Title: Highland Vacation Home Rentals from CA $107: Search Top Private Vacation Homes for Rent | Expedia.ca

  

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Photo by Karen Wirtz

# Highland Vacation Rentals

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## Check prices for these dates

Next weekend

[Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=115050&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Highland Vacation Homes

![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)

![Interior](https://images.trvl-media.com/lodging/97000000/96410000/96402700/96402683/w1282h818x1y2-a264c3c1.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)

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

### Our home is perfect for relaxing and having lots of fun, with near by activity’s

Highland

9.8/10

Exceptional

(6)

"My family and I had a great time at this property. Located on a beautiful property. Very relaxing and coordinating with the property owner was very easy. "

CA $314

CA $983 total

includes taxes & fees

Oct 9 - Oct 10

[](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/80000000/79880000/79874000/79873967/w906h683x60y0-2991689a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/80000000/79880000/79874000/79873967/w906h683x60y0-0b53ee10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/80000000/79880000/79874000/79873967/w906h683x59y0-70da373f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/80000000/79880000/79874000/79873967/e4830f65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

### Glamping Tent & Campsite by Minnewaska State Park

Kerhonkson

8.8/10

Excellent

(3)

"We had a great time. The tent and toilet were clean. We appreciated the water provided and the cookware. The only thing to note is that there is a bit of walking on a rocky trail before reaching the campsite (not next to the parking spot). The river was fun to explore but can be difficult for younger kids to get to. The campsite is close to Minnewaska State Park, very convenient. "

CA $119

CA $212 total

includes taxes & fees

Oct 15 - Oct 16

[](https://www.expedia.ca/Kerhonkson-Hotels-Glamping-Tent-Campsite-By-Minnewaska-State-Park.h79873967.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78180000/78173600/78173525/49a13516.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)

![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/79000000/78180000/78173600/78173525/1f4c1098.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Kingston

10/10

Exceptional

(28)

"Perfect cozy little spot for 2. Centrally located to explore surrounding areas"

CA $107

CA $353 total

includes taxes & fees

Oct 29 - Oct 30

[](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)

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

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/105000000/104090000/104080300/104080240/1879cd21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/105000000/104090000/104080300/104080240/362afdd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Kingston

10/10

Exceptional

(4)

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

CA $82

CA $322 total

includes taxes & fees

Oct 21 - Oct 22

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

![Interior](https://images.trvl-media.com/lodging/84000000/83440000/83439500/83439448/956d009d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace, books](https://images.trvl-media.com/lodging/84000000/83440000/83439500/83439448/f7dd1013.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83440000/83439500/83439448/774bff0e.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/84000000/83440000/83439500/83439448/d7732712.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks

Kerhonkson

10/10

Exceptional

(13)

"Can’t emphasize how nice the surrounding area and property itself are. Very relaxing while still being close to several small towns with great restaurants. Communication was excellent, overall a great experience! "

CA $162

CA $287 total

includes taxes & fees

Oct 9 - Oct 10

[](https://www.expedia.ca/Kerhonkson-Hotels-Dream-Art-Studio-In-The-Gunks.h83439448.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/97000000/96670000/96666900/96666877/affe6f29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/97000000/96670000/96666900/96666877/w906h683x59y0-5553baec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96670000/96666900/96666877/b7cb4de1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96670000/96666900/96666877/10847bd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### West Wing - a unique private space w/patio

Shokan

9.8/10

Exceptional

(17)

"Very clean house and great service "

CA $176

CA $275 total

includes taxes & fees

Oct 9 - Oct 10

[](https://www.expedia.ca/Shokan-Hotels-West-Wing-A-Unique-Private-Space-Wpatio.h96666877.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/94000000/93500000/93491200/93491157/f3a0c6f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/94000000/93500000/93491200/93491157/bb6b9558.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/94000000/93500000/93491200/93491157/298f7baf.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!

