Title: Highland Vacation Home Rentals from CA $264: Search Top Private Vacation Homes for Rent | Expedia.ca

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![Walking across the walkway over the Hudson, get there early to avoid parking issues. Great place to walk your dog!](https://images.trvl-media.com/place/115050/513f001c-86fc-4f9b-8930-057b5d34aed2.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Allison Alano Flores

![](https://images.trvl-media.com/place/115050/513f001c-86fc-4f9b-8930-057b5d34aed2.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=115050&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

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Highland vacation homes

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/7ad8e5a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/2bdd6486.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/b762fce3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/82ecc5c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Highland-Falls-Hotels-Sleek-Escape-Modern-3-BR-4-Min-From-West-Point.h110986250.Hotel-Information)

Highland Falls

10/10

Exceptional

(3 reviews)

"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"

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

Julio J.

CA $129

CA $559 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Highland-Falls-Hotels-Sleek-Escape-Modern-3-BR-4-Min-From-West-Point.h110986250.Hotel-Information)

![Apartment](https://images.trvl-media.com/lodging/124000000/123710000/123706400/123706320/ce02298f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/124000000/123710000/123706400/123706320/c81a0e54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/124000000/123710000/123706400/123706320/8067e3b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/124000000/123710000/123706400/123706320/2107cf79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hidden Lakefront Gem on a Gated Countryside Escape

[](https://www.expedia.ca/Monroe-Hotels-Rustic-Lakefront-Studio-With-Deck-Workspace.h123706320.Hotel-Information)

Monroe

CA $128

CA $322 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Monroe-Hotels-Rustic-Lakefront-Studio-With-Deck-Workspace.h123706320.Hotel-Information)

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

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/92f8429f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/e5f1d678.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/9832ea44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Highland Falls

10/10

Exceptional

(6 reviews)

"Good stay, awesome place"

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

Scott G.

CA $126

CA $481 total

includes taxes & fees

Jan 22 - Jan 23

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

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/89000000/88870000/88864900/88864808/1f5e7a7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels, soap, shampoo](https://images.trvl-media.com/lodging/89000000/88870000/88864900/88864808/w450h639x287y44-0aaac327.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/89000000/88870000/88864900/88864808/a5431ccf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/89000000/88870000/88864900/88864808/f4d68743.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Studio at the Inn at High Falls

[](https://www.expedia.ca/High-Falls-Hotels-The-Studio-At-The-Inn-At-High-Falls.h88864808.Hotel-Information)

High Falls

8.0/10

Very good

(34 reviews)

"Just wasn't our cup of tea. Quiet location, close to attractions, and easy to find. "

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

William K.

CA $156

CA $374 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/High-Falls-Hotels-The-Studio-At-The-Inn-At-High-Falls.h88864808.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/84000000/83440000/83439600/83439540/315d7b3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83440000/83439600/83439540/cdecc2e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83440000/83439600/83439540/2dce554c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83440000/83439600/83439540/842e96ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

[](https://www.expedia.ca/Kerhonkson-Hotels-Dream-House-In-The-Gunks.h83439540.Hotel-Information)

Kerhonkson

10/10

Exceptional

(32 reviews)

"I love the place, very comfortable and cozy, Thank you so very much, Enjoyed a lot , Julia"

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

Julia K.

CA $112

CA $264 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Kerhonkson-Hotels-Dream-House-In-The-Gunks.h83439540.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/6a09d677.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/3207c5e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/719e347a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/e5c54a16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Highland-Falls-Hotels-Lovely-3BR-Home-With-Parking-Walk-To-WP-Gate.h105177891.Hotel-Information)

Highland Falls

10/10

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

Briana T.

CA $211

CA $432 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Highland-Falls-Hotels-Lovely-3BR-Home-With-Parking-Walk-To-WP-Gate.h105177891.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109390000/109381700/109381685/bdac6c18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109390000/109381700/109381685/4388309b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/110000000/109390000/109381700/109381685/3c5edeb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109390000/109381700/109381685/fd769a19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### "Country outside the city " 3 bedrooms 2 full bathrooms 

[](https://www.expedia.ca/Holmes-Hotels-Country-Outside-The-City-3-Bedrooms-2-Full-Bathrooms.h109381685.Hotel-Information)

Holmes

9.6/10

Exceptional

(4 reviews)

"Great house! We had a fantastic weekend!! Thank you so much "

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

pamela w.

