Title: Hillsdale Vacation Home Rentals from CA $198: Search Top Private Vacation Homes for Rent | Expedia.ca

  

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# Hillsdale Vacation Rentals

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## Check prices for these dates

Next weekend

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=183683&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=183683&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=183683&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=183683&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Hillsdale Vacation Homes

![Exterior](https://images.trvl-media.com/lodging/101000000/100060000/100053100/100053078/ffa8b349.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/101000000/100060000/100053100/100053078/59725e4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, offices](https://images.trvl-media.com/lodging/101000000/100060000/100053100/100053078/b650005a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/101000000/100060000/100053100/100053078/f9a0c9d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Perfect House In Hillsdale, Brings Friends & Fam

Hillsdale

8.4/10

Very good

(5)

"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "

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

Stefanie K.

CA $594

CA $1,131 total

includes taxes & fees

Nov 29 - Nov 30

[](https://www.expedia.ca/Hillsdale-Hotels-Perfect-House-In-Hillsdale.h100053078.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/40000000/40000000/39992500/39992472/4bb55136.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/40000000/40000000/39992500/39992472/6b994e21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom](https://images.trvl-media.com/lodging/40000000/40000000/39992500/39992472/30c1c015.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom](https://images.trvl-media.com/lodging/40000000/40000000/39992500/39992472/080b28d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sioux Tipi on Chloe's Lake

Saugerties

9.8/10

Exceptional

(6)

"This was such a cool experience Id love to go back! "

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

Brandon

CA $154

CA $204 total

includes taxes & fees

Nov 17 - Nov 18

[](https://www.expedia.ca/Kingston-Hotels-Sioux-Tipi-On-Chloes-Lake.h39992472.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/60000000/60000000/59995300/59995220/4b325a19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Combined shower/tub, hair dryer, towels, soap](https://images.trvl-media.com/lodging/60000000/60000000/59995300/59995220/15670ab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/60000000/60000000/59995300/59995220/90-00a818b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/60000000/60000000/59995300/59995220/f501a761.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### All the comforts of home

Hudson

9.2/10

Wonderful

(26)

"Peaceful, friendly, clean, wish I had more time to explore and hope to return one day! Thank you!!"

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

Barbara V.

CA $149

CA $198 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Hudson-Hotels-All-The-Comforts-Of-Home.h59995220.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/43b40eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/c3446830.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/8de4c71d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/06261f5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Near Tanglewood: Historic Summer Retreat

New Lebanon

9.6/10

Exceptional

(22)

"Very cozy and comfortable with everything we needed to make our stay enjoyable. The kitchen was well stocked, the bedrooms a good size with comfortable mattresses. The deck and the yard were lovely. This location is gem!"

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

Patty W.

CA $201

CA $536 total

includes taxes & fees

Nov 5 - Nov 6

[](https://www.expedia.ca/New-Lebanon-Hotels-Near-Tanglewood-Historic-Summer-Retreat.h99243554.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/fbef3554.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/6d1211ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/f0ba5959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/65181381.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Berkshires Home Near Tanglewood, Trails & Wineries

Lebanon Springs

9.0/10

Wonderful

(19)

"It was great - just what we were looking for. "

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

Kaye S.

CA $216

CA $554 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/New-Lebanon-Hotels-Historic-Berkshires-Home-Near-Tanglewood.h84357520.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112330000/112329100/112329053/257c1efe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112330000/112329100/112329053/w1160h747x0y0-755e89fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/113000000/112330000/112329100/112329053/w1116h773x4y3-f65b8cab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/113000000/112330000/112329100/112329053/w1160h774x6y4-08649e94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 2-bedroom Waterfront home with boat access in Saugerties

Saugerties

9.2/10

Wonderful

(7)

"Beautiful place on the water. We had a blast!"

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

Rich M.

CA $222

CA $634 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Saugerties-Hotels-Charming-2-Bedroom-Waterfront-Home-With-Boat-Access-In-Saugerties.h112329053.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/52bc41a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/dcb799f2.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/85000000/84680000/84672900/84672833/c50e9e6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/caf5dd09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Home in Great Barrington

Great Barrington

9.8/10

Exceptional

(25)

"We had a lovely one week stay at this property. The location was very convenient to all the restaurants and shops. The fall foliage was spectacular and truly enjoyed biking and hiking in the Berkshires."

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

Farida K.

CA $254

CA $413 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Great-Barrington-Hotels-Home-In-Great-Barrington.h84672833.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115500000/115491000/115490904/e45ad0c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/116000000/115500000/115491000/115490904/fbe651db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115500000/115491000/115490904/0c8f026d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/116000000/115500000/115491000/115490904/cff06c8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Catskill Stay w/ Deck & Fire Pit

Catskill

8.0/10

Very good

(2)

"The house was great for a weekend trip with family. We enjoyed cooking in the kitchen, playing games in the cozy living room, and roasting up some s'mores around the bonfire at night. The location was great, close to a grocery store and some nature trails, which was important for us. We all got great sleep in the comfy bedrooms."

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

Erin S.

