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Top Holiday Rentals in Ossining

Stamford Suites
Exterior
Stamford Suites
2.5 star property
6.8 out of 10, 715 reviews
"Not a bad stay overall. Nice location opposite the police headquarters and courthouse. Friendly staff. Brianna the hostess was very nice. The suite was very large. The only thing is that the carpet needs changing. The continental breakfast wasn't appetizing but there's food all around the area. But all in all it was an enjoyable stay."
The price is 1 847 kr
includes taxes & fees
20 Jun - 21 Jun
Stamford Suites
Waterfront Retreat Center for Health & Wellness
Exterior
Waterfront Retreat Center for Health & Wellness
9.6 out of 10, Exceptional, 50 reviews
"We stayed at the New Dawn for a Memorial Service. The setting on the water was so peaceful and private, yet easy access for those of us traveling by public transportation from Manhattan and La Guardia airport. We had chairs lined up facing the water for a Celebration of Life Ceremony. The whole downstairs layout was just wonderful with indoor and outdoor areas for people to gather, sharing memories and grief. Food platters from Costco were easily arranged and the weather was perfect. It was so...
Waterfront Retreat Center for Health & Wellness
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, 96 reviews
"Comfortable apartment with a phenomenal view! The space could use a deep clean and some decluttering, but that view!!! Did I mention that the view was A-mazing?!?"
The price is 3 140 kr
includes taxes & fees
11 Jun - 12 Jun
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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Spacious 3BR Private Home * Direct Water View
Beach
Spacious 3BR Private Home * Direct Water View
10.0 out of 10, Exceptional, 12 reviews
"This is a very nice accommodation. Situated by the beautiful park and water. You can find shopping facilities within walking distance. The landlord was very reliable in making sure that our stay was very nice."
Spacious 3BR Private Home * Direct Water View
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
1 bedroom, desk, iron/ironing board, travel cot
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, 35 reviews
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Welcome to Villa Seabird, Luxury Escape on Long Island Sound
Interior
Welcome to Villa Seabird, Luxury Escape on Long Island Sound
10.0 out of 10, Exceptional, 3 reviews
"7 bedrooms, most with water views, were perfect for my siblings and me, our spouses and children, and our mother to spend a glorious weekend together! We hosted an unforgettable 80th bday party for our Mom with all our extended family and friends. Wow! The house is gorgeous! It is perfect for a event. The grand hall, the ability to open up the rooms to the backyard, and the VIEW, truly set the stage for a beautiful evening. The home is truly remarkable! My mom was overwhelmed and so thankful...
Welcome to Villa Seabird, Luxury Escape on Long Island Sound
The Subterranean Haven
Exterior
The Subterranean Haven
10.0 out of 10, Exceptional, 1 review
"The neighborhood is really nice and clean with a good variety of stores nearby. We found the subterranean haven to be a great location for unwinding and having small events. The George's are incredibly understanding, patient and flexible. We'd definitely recommend this host to anyone."
The price is 2 241 kr
includes taxes & fees
3 Jun - 4 Jun
The Subterranean Haven
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Terrace/patio
Lower Lvl Private 2BR/1BA Family/Pet Friendly
10.0 out of 10, Exceptional, 104 reviews
"Neighborhood great for walking dogs. Would have loved a sink besides bathroom. Overall great value."
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Country Carriage House ONLY 15 MIN TO NYC Great for Families, Couples, Reunions
Outdoor dining
Country Carriage House ONLY 15 MIN TO NYC Great for Families, Couples, Reunions
9.6 out of 10, Exceptional, 44 reviews
"We had a great time celebrating Thanksgiving with our adult children in the Carriage house. The location was great - beautiful neighborhood in small town with easy access to all the things we did in NYC. Lisa helped us when we didn’t have all the right kitchen tools for our meal and worked with us on our schedule for her dog business. It was a real pleasure spending our special family time in this home - comfortable and so many things to do (we played ping pong and pool). Thank you Lisa for a...
Country Carriage House ONLY 15 MIN TO NYC Great for Families, Couples, Reunions
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
Property grounds
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, 35 reviews
"Three nights here as we toured the area. Check in was easy. We were able to access the VRBO app 30 minutes prior to our arrival. By the time we reached the driveway, Ruben had sent the access code.The road to the house is gravel and only wide enough for one car. We were glad we had arrived during the day.The house has an antique store vibe. Lots of books for a rainy day activity. FYI, the photos on the listing are a bit different from what we saw in the rooms. The dining table is larger with...
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
Bright & Spacious Exec or Relo Home with 5BR & 2FB: Ideal for Extended Stays
Fridge, microwave, oven, stovetop
Bright & Spacious Exec or Relo Home with 5BR & 2FB: Ideal for Extended Stays
10.0 out of 10, Exceptional, 6 reviews
"The house is as beautiful as all the pictures, if not better. It was spotless and absolutely beautiful! And Leen was an amazing host. She walked you through everything and even though she has a 6 hour time difference from the home she is readily available to help with any questions and also has people close by if there is a need (which of course there wasn’t!). My family and I had an amazing time while there! Definitely stay here! You won’t be disappointed!!!"
Bright & Spacious Exec or Relo Home with 5BR & 2FB: Ideal for Extended Stays
Global Luxury Suites White Plains
Reception
Global Luxury Suites White Plains
3.5 star property
7.6 out of 10, Good, 17 reviews
"If this option is available in the city you are traveling to, take it! You get a home-y, modern APARTMENT with space, rather than a tiny, old hotel room. I always search Global Luxury Suites before searching anything else."
Global Luxury Suites White Plains
Lovely 2 Bedrooms Short term Rental Unit on a 2nd Floor
Fridge, microwave, oven, stovetop
Lovely 2 Bedrooms Short term Rental Unit on a 2nd Floor
10.0 out of 10, Exceptional, 1 review
"The owner is a verry nice person!!"
Lovely 2 Bedrooms Short term Rental Unit on a 2nd Floor
Cozy Spacious Guest Suite 15 minutes from NYC
Interior
Cozy Spacious Guest Suite 15 minutes from NYC
6.8 out of 10, 3 reviews
"Quiet neighborhood ample room to relax."
The price is 1 794 kr
includes taxes & fees
5 Jun - 6 Jun
Cozy Spacious Guest Suite 15 minutes from NYC
Stylish 3-bedroom 3rd fl Apt in Mount Vernon, NY
Smart TV
Stylish 3-bedroom 3rd fl Apt in Mount Vernon, NY
9.4 out of 10, Exceptional, 9 reviews
"The apartment was exactly as stated and shown in the photos"
Stylish 3-bedroom 3rd fl Apt in Mount Vernon, NY
Mini Garden-Apartment near New York City
Interior
Mini Garden-Apartment near New York City
Mini Garden-Apartment near New York City
Serenity Awaits at this Cozy Lakeside Bungalow
View from property
Serenity Awaits at this Cozy Lakeside Bungalow
10.0 out of 10, Exceptional, 17 reviews
"My husband, dog and I had a great Memorial Day weekend at this lakeside property. The house is a short drive away from NYC and is situated perfectly between the quaint towns of Ridgefield and Katonah. We had a good time enjoying the lake and nearby hikes."
Serenity Awaits at this Cozy Lakeside Bungalow
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
3 bedrooms, iron/ironing board, WiFi, bed sheets
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
10.0 out of 10, Exceptional, 1 review
"We went to the area to celebrate my husbands 30th birthday with some friends and absolutely loved the home. It was brand new and decorated immaculately. It comfortably fit our group and we thoroughly enjoyed our time there. The hosts were super accommodating and quick to respond. Would absolutely reccomend and go again!"
The price is 9 876 kr
includes taxes & fees
8 Jun - 9 Jun
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
Fridge, microwave, oven, stovetop
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
10.0 out of 10, Exceptional, 4 reviews
"We all slept well but beds do make lots of noise moving around on them. Bathrooms are clean and very nice."
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
Basement Apartment Close to Bus & Metro-North
Interior
Basement Apartment Close to Bus & Metro-North
The price is 1 635 kr
includes taxes & fees
5 Jun - 6 Jun
Basement Apartment Close to Bus & Metro-North
Don't see what you're looking for?
See all available properties in Ossining
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.

