Hillsdale Vacation Rentals from $148: Search Short-Term Rentals

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

Cozy Riverside Berkshires Retreat : This vacation home rental outside of Hillsdale is located on a river and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and kitchenware, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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Our top choices for Hillsdale vacation rentals

Classic Tent, Garden View | Outdoor dining

1. Gatherwild Ranch

Germantown

$194 nightly

Aug 26 - Aug 27

Total with taxes and fees

2. Micosta Leisure Inn

Hudson

philippe

$133 nightly

Aug 9 - Aug 10

Total with taxes and fees

3. Berkshire Mountain Lodge

Pittsfield

Joseph

$138 nightly

Aug 30 - Aug 31

Total with taxes and fees

4. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Catskill

Enior

$218 nightly

Sep 7 - Sep 8

Total with taxes and fees

5. Mtn-view Retreat in Huson Valley: Great for Groups

Hudson

$661 nightly

Aug 9 - Aug 10

Total with taxes and fees

6. Sleepy Hollow Lake Home w/ Deck, Pool Access!

Coxsackie

audrey

$548 nightly

Aug 19 - Aug 20

Total with taxes and fees

7. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Stephentown

$499 nightly

Aug 9 - Aug 10

Total with taxes and fees

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Top Hillsdale Hotel Reviews

Berkshire Mountain Lodge

8/10 Good

"We would come back here, even though there are quirky aspects to it that make it less than ideal. Overall, it's a good spot that seems like it was built in the fifties (has an old school vibe of a classic lodge), though it's only 20 years old.. What we liked: super clean, very spacious, a full kitchen, a comfortable bed, free parking, and a relatively reasonable rate. What needs improvement: We requested a quiet room and were put on the side where there is a noisy street. It was ok with earplugs. There is no housekeeping during the stay, which was fine for 3 nights, but would get old for longer. The door between the bedroom and living room needs to be fixed and didn't close fully. The toilet made a loud, running noise for 2 minutes with each flush. The handle on the fridge door broke off with normal use. We reported all of these, and none were addressed while we were there. The staff said they would send maintenance, but didn't, and didn't mention that they couldn't fix these items. Finally, we were charged a $22 resort fee that was supposed to include coffee. While they have a lovely espresso machine, no decaf was offered. As mentioned, even with the minor drawbacks, and knowing that it's more of a time share kind of place, where there's no sort of concierge service, it has many positive qualities that make it an overall good spot."

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

8/10 Good

"Stayed for two nights in a 2 bedroom villa. The place was very clean, beds and bedding were comfortable. The place could stand a refresh - more so the kitchen and bathrooms but not terribly awful by any means. The area of the property where we stayed was quiet and peaceful."

The Red Lion Inn

10/10 Excellent

"Escaped into another world on each floor's hallway-the memorabilia and artwork spoke of an honest, New England history. The atmosphere was perfect for a genuine, original immersion into New England's past and LOVED going up and down the 150yr old elevator! Meals delicious w/excellent service. Only one issue we had: the AC in the room was difficult to adjust and were quite chilled even w/turning the thermostat up to 80 deg!!!!!!!!! as suggested by the front desk. Shall make this a yearly visit!"

Quality Inn Great Barrington

10/10 Excellent

"Very nice front desk staff-courteous, upbeat, helpful. Room was clean but leftover trash in bin and no ice tray in refrigerator. VERY comfortable bed. Train in middle of the night was a throwback experience to a different age-i liked it but some would be frightened of the noise. Excellent location."

Find out more about Hillsdale

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Hillsdale in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $148 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

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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?

Cozy Riverside Berkshires Retreat: This vacation home rental outside of Hillsdale is located on a river and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and kitchenware, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Hillsdale?

With 49 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?

Copake Lake and Mosquito Island are a couple of lovely local spots to get outside and enjoy nature. 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.

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Check prices for these dates

Our top choices for Hillsdale vacation rentals

1. Gatherwild Ranch

2. Micosta Leisure Inn

3. Berkshire Mountain Lodge

4. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

5. Mtn-view Retreat in Huson Valley: Great for Groups

6. Sleepy Hollow Lake Home w/ Deck, Pool Access!

7. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Find vacation rentals that suit your style

Top Hillsdale Hotel Reviews

Berkshire Mountain Lodge

The Yankee Inn

Berkshires Untold

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

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

The Red Lion Inn

Best Western Plus Berkshire Hills Inn & Suites

Quality Inn Great Barrington

Quality Inn Lee - Lenox South

Find out more about Hillsdale

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