A calm lake with a rocky shoreline, surrounded by dense forest with autumn foliage.

Doodletown Holiday Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Doodletown holiday rentals

Property grounds

1. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (141 reviews)
"We had a great stay!!"
United States
Jasmine
The price is HK$1,553
HK$2,558 total
includes taxes & fees
11 Aug - 12 Aug
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
TV

2. Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is HK$898
HK$1,690 total
includes taxes & fees
11 Aug - 12 Aug
Cozy 1-bedroom retreat minutes from West Point!
Coffee/tea maker, fridge, microwave, oven

3. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (35 reviews)
"Our stay was very nice and described as listed! We recommend anyone who is interested to stay! "
United States
Aj L.
The price is HK$1,765
HK$3,293 total
includes taxes & fees
10 Aug - 11 Aug
Contemporary Cozy Cottage
TV

4. Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (24 reviews)
"Would definitely stay here again! It was a great experience!"
United States
Jodi P.
The price is HK$1,787
HK$2,937 total
includes taxes & fees
11 Aug - 12 Aug
Walk to WP Gate + Free Parking!
Exterior detail

5. Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (11 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is HK$1,742
HK$3,059 total
includes taxes & fees
10 Aug - 11 Aug
Fabulous 3bdrm Home w/parking!
Exterior detail

6. Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Putnam Valley
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is HK$1,700
HK$4,320 total
includes taxes & fees
11 Aug - 12 Aug
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Interior

7. Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
The price is HK$1,936
HK$3,405 total
includes taxes & fees
11 Aug - 12 Aug
Lovely 3BR Home with parking-Walk to WP Gate!
Coffee/tea maker, fridge, microwave, oven

8. Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Location was perfect for West Point visit. The space was clean and recently updated, the beds very comfortable, and perfect layout and spacious for 3-4 people. The host was welcoming and responsive."
United States
Maria L.
The price is HK$2,026
HK$3,246 total
includes taxes & fees
9 Sept - 10 Sept
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Smart TV

9. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (47 reviews)
"This apartment was perfect for what we needed! Beautifully renovated, comfortable bed, and very close to Beacon! "
United States
Abby W.
The price is HK$1,059
HK$2,316 total
includes taxes & fees
10 Aug - 11 Aug
Grant - A Tranquil One Bedroom Steps from River
Interior

10. Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
The price is HK$1,538
HK$1,774 total
includes taxes & fees
7 Sept - 8 Sept
Harriman Outdoor Center - Mountain Laurel Cabin
Outdoor spa tub

11. 3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Cornwall
10.0 out of 10, Exceptional, (11 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is HK$1,820
HK$3,521 total
includes taxes & fees
8 Sept - 9 Sept
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
TV, fireplace, DVD player

12. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
Monroe
10.0 out of 10, Exceptional, (8 reviews)
"We loved our stay! It was the perfect size for our small family. The property was extremely well maintained and there was a lot to do near by. We would definitely book here again!"
United States
Marc
The price is HK$1,294
HK$4,127 total
includes taxes & fees
11 Aug - 12 Aug
Hudson Valley Retreat w/ Pool Near Greenwood Lake
1 bedroom, free WiFi

13. 2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Fishkill
9.8 out of 10, Exceptional, (20 reviews)
"Schöne Zimmer, Internet war kostenpflichtig, funktionierte aber nicht. Das Personal war jedoch nett."
Germany
Anonymous traveller
The price is HK$639
HK$723 total
includes taxes & fees
1 Sept - 2 Sept
2 Queen Beds | Non-Smoking, Kitchen
Exterior

14. 2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Fishkill
9.4 out of 10, Exceptional, (20 reviews)
"great place tostay"
United States
Anonymous traveller
The price is HK$639
HK$739 total
includes taxes & fees
31 Aug - 1 Sept
2 Full Beds | Non-Smoking, Kitchen
Exterior

15. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.2 out of 10, Wonderful, (12 reviews)
"The chapel was just as it was pictured. It has been beautifully restored. It was a very unique experience."
United States
Stella
The price is HK$824
HK$1,553 total
includes taxes & fees
10 Aug - 11 Aug
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Interior

16. Luxury 10BR w/Pool, Hot Tub & Pizza Oven

Luxury 10BR w/Pool, Hot Tub & Pizza Oven
Stony Point
The price is HK$24,711
HK$35,485 total
includes taxes & fees
12 Aug - 13 Aug
Luxury 10BR w/Pool, Hot Tub & Pizza Oven
Smart TV, video games, DVD player, books

17. 'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Croton-on-Hudson
10.0 out of 10, Exceptional, (7 reviews)
"We had an extended stay at Croton Quarters, it was great! The hosts truly are pet-friendly, the location is ideal, and the property comfortable for a longer term visit. "
United States
Mateo A.
The price is HK$2,062
HK$3,704 total
includes taxes & fees
11 Aug - 12 Aug
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Outdoor dining

18. Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms

Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Lake Peekskill
The price is HK$1,942
HK$4,204 total
includes taxes & fees
19 Aug - 20 Aug
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Interior

19. Harriman Outdoor Center - Cranberry Cabin

Harriman Outdoor Center - Cranberry Cabin
Haverstraw
The price is HK$1,914
HK$2,220 total
includes taxes & fees
23 Aug - 24 Aug
Harriman Outdoor Center - Cranberry Cabin
Terrace/patio

20. River Views & Deck | River Suite on Washington

River Views & Deck | River Suite on Washington
Newburgh
The price is HK$1,283
HK$3,548 total
includes taxes & fees
1 Sept - 2 Sept
River Views & Deck | River Suite on Washington
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

Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

8/10 Good
"It was a fine motel and a good location"
Matthew 1-night trip
Posted 6 hours ago
Hampton Inn White Plains/Tarrytown

Find out more about Doodletown

Search for holiday rentals in Doodletown on Expedia! You can easily find your home rentals, villas, holiday apartments in Doodletown using one of the methods below:

  • View our selection of featured holiday rentals in Doodletown
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  • Enter your travel dates to view the best deals on holiday rentals in Doodletown while they last

Look no further and take a look at our great range of rental properties in Doodletown!

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?

Cozy Cabin with Sauna & Firepit!: This holiday home rental outside of Doodletown offers a fireplace, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, in addition to a kitchen with a stovetop and a microwave.

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 Blue Mountain Reservation. Bear Mountain State Park and Woodbury Common Premium Outlets 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.