Doodletown Holiday Rentals

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Holiday Rentals in Doodletown

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (122)
"It has an incredible mountain and water view. "
The price is AU$468
includes taxes & fees
13 Oct - 14 Oct
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (90)
"My family and I loved this property! We enjoyed walking around the woods and exploring. The house was well equipped and was really charming. We also loved sightseeing around the near by towns. Definitely a place to come back to stay again. "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

9.6 out of 10, Exceptional, (10)
"Easy check in and check out! Has all the bare minimums and a nicely upgraded bathroom. Didn’t feel super clean (the bathroom) when we got there but kitchen was clean and they kindly stocked a few groceries. Could not get the water hot for a shower which was bummer. Nice enough depending on what you are looking for! We had some sensory needs and so this ended up not being the best fit but the location was great. Thanks for having us. "
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

9.6 out of 10, Exceptional, (39)
"Plenty of seating & comfortable beds were a plus! The theatre room was really fun for grandkids!"
The price is AU$505
includes taxes & fees
3 Nov - 4 Nov
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Chestnut on Willow Lake

9.4 out of 10, Exceptional, (3)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
The price is AU$888
includes taxes & fees
22 Oct - 23 Oct
Chestnut on Willow Lake

Piermont Oasis

10.0 out of 10, Exceptional, (4)
"Easy check in; quick access to NYC. "
The price is AU$316
includes taxes & fees
15 Oct - 16 Oct
Piermont Oasis

Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St.

9.0 out of 10, Wonderful, (6)
"Large comfortable home in great location with multiple views of the Hudson. Our family had a pleasant stay and would definitely return to Castle in the Sky."
Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St.

The Woodbury Cottage

9.0 out of 10, Wonderful, (26)
"A cozy place to stay. "
The Woodbury Cottage

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

8.8 out of 10, Excellent, (5)
"We booked the property because our family is growing too large for all of the children and grandchildren to spend the holidays together. The “holiday house” as our 4 year old coined it was the perfect place to spend Christmas and Hanukkah. Large yet cozy and very well appointed. All of our communication with proprietors was prompt and helpful, and they had the driveway salted and plowed within hours of the (very picturesque) snowfall the day before Christmas. I would happily book here again. "
The price is AU$2,165
includes taxes & fees
16 Oct - 17 Oct
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

10.0 out of 10, Exceptional, (23)
"Clean, comfortable, beautiful views, cute little town. Super accommodating host. Couldn’t have asked for more. "
The price is AU$760
includes taxes & fees
14 Oct - 15 Oct
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Rustic Cabin in Fishkill!

10.0 out of 10, Exceptional, (2)
"The place was very nice, we met the owner and he was also bery accommodating. This is definitely a family friendly spot. "
The price is AU$549
includes taxes & fees
1 Nov - 2 Nov
Rustic Cabin in Fishkill!

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (308)
"We had the most relaxing 3 night stay at Don's vacation home. It is spacious and comfortable. Orange Lake right out the back door was a beautiful backdrop all throughout the day. Don gave us great recommendations for local restaurants too.It was the perfect weekend."
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

A luxurious stay.

6.0 out of 10, (2)
"If you want to go to a diagusting neighborhood then this is your place. We felt so unsafe we didn’t even stay there. We got a hotel. It is that bad. As nice as the inside is, the outside and neighborhood will have you running. Music blasting stinks of weed homeless people all over. Do not book this place. The owner didn’t even refund us our cleaning fee. Trust me STAY AWAY."
The price is AU$450
includes taxes & fees
12 Oct - 13 Oct
A luxurious stay.

Large,Cozy,Bright Apartment, Business Themed.

9.0 out of 10, Wonderful, (14)
"Very cozy stay with responsive host"
The price is AU$1,046
includes taxes & fees
12 Oct - 13 Oct
Large,Cozy,Bright Apartment, Business Themed.

Walk to WP Gate + Free Parking!

9.8 out of 10, Exceptional, (18)
"Great property and the hosts were very communicative."
The price is AU$460
includes taxes & fees
27 Oct - 28 Oct
Walk to WP Gate + Free Parking!

Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck

10.0 out of 10, Exceptional, (2)
"From the moment we arrived, we knew we had picked a gem. The house is absolutely lovely—tastefully decorated, comfortable, and full of charm. Every room feels fresh and inviting, and it’s clear the owners take great pride in maintaining their space.Cleanliness was outstanding throughout. We were especially touched by how genuinely friendly and responsive the owner was. From our first inquiry to the check-out process, they were prompt, helpful, and always checked to make sure we were comfortable....
The price is AU$1,348
includes taxes & fees
15 Oct - 16 Oct
Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck

Luxury 10BR Escape w/ Pool, Hot Tub & Game Lounge

Luxury 10BR Escape w/ Pool, Hot Tub & Game Lounge

Ideal Location 1block to Main St. Restaurants , Bars,Hudson River, Bus/ Train

9.4 out of 10, Exceptional, (3)
"We only stayed a couple days, but the location is quaint and apartment newly refurnished. The owner was very helpful and great to work with. Highly recommend!"
Ideal Location 1block to Main St. Restaurants , Bars,Hudson River, Bus/ Train

The Perfect Essential Getaway!

9.6 out of 10, Exceptional, (5)
"Owner was very responsive and accommodating on the app when I had questions. Place was great."
The price is AU$1,973
includes taxes & fees
12 Oct - 13 Oct
The Perfect Essential Getaway!

Spectacular Mansion w/Pool&Tennis

10.0 out of 10, Exceptional, (13)
"House was perfect for a group of 16 people. Pool, tennis courts and lawn were incredible. Highly recommend and would return! "
Spectacular Mansion w/Pool&Tennis
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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Top Doodletown Hotel Reviews

Find out more about Doodletown

Find out more about Doodletown

Everything you need to know about Doodletown 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 Doodletown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, 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 Doodletown holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Doodletown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Doodletown. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Doodletown 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 Doodletown holiday rentals we have selected for you start as low as AU$316 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Doodletown rentals

At Expedia, we put the best Doodletown 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 Doodletown 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 Doodletown 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 Doodletown. 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

Are there holiday rentals in Doodletown?

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

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

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn. : This holiday home rental outside of Doodletown is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of garden in this rental home to help you unwind.

What can I see and do in Doodletown?

Explore the area and family-friendly sights such as Rockland Bakery, or get out into nature at a spot like Lake Tiorati Beach. Woodbury Common Premium Outlets and Bear Mountain State Park are a couple of places you'll find in the wider area.

What are holiday rentals like in Doodletown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Doodletown. Holiday rentals feature amenities like kitchens and laundry facilities so you'll feel right at home. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for family trips or small group gatherings.