CA $280

CA $807 total

includes taxes & fees

Jan 26 - Jan 27

[](https://www.expedia.ca/Holmes-Hotels-Country-Outside-The-City-3-Bedrooms-2-Full-Bathrooms.h109381685.Hotel-Information)

![2 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/94000000/93500000/93491200/93491157/fefcbc55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, computer monitors](https://images.trvl-media.com/lodging/94000000/93500000/93491200/93491157/cbc374e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, computer monitors](https://images.trvl-media.com/lodging/94000000/93500000/93491200/93491157/bed3b59f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/94000000/93500000/93491200/93491157/c955f95c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Retro Retreat: renovated 2BR, desk, no chore list!

[](https://www.expedia.ca/Kingston-Hotels-Retro-Retreat-Renovated-2BR.h93491157.Hotel-Information)

Kingston

9.6/10

Exceptional

(15 reviews)

"Great, easy, full of everything you’d need. Stayed with 2 others for a work trip and it was perfect! "

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

Kelley Marie

CA $99

CA $392 total

includes taxes & fees

Feb 4 - Feb 5

[](https://www.expedia.ca/Kingston-Hotels-Retro-Retreat-Renovated-2BR.h93491157.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/79000000/78180000/78173600/78173525/92738c50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78180000/78173600/78173525/bd3ca6b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/79000000/78180000/78173600/78173525/fb0c2218.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78180000/78173600/78173525/c39f873f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Campfire Cottage: Fireplace, fire pit & no chores!

[](https://www.expedia.ca/Kingston-Hotels-Stylish-Cozy-Cabin.h78173525.Hotel-Information)

Kingston

10/10

Exceptional

(31 reviews)

"Great multi-week stay! Would certainly stay again. "

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

Jim R.

CA $111

CA $364 total

includes taxes & fees

Jan 21 - Jan 22

[](https://www.expedia.ca/Kingston-Hotels-Stylish-Cozy-Cabin.h78173525.Hotel-Information)

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

![TV](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/0c2d8c1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/ab2c7ac1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/116022ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fabulous 3bdrm Home w/parking!

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

Highland Falls

9.0/10

Wonderful

(4 reviews)

"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 $211

CA $421 total

includes taxes & fees

Jan 21 - Jan 22

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

![Property grounds](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522229/6b825ecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522229/ae162913.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522229/6f93013a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522229/973f29b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Highland-Falls-Hotels-3BR-West-Point-Retreat-3min-To-Back-Gate-King-Bed.h113522229.Hotel-Information)

Highland Falls

7.6/10

Good

(5 reviews)

"Wonderful stay! The property is within walking distance of the little downtown area & had driveway parking. It was clean & plenty spacious. Property owners had great communication! This is a property with 2 units, but we were not bothered by any extra noise. "

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

Waylon J.

CA $153

CA $605 total

includes taxes & fees

Jan 22 - Jan 23

[](https://www.expedia.ca/Highland-Falls-Hotels-3BR-West-Point-Retreat-3min-To-Back-Gate-King-Bed.h113522229.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/117000000/116760000/116758500/116758499/1fe9eea3_edited_074f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/117000000/116760000/116758500/116758499/92496678.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/117000000/116760000/116758500/116758499/92eb238a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116760000/116758500/116758499/5eb61507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

###  Cozy private suite in the heart of beautiful Gardiner.

[](https://www.expedia.ca/New-Paltz-Hotels-Cozy-Private-Suite-In-The-Heart-Of-Beautiful-Gardiner.h116758499.Hotel-Information)

New Paltz

10/10

Exceptional

(7 reviews)

"Check-in was easy. Hosts very responsive to any questions and helpful to local recommendations. "

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

Chanah B.

CA $177

CA $360 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/New-Paltz-Hotels-Cozy-Private-Suite-In-The-Heart-Of-Beautiful-Gardiner.h116758499.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104090000/104080300/104080240/29c91958.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/105000000/104090000/104080300/104080240/40cd82f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/105000000/104090000/104080300/104080240/w2175h1449x1y1-7a150bbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/105000000/104090000/104080300/104080240/a66de76c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

[](https://www.expedia.ca/Kingston-Hotels-Retro-Retreat-1br-Home-W-WFH-Desk.h104080240.Hotel-Information)

Kingston

10/10

Exceptional

(4 reviews)

"Beautiful house to stay in, convenient to numerous restaurants and hikes. Our host was very communicative and had great recommendations for the area!"

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

Brendan B.

CA $75

CA $316 total

includes taxes & fees

Feb 4 - Feb 5

[](https://www.expedia.ca/Kingston-Hotels-Retro-Retreat-1br-Home-W-WFH-Desk.h104080240.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/ef9b23f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/c86208ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/b07ff9fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/d5087de9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

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

Fishkill

9.4/10

Exceptional

(54 reviews)

"Quiet, clean and comfortable! Great stay!"

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

Joseph G.

