Title: Highland Vacation Rentals from CA $314: Short-Term Rentals for 2026 | 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

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2026-05-29&endDate=2026-05-31&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 rentals

![Property grounds](https://images.trvl-media.com/lodging/79000000/78770000/78763900/78763897/7eb8271b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/79000000/78770000/78763900/78763897/8759e018.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, blender, cookware/dishes/utensils](https://images.trvl-media.com/lodging/79000000/78770000/78763900/78763897/c01619d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/79000000/78770000/78763900/78763897/16466981.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails! 

[](https://www.expedia.ca/Highland-Hotels-Enjoy-A-Cozy.h78763897.Hotel-Information)

Highland

9.8/10

Exceptional

(26 reviews)

"Perfect location and stay"

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

kareem e.

CA $294

CA $444 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Highland-Hotels-Enjoy-A-Cozy.h78763897.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90260000/90253400/90253316/w910h683x57y0-c820193c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/90260000/90253400/90253316/4722395f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/90260000/90253400/90253316/dbbcd386.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/90260000/90253400/90253316/e9a4f2fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley

[](https://www.expedia.ca/Highland-Hotels-Step-Into-History-Unwind-At-Spring-Apt-A-Charming-At-Theof-NYHudson-Valley.h90253316.Hotel-Information)

Highland

10/10

Exceptional

(1 review)

"Everyone was just right! The home is perfect for a photo shoot. We weren't there for that, but we thought the setting was unique and beautiful! Everything we needed!!"

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

Rebecca D.

CA $274

CA $584 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Highland-Hotels-Step-Into-History-Unwind-At-Spring-Apt-A-Charming-At-Theof-NYHudson-Valley.h90253316.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)

![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)

![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)

### 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 $125

CA $477 total

includes taxes & fees

Feb 8 - Feb 9

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

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83440000/83439600/83439540/d9bc7fd6.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)

### 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 $63

CA $210 total

includes taxes & fees

Feb 8 - Feb 9

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

![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/95000000/94720000/94717500/94717464/dd930402.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/95000000/94720000/94717500/94717464/08ae7458.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/95000000/94720000/94717500/94717464/328adef2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/95000000/94720000/94717500/94717464/1cd6d553.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Highland-Falls-Hotels-Quiet-Apt-With-Coffee-Bar.h94717464.Hotel-Information)

Highland Falls

9.8/10

Exceptional

(16 reviews)

"Great Unit."

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

Rudy R.

CA $110

CA $365 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Highland-Falls-Hotels-Quiet-Apt-With-Coffee-Bar.h94717464.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/c39f873f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78180000/78173600/78173525/b2088330.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)

### 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 $101

CA $346 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/Kingston-Hotels-Stylish-Cozy-Cabin.h78173525.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 $69

CA $304 total

includes taxes & fees

Feb 8 - Feb 9

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

![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/111000000/110990000/110986300/110986250/82ecc5c3.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/111000000/110990000/110986300/110986250/2bdd6486.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 $160

CA $589 total

includes taxes & fees

Feb 10 - Feb 11

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

![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71560000/71554500/71554438/74754379.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71560000/71554500/71554438/f1f2157e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/72000000/71560000/71554500/71554438/a8ad041f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/72000000/71560000/71554500/71554438/43ce1dac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

[](https://www.expedia.ca/Kingston-Hotels-Chic-Hudson-Valley-Escape-With-Jacuzzi-Tub.h71554438.Hotel-Information)

Kingston

9.4/10

Exceptional

(28 reviews)

"Very clean very comfortable beds."

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

Millgate F.

