Shrub Oak Holiday Rentals

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Holiday Rentals in Shrub Oak

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 NZ$433
per night
27 May - 28 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."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Property grounds
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
10.0 out of 10, Exceptional, (35)
"This sweet little apartment was perfect for my solo stay. Comfortable, quiet, and very easy to get to. Lovely view from the deck. It had a feeling of security and privacy. Vicky was quick with answering my emails."
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
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Property grounds
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, (35)
"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
Exterior
Luxury home filled with books and art, with great access. Sleeps up to thirteen.
Luxury home filled with books and art, with great access. Sleeps up to thirteen.
Property grounds
Renovated 1850's Cottage on Storm King Mountain
9.8 out of 10, Exceptional, (8)
"It was a beautiful setting with water fall. The home itself needs a little work. It is well used and needs some TLC. Photos look much better then actual home."
Renovated 1850's Cottage on Storm King Mountain
View from property
Serenity Awaits at this Cozy Lakeside Bungalow
10.0 out of 10, Exceptional, (16)
"We really enjoyed staying at this cottage, much better than 2 rooms in a hotel. Very quiet, fully equipped kitchen.Easy to prepare meals when we wished. We visit the Ridgefield area several times per year and will definitely consider staying here again."
Serenity Awaits at this Cozy Lakeside Bungalow
Exterior
Cabin in the heart of the Hudson Valley, Cabin 4
8.4 out of 10, Very good, (11)
"Everything was as it says it was. Place was spotless. In the evening and morning you didn’t hear any traffic noise at all. Was quiet and peaceful. Communication with the property owner was outstanding."
The price is NZ$268
per night
4 Jun - 5 Jun
Cabin in the heart of the Hudson Valley, Cabin 4
Fridge, microwave, stovetop, dishwasher
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
10.0 out of 10, Exceptional, (21)
"This is an attractive, well-laid out house with an extremely accommodating owner. The home is pretty small—great for two or three with very little play area inside for kids—but there are several great outside areas on the deck, around the pool and stream. In terms of accessibility, three steps up to the doorway, a step down to the master bedroom and a step up to the ensuite master bath."
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Exterior
Cabin in the heart of the Hudson Valley, Cabin 2
9.4 out of 10, Exceptional, (3)
"Great tiny house for a stay upstate. Check in was easy and the place is clean!"
The price is NZ$268
per night
4 Jun - 5 Jun
Cabin in the heart of the Hudson Valley, Cabin 2
Property grounds
Lakefront New York Abode w/ Deck, Grill & Fire Pit
10.0 out of 10, Exceptional, (3)
"Clean, spacious, and many activities in a nice quiet town. The house comfortably fit our 10 people."
Lakefront New York Abode w/ Deck, Grill & Fire Pit
Property grounds
Spectacular Log Home Estate North Wing Apt
10.0 out of 10, Exceptional, (25)
"All as represented. Had everything we needed for a lovely home away from home!"
Spectacular Log Home Estate North Wing Apt
Dining
@iHeartNYState 4BR. Hot Tub Jacuzzi Fireplace
7.0 out of 10, Good, (4)
"Oven and stove top very dirty , SPA pool water not clean,no washer and dryer"
The price is NZ$965
per night
28 May - 29 May
@iHeartNYState 4BR. Hot Tub Jacuzzi Fireplace
Smart TV, books
Brand new private Studio in the heart of Tarrytown
10.0 out of 10, Exceptional, (4)
"It's very obvious that a lot of thought and care has gone into the creation of this lovely studio apartment. My husband and I stayed for two weeks while our home in a nearby town was undergoing renovations. We were very comfortable here and made welcome by the hosts, who were very accommodating and responsive to our inquiries and needs, both preceding and during our stay. The kitchen is very well-equipped with all manner of amenities, and we very easily cooked almost all our meals in the...
The price is NZ$531
per night
27 May - 28 May
Brand new private Studio in the heart of Tarrytown
Exterior
Stay on Main St! ~Walk to EVERYTHING West Point! Mountain Views/private parking
9.2 out of 10, Wonderful, (13)
"Our family of 4 stayed here for a couple nights while visiting family. Super clean, well stocked, easy apartment! The owner was incredibly helpful and we couldn’t have asked for more! Looking forward to coming back!"
Stay on Main St! ~Walk to EVERYTHING West Point! Mountain Views/private parking
Fridge, microwave, oven, stovetop
Cabin in the Heart of the Hudson Valley, Cabin 1
10.0 out of 10, Exceptional, (11)
"My husband and I didn’t think there were any more old-fashioned “tourist cabins” left along America’s secondary highways. They were ubiquitous in the 1940’s and 50’s. We were happy to find this immaculate, comfortable cabin enclave near the Beacon-Newburgh Bridge in Orange County and enjoyed our short stay. The family who started the business - in the 1920’s! - is featured along with framed archival postcards on the walls, reminding us that this business is a rare survivor of the kinds of...
The price is NZ$362
per night
27 May - 28 May
Cabin in the Heart of the Hudson Valley, Cabin 1
Property grounds
Stay in the HEART of West Point~Walk 2 mins to academy!
9.8 out of 10, Exceptional, (23)
"Great location close to West Point. Next to bar which can be a bit noisy. Step stairs so not for the eldery or physically appeared. Resturants are close and Ice Cream and bakery near by."
Stay in the HEART of West Point~Walk 2 mins to academy!
Outdoor pool
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
10.0 out of 10, Exceptional, (17)
"House is very cute. The scenery in early spring was amazing. Very quiet neighborhood. Conveniently located. Very clean. Beds were very comfortable. Had everything we needed."
The price is NZ$484
per night
28 May - 29 May
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
Fridge, microwave, oven, stovetop
Cozy country efficiency in the Hudson Valley
9.8 out of 10, Exceptional, (39)
"Quiet, clean and very comfortable. Beautiful property located just minutes from town. Will definitely stay here again."
The price is NZ$353
per night
4 Jun - 5 Jun
Cozy country efficiency in the Hudson Valley
Outdoor dining
Lakeview Estate - Chef's Kitchen - NYC Getaway
10.0 out of 10, Exceptional, (18)
"Beautiful, spacious property with all the amenities we needed and more. I would recommend and we will certainly return!"
The price is NZ$1,333
per night
27 May - 28 May
Lakeview Estate - Chef's Kitchen - NYC Getaway
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See all available properties in Shrub Oak
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.

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3.5 star property
9.2 out of 10, Wonderful, (53)
"Marriott Westchester is a lovely hotel. The rooms are excellent. The infinity shower, tea tree body wash, and the soft beds. I did not want to leave. The breakfast was included and it was delicious. A la carte menu for room service. Rice bowl, steak egg rolls. yum yum...... "
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16 Jun - 17 Jun
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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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Shrub Oak holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Shrub Oak. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Shrub Oak. Seeing all the best attractions is bound to make you fall in love with Shrub Oak. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Shrub Oak short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Shrub Oak?

Yes, there are holiday rentals close to the most popular sights in Shrub Oak, or you can select a more secluded option if you're looking for a relaxing stay.

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

Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits: This holiday home rental outside of Shrub Oak 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.

What can I see and do in Shrub Oak?

Explore the area and family-friendly sights such as SplashDown Beach, or get out into nature at a spot like Donald J. Trump State Park. Woodbury Common Premium Outlets and Jefferson Valley Mall are a couple of places you'll find in the wider area.

What’s a holiday rental in Shrub Oak like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Shrub Oak. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from public hotel lifts and busy front desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for family gatherings.

Recent reviews of Shrub Oak properties
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