Doodletown Vacation Rentals from $186: Search Short-Term Rentals

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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!

Highland Falls

Andrew L.

$294 nightly

Nov 10 - Nov 11

Total with taxes and fees

A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

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

Highland Falls

Morgan S.

$394 nightly

Nov 10 - Nov 11

Total with taxes and fees

A house with a view of a bridge and mountains.

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

Fort Montgomery

Jasmine

$257 nightly

Nov 16 - Nov 17

Total with taxes and fees

A hallway with a wooden door, a black table with a sign, and large green plants.

4. 3BR Near West Point | Coffee Bar | Sleeps 6

Highland Falls

mario b.

$383 nightly

Nov 10 - Nov 11

Total with taxes and fees

A modern kitchen with stainless steel appliances, wooden cabinets, and a contemporary light fixture.

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

Highland Falls

Maria L.

$217 nightly

Nov 10 - Nov 11

Total with taxes and fees

A house with a white front door, a small porch with a white railing, and a window with a green curtain.

6. Fabulous 3bdrm Home w/parking!

Highland Falls

Beth M.

$256 nightly

Nov 10 - Nov 11

Total with taxes and fees

A blue house with a white porch, a welcome sign, and a mailbox.

7. 3BR West Point Retreat-3min to Back Gate+ King Bed

Highland Falls

Christine T.

$388 nightly

Nov 11 - Nov 12

Total with taxes and fees

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

Highland Falls

Zack C.

$171 nightly

Nov 10 - Nov 11

Total with taxes and fees

A living room with a wooden floor, a black sofa, a coffee table, and a ceiling fan.

9. Perfect 2BR with Free Parking! Walk to West Point!

Highland Falls

$233 nightly

Nov 10 - Nov 11

Total with taxes and fees

A room with a wooden floor, a white door with a number, and a window with blinds.

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

Highland Falls

Briana T.

$256 nightly

Nov 10 - Nov 11

Total with taxes and fees

A dining area with a table, chairs, a vase with flowers, a hanging light fixture, and wall decorations.

11. Mountain-View 2BR Steps from Thayer Gate

Highland Falls

$218 nightly

Nov 10 - Nov 11

Total with taxes and fees

A wooden coffee table with two decorative planters in a living room.

12. Walk to WP Gate + Free Parking!

Highland Falls

Jerell T.

$235 nightly

Nov 10 - Nov 11

Total with taxes and fees

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

13. Hudson Valley/West Point Retreat w/ parking!

Highland Falls

$266 nightly

Nov 10 - Nov 11

Total with taxes and fees

A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

14. Contemporary Cozy Cottage

Lake Peekskill

Heather M.

$341 nightly

Nov 10 - Nov 11

Total with taxes and fees

A deck with Adirondack chairs, a fire pit, and a grill.

15. 3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

Cornwall

Elisabeth

$357 nightly

Nov 10 - Nov 11

Total with taxes and fees

A dining table set with plates, cutlery, and glasses, with a bowl of fruit and a wine glass in the background.

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

CROTON HDSN

Margaret S.

$312 nightly

Nov 12 - Nov 13

Total with taxes and fees

A stone staircase leading to a house with a stone wall and a metal gate.

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

Croton-on-Hudson

Eva C.

$343 nightly

Nov 10 - Nov 11

Total with taxes and fees

A modern bedroom with a blue sofa, a bed, a TV, and a window with a view.

18. Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer

Beacon

Maryanne

$205 nightly

Nov 24 - Nov 25

Total with taxes and fees

A modern living room with a stone fireplace, a leather sofa, a yellow armchair, a flat-screen TV, and a bookshelf.

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

Croton-on-Hudson

Mateo A.

$371 nightly

Nov 19 - Nov 20

Total with taxes and fees

A spacious living room with a fireplace, a ceiling fan, and a large window.

20. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Monroe

Scott

$457 nightly

Nov 30 - Dec 1

Total with taxes and fees

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Find vacation rentals that suit your style

Top Doodletown Hotel Reviews

A buffet with various food items, including omelets and baked goods, served in metal containers.

Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

Peekskill

10/10 Excellent

David Allen

A hotel entrance with stone pillars, a covered walkway, and a bench.

Sleep Inn & Suites Monroe - Woodbury

Monroe

10/10 Excellent

Meredith

A large, multi-story stone building with a prominent arched entrance and multiple windows.

Overlook Lodge at Bear Mountain

Bear Mountain

10/10 Excellent

The property is well tucked away in the wilderness of Bear Mountain State Park. It's designed to blend with the surrounding nature. The hotel has very rustic look and feel but in a good way. It definitely gives nostalgic vibes of being in a log and stone cabin in the woods. The rooms and property are very clean and cozy and updated without ruining the rustic feel. The only two complaints I have about the property and it's very minor is that 1) the walls are extremely thin and noise from...

Arie

A lobby with a grand chandelier, two large arched windows, and a central fireplace with a portrait above it.

The Thayer Hotel at West Point

West Point

10/10 Excellent

Amy

A Holiday Inn Express hotel with a covered entrance, a parking lot, and a well-lit facade.

Holiday Inn Express Hotel & Suites Chester by IHG

Chester

10/10 Excellent

Edward J

A large, two-story white house with a wrap-around porch and a small front garden.

The Dominion House Bed & Breakfast

Chester

10/10 Excellent

Cindy

A Red Roof Inn & Suites building with a two-story structure, a balcony, and an American flag.

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

New Windsor

10/10 Excellent

Belinda

A hotel indoor pool with lounge chairs, a hot tub, and a warning sign.

Homewood Suites Stewart Airport

New Windsor

10/10 Excellent

Needed a place to stay when moving to the area. This hotel was conveniently located and very affordable - especially considering what you get! The suites were fantastic - spacious, everything we needed, kitchenettes. On top of that they serve a good hot breakfast every morning and a manager's reception (which is essentially a meal) four nights a week. What a deal! Friendly, helpful staff too. I truly don't have anything negative to say about this hotel.

Anonymous traveler

A hotel room with a green sofa, a small table, a bed with a headboard, a desk with a lamp, and a framed picture on the wall.

Quality Inn & Suites Fishkill South near I-84

Fishkill

10/10 Excellent

Lynn

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 $186 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.

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.

Doodletown Vacation Rentals

Check prices for these dates

Our top choices for Doodletown vacation rentals

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

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

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

4. 3BR Near West Point | Coffee Bar | Sleeps 6

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

6. Fabulous 3bdrm Home w/parking!

7. 3BR West Point Retreat-3min to Back Gate+ King Bed

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

9. Perfect 2BR with Free Parking! Walk to West Point!

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

11. Mountain-View 2BR Steps from Thayer Gate

12. Walk to WP Gate + Free Parking!

13. Hudson Valley/West Point Retreat w/ parking!

14. Contemporary Cozy Cottage

15. 3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

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

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

18. Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer

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

20. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Find vacation rentals that suit your style

Top Doodletown Hotel Reviews

Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

10/10 Excellent

Find out more about Doodletown

Everything you need to know about Doodletown vacation rentals

Doodletown vacation rentals: An excellent choice for every season

How to find incredible deals on Doodletown rentals

Frequently Asked Questions

Are there vacation rentals in Doodletown?

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

What can I see and do in Doodletown?

What are vacation rentals like in Doodletown?

Explore a world of travel with Expedia