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Check prices for these dates

Next weekend
5 Sept - 7 Sept
In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct

Featured Cottages in Hillsdale

Our top choices for Hillsdale cottages

Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires
Dining

Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

2.0 star property
9.0 out of 10, Wonderful, (4)
"Cozy, serene and bucolic waterfront hideaway within driving distance of Tanglewood, Shakespeare & Company, Jacob's Pillow and all the wonderful food and cultural Berkshire gems! Julie and Russ were amazing hosts. Great communication and wonderful restaurant and museum suggestions. Definitely planning another long weekend retreat!"
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires
Charming Cottage in Private Lake Community (Pet-Friendly!)
Fridge, microwave, oven, stovetop

Charming Cottage in Private Lake Community (Pet-Friendly!)

10.0 out of 10, Exceptional, (33)
"We enjoyed ourselves,relaxed,visited had a very enjoyable bisit"
Charming Cottage in Private Lake Community (Pet-Friendly!)
Summer Lake Cottage, private beach, Berkshire Hills, small village
Exterior

Summer Lake Cottage, private beach, Berkshire Hills, small village

9.4 out of 10, Exceptional, (81)
"Wonderful lake retreat 🥾"
Summer Lake Cottage, private beach, Berkshire Hills, small village
Heaven Can't Wait, On Beautiful Kinderhook Lake!!
Property grounds

Heaven Can't Wait, On Beautiful Kinderhook Lake!!

9.8 out of 10, Exceptional, (86)
"Home our mother's 83rd birthday party cookout at the lake house with a few family members and it was a great day. Everyone loved the house. We enjoyed the stay"
Heaven Can't Wait, On Beautiful Kinderhook Lake!!
Rose Cottage
Outdoor dining

Rose Cottage

9.8 out of 10, Exceptional, (6)
"It's so peaceful there. It was lovely."
Rose Cottage
The Blue Elm - A Historic Berkshire Cottage
Exterior

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (10)
"Housing is just as beautiful as the pictures show and the residential neighborhood is quiet, conveniently situated. Hosts are very responsive. We really enjoyed our stay!! "
The price is AU$643
includes taxes & fees
28 Aug - 29 Aug
The Blue Elm - A Historic Berkshire Cottage
4 Mi to Dtwn Catskill: Mtn-view Home
House (4 Bedrooms) | Interior

4 Mi to Dtwn Catskill: Mtn-view Home

3.0 star property
4 Mi to Dtwn Catskill: Mtn-view Home
Perfect Vacation Get Away - Historical New Marlborough
Property grounds

Perfect Vacation Get Away - Historical New Marlborough

9.2 out of 10, Wonderful, (57)
"Lovely place!"
Perfect Vacation Get Away - Historical New Marlborough
Charming Cottage in the Heart of Catskill & Pet Friendly
Outdoor dining

Charming Cottage in the Heart of Catskill & Pet Friendly

10.0 out of 10, Exceptional, (14)
"Really enjoyed my stay! Very thoughtful host. "
Charming Cottage in the Heart of Catskill & Pet Friendly
Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake
Interior

Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake

10.0 out of 10, Exceptional, (7)
"Very cozy, very nice views, tranquil, serene. "
Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake
Experience Peace in this Beautiful country cottage nestled beneath the mountains
Property grounds

Experience Peace in this Beautiful country cottage nestled beneath the mountains

10.0 out of 10, Exceptional, (6)
"Nice house, well stocked and nice outdoor area/deck."
The price is AU$496
includes taxes & fees
3 Sept - 4 Sept
Experience Peace in this Beautiful country cottage nestled beneath the mountains
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Fridge, microwave, stovetop, dishwasher

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

10.0 out of 10, Exceptional, (3)
"We were there for 2 nights for visiting day at a camp in the Berkshires. The home is very comfortable and clean. We enjoyed our stay! "
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Reset and Relax in Luxury Cottage
Property grounds

Reset and Relax in Luxury Cottage

10.0 out of 10, Exceptional, (40)
"Amazing floors, bathroom showers (wow!), and an awesome kitchen."
Reset and Relax in Luxury Cottage
Hits Adjacent | Pet Friendly | Caraway Cottage
TV, fireplace, offices

Hits Adjacent | Pet Friendly | Caraway Cottage

10.0 out of 10, Exceptional, (11)
"We enjoyed our stay, nice location "
The price is AU$696
includes taxes & fees
1 Sept - 2 Sept
Hits Adjacent | Pet Friendly | Caraway Cottage
Creekside Cottage The Fitz House Red Hook NY
Exterior

Creekside Cottage The Fitz House Red Hook NY

10.0 out of 10, Exceptional, (4)
"We had a wonderful stay. Communication with host was excellent. Highly recommend the location for a couple."
Creekside Cottage The Fitz House Red Hook NY
Fun Getaway Lakehouse in the Hudson Valley
Terrace/patio

Fun Getaway Lakehouse in the Hudson Valley

10.0 out of 10, Exceptional, (15)
"We enjoyed our stay with friends. Conveniently located near the water, great amenities and very clean. The host was incredibly responsive and kind throughout!"
Fun Getaway Lakehouse in the Hudson Valley
Saugerties Cottage - relaxing home in nature, close to downtown, HITS & hikes
Property grounds

Saugerties Cottage - relaxing home in nature, close to downtown, HITS & hikes

10.0 out of 10, Exceptional, (5)
"quiet sanctuary close to Woodstock and saugerties"
Saugerties Cottage - relaxing home in nature, close to downtown, HITS & hikes
Country Cottage with beautiful views and easy access to Catskills activities.
Terrace/patio

Country Cottage with beautiful views and easy access to Catskills activities.

10.0 out of 10, Exceptional, (10)
"Great spot!"
The price is AU$337
includes taxes & fees
3 Sept - 4 Sept
Country Cottage with beautiful views and easy access to Catskills activities.
Charming Artist's Retreat
Exterior

Charming Artist's Retreat

9.8 out of 10, Exceptional, (140)
"Enjoyed our stay!"
Charming Artist's Retreat
Entire cottage in Berkshire Villiage
Books, stereo

Entire cottage in Berkshire Villiage

3.0 star property
9.8 out of 10, Exceptional, (6)
"The cottage was clean and as described. The street was very quiet."
Entire cottage in Berkshire Villiage
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 Hillsdale Hotel Reviews

Find out more about Hillsdale

Find out more about Hillsdale

Hillsdale Cottages information

Number of reviews
361
Accommodation
162 Cottages
Lowest Price
AU$337
Highest Price
AU$696

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Explore a world of travel with Expedia

Frequently asked questions

What is there to do in Hillsdale near my cottage?
Once you've unpacked your bags and settled in, head out and discover the fantastic things Hillsdale has for you to experience. Catamount Aerial Adventure Park is a great attraction to add to your itinerary.