CA $199

CA $611 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Catskill-Hotels-Catskill-Stay-W-Deck-Fire-Pit.h115490904.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658957/c0195267.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658957/4c35929b.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/121000000/120660000/120659000/120658957/c605aa42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658957/62efe3e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hudson Hot Tub & Pet Escape

Stottville

CA $153

CA $381 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Hudson-Hotels-Hudson-Hot-Tub-Pet-Escape.h120658957.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/104000000/103820000/103820000/103819908/c945b9f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/104000000/103820000/103820000/103819908/fee8af1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103820000/103820000/103819908/6b996d30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/104000000/103820000/103820000/103819908/d16bb4cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Luxurious Cabin, Catskills - The Tiny Nook

Catskill

10/10

Exceptional

(6)

"Great place. Exactly like the pictures. "

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

robert a.

CA $224

CA $477 total

includes taxes & fees

Nov 12 - Nov 13

[](https://www.expedia.ca/Catskill-Hotels-The-Tiny-Nook-Escape-The-City-Life-Relaxing-Getaway-Tucked-In-Catskills.h103819908.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/665b8282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, computer monitors](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/af920cc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/f26544ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/8f9296e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cheerful 3-bedroom cottage with woodstove

Sheffield

10/10

Exceptional

(40)

"The property was centrally located for skiing, and was a comfortable stay."

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

Kelly R.

CA $276

CA $632 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Sheffield-Hotels-Cheerful-3-Bedroom-Cottage-With-Woodstove.h75599864.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/84000000/83470000/83464900/83464810/6a099f33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83470000/83464900/83464810/08b843db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83470000/83464900/83464810/d75f5082.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/84000000/83470000/83464900/83464810/d929aaa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy & Comfortable Water-view Home in Saugerties

Saugerties

9.6/10

Exceptional

(5)

"Let me start off with how peaceful it was in the morning just sitting at the dining table facing the front sliding doors where the scenery was of a little lake across the street. We decided to book this house for Mother's day to enjoy a weekend away from the city life and it was perfect. The men in our family enjoyed the pool table, my grandfather was able to watch TV from the living room while the ladies enjoyed drinks in the kitchen area and still feeling like we were all in the same room. We...

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

Sara S.

CA $294

CA $938 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Saugerties-Hotels-The-Longview-House-Near-Saugerties-Lighthouse.h83464810.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/117000000/116730000/116728300/116728281/1f7567aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/117000000/116730000/116728300/116728281/1c68b50d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116730000/116728300/116728281/4ea11255.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, computer monitors](https://images.trvl-media.com/lodging/117000000/116730000/116728300/116728281/a00a49e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hot tub on water, 5min HITS, 20mi to Hunter skiing

Malden

10/10

Exceptional

(3)

"I recently had the pleasure of staying at this stunning property hosted by Matthew, Tonya, and David, and I cannot recommend them highly enough! From the moment we arrived, it was clear that they had gone above and beyond to ensure a seamless and fantastic experience for their guests.The breathtaking views of the Hudson River from the property were nothing short of spectacular, providing a perfect backdrop for relaxation and enjoyment. Every detail of the home was thoughtfully considered,...

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

don m.

CA $309

CA $1,078 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Malden-Hotels-River-Front-Luxury-Hot-Tub.h116728281.Hotel-Information)

![Game room](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/406cc767.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, eco-friendly cleaning products](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/780d89c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/c57b8d60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/862ec0e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pet Friendly Riverfront Home in Great Barrington

Great Barrington

8.8/10

Excellent

(3)

"Close to a great bakery and near to a farm market and shopping mall. "

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

Cristine C.

CA $268

CA $396 total

includes taxes & fees

Nov 14 - Nov 15

[](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/505c31c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/8d87241a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/64f95c5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/53261c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Great Barrington Get Away

Great Barrington

9.4/10

Exceptional

(25)

"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"

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

Elizabeth G.

CA $399

CA $726 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Great-Barrington-Hotels-Great-Barrington-Get-Away.h29615546.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821595/329257ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821595/a7b21f81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821595/a0287de3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821595/04c3bec8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bungalow in the Berkshires

Lee

10/10

Exceptional

(4)

"We had a lovely stay. Easy check in and communication was great. "

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

Dale G.

CA $385

CA $540 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Lee-Hotels-Bungalow-In-The-Berkshires.h111821595.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/a38bbe4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/44aa4835.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/adca2c72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/811d3663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

7.8/10

Good

(6)

"Very clean and spacious! We enjoyed our stay with our small pup!"

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

Ann C.

CA $376

CA $691 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-Home-W-Lake-And-Mountain-Views-Near-Skiing.h106650307.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/33000000/32810000/32807400/32807378/e3e0e9fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/33000000/32810000/32807400/32807378/d9fe6b36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/33000000/32810000/32807400/32807378/094a3cc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/33000000/32810000/32807400/32807378/8e812ffc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Valatie

10/10

Exceptional

(54)

"Great spot on the lake. Super quiet and relaxing."

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

vincent m.