CA $344

CA $441 total

includes taxes & fees

Jan 18 - Jan 19

[](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/99000000/98780000/98779400/98779366/d143cbe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/99000000/98780000/98779400/98779366/8ea1adb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/99000000/98780000/98779400/98779366/50bbfc33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/99000000/98780000/98779400/98779366/c24c61a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Esopus Creek modern Tiny house Retreat!

[](https://www.expedia.ca/Kingston-Hotels-Esopus-Creek-Modern-Tiny-House-Retreat.h98779366.Hotel-Information)

Kingston

9.8/10

Exceptional

(66 reviews)

"We came for our daughter’s wedding in town . The place was conveniently located near the wedding siteIt was small and just perfect for 3 members of my family -Woke up to birds chirping Would surely plan for a second stay "

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

Pratistha L.

CA $206

CA $335 total

includes taxes & fees

Jan 28 - Jan 29

[](https://www.expedia.ca/Kingston-Hotels-Esopus-Creek-Modern-Tiny-House-Retreat.h98779366.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/111000000/110650000/110643700/110643700/b8d7ac80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/111000000/110650000/110643700/110643700/8dd5c447.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/111000000/110650000/110643700/110643700/905a40e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110650000/110643700/110643700/268b639b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Escape -Strong Wi-Fi -Prime Location

[](https://www.expedia.ca/Poughkeepsie-Hotels-Cozy-Escape-Strong-Wi-Fi-Prime-Location.h110643700.Hotel-Information)

Poughkeepsie

6.8/10

(5 reviews)

"The property was perfect for our little weekend getaway. It was very clean and cozy and the host Christina made it so easy for check in and was available for any questions. We would definitely stay again."

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

Andrea C.

CA $124

CA $441 total

includes taxes & fees

Feb 3 - Feb 4

[](https://www.expedia.ca/Poughkeepsie-Hotels-Cozy-Escape-Strong-Wi-Fi-Prime-Location.h110643700.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100540000/100535600/100535519/1eef3e41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100540000/100535600/100535519/1223c490.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, offices](https://images.trvl-media.com/lodging/101000000/100540000/100535600/100535519/3238f3a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100540000/100535600/100535519/3b0b1bad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything

[](https://www.expedia.ca/Kerhonkson-Hotels-Cozy-Hudson-Valley-Retreat-1950s-Ranch-Close-To-Everything.h100535519.Hotel-Information)

Kerhonkson

9.8/10

Exceptional

(24 reviews)

"Comfortable stay- very clean and kind host! Would highly recommend! "

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

Gretchen M.

CA $237

CA $409 total

includes taxes & fees

Jan 24 - Jan 25

[](https://www.expedia.ca/Kerhonkson-Hotels-Cozy-Hudson-Valley-Retreat-1950s-Ranch-Close-To-Everything.h100535519.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122930000/122929100/122929001/120febc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122930000/122929100/122929001/7c3fd8d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/123000000/122930000/122929100/122929001/bb90272b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/123000000/122930000/122929100/122929001/2f9d1a89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Cornwall-Hotels-Storm-King-At-Narnia-Welcome-To-A-Slice-Of-Paradise-In-The-Hudson-Valley.h122929001.Hotel-Information)

Cornwall

10/10

Exceptional

(2 reviews)

"We really enjoyed our short stay at the house - it was extremely clean, the beds were comfortable, and the whole house was warm and cozy. There were thoughtful little touches all around the house - from fluffy socks for us to extra blankets, motion-sensor nightlights, and a fully equipped kitchen. Everything is newly renovated and updated. Views of the surrounding mountains are beautiful and the location is quiet and peaceful. We would visit again! "

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

Anne R.

CA $300

CA $591 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Cornwall-Hotels-Storm-King-At-Narnia-Welcome-To-A-Slice-Of-Paradise-In-The-Hudson-Valley.h122929001.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/103000000/102530000/102523100/102523082/abda313d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining tables](https://images.trvl-media.com/lodging/103000000/102530000/102523100/102523082/9ef38a5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/103000000/102530000/102523100/102523082/85812d6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/103000000/102530000/102523100/102523082/a01882c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Brand New House with Huge patio overlooks Esopus Creek at Lake Katrine

[](https://www.expedia.ca/Lake-Katrine-Hotels-Brand-New-House-With-Huge-Patio-Overlooks-Esopus-Creek-At-Lake-Katrine.h102523082.Hotel-Information)

Lake Katrine

10/10

Exceptional

(17 reviews)

"Perfect getaway!"

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

Lynn A.

