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Hinsdale Vacation Rentals

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Vacation Rentals in Hinsdale

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Hinsdale
9.8 out of 10, Exceptional, (19)
"Rich was an amazing host. Beautiful lake and sunsets. I would love to stay there again"
United States
maria f.
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

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

Hinsdale
9.8 out of 10, Exceptional, (34)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
$375 nightly
The price is $419
Dec 8 - Dec 9
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2167)
"Great stay and beautiful scenery close to Jiminy’s Peak Ski slopes. They have a heated pool for winter weather and extra outdoor for the summer plus other family oriented amenities"
United States
Karla
$111 nightly
The price is $124
Dec 8 - Dec 9
Total with taxes and fees
Vacation Village in the Berkshires

Huttopia Berkshires

1.0 star property
Williamstown
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
$151 nightly
The price is $169
Dec 16 - Dec 17
Total with taxes and fees
Huttopia Berkshires

Jiminy Peak Mountain Resort

3.0 star property
Hancock
8.2 out of 10, Very Good, (987)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
$189 nightly
The price is $211
Dec 8 - Dec 9
Total with taxes and fees
Jiminy Peak Mountain Resort

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (135)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
United States
Cyril
The Ponds at Foxhollow

Pet Friendly Riverfront Home in Great Barrington

Great Barrington
9.4 out of 10, Exceptional, (6)
$253 nightly
The price is $283
Dec 8 - Dec 9
Total with taxes and fees
Pet Friendly Riverfront Home in Great Barrington

Peace and quiet on the lake

Sherwood Forest
9.6 out of 10, Exceptional, (230)
"Great communication, comfortable home, love the location"
United States
Susan C.
Peace and quiet on the lake

The Kemble- Built by a US Secretary of State in Lenox

Lenox
10.0 out of 10, Exceptional, (17)
"Perfect house for our family reunion. Everything was perfect."
United States
Michael C.
The Kemble- Built by a US Secretary of State in Lenox

Spacious 5-bedroom house in charming Lee with WiFi

Lee
8.0 out of 10, Very Good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
$666 nightly
The price is $743
Dec 14 - Dec 15
Total with taxes and fees
Spacious 5-bedroom house in charming Lee with WiFi

Bear Creek Cabin

Charlemont
10.0 out of 10, Exceptional, (43)
"We enjoyed our stay!!"
United States
Hillary S.
$536 nightly
The price is $599
Dec 8 - Dec 9
Total with taxes and fees
Bear Creek Cabin

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Great Barrington
10.0 out of 10, Exceptional, (28)
"Wonderful old house, very comfortable space for a large family gathering. The kitchen was well-equipped, and exceptionally clean. The host was communicative and responsive, although everything was so well-thought out on his part, we didn't have much need to talk to the hosts. Excellent location, less than five minutes to Great Barrington, and twenty to Tanglewood and Lenox. "
United States
Johnathan B.
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Experience Three Sisters Sanctuary in Goshen, MA

2.0 star property
Goshen
10.0 out of 10, Exceptional, (2)
"We had such a great time staying here as always. "
United States
David F.
Experience Three Sisters Sanctuary in Goshen, MA

Amore Estate - beautiful room with many places to explore and relax in.

Lenox
9.2 out of 10, Wonderful, (33)
"Beautiful property. The house and grounds, including a beautiful pool were amazing. Loved sitting on the porch and watching the birds.So much to do in the Berkshires, would definitely like to come back."
United States
Jacquie S.
Amore Estate - beautiful room with many places to explore and relax in.

Comfortable Berkshires retreat on mtn resort, SISO

Hancock
9.0 out of 10, Wonderful, (7)
"Kind and responsive host."
United States
Javier
$722 nightly
The price is $733
Dec 8 - Dec 9
Total with taxes and fees
Comfortable Berkshires retreat on mtn resort, SISO

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Stockbridge
10.0 out of 10, Exceptional, (135)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Sherwood Forest
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$337 nightly
The price is $376
Dec 8 - Dec 9
Total with taxes and fees
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Great Barrington
10.0 out of 10, Exceptional, (53)
"Great house for a large group. Lots of seating areas indoors and outdoors to accommodate kids and adults. House was very clean and kitchen was well stocked for cooking. We loved that the bedrooms were nicely separated for privacy, particularly the bunk rooms and nearby game room. Great for the late nighters in the bunch!Beautiful property and less than 10 mins to town."
United States
Carol R.
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Hancock Village Inn Near Jiminy Peak

Hancock
10.0 out of 10, Exceptional, (16)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
$1,026 nightly
The price is $1,111
Dec 9 - Dec 10
Total with taxes and fees
Hancock Village Inn Near Jiminy Peak

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Pittsfield
9.8 out of 10, Exceptional, (150)
"We had a fabulous stay at this lovely home in the Berkshires! The house was well equipped with everything needed to make our stay with our family so enjoyable. Great communication with the host in helping to resolve a small issue with loss of power on 2nd floor but was easily resolved."
United States
Sarah A.
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
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 Hinsdale Hotel Reviews

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 $124 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.

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 Kennedy Park. Bas Ridge Golf Course and Crane Museum of Papermaking 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.