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In two weeks
Sep 19 - Sep 21
In two months
Oct 31 - Nov 2
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Nov 28 - Nov 30
In four months
Dec 26 - Dec 28

Cottages in Hillsdale

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

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

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
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, (88)
"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
Exterior

Rose Cottage

9.0 out of 10, Wonderful, (7)
"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 ￥29,436
￥59,514 total
includes taxes & fees
Sep 4 - Sep 5
The Blue Elm - A Historic Berkshire Cottage
Charming Cottage in the Heart of Catskill & Pet Friendly
Exterior

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
Perfect Vacation Get Away - Historical New Marlborough
Exterior

Perfect Vacation Get Away - Historical New Marlborough

9.2 out of 10, Wonderful, (57)
"Lovely place!"
The price is ￥22,077
￥40,688 total
includes taxes & fees
Oct 1 - Oct 2
Perfect Vacation Get Away - Historical New Marlborough
Reset and Relax in Luxury Cottage
Property grounds

Reset and Relax in Luxury Cottage

10.0 out of 10, Exceptional, (40)
"We had a great long weekend at this wonderful property. The absolute cleanest property we ever visited. The owner made sure everything was ready and stayed in touch to check for any concerns. Great location as a base to explore Rhinebeck, Red Hook and Hyde park. Or just sit and relax. "
Reset and Relax in Luxury Cottage
4 Mi to Dtwn Catskill: Mtn-view Home
House (4 Bedrooms) | Front of property

4 Mi to Dtwn Catskill: Mtn-view Home

3.0 star property
4 Mi to Dtwn Catskill: Mtn-view Home
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
Experience Peace in this Beautiful country cottage nestled beneath the mountains
Exterior

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 ￥19,604
￥46,288 total
includes taxes & fees
Sep 3 - Sep 4
Experience Peace in this Beautiful country cottage nestled beneath the mountains
Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake
Outdoor dining

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
Private hot tub + Modern Cottage
Exterior

Private hot tub + Modern Cottage

9.8 out of 10, Exceptional, (7)
"The property had everything we needed. We enjoyed our stay immensely."
Private hot tub + Modern Cottage
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Outdoor dining

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
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
Hits Adjacent | Pet Friendly | Caraway Cottage
Exterior

Hits Adjacent | Pet Friendly | Caraway Cottage

10.0 out of 10, Exceptional, (11)
"We enjoyed our stay, nice location "
The price is ￥36,795
￥71,783 total
includes taxes & fees
Sep 14 - Sep 15
Hits Adjacent | Pet Friendly | Caraway Cottage
Saugerties Cottage - relaxing home in nature, close to downtown, HITS & hikes
Exterior

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.
Exterior

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

10.0 out of 10, Exceptional, (11)
"Great spot!"
The price is ￥16,190
￥28,023 total
includes taxes & fees
Oct 1 - Oct 2
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
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
Accommodation
168 Cottages
Lowest Price
￥16,190
Highest Price
￥36,795

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Explore a world of travel with Expedia

Frequently asked questions

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What is there to do in Hillsdale near my cottage?
The ideal travel accessory is a well-thought-out travel plan. Catamount Aerial Adventure Park is a wonderful spot to kick off your exploration of Hillsdale.