CA $117

CA $319 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Kingston-Hotels-Chic-Hudson-Valley-Escape-With-Jacuzzi-Tub.h71554438.Hotel-Information)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/110000000/109790000/109781600/109781517/147d3620.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/110000000/109790000/109781600/109781517/c3a6ab07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109790000/109781600/109781517/446f5ba8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/110000000/109790000/109781600/109781517/966dbd3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kapitan’s cottage a Rustic Private Catskill Getaway Near Kingston

[](https://www.expedia.ca/Kingston-Hotels-Private-In-Nature-Upstate-Rustic-Kapitans-Cottage-Pet-Friendly.h109781517.Hotel-Information)

Kingston

9.6/10

Exceptional

(9 reviews)

"Thoughtfully furnished, beautifully renovated, and well-located cottage off a private and scenic road that is close to Kingston yet feels rural and quiet. Hosts were warm and responsive. Would be glad to return (and hope to soon). "

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

Antonina W.

CA $187

CA $483 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Kingston-Hotels-Private-In-Nature-Upstate-Rustic-Kapitans-Cottage-Pet-Friendly.h109781517.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/70000000/69550000/69544900/69544886/ac221ad2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/70000000/69550000/69544900/69544886/d10065ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/70000000/69550000/69544900/69544886/5710350e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/70000000/69550000/69544900/69544886/9236bc83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

[](https://www.expedia.ca/Beacon-Hotels-Luxe-Studio-2-On-Main-Street-Luxury-Steam-Shower.h69544886.Hotel-Information)

Beacon

10/10

Exceptional

(33 reviews)

"Great time and great place to stay "

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

S S.

CA $159

CA $344 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Beacon-Hotels-Luxe-Studio-2-On-Main-Street-Luxury-Steam-Shower.h69544886.Hotel-Information)

![Fireplace, books](https://images.trvl-media.com/lodging/84000000/83440000/83439100/83439008/cd189b6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/84000000/83440000/83439100/83439008/c4f41298.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83440000/83439100/83439008/7cf93160.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83440000/83439100/83439008/5dd44347.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

[](https://www.expedia.ca/Kerhonkson-Hotels-Dream-Cottage-In-The-Gunks.h83439008.Hotel-Information)

Kerhonkson

9.4/10

Exceptional

(12 reviews)

"Charming and relaxing cottage. Perfect location for hiking or enjoying Lake Minnewaska or Mohonk Preserve. "

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

Patrick S.

CA $117

CA $269 total

includes taxes & fees

Feb 11 - Feb 12

[](https://www.expedia.ca/Kerhonkson-Hotels-Dream-Cottage-In-The-Gunks.h83439008.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/84000000/83450000/83440300/83440247/d10caf62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace, books](https://images.trvl-media.com/lodging/84000000/83450000/83440300/83440247/f359a159.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/84000000/83450000/83440300/83440247/7443da23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83450000/83440300/83440247/bb0bc46c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Apartment with Sauna in Historic Stone Ridge

[](https://www.expedia.ca/Stone-Ridge-Hotels-Cozy-Apartment-With-Sauna-In-Historic-Stone-Ridge.h83440247.Hotel-Information)

Stone Ridge

9.0/10

Wonderful

(15 reviews)

"Clean cozy will be staying again"

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

Michael C.

CA $78

CA $211 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Stone-Ridge-Hotels-Cozy-Apartment-With-Sauna-In-Historic-Stone-Ridge.h83440247.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/83000000/82500000/82491600/82491535/ebe69c53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/83000000/82500000/82491600/82491535/095616e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/83000000/82500000/82491600/82491535/6cc368ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/83000000/82500000/82491600/82491535/3ab297f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private Studio Close to Downtown Rhinebeck

[](https://www.expedia.ca/Rhinebeck-Hotels-Private-Studio-Close-To-Downtown-Rhinebeck.h82491535.Hotel-Information)

Rhinebeck Village

9.8/10

Exceptional

(27 reviews)

"Beautiful place has a great stay!"

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

Heather O.