CA $378

CA $752 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Albany-Hotels-Escape-To-Lakefront-Leisurehudson.h32807378.Hotel-Information)

![TV, video games](https://images.trvl-media.com/lodging/121000000/120450000/120449800/120449785/370d084b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/121000000/120450000/120449800/120449785/fd2ef68b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120450000/120449800/120449785/34e259bf.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/121000000/120450000/120449800/120449785/588af754.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### New! The Den on Denniston, with game room, movie theater, fire pit and more. Close To HITS Horse show & Hunter Mountain skiing

Saugerties

CA $214

CA $648 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Saugerties-Hotels-New-Denniston-Den.h120449785.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/104000000/103620000/103611900/103611832/w906h683x60y0-974ef863.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/104000000/103620000/103611900/103611832/dc67334d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/104000000/103620000/103611900/103611832/909d9f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/104000000/103620000/103611900/103611832/da5a53c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1BR Hudson Apartment, 3Min Walk To Warren St For Two - Apartment 1 - Pet Allowed

Hudson

CA $287

CA $535 total

includes taxes & fees

Nov 5 - Nov 6

[](https://www.expedia.ca/Hudson-Hotels-1BR-Hudson-Apartment.h103611832.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=2025-11-15&endDate=2025-11-16&regionId=183683&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&openPlayBack=true)

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## Top Hillsdale Hotel Reviews

![Holiday Inn & Suites Pittsfield-Berkshires by IHG](//images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg)

### Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent

"The restaurant was so delicious …the fries were the best fries I have ever had …will never forget how tasty they were !!!"

[](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information)

![The Red Lion Inn](//images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg)

### The Red Lion Inn

10/10 Excellent

"The Red Lion Hotel was a great place to stay!! I would definitley come back again and stay there! I loved the bar downstairs and the restaurant! Our room was perfect and we had lots of room! The bed was super comfy - a marshmallow bed!! LOL! The location was nice to walk to the different shops in town! Fun place! "

[](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information)

![Berkshires Untold](//images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg)

### Berkshires Untold

10/10 Excellent

"This property was great for our weekend getaway. It is conveniently located "

[](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information)

![Berkshire Mountain Lodge](//images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg)

### Berkshire Mountain Lodge

10/10 Excellent

"Excellent all the way around"

[](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information)

![Quality Inn](//images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg)

### Quality Inn

10/10 Excellent

"It was really nice staying here. The room was clean, bed was comfortable, and there was a mini-fridge that wasn't full of expensive drinks you're not supposed to touch! It was mostly quiet, except for the trains at night that pass behind the building. It is very close by to shops, cool architecture, and a nice walking path. Very safe area too. The breakfast wasn't the best, but it's free, and you can easily pop in to nearby restaurants if you want something better. The staff are very friendly and helpful. I would recommend staying here! It's a nice place to stay for the price."

[](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information)

![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](//images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c_y.jpg)

### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent

"Very clean and roomy lodge (2 bedrooms); conveniently located; has kitchen; recreational facilities a bit dated. Will come back again. "

[](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information)

![Holiday Inn Express Hotel & Suites Great Barrington by IHG](//images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg)

### Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent

"Excellent front desk staff. Ask for Steve. Very convenient to Monument Mountain and local ski resorts."

[](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information)

![Overlook Hotel](//images.trvl-media.com/lodging/119000000/118060000/118056600/118056521/88412f44_y.jpg)

### Overlook Hotel

10/10 Excellent

"We were in town for a wedding and elected to stay at the family owned Overlook Hotel. This hotel is under renovation and coming along nicely. The rehabilitated buildings come with luxurious fixtures and relaxing decor. A perfect retreat! Being that it is just up and running, some ammentities will need to catch up. If your stay in the near future requires anything in particular, be sure to communicate with the owners- i am certain the be sure you have all you need!"

[](https://expedia.ca/Saugerties-Hotels-Overlook-Hotel.h118056521.Hotel-Information)

![Holiday Inn Express Hotel & Suites West Coxsackie by IHG](//images.trvl-media.com/lodging/3000000/2600000/2591600/2591583/2081618e_y.jpg)

### Holiday Inn Express Hotel & Suites West Coxsackie by IHG

10/10 Excellent

"Perfect spot for an overnight stay when coming to the area"

[](https://expedia.ca/Albany-Hotels-Holiday-Inn-Express-Hotel-Suites-West-Coxsackie.h2591583.Hotel-Information)

## Find out more about Hillsdale

## Hillsdale Vacation Homes information

| Number of reviews | 249 |
| --- | --- |
| Accommodation | 673 Vacation Homes |
| Lowest Price | CA $198 |
| Highest Price | CA $1,131 |

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-   [Chatham Vacation Rentals](https://www.expedia.ca/Chatham-Vacation-Rentals.d6046736.Travel-Guide-VacationRentals)
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-   [Things to do in Hudson](https://www.expedia.ca/Things-To-Do-In-Hudson.d55762.Travel-Guide-Activities)

-   [Book Vacation Homes in Hillsdale on Expedia.com](https://www.expedia.com/Hillsdale-Private-Vacation-Homes.d183683-aaPrivateVacationHomes.Travel-Guide-Accommodation)