Title: Town of Highlands Vacation Home Rentals from CA $211: Search Top Private Vacation Homes for Rent | Expedia.ca

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![George W. Perkins Memorial Drive with Hudson River and Bear Mountain Bridge, NY](https://images.trvl-media.com/place/183639/985ee9c0-c331-4997-9abd-dfd80d6d3cf2.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Town of Highlands Vacation Rentals

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## Check prices for these dates

Next weekend

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248635976002149&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976002149&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976002149&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976002149&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Cities in Town of Highlands

![](https://mediaim.expedia.com/destination/1/d0cc470cce0c12eec31b3f6f28539bc4.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### West Point

[](https://expedia.ca/West-Point-Private-Vacation-Homes.d9700-aaPrivateVacationHomes.Travel-Guide-Accommodation)

![](https://mediaim.expedia.com/destination/2/0dd0b78def315096bc47a57bca0e3daf.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Highland Falls

[](https://expedia.ca/Highland-Falls-Private-Vacation-Homes.d9540-aaPrivateVacationHomes.Travel-Guide-Accommodation)

## Our top choices for Town of Highlands vacation homes

![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/2af1ac8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/86da8ea2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/fbb02298.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, coffee/tea maker, electric kettle](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/7aae90a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Fishkill

[](https://www.expedia.ca/Fishkill-Hotels-Large-Relaxing-Family-Retreat-In-The-Hudson-Valley-With-Theatre-And-Gazebo.h111183358.Hotel-Information)

9.4/10

Exceptional

(53)

"Quiet, clean and comfortable! Great stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joseph G.

CA $339

CA $433 total

includes taxes & fees

Jan 4 - Jan 5

[](https://www.expedia.ca/Fishkill-Hotels-Large-Relaxing-Family-Retreat-In-The-Hudson-Valley-With-Theatre-And-Gazebo.h111183358.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/117000000/116300000/116295600/116295595/7917335b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/117000000/116300000/116295600/116295595/6b71b73b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/117000000/116300000/116295600/116295595/b850bea4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116300000/116295600/116295595/e62b431c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Warwick

[](https://www.expedia.ca/Warwick-Hotels-Room-2-At-The-Warwick-Inn-Cozy-Elegance-In-The-Heart-Of-Town.h116295595.Hotel-Information)

9.0/10

Wonderful

(8)

"This was our second stay at The Warwick Inn, and it was just as wonderful as the first. The inn is a beautifully kept old Victorian house, decorated so charmingly and kept impeccably clean. It has such a cozy, quiet atmosphere that makes it easy to relax and unwind. The restaurant downstairs is fantastic and so convenient, adding to the overall experience. If you’re looking for a unique, comfortable, and peaceful place to stay in Warwick, this inn is a gem."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kalley

CA $123

CA $214 total

includes taxes & fees

Jan 5 - Jan 6

[](https://www.expedia.ca/Warwick-Hotels-Room-2-At-The-Warwick-Inn-Cozy-Elegance-In-The-Heart-Of-Town.h116295595.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/64000000/63530000/63528000/63527962/9f0ce022.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/64000000/63530000/63528000/63527962/22655253.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/64000000/63530000/63528000/63527962/c553f5f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/64000000/63530000/63528000/63527962/70096d79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Newburgh

[](https://www.expedia.ca/Newburgh-Hotels-Large.h63527962.Hotel-Information)

9.0/10

Wonderful

(15)

"Very cozy stay with responsive host"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Adhith P.

CA $493

CA $657 total

includes taxes & fees

Jan 2 - Jan 3

[](https://www.expedia.ca/Newburgh-Hotels-Large.h63527962.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863201/07973626.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863201/dc1cc284.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863201/c485256a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/115000000/114870000/114863300/114863201/fa190f5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Newburgh

[](https://www.expedia.ca/Newburgh-Hotels-Ultimate-Lakeside-Getaway-On-5-Acres-Private-Dock.h114863201.Hotel-Information)

10/10

Exceptional

(22)

"Great host, amazing area, perfect get away!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Gianna W.

