Cottages in Town of Wappinger
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Cottages in Town of Wappinger

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your current months are November, 2026 and December, 2026.

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Top cities in Town of Wappinger

A lake surrounded by forested hills with autumn foliage.

Wappingers Falls

Chelsea

Castle Point

Myers Corner

Hughsonville

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Our top choices for Town of Wappinger cottages

A white single-story house with a stone pathway leading to the front door, surrounded by trees and a well-maintained lawn.

A bedroom with two beds, a nightstand, a dresser, and large windows with curtains.

A covered patio with stone flooring, outdoor furniture, and potted plants.

A spacious kitchen with white cabinetry, a central island, and a large window providing a view of the outdoors.

1. Historic 1800s Cornwall-on-hudson Cottage!

Historic 1800s Cornwall-on-hudson Cottage!

3.0 star property

Cornwall

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"We loved everything about this property. The host was easy to connect with. The cottage was well stocked and spotless. The cottage and yard were absolutely beautiful. Would definitely book again."

Anthony

Historic 1800s Cornwall-on-hudson Cottage!

A covered outdoor seating area with a sofa, chairs, and a table.

A rustic interior with exposed wooden beams, a sofa, a chair, a table, and a fireplace.

A wooden boardwalk through a forested area with a house in the background.

A cozy living room with a stone fireplace, a colorful glass coffee table, and a grey sofa.

2. Historic Barn Retreat w/ Pool & Pond Views Longview Pond Lodge by Avantstay

Historic Barn Retreat w/ Pool & Pond Views Longview Pond Lodge by Avantstay

3.0 star property

Clinton Corners

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"It was amazing Such a lovely place we were there with our family 6 persons The house has everything very clean lots of space . Everything was amazing We would love to go again Thank you 🙏❤️"

Dieter

Historic Barn Retreat w/ Pool & Pond Views Longview Pond Lodge by Avantstay

A single-story house with a covered porch, a brick foundation, and a lawn in front.

A living room with a ceiling fan, a sofa, a coffee table, a chair, and a floor lamp.

A bedroom with a large bed, a dresser, a chair, and a desk.

A dining area with a wooden table, chairs, a chandelier, and a decorative mirror.

3. Charming Gardiner Home w/ Yard & Sunroom

Charming Gardiner Home w/ Yard & Sunroom

3.0 star property

Gardiner

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

Charming Gardiner Home w/ Yard & Sunroom

A wooden porch with two rocking chairs and a window overlooking a forest.

A wooden cabin bedroom with a bed, dresser, shelves, and a ceiling fan.

A wooden cabin with a porch, large windows, and a door.

A modern living room with a fireplace, a sofa, and a dining area with a bar.

4. Pool+hot Tub, Firepit Near Hikes, Shops, Dining Cragswood Lodge by Avantstay

Pool+hot Tub, Firepit Near Hikes, Shops, Dining Cragswood Lodge by Avantstay

3.0 star property

New Paltz

Pool+hot Tub, Firepit Near Hikes, Shops, Dining Cragswood Lodge by Avantstay

A wooden deck with wicker furniture and a table set with drinks and snacks.

A dining room with a large table, chairs, and a view through large windows.

A living room with a brown leather sofa, a green sofa, a glass coffee table with apples, and framed botanical prints on the wall.

A modern house with a dark exterior, a concrete staircase, and a small garden area with plants.

5. Charcoal Chalet by Avantstay A+ Design w/ Firepit

Charcoal Chalet by Avantstay A+ Design w/ Firepit

3.0 star property

New Paltz

7.0 out of 10, Good, (2 reviews)

7.0/10

Good

(2 reviews)

"We enjoyed the quiet and beautiful outdoors area. The house was very nice, clean and had everything we needed such as laundry facilities and detergent, cookware, utensils, coffee, tea, sugar and so much more. We felt very at home in this house. The dining room was beautiful with the long table and many windows overlooking the back yard. It was perfect for a small dinner gathering. Parking was great and the area felt safe and was quiet. I will most likely book again for next year."

