Hillsdale Vacation Rentals

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Vacation Rentals in Hillsdale

Micosta Leisure Inn
Balcony
Micosta Leisure Inn
3.0 star property
8.8 out of 10, Excellent, (71)
"super nice and clean I think I will return the only thing is that it is under construction."
The price is CA $171
CA $193 total
includes taxes & fees
May 14 - May 15
Micosta Leisure Inn
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
7 bedrooms, iron/ironing board, cribs/infant beds, travel crib
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (29)
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
Property grounds
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
10.0 out of 10, Exceptional, (64)
"This is our 4th time staying here! And it won't be the last. Weather perfect for sitting on the deck with coffee and cocktails watching the creek slowly flow by. Beds are super comfortable with the BEST pillows. Everything you need for a relaxing stay. O.J, incredible bread with butter and strawberry preserves to greet you! Only a mile from town. An easy walk. Will see you again soon!"
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
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Fox Hollow Luxury Ranch Laurel Lake
Fridge, microwave, oven, stovetop
Fox Hollow Luxury Ranch Laurel Lake
9.4 out of 10, Exceptional, (12)
"Generous facility, nicely located, accommodating host."
Fox Hollow Luxury Ranch Laurel Lake
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Interior
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Charming Artist's Retreat
Fridge, microwave, oven, stovetop
Charming Artist's Retreat
10.0 out of 10, Exceptional, (112)
"The property is lovely and the entire experience of working with Maureen was amazing. Looking forward to a return trip!"
Charming Artist's Retreat
Quintessential 6-BR Berkshires Lodge
Exterior
Quintessential 6-BR Berkshires Lodge
10.0 out of 10, Exceptional, (4)
"We had a great time. Place is amazing. Highly recommend. We had four different families and we never felt cramped. Lovely open main room allowed us to stay connected. Bedrooms were nice and spacious, good bed options. Nice decor."
Quintessential 6-BR Berkshires Lodge
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Private kitchen
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
10.0 out of 10, Exceptional, (10)
"We had a lovely weekend at this updated farm house. The house is a great combination of old comfortable farm house and updated and clean kitchens and bathrooms. We loved having Artie, the kitty, as our welcoming party."
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Rockspring by AvantStay | Huge Berkshires Estate
Interior
Rockspring by AvantStay | Huge Berkshires Estate
8.8 out of 10, Excellent, (10)
"We stayed with friends and family and had plenty of room. The separate game room is great! The house was as pictured and described. It is close to a few ski mountains and Great Barrington. We would happily stay at RockSpring or a different AvantStay again!"
Rockspring by AvantStay | Huge Berkshires Estate
Charming Cottage in Private Lake Community (Pet-Friendly!)
Fridge, microwave, oven, stovetop
Charming Cottage in Private Lake Community (Pet-Friendly!)
9.6 out of 10, Exceptional, (14)
"Clean and comfortable. We had a great time visiting with friends and family at my daughters baby shower!"
Charming Cottage in Private Lake Community (Pet-Friendly!)
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
Fridge, microwave, oven, stovetop
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
6.0 out of 10, (2)
"Be aware they will not proactively provide you with a local host name or contact info. It was very difficult to get Vacasa support to help me get this info to resolve wifi issue - like hours long to get them to just give me the property managers info and even then, they wouldn't give it to me, just had them contact me. Otherwise, amazing pool and great location. Outdated indoors but clean to the extent that it could be. Utensils were dirty and tons of flies in the house upon arrival - like 50...
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
Serene Acreage - Pond - Hiking Trails Nearby
Property grounds
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, (4)
"Perfect place to relax and have dogs as part of a mini vacation. Very clean, organized, and provided helpful local information. Will definitely stay there again."
Serene Acreage - Pond - Hiking Trails Nearby
Private Estate, Heated YEARROUND Outdoor Pool
Fridge, microwave, oven, stovetop
Private Estate, Heated YEARROUND Outdoor Pool
10.0 out of 10, Exceptional, (8)
"The pictures simply do not do this place justice, it’s an incredible home. Our friend group was cozy all weekend! We loved the hot tub/pool, the really interesting artwork, the driving range mat and basketball hoop. Plenty of towels and kitchen supplies. The in law apartment (which we didn’t use as sadly part of our group was unable to join us) is attached to the main home and is so cute. We had a small issue upon arrival and the hosts were immediately responsive with us troubleshooting and...
Private Estate, Heated YEARROUND Outdoor Pool
Romantic Log Cabin on Privately-Owned Lake with Fireplace
Bar (on property)
Romantic Log Cabin on Privately-Owned Lake with Fireplace
9.8 out of 10, Exceptional, (68)
"The cabin was wonderful and was stocked will everything we needed and more. The lake was both beautiful and private to just this cabin. The grounds had several trails that we enjoyed."
Romantic Log Cabin on Privately-Owned Lake with Fireplace
Hamptons on the Hudson in South Saugerties
Property grounds
Hamptons on the Hudson in South Saugerties
9.8 out of 10, Exceptional, (6)
"Rainy but had a great time at the Wool and Sheep Festival.The fall colors were beautiful."
Hamptons on the Hudson in South Saugerties
Moose Lodge by AvantStay | Luxe Berkshires Escape
Outdoor dining
Moose Lodge by AvantStay | Luxe Berkshires Escape
10.0 out of 10, Exceptional, (11)
"We had a wonderful time at the Moose Lodge. It was perfect for our family. Very clean, everything we needed and the property managers were extremely communicative. Thank you!"
Moose Lodge by AvantStay | Luxe Berkshires Escape
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
TV, fireplace, DVD player, books
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, (39)
"This house was the perfect get away house for out family! The place was clean and the kitchen well stocked! We had wonderful large family dinners and enjoyed heading into town for meals and fun too. We had the best hikes with are wonderful dog that we got to include, it was a very special week. Great location and the most peaceful and amazing views from the deck and the dock. Would stay here again for sure! Thank you for sharing your home."
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Sexiest Lil Cabin in Saugerties, NY
Exterior
Sexiest Lil Cabin in Saugerties, NY
8.4 out of 10, Very good, (6)
"We loved our stay here, it was the perfect short getaway. Thanks Alexandria!"
The price is CA $150
CA $178 total
includes taxes & fees
May 14 - May 15
Sexiest Lil Cabin in Saugerties, NY
Stockbridge Home, Come Experience The Berkshires!
Fridge, microwave, oven, stovetop
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (11)
"We have a lovely stay, house is super clean and has all you need to relax and enjoy the space. I loved the fact we could take our small dog with us to make it a lovely family’s vacation. The house is central to everything and all towns in the Berkshires which we appreciated so much. We will return and would recommend to other highly also."
Stockbridge Home, Come Experience The Berkshires!
Peaceful, Post and Beam Loft, Sleeps 9
TV, DVD player
Peaceful, Post and Beam Loft, Sleeps 9
10.0 out of 10, Exceptional, (8)
"beautifully stay for couples."
Peaceful, Post and Beam Loft, Sleeps 9
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See all available properties in Hillsdale
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.