[](https://www.expedia.ca/Newburgh-Hotels-Ultimate-Lakeside-Getaway-On-5-Acres-Private-Dock.h114863201.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/117000000/116300000/116293600/116293556/e4cec53f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116300000/116293600/116293556/d8b7ae3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/117000000/116300000/116293600/116293556/4cc093aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116300000/116293600/116293556/w1024h682x0y3-ac855643.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Warwick

[](https://www.expedia.ca/Warwick-Hotels-Room-1-At-The-Warwick-Inn-Cozy-Elegance-In-The-Heart-Of-Town.h116293556.Hotel-Information)

9.4/10

Exceptional

(8)

"I really enjoyed my stay. The room was very clean, the inn is well located in town and it is great having the restaurant below. Would stay here again! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Erin R.

CA $121

CA $211 total

includes taxes & fees

Jan 5 - Jan 6

[](https://www.expedia.ca/Warwick-Hotels-Room-1-At-The-Warwick-Inn-Cozy-Elegance-In-The-Heart-Of-Town.h116293556.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/121000000/120640000/120638400/120638396/82fb52cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120640000/120638400/120638396/1a4d5020.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120640000/120638400/120638396/0151cfea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120640000/120638400/120638396/29a6ed4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Wallkill

[](https://www.expedia.ca/Wallkill-Hotels-Cozy-Private-Suite-In-A-Country-Home-Near-New-Paltz.h120638396.Hotel-Information)

10/10

Exceptional

(2)

"Clean, private, had no issues and the check in was easy. Had a great stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Justin O.

[](https://www.expedia.ca/Wallkill-Hotels-Cozy-Private-Suite-In-A-Country-Home-Near-New-Paltz.h120638396.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/25000000/24920000/24911200/24911110/3deb5ed4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/25000000/24920000/24911200/24911110/5f06c884.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/25000000/24920000/24911200/24911110/004a0ae8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/25000000/24920000/24911200/24911110/ae7ed8ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Newburgh

[](https://www.expedia.ca/Newburgh-Hotels-Private-Lakefront-Home-With-Kayaks-Stunning-Sunsets-Panoramic-View.h24911110.Hotel-Information)

10/10

Exceptional

(314)

"Excellent communication with great host. Pleasant, peaceful stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Frank D.

[](https://www.expedia.ca/Newburgh-Hotels-Private-Lakefront-Home-With-Kayaks-Stunning-Sunsets-Panoramic-View.h24911110.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/d9fd7f11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/32d0bc6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/3745699f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/c7d67b21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Lake Peekskill

[](https://www.expedia.ca/Lake-Peekskill-Hotels-Contemporary-Cozy-Cottage.h102145832.Hotel-Information)

10/10

Exceptional

(30)

"Very clean comfortable quiet place"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Mauro C.

CA $308

CA $572 total

includes taxes & fees

Jan 5 - Jan 6

[](https://www.expedia.ca/Lake-Peekskill-Hotels-Contemporary-Cozy-Cottage.h102145832.Hotel-Information)

![Children's area](https://images.trvl-media.com/lodging/113000000/112590000/112586800/112586795/b2662bbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/113000000/112590000/112586800/112586795/9d74f7a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112590000/112586800/112586795/244ebd87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/113000000/112590000/112586800/112586795/fc97efe8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Fishkill

[](https://www.expedia.ca/Fishkill-Hotels-Hickory-On-Willow-Lake.h112586795.Hotel-Information)

9.6/10

Exceptional

(5)

"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rachel C.

CA $716

CA $1,007 total

includes taxes & fees

Jan 5 - Jan 6

[](https://www.expedia.ca/Fishkill-Hotels-Hickory-On-Willow-Lake.h112586795.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/97000000/96850000/96842000/96841918/10c9994b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/97000000/96850000/96842000/96841918/53df77e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96850000/96842000/96841918/c9e7f08f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/97000000/96850000/96842000/96841918/45c2db90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Nyack

[](https://www.expedia.ca/Nyack-Hotels-Castle-In-The-Sky-Beautifully-Renovated-Victorian-One-Block-From-Main-St.h96841918.Hotel-Information)

9.0/10

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."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dr. Andrea W.

[](https://www.expedia.ca/Nyack-Hotels-Castle-In-The-Sky-Beautifully-Renovated-Victorian-One-Block-From-Main-St.h96841918.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/e73b5292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/424d87c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/339c4da4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/ee686000.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Highland Falls

[](https://www.expedia.ca/Highland-Falls-Hotels-House-On-The-Babbling-Brook-Quiet-2BR-King-Bed.h113522235.Hotel-Information)

10/10

Exceptional

(5)

"Good stay, awesome place"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Scott G.