Kingston

9.4/10

Exceptional

(12)

"Very clean and nice inside. Host was very communicative. "

CA $121

CA $414 total

includes taxes & fees

Oct 21 - Oct 22

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

![1 bedroom, desk, free WiFi](https://images.trvl-media.com/lodging/116000000/115350000/115342500/115342421/e4118fbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115350000/115342500/115342421/02d3f9de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/116000000/115350000/115342500/115342421/0d014c6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/115350000/115342500/115342421/dcc9a5b6_edited_40c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

Red Hook

9.6/10

Exceptional

(8)

"It was a perfect quiet spot surrounded by trees in a beautiful, safe neighborhood. I loved how close it was to a bagel shop and some cool eateries just a few minutes downtown. The whole area is beautiful in general. "

CA $202

CA $341 total

includes taxes & fees

Oct 15 - Oct 16

[](https://www.expedia.ca/Red-Hook-Hotels-THE-ARTISTS-LOFT-Peaceful-1-Bedroom-Apartment-In-Lovely-Red-Hook-With-AC.h115342421.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/89000000/88870000/88864900/88864808/a5431ccf.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)

![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)

![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)

### The Studio at the Inn at High Falls

High Falls

8.2/10

Very good

(31)

"I had a great stay here, it’s just as listed; simple but has everything that I needed, check in was easy, communication was good, and bed was comfortable!"

CA $157

CA $376 total

includes taxes & fees

Oct 13 - Oct 14

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

![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101540000/101530700/101530700/w977h683x24y0-0a1c4108.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/102000000/101540000/101530700/101530700/w679h683x174y0-b11ecb64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/102000000/101540000/101530700/101530700/w984h683x20y0-1854a468.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101540000/101530700/101530700/w507h683x258y0-71f7754d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat

Poughkeepsie

10/10

Exceptional

(4)

"Our stay was only a couple nights but it was what we expected. I would recommend this property. Had a great stay."

CA $453

CA $868 total

includes taxes & fees

Oct 12 - Oct 13

[](https://www.expedia.ca/Poughkeepsie-Hotels-Beautiful.h101530700.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/119000000/118170000/118164800/118164776/87b6b115.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/119000000/118170000/118164800/118164776/3add8621.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/119000000/118170000/118164800/118164776/74e2e6be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/119000000/118170000/118164800/118164776/afe3fdf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

new paltz

CA $283

CA $898 total

includes taxes & fees

Oct 13 - Oct 14

[](https://www.expedia.ca/New-Paltz-Hotels-Welcome-To-New-Paltz-Charming-3-Bedroom-House-With-AC.h118164776.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/cf889632.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110990000/110986300/110986250/04bc58ee.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/111000000/110990000/110986300/110986250/03441cf9.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 !

Highland Falls

10/10

Exceptional

(1)

"Looked like this property was recently renovated. Very clean and nice. "

CA $251

CA $695 total

includes taxes & fees

Oct 29 - Oct 30

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

![Interior](https://images.trvl-media.com/lodging/101000000/100540000/100535600/100535519/5bc13913.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

![Interior](https://images.trvl-media.com/lodging/101000000/100540000/100535600/100535519/3b0b1bad.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)

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

Kerhonkson

9.8/10

Exceptional

(18)

"Comfortable accommodations. Everything you need for a relaxing holiday "

CA $279

CA $459 total

includes taxes & fees

Nov 3 - Nov 4

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110960000/110952900/110952803/44ca83df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/111000000/110960000/110952900/110952803/cff51064.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/111000000/110960000/110952900/110952803/ae46a491.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/111000000/110960000/110952900/110952803/d2501def.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Tavern

Kingston

10/10

Exceptional

(1)

"We had a great time staying here! The house is a gorgeous historic house with modern amenities. It was a short drive to Kingston which was super convenient. We loved that we could bring our dog with us as well. It is on a main road, but we didn't find that to be a disturbance at all. I would definitely come back here again!!"

CA $218

CA $674 total

includes taxes & fees

Oct 28 - Oct 29

[](https://www.expedia.ca/Kingston-Hotels-NEW-Luxe-Historical-Style-In-Stone-Ridge.h110952803.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/109000000/108480000/108478400/108478343/6b2d2281.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108480000/108478400/108478343/897509a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108480000/108478400/108478343/b8f28b41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/109000000/108480000/108478400/108478343/a1036266.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### West Point Family Retreat, 5 min walk to Thayer!

Highland Falls

9.8/10

Exceptional

(6)

"Nice houseAwesome kitchen Granddaughter loved the bunk bed and the many games"

CA $627

CA $1,142 total

includes taxes & fees

Oct 19 - Oct 20

[](https://www.expedia.ca/Highland-Falls-Hotels-West-Point-Family-Retreat.h108478343.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112270000/112268900/112268824/a21059b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112270000/112268900/112268824/84d981c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, offices](https://images.trvl-media.com/lodging/113000000/112270000/112268900/112268824/580a3b7c.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)

### Treetops

Pine Bush

10/10

Exceptional

(2)

"I love Cragsmoor and your house is perfect for my family. Thank you!"