Other types of properties in Ossining you may be interested in

Armoni Inn & Suites
Restaurant
Armoni Inn & Suites
3.5 star property
6.2 out of 10, 1,177 reviews
"It is a nice area. I give 4 out of 5 for the cleanness."
The price is 942 kr
includes taxes & fees
23 Jun - 24 Jun
Armoni Inn & Suites
Royal Regency Hotel
Interior
Royal Regency Hotel
3.5 star property
8.0 out of 10, Very good, 1,499 reviews
"Great stay "
The price is 4 522 kr
includes taxes & fees
8 Jun - 9 Jun
Royal Regency Hotel
Amsterdam Hotel
Front of property
Amsterdam Hotel
2.0 star property
8.4 out of 10, Very good, 1,505 reviews
"Very comfortable stay with friendly and helpful staff."
The price is 1 223 kr
includes taxes & fees
2 Jun - 3 Jun
Amsterdam Hotel
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.

Frequently asked questions

Can I find a holiday rental in Ossining?

Yes, there are holiday rentals close to the most popular sights in Ossining, or you can select a more secluded option if you're looking for a relaxing stay. Ossining is known for its restaurants and parks. Make sure you have time to check out the golf courses and university setting during your trip.

How many holiday rentals will I find in Ossining?

With 7 Expedia holiday rentals, you're guaranteed to find just the right place for your Ossining stay.

What’s there to see and do in Ossining?

Cultural attractions include Sing Sing Prison Museum and Ossining Historical Society, whereas Louis Engel Waterfront Park and Teatown Lake Reservation are a couple of picturesque spots to enjoy the outdoors. Sing Sing Correctional Facility and Thomas J. Watson Research Center are other places to visit while you're in town.

What’s a holiday rental in Ossining like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Ossining. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for a family getaway.

Recent reviews of Ossining properties
Expedia verified reviews

Courtyard by Marriott Yonkers Westchester County

Courtyard by Marriott Yonkers Westchester County

5/5 Excellent
"Friendly staff comfortable bed "
A verified traveller stayed at Courtyard by Marriott Yonkers Westchester County
Posted 17 hours ago
Courtyard by Marriott Yonkers Westchester County