Holiday rentals in Ossining

4.85 out of 5 average rating, 133 reviews

Home in Baldwin

Clarissa's Paradise

JamalRating, 5 stars2 months ago

First of all I would like to thank Carmen for letting me stay at her beautiful home. I enjoyed the time I spent at the air bnb even though it was a very busy weekend for me. Carmen home was clean and comfortable, also a very convenient location close to so many places. The home is also pretty spacious I was able to have a nice family dinner and gathering there. I would definitely recommend staying at this beautiful air bnb, Carmen was a great host Thankyou again.

5 out of 5 average rating, 43 reviews

Home in Ocean Beach

Sunny Spacious Pet Friendly Steps from the Beach

LoriRating, 5 stars6 months ago

Excellent stay! Hosts were responsive and very helpful. The house is absolutely beautiful, the pictures do not do it justice. The location is perfect and we had a wonderful time. The house was very clean and had beautiful decor. Highly recommend! Five stars one of my favorite and I will definitely be back. Thank you to Susan and Zoe for a wonderful stay.

4.95 out of 5 average rating, 355 reviews

Home in Kerhonkson

Beautiful Salt Water Pool & Fully Fenced 10 Acres

EppiRating, 5 stars5 days ago

FENCED. YARD!! Apart from the clean, spacious, well appointed home, the yard was the best part. And it wasn’t just boring and flat and grassy-think boulders for climbing and jumping, hills for racing, “secret passageways” for exploring. Just be prepared to look for ticks. Clearly an excellent choice for families with children, and our dog loved it most. The home has lots of character, good books to read, games for passing time. While venturing out for hikes, we enjoyed the views along the windy roads with charming homes and mountain scenery. The kitchen had so many pots and pans and plenty of dishes. Lillian was always responsive and quick. Good choice for a peaceful getaway.

Cottage in Greenwood Lake

4.93 out of 5 average rating, 87 reviews

Cottage with Picturesque Views

CalaRating, 5 stars2 months ago

This place is literally a piece of heaven! During our stay, we had a full frontal of the frozen lake, it was pure magic! Waking up to the beautiful view of the lake was magic. If you are trying to disconnect, relax, reconnect with your loved one, this is your spot! The details in this rental were to die for! From the beautiful kitchen, to the rooms, there is not a single spot in this rental that was overlooked by design!! There is also ample space outside to hang out and grill! It was a beautiful and relaxing winter stay, the host was extremely responsive, even went out his way to grab allergy medicine for me through one of the snowy days.. thank you so much for your kindness! This place is absolutely heaven! I am definitely coming back!

4.99 out of 5 average rating, 174 reviews

Flat in Long Beach

Incredible Long Beach Private Rental

AllanRating, 5 stars4 months ago

Absolutely superb hosts and such a great location. Steven couldn’t have been a better host, our kids and us loved his place and would highly recommend. Thoughtful touches everywhere and very clean. Hope we can stay again sometime.

4.92 out of 5 average rating, 140 reviews

Home in Hopatcong

Lakefront Hopatcong w/dock kayaks fishing near NYC

AmandaRating, 5 stars2 days ago

Had an amazing stay at this beautiful property. It was spacious, clean, and had everything we needed. The host was responsive and super helpful with everything. The views and location were truly incredible. I recommend this house to anyone who is looking to stay in this area.

5 out of 5 average rating, 211 reviews

Cabin in Kingston

Lakeside Cottage: Boulder's Bluff

AlexRating, 5 stars5 months ago

We loved our stay at Ed's cabin. it is a real gem and perfect for a long weekend away. we loved the fireplace, the rocking chairs, the windows with views out onto the lake that make you feel like you're right over the lake and in the trees. there were nice restaurants and hikes in the area, but we were perfectly content watching the lake and reading from the cabin. Ed was perfectly accommodating and extremely generous with his space, couldn't recommend more highly.

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Popular amenities for Ossining holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Ossining's top sights

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

Baked by Susan9 locals recommend

Other great holiday rentals in Ossining

Flat in Downtown Stamford

4.83 out of 5 average rating, 6 reviews

Sunny 1BR Apartment

JoanRating, 5 stars3 months ago

Clean , modern apt. Very easy to navigate with the technology. Staff very friendly and helpful. A bit noisy on street outside with traffic. Will definitely rent again with URBY, but request a courtyard side unit

4.97 out of 5 average rating, 181 reviews

Home in Millerton

Vacation Home In Millerton

SarahRating, 5 stars1 week ago

We had a wonderful week at Corina's house while out for a family event! The house was spotless and the kitchen was stocked with everything we could need. The outside space was just as amazing. We had a great campfire one night, enjoyed using the grill, and our dog loved being able to run around the large yard. I'm sure we'll be back next year!

5 out of 5 average rating, 14 reviews

Home in South Fallsburg

Renovated & Spacious 3BR Catskills Retreat

NicolaRating, 5 stars1 month ago

Alan was a pleasure to work with. He promptly answers all my messages. We worked with him for our company stays. we stayed well over a month in 2 of his home. Check out all his homes for rent.

Apartment in Vernon Township

4.96 out of 5 average rating, 74 reviews

Peaceful Mountain Retreat

JulieRating, 5 stars1 week ago

Great condo for a family of five. Plenty of space and everything was clean and inviting. our kids especially loved the loft stocked with games and toys.

Apartment in Vernon Township

4.73 out of 5 average rating, 111 reviews

200 yds Minerals - great for hotel weddings

SaraRating, 5 stars5 months ago

We had a great time! The unit is an easy walk to Minerals, and the layout was perfect for our needs. Joann was a fantastic host and we can’t wait to stay again!

4.82 out of 5 average rating, 96 reviews

Home in Cornwall

State Forest Getaway

GideonRating, 5 stars1 week ago

Elena's house turned out to be a great vacation spot for us. It was conveniently located, very well maintained and guest friendly. Though rustic on the outside, the interior was completely redone, offering all modern amenities you might want. Kitchen was better equipped than most Airbnb's we've stayed at and was fun for us to cook in Without getting into much detail I'll just say that should we be in the area again we'll definitely return to this Airbnb and always recommend it to others

Cottage in Greenwood Lake

4.96 out of 5 average rating, 48 reviews

5 bedroom 7 beds Cottage Sauna, Hike, Winery & Ski

JasonRating, 5 stars1 week ago

We had a great time at Carmine's place, highly recommend.