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Top Holiday Rentals in Ossining

Beach
Spacious 3BR Private Home * Direct Water View
10.0 out of 10, Exceptional, (12)
"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
Exterior
The Subterranean Haven
10.0 out of 10, Exceptional, (1)
"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 £204
includes taxes & fees
8 May - 9 May
The Subterranean Haven
Terrace/patio
Lower Lvl Private 2BR/1BA Family/Pet Friendly
10.0 out of 10, Exceptional, (102)
"Beautiful, ultra comfy and clean space, great beds, amazing gym and home theatre, easy check-in and excellent, rapid responses from host. Wish I could have stayed longer."
Lower Lvl Private 2BR/1BA Family/Pet Friendly
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Fridge, microwave, oven, stovetop
Bright & Spacious Exec or Relo Home with 5BR & 2FB: Ideal for Extended Stays
10.0 out of 10, Exceptional, (6)
"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
Fridge, microwave, oven, stovetop
Lovely 2 Bedrooms Short term Rental Unit on a 2nd Floor
10.0 out of 10, Exceptional, (1)
"The owner is a verry nice person!!"
Lovely 2 Bedrooms Short term Rental Unit on a 2nd Floor
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)
"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 £739
includes taxes & fees
5 May - 6 May
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
View from property
Serenity Awaits at this Cozy Lakeside Bungalow
10.0 out of 10, Exceptional, (15)
"We so enjoyed our stay! The house was perfect for our family, conveniently located close to extended family and with the most beautiful view. The house had everything we needed and provided the perfect home base for spring break in our hometown. We even got to experience an earth quake ;) thank you!!"
Serenity Awaits at this Cozy Lakeside Bungalow
1 bedroom, WiFi, bed sheets
Charming Private Oasis in Old Greenwich – A Commuter's Dream!
10.0 out of 10, Exceptional, (1)
"the owners were on property and very accommodating, the unit was pristine with lots of little extras. would definitely stay there again. "
Charming Private Oasis in Old Greenwich – A Commuter's Dream!
Balcony
GORGEOUS WATER FRONT HOUSE / HUGE GARDEN & SEA ACCESS
10.0 out of 10, Exceptional, (9)
"Our family gathered for a dinner with 22 people on the patio and the setting and house made that possible and it was lovely. 30 family members came to practice a dance on the back lawn and we had space in the house for them to relax and visit. Our family of 10 was very comfortable and found the accommodations tasteful and renovations were lovely! I would give a 5+ rating and thanks to Alex, who was so helpful before we arrived, with questions about the house."
GORGEOUS WATER FRONT HOUSE / HUGE GARDEN & SEA ACCESS
Fridge, microwave, oven, stovetop
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (61)
"The property and house were beautiful, out of the way but beautiful. The fire pit, sunroom, and porch were amazing. It was great for decompressing after a West Point graduation. Thank you for sharing your little piece of heaven."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Exterior
COZY PRIVATE STUDIO w/ Free Off-Street Parking & Washer/Dryer
10.0 out of 10, Exceptional, (2)
"I came in town for an event I was doing and this property is always my first look. The location is Great to get on and off the highway/parkway pretty easily and it’s plenty to do near by. I’ll be back!!!"
COZY PRIVATE STUDIO w/ Free Off-Street Parking & Washer/Dryer
Beach nearby, sun-loungers, beach towels
NAUTICAL FAIRYTALE BEACH HOUSE / ACROSS THE ROAD FROM THE BEACH,45 MIN TO NYC
10.0 out of 10, Exceptional, (11)
"Enjoyed the house and the location! Would stay again!"
NAUTICAL FAIRYTALE BEACH HOUSE / ACROSS THE ROAD FROM THE BEACH,45 MIN TO NYC
Fridge, microwave, stovetop, coffee/tea maker
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
10.0 out of 10, Exceptional, (3)
"We went to a show at the Capital Theater and this place was very convenient. Had a nice dinner in walking distance as well. The building is old and kind of gross, but the apartment itself was very nice, modern, and clean."
The price is £221
includes taxes & fees
31 May - 1 Jun
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
Beach
The Safe House - High Tech Apt #2 - 3 Beds
10.0 out of 10, Exceptional, (29)
"Since it was first time with VRBO, I was a little nervous about the whole process going into it. Rob was great to answer questions and deal with both myself and my granddaughter.It was an ideal location for visiting the Hudson River Valley and along the coast to Newport. We flew into White Plains and it is just a 20 minute ride away. The apartment was clean and convenient. We only ate 3 meals in 5 days away from there. The beds were comfortable and the shower was very nice. I liked the shower...
The price is £235
includes taxes & fees
30 May - 31 May
The Safe House - High Tech Apt #2 - 3 Beds
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (96)
"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 £219
includes taxes & fees
6 May - 7 May
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
1 bedroom, desk, iron/ironing board, travel cot
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (35)
"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."
The price is £212
includes taxes & fees
6 May - 7 May
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Exterior
Waterfront Retreat Center for Health & Wellness
9.6 out of 10, Exceptional, (49)
"Beautiful location and old, well-maintained house. Really perfect for our family group of 17"
Waterfront Retreat Center for Health & Wellness
Outdoor dining
Country Carriage House ONLY 15 MIN TO NYC Great for Families, Couples, Reunions
9.6 out of 10, Exceptional, (44)
"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...
The price is £770
includes taxes & fees
8 May - 9 May
Country Carriage House ONLY 15 MIN TO NYC Great for Families, Couples, Reunions
Property grounds
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, (34)
"Comfy place and great communication. Would stay again!"
The price is £280
includes taxes & fees
6 May - 7 May
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
Smart TV
Stylish 3-bedroom 3rd fl Apt in Mount Vernon, NY
9.4 out of 10, Exceptional, (9)
"The apartment was exactly as stated and shown in the photos"
Stylish 3-bedroom 3rd fl Apt in Mount Vernon, NY
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.

Ossining Holiday Rental Travel Info

Other types of properties in Ossining you may be interested in

Front of property
Amsterdam Hotel
2.0 star property
8.4 out of 10, Very good, (1499)
"The stay was very enjoyable and located in a very conscientious area."
The price is £85
includes taxes & fees
9 May - 10 May
Amsterdam Hotel
Desk, laptop workspace, blackout curtains, iron/ironing board
Baymont by Wyndham White Plains - Elmsford
2.5 star property
8.2 out of 10, Very good, (1005)
"Great experience. Very clean and staff was friendly. "
The price is £113
includes taxes & fees
27 May - 28 May
Baymont by Wyndham White Plains - Elmsford
Interior
Royal Regency Hotel
3.5 star property
8.0 out of 10, Very good, (1423)
"The staff is very nice, especially Leslie. She is very helpful And respectful"
The price is £153
includes taxes & fees
12 May - 13 May
Royal Regency 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.

Everything you need to know about Ossining holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Ossining holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ossining holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Ossining holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ossining. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Ossining holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Ossining holiday rentals we have selected for you start as low as £204 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Ossining rentals

At Expedia, we put the best Ossining holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Ossining rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ossining holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ossining. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.

What are some of the best holiday rentals that Ossining has to offer?

Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits: This holiday home rental outside of Ossining is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Ossining?

With 8 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 Nelson Park and Louis Engel Waterfront Park 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.

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