CA $116

CA $325 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Rhinebeck-Hotels-Private-Studio-Close-To-Downtown-Rhinebeck.h82491535.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/84000000/83430000/83426500/83426410/10d69ba6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83430000/83426500/83426410/0c3ccbf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/84000000/83430000/83426500/83426410/cb371140.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/84000000/83430000/83426500/83426410/fd01a6d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dream getaway apartment in the foot of Gunks Ridge

[](https://www.expedia.ca/Wallkill-Hotels-Dream-Getaway-Apartment-In-The-Foot-Of-Gunks-Ridge.h83426410.Hotel-Information)

Wallkill

9.6/10

Exceptional

(24 reviews)

"Serg’s place was comfortable and clean! It was a perfect location for me and my friends to stay while rock climbing in the Gunks. We did not feel cramped or unsafe and the complementary tea was a hit! One thing to note is that both of the beds were low to the ground (below knee level) so if someone has knee or back problems, it might be difficult to stand up out of bed. "

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

Mary S.

CA $75

CA $222 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Wallkill-Hotels-Dream-Getaway-Apartment-In-The-Foot-Of-Gunks-Ridge.h83426410.Hotel-Information)

![Apartment](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711154/901afe1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711154/91a23b03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711154/7aa0c18f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/124000000/123720000/123711200/123711154/d8a9dc23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Calm Boutique Lake Studio Fast Wifi Great WFH

[](https://www.expedia.ca/Monroe-Hotels-Cozy-Modern-Studio-Near-Lake-Porch-Fire-Pit.h123711154.Hotel-Information)

Monroe

CA $113

CA $294 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Monroe-Hotels-Cozy-Modern-Studio-Near-Lake-Porch-Fire-Pit.h123711154.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)

![Exterior](https://images.trvl-media.com/lodging/94000000/93500000/93491200/93491157/f50280fc.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)

### 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 $132

CA $430 total

includes taxes & fees

Feb 8 - Feb 9

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

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/95000000/94720000/94717500/94717468/7b3193ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/95000000/94720000/94717500/94717468/8a733476.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/95000000/94720000/94717500/94717468/7fbb18e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/95000000/94720000/94717500/94717468/9fa76c16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Local Artist Inspired | Walk to WestPoint + King Bed

[](https://www.expedia.ca/Highland-Falls-Hotels-Local-Artist-Inspired-Walk-To-WestPoint-King-Bed.h94717468.Hotel-Information)

Highland Falls

9.4/10

Exceptional

(11 reviews)

"Great place to stay if you have a West Point student - super close to all West Point related activities. The place itself needs some work but it’s functional."

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

Jesse C.

CA $141

CA $560 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Highland-Falls-Hotels-Local-Artist-Inspired-Walk-To-WestPoint-King-Bed.h94717468.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/93000000/92360000/92356000/92355918/d8c6c1e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92360000/92356000/92355918/3837d8ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/93000000/92360000/92356000/92355918/d912385e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92360000/92356000/92355918/b2e6343d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mid-Century DJ’s Dream

[](https://www.expedia.ca/Hyde-Park-Hotels-Mid-Century-DJs-Dream.h92355918.Hotel-Information)

Staatsburg

10/10

Exceptional

(44 reviews)

"Great host and excellent accommodations! "

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

Elaine L.

CA $153

CA $266 total

includes taxes & fees

Feb 11 - Feb 12

[](https://www.expedia.ca/Hyde-Park-Hotels-Mid-Century-DJs-Dream.h92355918.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107970000/107964300/107964203/bf85ab49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/108000000/107970000/107964300/107964203/96050ad7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107970000/107964300/107964203/9714c3f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/108000000/107970000/107964300/107964203/e7e8be7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

[](https://www.expedia.ca/Gardiner-Hotels-Modern-Zen-Chalet-At-The-Foot-Of-Gunks-W-Mt-View.h107964203.Hotel-Information)

Gardiner

10/10

Exceptional

(8 reviews)

"Great weekend getaway to reconnect with old friends!"

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

Lisa D.

CA $281

CA $462 total

includes taxes & fees

Feb 26 - Feb 27

[](https://www.expedia.ca/Gardiner-Hotels-Modern-Zen-Chalet-At-The-Foot-Of-Gunks-W-Mt-View.h107964203.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=2026-02-21&endDate=2026-02-22&regionId=115050&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

[](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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=CABIN)

Apartments

[](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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=APARTMENT)

Private vacation homes

[](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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=VACATION_HOME)

Cottages

[](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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=COTTAGE)

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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&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=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=CHALET)

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## Top Highland Hotel Reviews

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

### Hampton Inn Kingston

10/10 Excellent

"Cleanliness and comfortable bed"

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

"Best staff ever great location."

