Holiday Homes in Hinsdale

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Our top choices for Hinsdale holiday homes

Berkshires Cottage! Dog friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires Cottage! Dog friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (14 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is AU$540
includes taxes & fees
15 Mar - 16 Mar
Berkshires Cottage! Dog friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Florida Mountain Log Cabin

Florida Mountain Log Cabin
Florida
10.0 out of 10, Exceptional, (4 reviews)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is AU$477
includes taxes & fees
15 Mar - 16 Mar
Florida Mountain Log Cabin

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (28 reviews)
"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "
United States
maureen k.
The price is AU$384
includes taxes & fees
15 Mar - 16 Mar
Home in Great Barrington

Charlemont Chalet - A 15 Acre Private Retreat

Charlemont Chalet - A 15 Acre Private Retreat
Charlemont
The price is AU$858
includes taxes & fees
15 Mar - 16 Mar
Charlemont Chalet - A 15 Acre Private Retreat

North Getaway Cottage

North Getaway Cottage
Williamstown
9.2 out of 10, Wonderful, (24 reviews)
"We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!"
United States
Carole S.
The price is AU$613
includes taxes & fees
16 Mar - 17 Mar
North Getaway Cottage

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

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is AU$688
includes taxes & fees
15 Mar - 16 Mar
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (34 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
The price is AU$770
includes taxes & fees
15 Mar - 16 Mar
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is AU$476
includes taxes & fees
23 Mar - 24 Mar
3-bedroom house in beautiful Berkshires, close to amenities!

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.0 out of 10, Wonderful, (12 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is AU$427
includes taxes & fees
14 Mar - 15 Mar
Cozy Riverside Berkshires Retreat

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is AU$571
includes taxes & fees
29 Mar - 30 Mar
Near Tanglewood: Historic Summer Retreat

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (21 reviews)
"Comfy beds, clean, great big deck with a view. "
United States
Corinne T.
The price is AU$667
includes taxes & fees
15 Mar - 16 Mar
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Luxury Barn Retreat — All-Season Escape Awaits!

Luxury Barn Retreat — All-Season Escape Awaits!
East Chatham
10.0 out of 10, Exceptional, (2 reviews)
"Accommodations were even better than we expected. The rooms were very clean, and there are unique (and sometimes whimsical, other times thought-provoking) decorations/pictures throughout the barn. The kitchen was basically a chef’s kitchen- all appliances were top notch. The backyard was spacious, and even contained a (non-working) pay phone booth! My wife loved the swinging two-seat chair on the porch! "
United States
Timothy S.
The price is AU$870
includes taxes & fees
18 Mar - 19 Mar
Luxury Barn Retreat — All-Season Escape Awaits!

Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (2 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is AU$609
includes taxes & fees
15 Mar - 16 Mar
Riverbend Berkshire East Basecamp - 3 bedrooms available

The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful view, peaceful quiet area, cosy cabin."
United States
Anonymous traveller
The price is AU$512
includes taxes & fees
18 Mar - 19 Mar
The Greylock Cabin

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (10 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is AU$778
includes taxes & fees
16 Mar - 17 Mar
Treetop Hideaway in Tyringham

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.6 out of 10, Exceptional, (4 reviews)
"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."
United States
Paulo I.
The price is AU$625
includes taxes & fees
15 Mar - 16 Mar
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (4 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is AU$1,823
includes taxes & fees
22 Mar - 23 Mar
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
8.0 out of 10, Very good, (1 review)
"excellent communication with property manager."
United States
Nancy H.
The price is AU$790
includes taxes & fees
15 Mar - 16 Mar
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is AU$1,001
includes taxes & fees
23 Mar - 24 Mar
Spacious 5-bedroom house in charming Lee with WiFi

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Hancock
9.8 out of 10, Exceptional, (74 reviews)
"Had the best weekend skiing and enjoying family time in this amazing 3 story condo. Plenty of room for kids and grandkids to spread out. Short walk to the slopes made it so convenient for the skiers and a short ride down the mountain for the Littles in ski school. The unit was fully equipped with everything we needed. The views of the mountain breathtaking and the cozy fire at night was a nice bonus! Howie is an amazing host. Very responsive and helpful with all my questions. We will for sure be...
United States
Kim
The price is AU$775
includes taxes & fees
16 Mar - 17 Mar
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
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

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Hinsdale Holiday Homes information

Number of reviews
268
Accommodation
344 Holiday Homes
Lowest Price
AU$384
Highest Price
AU$1,823