CA $241

CA $811 total

includes taxes & fees

Oct 23 - Oct 24

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

![Outdoor dining](https://images.trvl-media.com/lodging/99000000/98780000/98779400/98779366/8c96124e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/99000000/98780000/98779400/98779366/abf51a3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/99000000/98780000/98779400/98779366/2914f4fc.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)

### Esopus Creek modern Tiny house Retreat!

Kingston

9.8/10

Exceptional

(57)

"The property was beautiful. Quiet area but close enough to all the places we wanted to go. Our hosts were very gracious, attentive and friendly. Enjoyed our weekend retreat. "

CA $207

CA $335 total

includes taxes & fees

Oct 14 - Oct 15

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

![Exterior](https://images.trvl-media.com/lodging/89000000/88190000/88181200/88181115/280bea60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/89000000/88190000/88181200/88181115/0dcdc2c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88190000/88181200/88181115/21fb1fff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/89000000/88190000/88181200/88181115/cbf53a35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Hopewell Junction

9.0/10

Wonderful

(10)

"We had a fantastic stay at The Chapel. It was just the fun, different kind of place we were looking for. Pat and Christine were great hosts. We really appreciated their suggestions of hikes and places to visit. We actually had our trip planned out before, but changed it due to their suggestions. We had NO regrets. The bed was super comfy and we loved the s'more makings. "

CA $212

CA $360 total

includes taxes & fees

Oct 12 - Oct 13

[](https://www.expedia.ca/Hopewell-Junction-Hotels-Cozy-1845-Chapel-Escape-Near-Appalachian-Trail-And-Fahnestock-Park.h88181115.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/117000000/116370000/116362400/116362325/60f2c951.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/117000000/116370000/116362400/116362325/1522d348.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/117000000/116370000/116362400/116362325/77fcc776.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116370000/116362400/116362325/a4cc8a05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit

Montgomery

10/10

Exceptional

(1)

"Guido was very responsive and thoughtful! My partner and I stayed with our small dog and it was safe, clean, well stocked and in a beautiful area. Highly recommend to those looking to stay in the area!"

CA $211

CA $335 total

includes taxes & fees

Oct 23 - Oct 24

[](https://www.expedia.ca/Montgomery-Hotels-Cozy-Cabin-Gateway-I-15-Acres-W-Pool-Firepit.h116362325.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/103000000/102530000/102523100/102523082/7e5fe9d7.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/103000000/102530000/102523100/102523082/adb21577.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)

![Living area](https://images.trvl-media.com/lodging/103000000/102530000/102523100/102523082/4ee2e954.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Lake Katrine

10/10

Exceptional

(16)

"Immaculate house beautiful furnishings Very comfortable Everything you need for a relaxing stay Fully equipped"

CA $250

CA $584 total

includes taxes & fees

Oct 9 - Oct 10

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

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## Top Highland Hotel Reviews

![Quality Inn & Suites Fishkill South near I-84](//images.trvl-media.com/lodging/2000000/1770000/1766700/1766609/12805cb0_y.jpg)

### Quality Inn & Suites Fishkill South near I-84

10/10 Excellent

"Spacious Bathroom "

[](https://expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Suites-Fishkill-South-Near-I-84.h1766609.Hotel-Information)

![SureStay Plus Hotel by Best Western Highland Poughkeepsie](//images.trvl-media.com/lodging/1000000/920000/918800/918797/960f4844_y.jpg)

### SureStay Plus Hotel by Best Western Highland Poughkeepsie

10/10 Excellent

"Pets welcome "

[](https://expedia.ca/Poughkeepsie-Hotels-SureStay-Plus-Hotel-By-Best-Western-Highland-Poughkeepsie.h918797.Hotel-Information)

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

### Hampton Inn & Suites Poughkeepsie

10/10 Excellent

"The room was very large and the price was great."

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

![Inn at Bellefield / Hyde Park, Residence Inn by Marriott](//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

"This hotel is well located to local historic sites. The room was spacious and sparkling clean. Breakfast was plentiful and delicious. Parking was convenient. The bar and tender were great. The concierge gave great alternative day trips because of the closure of the FDR Library and those suggestions were well worth it. Happy to have stayed here."

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

![Super 8 by Wyndham Kingston](//images.trvl-media.com/lodging/1000000/900000/897900/897881/a6dbd2e2_y.jpg)

### Super 8 by Wyndham Kingston

10/10 Excellent

"The room was clean and the hotel was quiet, just what you want when trying to get a good nights sleep. The “free breakfast “ consisted of watered down orange juice or lemonade, coffee some teas and pre made mini blueberry muffins. But I wasn’t looking for a great breakfast just a good hotel to stay in for a few days and not pay the expensive price it would have cost to stay in Woodstock."