Hillsdale Vacation Rental Travel Info

Number of vacation rentals
4
Popular accommodation
Hillsdale private vacation homes
Known landmarks
Catamount Aerial Adventure Park and High Falls Trail
International airport
Albany, NY (ALB-Albany Intl.)

Other types of properties in Hillsdale you may be interested in

Life House Berkshires
Lobby
Life House Berkshires
3.5 star property
9.0 out of 10, Wonderful, (236)
"It’s the perfect place to go for a weekend or weeklong stay and be as isolated as social as you want. The towns nearby are fantastic. Will definitely be back a lot "
The price is CA $135
CA $151 total
includes taxes & fees
May 20 - May 21
Life House Berkshires
The Red Lion Inn
Outdoor pool, sun loungers
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (881)
"Great service from the staff and a beautiful place to relax and unwind"
The price is CA $171
CA $222 total
includes taxes & fees
May 21 - May 22
The Red Lion Inn
Quality Inn
Lobby
Quality Inn
2.5 star property
8.0 out of 10, Very good, (890)
"Ok for the money."
The price is CA $134
CA $150 total
includes taxes & fees
May 19 - May 20
Quality Inn
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.

Everything you need to know about Hillsdale vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Hillsdale vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Hillsdale vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Hillsdale vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hillsdale. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Hillsdale vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Hillsdale vacation rentals we have selected for you start as low as CA $150 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Hillsdale rentals

At Expedia, we put the best Hillsdale vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Hillsdale rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Hillsdale vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Hillsdale. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a vacation rental in Hillsdale?

Yes, we have vacation rentals close to the most popular attractions in Hillsdale, or you can go with a more remote option if you'd like a relaxing place to stay. Hillsdale is known for its coffeehouses and ski areas.

What are some of the best vacation rentals that Hillsdale has to offer?

Fox Hollow Luxury Ranch Laurel Lake: This vacation home rental outside of Hillsdale is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Hillsdale?

With 46 Expedia vacation rentals, you're sure to find just the right place for your Hillsdale stay.

What’s there to see and do in Hillsdale?

Explore the area and family-friendly sights such as Hornets Nest Paintball, or get out into nature at a spot like Copake Lake. While here, Catamount Aerial Adventure Park and Catamount Ski Area are other places worth a visit.

What’s a vacation rental in Hillsdale like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Hillsdale. Vacation rentals offer extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for families.

Recent reviews of Hillsdale properties
Expedia verified reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

5/5 Excellent
"Would definitely come back"
A verified traveller stayed at The Yankee, Trademark Collection by Wyndham
Posted 2 days ago
The Yankee, Trademark Collection by Wyndham