CA $249

CA $582 total

includes taxes & fees

Jan 21 - Jan 22

[](https://www.expedia.ca/Lake-Katrine-Hotels-Brand-New-House-With-Huge-Patio-Overlooks-Esopus-Creek-At-Lake-Katrine.h102523082.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112270000/112268900/112268824/ba9be98b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/113000000/112270000/112268900/112268824/49d4b784.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112270000/112268900/112268824/211a8ab3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/113000000/112270000/112268900/112268824/9621850a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bright Contemporary Near The Best Hiking Trails

[](https://www.expedia.ca/Cragsmoor-Hotels-NEW-Sunny-Family-Cabin-Near-The-Best-Hiking-Trails.h112268824.Hotel-Information)

Pine Bush

10/10

Exceptional

(3 reviews)

"Nice property, very close to Sam’s Point trailheads. We were there to hike, so this was perfect. We would definitely book again."

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

Amy L.

CA $159

CA $708 total

includes taxes & fees

Jan 26 - Jan 27

[](https://www.expedia.ca/Cragsmoor-Hotels-NEW-Sunny-Family-Cabin-Near-The-Best-Hiking-Trails.h112268824.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=2026-01-30&endDate=2026-01-31&regionId=115050&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

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Cottages

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Apartments

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Private vacation homes

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Villas

[](https://www.expedia.ca/Hotel-Search?destination=Highland%2C+New+York%2C+United+States+of+America&regionId=115050&latLong=41.720928%2C-73.960136&adults=2&startDate=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&lodging=VILLA)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Highland%2C+New+York%2C+United+States+of+America&regionId=115050&latLong=41.720928%2C-73.960136&adults=2&startDate=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&lodging=CONDO)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Highland%2C+New+York%2C+United+States+of+America&regionId=115050&latLong=41.720928%2C-73.960136&adults=2&startDate=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&lodging=CHALET)

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## Top Highland Hotel Reviews

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

### Hampton Inn & Suites Poughkeepsie

10/10 Excellent

"Team is friendly, professional and helpful. Room was clean and comfy. Breakkfast is well maintained with a variety of options. Love the make your own waffles and the potatoes andyogurt selections. "

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

![Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/e8f6eb1b_y.jpg)

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

10/10 Excellent

"Good stay"

[](https://expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information)

![Hampton Inn by Hilton New Paltz](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/bd59d6cb_y.jpg)

### Hampton Inn by Hilton New Paltz

10/10 Excellent

"Great front desk assistant. "

[](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.Hotel-Information)

![Residence Inn by Marriott Kingston](https://images.trvl-media.com/lodging/16000000/15720000/15715300/15715238/3f674783_y.jpg)

### Residence Inn by Marriott Kingston

10/10 Excellent

"Clean room. Spacious. Lovely friendly respectful staff unlike my experience at Hampton Inn across the road :("

[](https://expedia.ca/Kingston-Hotels-Residence-Inn-By-Marriott-Kingston.h15715238.Hotel-Information)

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

### Courtyard by Marriott Poughkeepsie

10/10 Excellent

"Easy parking, check-in. Nice rooms"

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

![Minnewaska Lodge](https://images.trvl-media.com/lodging/2000000/1210000/1201800/1201707/3be04d40_y.jpg)

### Minnewaska Lodge

10/10 Excellent

"The room was spotless and the personnel really helpful "

[](https://expedia.ca/Poughkeepsie-Hotels-Minnewaska-Lodge.h1201707.Hotel-Information)

![Hampton Inn Kingston](https://images.trvl-media.com/lodging/2000000/1670000/1662000/1661941/21cb7965_y.jpg)

### Hampton Inn Kingston

10/10 Excellent

"Excellent "

[](https://expedia.ca/Kingston-Hotels-Hampton-Inn-Kingston.h1661941.Hotel-Information)

![Inn at Bellefield / Hyde Park, Residence Inn by Marriott](https://images.trvl-media.com/lodging/100000000/99860000/99850800/99850733/w4000h2662x0y0-e2ffacae_y.jpg)

### Inn at Bellefield / Hyde Park, Residence Inn by Marriott

10/10 Excellent

"."

[](https://expedia.ca/Hyde-Park-Hotels-Inn-At-Bellefield-Hyde-Park.h99850733.Hotel-Information)

![Hampton Inn Fishkill](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/f57ee72e_y.jpg)

### Hampton Inn Fishkill

10/10 Excellent

"Hotel was clean. Staff was nice."

[](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Fishkill.h119273.Hotel-Information)

## Find out more about Highland

## Highland Vacation Homes information

| Number of reviews | 309                |
| ----------------- | ------------------ |
| Accommodation     | 590 Vacation Homes |
| Lowest Price      | CA $264            |
| Highest Price     | CA $807            |

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- [Flights to Milton ](https://www.expedia.ca/Cheap-Flights-To-Milton.d6288971.Travel-Guide-Flights)
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