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

Doodletown Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Doodletown vacation rentals

A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

1. Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.4 out of 10, Exceptional, (24 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
$285 nightly
The price is $290
Sep 27 - Sep 28
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

2. House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
9.8 out of 10, Exceptional, (12 reviews)
"We had a very comfortable stay. Nice quaint village. Area was quiet and easy to get to."
United States
Leann M.
$378 nightly
The price is $404
Sep 27 - Sep 28
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!
A house with a view of a bridge and mountains.

3. 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, (146 reviews)
"We had a great stay!!"
United States
Jasmine
$280 nightly
The price is $331
Sep 28 - Sep 29
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

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

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
9.0 out of 10, Wonderful, (4 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
$234 nightly
The price is $260
Oct 5 - Oct 6
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!
A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

5. Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.4 out of 10, Exceptional, (20 reviews)
"Great location! Easy checkin, checkout process. We would stay again"
United States
Morgan S.
$433 nightly
The price is $444
Sep 29 - Sep 30
Total with taxes and fees
Local Artist Inspired | Walk to WestPoint + King Bed
A hallway with a wooden door, a black table with a sign, and large green plants.

6. 3BR Near West Point | Coffee Bar | Sleeps 6

3BR Near West Point | Coffee Bar | Sleeps 6
Highland Falls
10.0 out of 10, Exceptional, (1 review)
"We had a great stay at Joseph’s home. The property was very clean, spacious, and well prepared for guests. My work team and I felt comfortable right away, and the house had everything we needed for both a productive and relaxing stay.Joseph was always kind, professional, and quick to respond, which made a big difference. I would recommend this property without hesitation."
United States
ROHID S.
$432 nightly
The price is $443
Oct 6 - Oct 7
Total with taxes and fees
3BR Near West Point | Coffee Bar | Sleeps 6
A bedroom with a bed, a ceiling fan, a nightstand, a window with curtains, and a wall with framed pictures.

7. Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.4 out of 10, Exceptional, (8 reviews)
"Great location and super host. "
United States
James U.
$447 nightly
The price is $459
Oct 6 - Oct 7
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !

8. Walk-to-Lake Cottage With Grill for Peaceful Fall Days

Walk-to-Lake Cottage With Grill for Peaceful Fall Days
Putnam Valley
9.8 out of 10, Exceptional, (25 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
$464 nightly
The price is $512
Sep 28 - Sep 29
Total with taxes and fees
Walk-to-Lake Cottage With Grill for Peaceful Fall Days
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

9. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (40 reviews)
"Our stay was very nice and described as listed! We recommend anyone who is interested to stay! "
United States
Aj L.
$367 nightly
The price is $420
Sep 30 - Oct 1
Total with taxes and fees
Contemporary Cozy Cottage
A neatly made bed with a black and white duvet, a wooden headboard, and a bedside table with a lamp. There are three framed artworks on the wall above the bed.

10. 'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Croton-on-Hudson
10.0 out of 10, Exceptional, (3 reviews)
"Great stay!"
United States
Ann S.
$276 nightly
The price is $316
Sep 27 - Sep 28
Total with taxes and fees
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
A modern kitchen with stainless steel appliances, wooden cabinets, and a contemporary light fixture.

11. 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.
$361 nightly
The price is $407
Oct 6 - Oct 7
Total with taxes and fees
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
A modern living room with a stone fireplace, a leather sofa, a yellow armchair, a flat-screen TV, and a bookshelf.

12. '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, (8 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.
$359 nightly
The price is $410
Sep 30 - Oct 1
Total with taxes and fees
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
A living room with a fireplace, a painting, shelves with decorative items, and a television.

13. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (49 reviews)
"We enjoyed our stay, property was as described. It's convenient to many of the Hudson Valley small towns, including West Point."
United States
Mike W.
$249 nightly
The price is $282
Sep 28 - Sep 29
Total with taxes and fees
Grant - A Tranquil One Bedroom Steps from River
A deck with Adirondack chairs, a fire pit, and a grill.

14. 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, (15 reviews)
"Everything you could ask for!!"
United States
Elisabeth
$351 nightly
The price is $415
Sep 27 - Sep 28
Total with taxes and fees
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
A room with a wooden floor, a white door with a number, and a window with blinds.

15. 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.
$403 nightly
The price is $466
Oct 6 - Oct 7
Total with taxes and fees
Lovely 3BR Home with parking-Walk to WP Gate!
A wooden coffee table with two decorative planters in a living room.

16. Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (26 reviews)
"Clean and modern with good amenities. Would stay here again. "
United States
Daniel C.
$395 nightly
The price is $447
Oct 6 - Oct 7
Total with taxes and fees
Walk to WP Gate + Free Parking!
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

17. Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (12 reviews)
"House was exactly as described. Would stay again."
United States
Beth M.
$430 nightly
The price is $484
Oct 6 - Oct 7
Total with taxes and fees
Fabulous 3bdrm Home w/parking!
A stone staircase leading to a house with a stone wall and a metal gate.

18. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
Croton-on-Hudson
9.6 out of 10, Exceptional, (24 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
$372 nightly
The price is $425
Sep 26 - Sep 27
Total with taxes and fees
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
A wooden cabin with large windows, a wooden bench, and a view of the forest.

19. Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
$224 nightly
The price is $227
Sep 28 - Sep 29
Total with taxes and fees
Harriman Outdoor Center - Mountain Laurel Cabin
A dining table set with plates, cutlery, and glasses, with a bowl of fruit and a wine glass in the background.

20. Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (93 reviews)
"Our stay was just perfect! We chose the location based on being close-ish to family in northern Westchester and friends in the city and it was perfect. Maria is an excellent host and super attentive and helpful when needed. The apartment was the perfect size for our family and super cozy after a long day. We'd definitely stay again!"
United States
Aimee S.
$328 nightly
The price is $375
Oct 4 - Oct 5
Total with taxes and fees
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
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

Sheraton Tarrytown Hotel

Sheraton Tarrytown Hotel

10/10 Excellent
"The hospitality of the staff and great convenient location, close to shops, supermarkets, restaurants, etc."
Myrna 3-night trip
Posted 3 hours ago
Sheraton Tarrytown Hotel

Find out more about Doodletown

Everything you need to know about Doodletown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Doodletown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Doodletown vacation 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 low season months. For more hustle and bustle, you may prefer to visit Doodletown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $82 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Doodletown rentals

At Expedia, we put the best Doodletown vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Doodletown?

Yes, you can find vacation rentals near popular sights in Doodletown, or you can go with a secluded option if you're looking for relaxation. Doodletown is known for its parks.

What are some of the best vacation home rentals in Doodletown?

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: This vacation home rental outside of Doodletown is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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. Bear Mountain State Park and Woodbury Common Premium Outlets are a couple of places you'll find in the larger area.

What are vacation rentals like in Doodletown?

Vacation rentals are private properties you can book for a short or long stay in Doodletown. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for a family trip or a small group gathering.