Christina

Charcoal Chalet by Avantstay A+ Design w/ Firepit

An outdoor dining area with a table set for two, a hot tub, and a view of a modern building with large windows.

A modern kitchen with a large island, wooden ceiling beams, and pendant lighting.

A modern kitchen with a large island, bar stools, and a staircase leading to an upper level.

A modern house with a large chimney, large windows, and a well-lit exterior at dusk.

6. Luxe Mountain Getaway on Private Rd Near Rhinebeck

Luxe Mountain Getaway on Private Rd Near Rhinebeck

3.0 star property

Hyde Park

Luxe Mountain Getaway on Private Rd Near Rhinebeck

A covered porch with wooden flooring, a green sofa, and a table with a green vase.

A spacious living room with a stone fireplace, leather furniture, and large windows offering a view of the outdoors.

A spacious kitchen with wooden cabinets, a central island with bar stools, and pendant lighting.

A spacious living room with a large wooden ceiling, a leather sofa, a wooden armchair, and a coffee table.

7. Luxe Family Home on Orange Lake w/ Private Dock!

Luxe Family Home on Orange Lake w/ Private Dock!

3.0 star property

Newburgh

Luxe Family Home on Orange Lake w/ Private Dock!

A modern living room with a TV, a dining area with a table and chairs, and a kitchen in the background.

A kitchen with wooden cabinets, a stainless steel stove, a dishwasher, and a dining table with a basket of fruit.

A living room with a sofa, coffee table, TV, bookshelf, and fireplace.

8. Charming Highland Falls Home < 2 Mi to West Point!

Charming Highland Falls Home < 2 Mi to West Point!

3.0 star property

Highland Falls

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Fabulous place - great for our family weekend at West Point. Plenty of room, lovely kitchen, and lots of seating - whole group of us could watch the baseball playoffs. Terrific - not a single problem or complaint!!"

Mia

Charming Highland Falls Home < 2 Mi to West Point!

A two-story house with a red front door, a small porch, and a garden with a stone pathway.

A living room with two grey sofas, a coffee table, a chandelier, and a window with blinds.

A modern kitchen with stainless steel appliances, wooden cabinets, and a large window providing natural light.

A modern kitchen with dark cabinets, a built-in oven, and a refrigerator.

9. 4 Mi to Hudson River: Cozy Newburgh Home!

4 Mi to Hudson River: Cozy Newburgh Home!

3.0 star property

Newburgh

8.0 out of 10, Very good, (1 review)

8.0/10

Very good

(1 review)

4 Mi to Hudson River: Cozy Newburgh Home!

An outdoor patio with a stone wall, a wooden fence, and a table with chairs.

A living room with a leather sofa, a round coffee table, a bench, and a ceiling fan.

A modern kitchen with a round marble table, black chairs, and a stainless steel refrigerator.

A bedroom with a large bed, a dresser, a mirror, and three windows.

10. Updated Home w/ Patio Half Mile to West Point

Updated Home w/ Patio Half Mile to West Point

3.0 star property

Highland Falls

Updated Home w/ Patio Half Mile to West Point

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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Cottages in Town of Lewisboro
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Cottages in Town of Wappinger

Change your mind

Treat yourself

Be picky

Top cities in Town of Wappinger

Wappingers Falls

Find holiday rentals that suit your style

Check prices for these dates

Our top choices for Town of Wappinger cottages

1. Historic 1800s Cornwall-on-hudson Cottage!

2. Historic Barn Retreat w/ Pool & Pond Views Longview Pond Lodge by Avantstay

3. Charming Gardiner Home w/ Yard & Sunroom

4. Pool+hot Tub, Firepit Near Hikes, Shops, Dining Cragswood Lodge by Avantstay

5. Charcoal Chalet by Avantstay A+ Design w/ Firepit

6. Luxe Mountain Getaway on Private Rd Near Rhinebeck

7. Luxe Family Home on Orange Lake w/ Private Dock!

8. Charming Highland Falls Home < 2 Mi to West Point!

9. 4 Mi to Hudson River: Cozy Newburgh Home!

10. Updated Home w/ Patio Half Mile to West Point

Explore a world of travel with Expedia