CA $133

CA $483 total

includes taxes & fees

Jan 4 - Jan 5

[](https://www.expedia.ca/Highland-Falls-Hotels-House-On-The-Babbling-Brook-Quiet-2BR-King-Bed.h113522235.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90340000/90332000/90331975/434df93a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/91000000/90340000/90332000/90331975/76c8412d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90340000/90332000/90331975/18f12633.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90340000/90332000/90331975/03e4686c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Marlboro

[](https://www.expedia.ca/Marlboro-Hotels-Hudson-Valley-Hilltop-Escape-WHot-Tub.h90331975.Hotel-Information)

10/10

Exceptional

(5)

"Thank you for sharing your home with us. We thoroughly enjoyed our stay. The home is like a retreat - well thought out amenities & hospitality (love the dimmer switches throughout & book selections). Would definitely stay again. — WP Family "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Angie W.

[](https://www.expedia.ca/Marlboro-Hotels-Hudson-Valley-Hilltop-Escape-WHot-Tub.h90331975.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/103000000/102190000/102188900/102188852/a4b35b8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/103000000/102190000/102188900/102188852/f5af14ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102190000/102188900/102188852/3bbe0756.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/103000000/102190000/102188900/102188852/56621b5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Beacon

[](https://www.expedia.ca/Beacon-Hotels-Majestic-RiverView-Estate-Breathtaking-Views.h102188852.Hotel-Information)

9.8/10

Exceptional

(10)

"Great house for a large group - stayed here with friends for a wedding and was only a short walk away from downtown Beacon. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Avatar S.

[](https://www.expedia.ca/Beacon-Hotels-Majestic-RiverView-Estate-Breathtaking-Views.h102188852.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/45000000/44130000/44126500/44126447/59415cb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![WiFi, bed sheets](https://images.trvl-media.com/lodging/45000000/44130000/44126500/44126447/w1421h960x0y0-1bf6f7e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/45000000/44130000/44126500/44126447/1b246a76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/45000000/44130000/44126500/44126447/2fce8b60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Poughkeepsie

[](https://www.expedia.ca/Poughkeepsie-Hotels-The-Queen-City-Cottage.h44126447.Hotel-Information)

7.4/10

Good

(16)

"We had a great stay! Good location and the house was very clean. Would definitely stay here again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Payton W.

[](https://www.expedia.ca/Poughkeepsie-Hotels-The-Queen-City-Cottage.h44126447.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/27000000/26690000/26681500/26681452/e2144f45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/27000000/26690000/26681500/26681452/bfac06f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/27000000/26690000/26681500/26681452/494a6c16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/27000000/26690000/26681500/26681452/379cf32c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Highland Falls

[](https://www.expedia.ca/Newburgh-Hotels-Our-Rockbound-Highland-Home-2-Blocks-From-Thayer-Gate-12-Block-To-Main-St.h26681452.Hotel-Information)

10/10

Exceptional

(39)

"Everything was good. Heather was very attentive."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jeannette P.

[](https://www.expedia.ca/Newburgh-Hotels-Our-Rockbound-Highland-Home-2-Blocks-From-Thayer-Gate-12-Block-To-Main-St.h26681452.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/97000000/96410000/96402700/96402683/w1267h816x1y0-efb023de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96410000/96402700/96402683/w1280h786x2y0-10a0429d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, foosball, table tennis](https://images.trvl-media.com/lodging/97000000/96410000/96402700/96402683/w1250h789x1y5-d69ff69b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/97000000/96410000/96402700/96402683/dc2d11be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Highland

[](https://www.expedia.ca/Highland-Hotels-Our-Home-Is-Perfect-For-Relaxing-And-Having-Lots-Of-Fun.h96402683.Hotel-Information)

9.6/10

Exceptional

(11)

"Enjoyed the stay. Nice place to relax for a weekend."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Marie J.

[](https://www.expedia.ca/Highland-Hotels-Our-Home-Is-Perfect-For-Relaxing-And-Having-Lots-Of-Fun.h96402683.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106650000/106647200/106647189/5b4bebd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106650000/106647200/106647189/74a38716.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106650000/106647200/106647189/bc63286a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106650000/106647200/106647189/e6f59d49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Goshen

[](https://www.expedia.ca/Goshen-Hotels-Luxury-3-Bedroom-Fully-Renovated-House-In-Goshen-With-Brand-New-Furniture.h106647189.Hotel-Information)

9.0/10

Wonderful

(12)

"Great location!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alozie E.

