Photo by Linda Zanetti

Search Guest Houses in Ossining

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 5 Guest Houses in Ossining with updated reviews, rates, and availability.

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

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

9.8 out of 10, Exceptional, (10)
"Our stay at the cottage was really great, Orestes is an amazing host. The cottage was cozy, clean, and quiet and very dog friendly. Highly recommended!"
The Cottage by the Lake: Hudson Valley Indulgence/1 hr. from NYC/welcome pets!.
Peaceful Light-Filled Guesthouse 1 Hour From NYC
Outdoor pool, a heated pool

Peaceful Light-Filled Guesthouse 1 Hour From NYC

10.0 out of 10, Exceptional, (6)
"We had an absolutely delightful stay at the charming sanctuary that is Sweetbriar guesthouse. The hosts have thought of everything to ensure guests are comfortable. The guesthouse is clean and organized and the views from the picture windows are gorgeous!"
Peaceful Light-Filled Guesthouse 1 Hour From NYC
Mid Century Modern ZEN House with Pool. 50 min from New York City
Interior

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

10.0 out of 10, Exceptional, (19)
"Incredible property, great location, and amazing host. We will definitely be coming back!!!"
The price is AED 1,671
AED 3,085 total
includes taxes & fees
16 Jun - 17 Jun
Mid Century Modern ZEN House with Pool. 50 min from New York City
The West Lane Inn - King Room
1 bedroom, iron/ironing board, internet, bed sheets

The West Lane Inn - King Room

10.0 out of 10, Exceptional, (1)
" the complimentary breakfast"
The price is AED 1,457
AED 1,667 total
includes taxes & fees
2 Jun - 3 Jun
The West Lane Inn - King Room
Beautiful Stamford Loft! Near Downtown+Parking+45min to NYC
2 bedrooms, iron/ironing board, free WiFi, bed sheets

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

9.6 out of 10, Exceptional, (15)
"Beautiful location. Clean, comfortable, private, excellent ammenities. The lite extras made it extra specisl."
Beautiful Stamford Loft! Near Downtown+Parking+45min to NYC
Ultra-Modern Luxe Sleek & Stunning Stay
Blackout drapes, iron/ironing board, free WiFi

Ultra-Modern Luxe Sleek & Stunning Stay

2.0 star property
The price is AED 2,204
AED 2,454 total
includes taxes & fees
2 Jun - 3 Jun
Ultra-Modern Luxe Sleek & Stunning Stay
Prime Luxury with Balcony Wood Fireplace
Living area

Prime Luxury with Balcony Wood Fireplace

2.0 star property
The price is AED 2,384
AED 2,667 total
includes taxes & fees
2 Jun - 3 Jun
Prime Luxury with Balcony Wood Fireplace
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free