[](https://expedia.ca/Kingston-Hotels-Super-8-By-Wyndham-Kingston.h897881.Hotel-Information)

![Holiday Inn Express Poughkeepsie by IHG](//images.trvl-media.com/lodging/1000000/20000/12200/12157/9d729415_y.jpg)

### Holiday Inn Express Poughkeepsie by IHG

10/10 Excellent

"Good stay. Nothing really special about the place except the breakfast which had more choices than usual."

[](https://expedia.ca/Poughkeepsie-Hotels-Holiday-Inn-Express-Poughkeepsie.h12157.Hotel-Information)

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

### DoubleTree by Hilton Poughkeepsie Convention Center

10/10 Excellent

"Lovely clean spacious room with beautiful view of the Hudson River and its bridges. Friendly welcoming staff."

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

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

### Hampton Inn by Hilton New Paltz

10/10 Excellent

"Hotel and Room was very clean. "

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

![The Crossroads Hotel, Newburgh](//images.trvl-media.com/lodging/1000000/20000/14500/14410/5440914b_y.jpg)

### The Crossroads Hotel, Newburgh

10/10 Excellent

"Room was very clean but a little worn. Bed and linens were comfortable. Bathroom was clean. Very quiet. Staff were very welcoming, polite and accommodating. "

[](https://expedia.ca/Newburgh-Hotels-The-Crossroads-Hotel.h14410.Hotel-Information)

## Find out more about Highland

## Highland Vacation Homes information

| Number of reviews | 15,177 |
| --- | --- |
| Accommodation | 609 Vacation Homes |
| Lowest Price | CA $107 |
| Highest Price | CA $253 |

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-   [Hotels near Vassar Brothers Medical Center](https://www.expedia.ca/Vassar-Brothers-Medical-Center-Hotels.0-l553248626761242223-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Vassar College](https://www.expedia.ca/Vassar-College-Hotels.0-l6085394-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Walkway Over the Hudson State Historic Park](https://www.expedia.ca/Walkway-Over-The-Hudson-State-Historic-Park-Hotels.0-l6222117-0.Travel-Guide-Filter-Hotels)

-   [Flights to Milton](https://www.expedia.ca/Cheap-Flights-To-Milton.d6288971.Travel-Guide-Flights)
-   [Flights to Poughkeepsie](https://www.expedia.ca/Cheap-Flights-To-Poughkeepsie.d6056317.Travel-Guide-Flights)
-   [Flights from Poughkeepsie](https://www.expedia.ca/lp/flights/6056317/flights-from-poughkeepsie)
-   [Flights from Milton](https://www.expedia.ca/lp/flights/6288971/flights-from-milton)
-   [Flights from Toronto (YYZ) to New York (NYC)](https://www.expedia.ca/lp/flights/yyz/nyc/toronto-to-new-york)

-   [Culinary Institute of America](https://www.expedia.ca/Culinary-Institute-Of-America-Hyde-Park.d6093745.Vacation-Attraction)
-   [Franklin D. Roosevelt Presidential Library and Museum](https://www.expedia.ca/Franklin-D-Roosevelt-Presidential-Library-And-Museum-Hyde-Park.d6127069.Vacation-Attraction)
-   [Poughkeepsie Vacations](https://www.expedia.ca/Poughkeepsie.d6056317.Destination-Travel-Guides)
-   [Visit Poughkeepsie](https://www.expedia.ca/Poughkeepsie.dx6056317)

-   [Car rental Poughkeepsie](https://www.expedia.ca/Car-Rentals-In-Poughkeepsie.d6056317.Car-Rental-Guide)
-   [Hertz Rental Cars in Poughkeepsie](https://www.expedia.ca/Hertz-Car-Rentals-In-Poughkeepsie.d6056317-c40.Car-Rental-Guide-Suppliers)
-   [Rent A Wreck Rental Cars in Poughkeepsie](https://www.expedia.ca/Rent-A-Wreck-Car-Rentals-In-Poughkeepsie.d6056317-c33.Car-Rental-Guide-Suppliers)

-   [Things to do in Poughkeepsie](https://www.expedia.ca/Things-To-Do-In-Poughkeepsie.d6056317.Travel-Guide-Activities)

-   [Book Vacation Homes in Highland on Expedia.com](https://www.expedia.com/Highland-Private-Vacation-Homes.d115050-aaPrivateVacationHomes.Travel-Guide-Accommodation)