CA $394

CA $600 total

includes taxes & fees

Jan 2 - Jan 3

[](https://www.expedia.ca/Goshen-Hotels-Luxury-3-Bedroom-Fully-Renovated-House-In-Goshen-With-Brand-New-Furniture.h106647189.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118790000/118789700/118789607/db87b742.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/119000000/118790000/118789700/118789607/e6bd76c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/119000000/118790000/118789700/118789607/d0f943d9_edited_6f50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/119000000/118790000/118789700/118789607/56a9517c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Greenwood Lake

[](https://www.expedia.ca/Greenwood-Lake-Hotels-Ann-Creek-Charming-2-BR-Fully-Renovated-House-At-Greenwood-Lake-Dog-Friendly.h118789607.Hotel-Information)

9.8/10

Exceptional

(8)

"Awesome place. Cozy and great communication with owners. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dominick P.

[](https://www.expedia.ca/Greenwood-Lake-Hotels-Ann-Creek-Charming-2-BR-Fully-Renovated-House-At-Greenwood-Lake-Dog-Friendly.h118789607.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71960000/71952400/71952323/f6623e06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/72000000/71960000/71952400/71952323/0229fe97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/72000000/71960000/71952400/71952323/550eef50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/72000000/71960000/71952400/71952323/5aa43ade.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Carmel Hamlet

[](https://www.expedia.ca/Carmel-Hotels-Lost-In-The-Woods.h71952323.Hotel-Information)

10/10

Exceptional

(96)

"We love staying here, it's so peaceful. A great place to stay when in the Hudson Valley."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Chad H.

[](https://www.expedia.ca/Carmel-Hotels-Lost-In-The-Woods.h71952323.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/1ffbe7a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/26b38c44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/be15b260.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/8cbcd139.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Highland Falls

[](https://www.expedia.ca/Highland-Falls-Hotels-Fabulous-3bdrm-Home-Wparking.h114378708.Hotel-Information)

9.0/10

Wonderful

(4)

"Clean home, conveniently located to West Point. Very comfortable beds. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Danielle B.

CA $246

CA $439 total

includes taxes & fees

Jan 5 - Jan 6

[](https://www.expedia.ca/Highland-Falls-Hotels-Fabulous-3bdrm-Home-Wparking.h114378708.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-15&endDate=2026-01-16&regionId=553248635976002149&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

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Apartments

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Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Town+of+Highlands%2C+New+York%2C+United+States+of+America&regionId=553248635976002149&latLong=41.349152%2C-73.974518&adults=2&startDate=2026-03-31&d1=2026-03-31&endDate=2026-04-03&d2=2026-04-03&lodging=CABIN)

Private vacation homes

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Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Town+of+Highlands%2C+New+York%2C+United+States+of+America&regionId=553248635976002149&latLong=41.349152%2C-73.974518&adults=2&startDate=2026-03-31&d1=2026-03-31&endDate=2026-04-03&d2=2026-04-03&lodging=COTTAGE)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Town+of+Highlands%2C+New+York%2C+United+States+of+America&regionId=553248635976002149&latLong=41.349152%2C-73.974518&adults=2&startDate=2026-03-31&d1=2026-03-31&endDate=2026-04-03&d2=2026-04-03&lodging=CONDO)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Town+of+Highlands%2C+New+York%2C+United+States+of+America&regionId=553248635976002149&latLong=41.349152%2C-73.974518&adults=2&startDate=2026-03-31&d1=2026-03-31&endDate=2026-04-03&d2=2026-04-03&lodging=VILLA)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Town+of+Highlands%2C+New+York%2C+United+States+of+America&regionId=553248635976002149&latLong=41.349152%2C-73.974518&adults=2&startDate=2026-03-31&d1=2026-03-31&endDate=2026-04-03&d2=2026-04-03&lodging=CHALET)

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## Top Town of Highlands Hotel Reviews

![Courtyard by Marriott Poughkeepsie](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/990080f2_y.jpg)

### Courtyard by Marriott Poughkeepsie

10/10 Excellent

"The space was good enough and shower was a nice size"

[](https://expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.Hotel-Information)

![Hyatt Place Poughkeepsie / Hudson Valley](https://images.trvl-media.com/lodging/38000000/37970000/37960500/37960419/9bb388bd_y.jpg)

### Hyatt Place Poughkeepsie / Hudson Valley

10/10 Excellent

"I was unable to attend breakfast this time as I had to run off in the morning but I enjoyed a nice hot shower."

