Hinsdale Vacation Rentals from $109: Search Short-Term Rentals

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Our top choices for Hinsdale vacation rentals

1. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Hinsdale

Gerard C.

$475 nightly

Aug 12 - Aug 13

Total with taxes and fees

2. Hummingbird Haven is a woodland retreat surrounded by Nature and Local Charm.

Hinsdale

Joseph L.

$533 nightly

Aug 10 - Aug 11

Total with taxes and fees

3. Berkshire Mountain Lodge

Pittsfield

Joseph

$138 nightly

Aug 30 - Aug 31

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

4. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Dalton

Susan M.

$291 nightly

Aug 10 - Aug 11

Total with taxes and fees

5. Vacation Village in the Berkshires

Williamstown

Brooks

$106 nightly

Sep 7 - Sep 8

Total with taxes and fees

6. Huttopia Berkshires

Williamstown

GEORGINA

$97 nightly

Sep 7 - Sep 8

Total with taxes and fees

7. Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Hancock

Alicia S.

$241 nightly

Aug 11 - Aug 12

Total with taxes and fees

8. WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

Hancock

Matthew B.

$233 nightly

Aug 10 - Aug 11

Total with taxes and fees

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Top Hinsdale Hotel Reviews

Berkshire Mountain Lodge

8/10 Good

"Very nice space with a full kitchen. You can definitely stay here for a week comfortably. Personally, I didn’t think the bed or the pillows were that comfortable but other than that, it was great."

Jiminy Peak Mountain Resort

8/10 Good

"Jiminy Peak is located in an absolutely beatiful location in the Berkshires. And it has fun family-friendly summertime activities. But it could use some sprucing up. The pool liner is a little wrinkly and the hot tub is quite stained near the water line. In addition, our room had a nice 2-foot gouge in the wall seemingly caused by the corner of the armchair beneath it. It seems that could/should have been repaired before out arrival. And the dated counertops and fixtures are showing their age. That said, so am I! On the plus side: the iconic scenery, the friendly helpful staff, and the amenities. All in all, a good value for a family getaway. I would definitely recommend the prolerty overall."

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

10/10 Excellent

"My husband and I spent a wonderful summer weekend staying at this quiet, off-the-beaten-track room. The ability to relax on the porch or on the private dock (and on the water) is an experience far superior than any hotel stay. Rich was the consummate host, gracious, caring, easily accessible, and open to sharing activities to enjoy in the area. We stayed here to attend a few Tanglewood concerts, but there's so much to do and see in and around Hinsdale. We look forward to returning."

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 Hinsdale

Everything you need to know about Hinsdale 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 Hinsdale 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 Hinsdale vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Hinsdale vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hinsdale. 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 Hinsdale 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 $109 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 Hinsdale rentals

At Expedia, we put the best Hinsdale 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 Hinsdale 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 Hinsdale 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 Hinsdale. 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 Hinsdale?

Yes, we offer vacation rentals close to the most popular attractions in Hinsdale, or you can go with a secluded option if you're looking for relaxation. Hinsdale is known for its golf courses and restaurants. Make sure you have time to check out the shopping while you're in the area.

What's the top vacation rental in Hinsdale?

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets. : Visitors give good reviews to this Hinsdale vacation home rental, which offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals are there in Hinsdale?

Expedia has 8 vacation rentals for your stay in Hinsdale.

What can I see and do in Hinsdale?

While exploring the area, visit family-friendly sights like Berkshire Museum, or get outside and enjoy nature at Ashmere Lake. Bas Ridge Golf Course and Wahconah Falls State Park are a couple of places you'll find in the larger area.

What are vacation rentals like in Hinsdale?

Vacation rentals are privately owned properties you can reserve for a couple days or more in Hinsdale. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a family getaway.

Room 1

Check prices for these dates

Our top choices for Hinsdale vacation rentals

1. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

2. Hummingbird Haven is a woodland retreat surrounded by Nature and Local Charm.

3. Berkshire Mountain Lodge

4. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

5. Vacation Village in the Berkshires

6. Huttopia Berkshires

7. Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

8. WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

9. NEW RENO - Chalet-style farm loft near Tanglewood

10. Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

11. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

12. Penthouse Apartment on Park Street

13. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

14. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

15. Berkshires Apartment at the Stephentown Hotel

16. Real Estate: Therapy - Lake, Laundry, Love it

17. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

18. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

19. Getaway Near Mass MoCA, Great Hiking, Scenic Views

20. stylish Berkshires Retreat

Find vacation rentals that suit your style

Top Hinsdale Hotel Reviews

Berkshire Mountain Lodge

Berkshires Untold

Jiminy Peak Mountain Resort

The Yankee Inn

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

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

The Red Lion Inn

Best Western Plus Berkshire Hills Inn & Suites

Quality Inn Great Barrington

Find out more about Hinsdale

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