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

"The staff is incredibly courteous and helpful. The room is immaculate. Every amenity and convenience is considered in making your stay a pleasure. "

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

"My stay was wonderful. Even though the TVs were down the stay was still pleasant. The staff was friendly and sympathetic to the inconvenience. The food from the lobby was excellent!! Best burger I’ve had by far! Breakfast was amazing as well! I’d definitely stay again"

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

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

### Minnewaska Lodge

10/10 Excellent

"Awesome"

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

![Woodstock Way Hotel](https://images.trvl-media.com/lodging/92000000/91580000/91577900/91577819/a7440a5e_y.jpg)

### Woodstock Way Hotel

10/10 Excellent

"For"

[](https://expedia.ca/Woodstock-Hotels-Woodstock-Way-Hotel.h91577819.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

"Nice staff and beds!"

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

![Best Western Plus Kingston Hotel And Conference Center](https://images.trvl-media.com/lodging/1000000/10000/6100/6056/d4db98bc_y.jpg)

### Best Western Plus Kingston Hotel And Conference Center

10/10 Excellent

"Very nice. Was not expecting to pay for breakfast, so i skipped out."

[](https://expedia.ca/Kingston-Hotels-Best-Western-Plus-Kingston-Hotel-And-Conference-Center.h6056.Hotel-Information)

![DoubleTree by Hilton Poughkeepsie Convention Center](https://images.trvl-media.com/lodging/1000000/20000/14600/14563/acc87956_y.jpg)

### DoubleTree by Hilton Poughkeepsie Convention Center

10/10 Excellent

"Room was clean and comfortable. Staff was so friendly. Would definitely stay here again "

[](https://expedia.ca/Poughkeepsie-Hotels-Poughkeepsie-Grand-Hotel.h14563.Hotel-Information)

## Find out more about Highland

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Highland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Vacation Homes in Highland ](https://expedia.ca/Highland-Private-Vacation-Homes.d115050-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Highland ](https://expedia.ca/Highland-Apartments.d115050-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Highland ](https://expedia.ca/Highland-Cottages.d115050-aaCottages.Travel-Guide-Accommodation)
- [Cabin Rentals in Highland ](https://expedia.ca/Highland-Cabins.d115050-aaCabins.Travel-Guide-Accommodation)
- [B&B in Highland ](https://expedia.ca/Highland-Bed-And-Breakfast.d115050-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Farmstay in Highland ](https://expedia.ca/Highland-Agritourism.d115050-aaAgritourism.Travel-Guide-Accommodation)
- [Motels in Highland ](https://expedia.ca/Highland-Motels.d115050-aaMotels.Travel-Guide-Accommodation)
- [Villas in Highland ](https://expedia.ca/Highland-Villas.d115050-aaVillas.Travel-Guide-Accommodation)
- [Guest Houses in Highland ](https://expedia.ca/Highland-Guest-Houses.d115050-aaGuestHouses.Travel-Guide-Accommodation)
- [Lodges in Highland ](https://expedia.ca/Highland-Lodges.d115050-aaLodges.Travel-Guide-Accommodation)
- [RV Parks in Highland ](https://expedia.ca/Highland-RV-Parks.d115050-aaRVParks.Travel-Guide-Accommodation)
- [Inns in Highland ](https://expedia.ca/Highland-Inns.d115050-aaInns.Travel-Guide-Accommodation)
- [Chalets in Highland ](https://expedia.ca/Highland-Chalets.d115050-aaChalets.Travel-Guide-Accommodation)
- [Condo Rentals in Highland ](https://expedia.ca/Highland-Condos.d115050-aaCondos.Travel-Guide-Accommodation)
- [Hostels in Highland ](https://expedia.ca/Highland-Hostels.d115050-aaHostels.Travel-Guide-Accommodation)
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## Frequently asked questions

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