[](https://expedia.ca/Poughkeepsie-Hotels-Hyatt-Place-Poughkeepsie.h37960419.Hotel-Information)

![Crowne Plaza Suffern - Mahwah by IHG](https://images.trvl-media.com/lodging/1000000/10000/2400/2358/e31233cf_y.jpg)

### Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent

"Was greeted and taken care of well at check in and given a preference of which floor I’d like to stay on, room was clean a couple hair strand on the lounge sofa chair and no garbage bags in the trash bins, and bathroom was a bit cold but I come prepared for situations such as those and the only thing I didn’t like was the heater will only stay on when on high and cut off once switched to low. I’d stayed he a few times in the past it’s been a while I know last time I was on the ground floor in the winter time like this but the heating was poor so, over all I’m happy with my stay and comfortable. "

[](https://expedia.ca/Nyack-Hotels-Crowne-Plaza-Suffern-Mahwah.h2358.Hotel-Information)

![West Gate Inn Nyack](https://images.trvl-media.com/lodging/6000000/5850000/5843400/5843352/393dcf26_y.jpg)

### West Gate Inn Nyack

10/10 Excellent

"Overalls with excellence in customer service."

[](https://expedia.ca/Nyack-Hotels-West-Gate-Inn-Nyack.h5843352.Hotel-Information)

![Holiday Inn Express Hotel & Suites Chester by IHG](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/02f3df9e_y.jpg)

### Holiday Inn Express Hotel & Suites Chester by IHG

10/10 Excellent

"Very clean room - great stay would stay again! "

[](https://expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information)

![Sonesta Simply Suites Nanuet](https://images.trvl-media.com/lodging/1000000/700000/694300/694250/a9ba8283_y.jpg)

### Sonesta Simply Suites Nanuet

10/10 Excellent

"I enjoyed the hotel very much and the service that it provided."

[](https://expedia.ca/Nyack-Hotels-Sonesta-Simply-Suites-Nanuet.h694250.Hotel-Information)

![Sleepy Hollow Hotel](https://images.trvl-media.com/lodging/1000000/10000/4000/3956/ee0f5c7a_y.jpg)

### Sleepy Hollow Hotel

10/10 Excellent

"I loved my stay Staff was respectful and very hospitable Pool was warm And there was a lot of parking space available "

[](https://expedia.ca/White-Plains-Hotels-Sleepy-Hollow-Hotel-Conference-Center.h3956.Hotel-Information)

![Hotel Nyack, a JdV by Hyatt Hotel](https://images.trvl-media.com/lodging/12000000/11950000/11943100/11943081/a38df02c_y.jpg)

### Hotel Nyack, a JdV by Hyatt Hotel

10/10 Excellent

"Friendly staff, clean and comfortable room. Also very convenient "

[](https://expedia.ca/Nyack-Hotels-Hotel-Nyack.h11943081.Hotel-Information)

![Hampton Inn & Suites Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/47fa2e85_y.jpg)

### Hampton Inn & Suites Poughkeepsie

10/10 Excellent

"Great service staff is excellent "

[](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information)

## Find out more about Town of Highlands

## Town of Highlands Vacation Homes information

| Number of reviews | 642                |
| ----------------- | ------------------ |
| Accommodation     | 292 Vacation Homes |
| Lowest Price      | CA $211            |
| Highest Price     | CA $1,007          |

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- [Flights to Bear Mountain ](https://www.expedia.ca/Cheap-Flights-To-Bear-Mountain.d183639.Travel-Guide-Flights)
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- [Flights from Toronto (YYZ) to New York (NYC) ](https://www.expedia.ca/lp/flights/yyz/nyc/toronto-to-new-york)

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- [Things to do in Bear Mountain ](https://www.expedia.ca/Things-To-Do-In-Bear-Mountain.d183639.Travel-Guide-Activities)
- [Things to do in West Point ](https://www.expedia.ca/Things-To-Do-In-West-Point.d9700.Travel-Guide-Activities)

- [Book Vacation Homes in Town of Highlands on Expedia.com ](https://www.expedia.com/Town-Of-Highlands-Private-Vacation-Homes.d553248635976002149-aaPrivateVacationHomes.Travel-Guide-Accommodation)