night
$375 total
Apr 5 - Apr 6
Total with taxes and fees
You can put free parking to good use if you drive.
Pet friendly
Parking included
Mid Century Modern ZEN House with Pool. 50 min from New York City

Mid Century Modern ZEN House with Pool. 50 min from New York City

Stamford CT
Guests of this guesthouse enjoy features like an outdoor pool, a gym, and local meal delivery service. Additional amenities include barbecue grills and a garden.
Pool
Free WiFi
Ultra-Modern Luxe Sleek & Stunning Stay

Ultra-Modern Luxe Sleek & Stunning Stay

2 out of 5
66 Dekalb Ave White Plains NY
Guests of Ultra-Modern Luxe Sleek & Stunning Stay enjoy features like free WiFi in public areas. If you decide to drive, there's free parking. Dry cleaning/laundry services make packing light an option.
Pet friendly
Parking included
Beautiful Stamford Loft! Near Downtown+Parking+45min to NYC

Beautiful Stamford Loft! Near Downtown+Parking+45min to NYC

Stamford CT
At this guesthouse, guests have access to a garden.
Free WiFi
Air conditioning
Prime Luxury with Balcony Wood Fireplace

Prime Luxury with Balcony Wood Fireplace

2 out of 5
51 Vernon Ave Yonkers NY
Guests of Prime Luxury with Balcony Wood Fireplace enjoy features like free WiFi in public areas. Free parking is available if you drive. Dry cleaning/laundry services make packing light an option.
Pet friendly
Parking included
Don't see what you're looking for?
See all available properties in Ossining
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in Ossining

    Windrose On Hudson

    Windrose On Hudson

    1 Shady Lane Farm Road Ossining NY
    $172 nightly
    The price is $191 total per night from May 3 to May 4
    $191 total
    May 3 - May 4
    Total with taxes and fees
    8.4/10 Very Good! (120 reviews)
    Baymont by Wyndham White Plains - Elmsford

    Baymont by Wyndham White Plains - Elmsford

    540 Saw Mill River Rd Elmsford NY
    $123 nightly
    The price is $141 total per night from Apr 12 to Apr 13
    $141 total
    Apr 12 - Apr 13
    Total with taxes and fees
    8.2/10 Very Good! (1,623 reviews)
    LIV Hotel Bronx - Newly Built

    LIV Hotel Bronx - Newly Built

    3530 Webster Ave Bronx NY
    $134 nightly
    The price is $157 total per night from Apr 5 to Apr 6
    $157 total
    Apr 5 - Apr 6
    Total with taxes and fees
    8.2/10 Very Good! (434 reviews)

Ossining Guest Houses essential information

Accommodation
6 Guest Houses
Lowest Price
$141
Highest Price
$396
Popular accommodation
The Cottage by the Lake: Hudson Valley Indulgence/1 hr. from NYC/welcome pets!., Upscale 3BR NY Home with Free Parking, Peaceful Light-Filled Guesthouse 1 Hour From NYC, Upscale Modern Luxury 3BR Home , Luxury 3BR NY Home with Free Parking, Mid Century Modern ZEN House with Pool. 50 min from New York City, Ultra-Modern Luxe Sleek & Stunning Stay, Beautiful Stamford Loft! Near Downtown+Parking+45min to NYC, Prime Luxury with Balcony Wood Fireplace

More to Explore