Search Cottages in Hillsdale

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 158 Cottages in Hillsdale with updated reviews, rates, and availability.

Charming Artist's Retreat
Fridge, microwave, oven, stovetop

Charming Artist's Retreat

10.0 out of 10, Exceptional, (137)
"Enjoyed our stay!"
Charming Artist's Retreat
Quiet rustic cottage with shared lake access
Fridge, microwave, oven, stovetop

Quiet rustic cottage with shared lake access

10.0 out of 10, Exceptional, (107)
"Lovely lake house at the end of a long private road, perfect for a quiet getaway, close to all kinds of hiking and other natural attractions. Our hosts were super friendly and responsive. Highly recommended."
Quiet rustic cottage with shared lake access
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
Interior

Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location

Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Interior

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

9.2 out of 10, Wonderful, (11)
"A short getaway with family. "
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Reset and Relax in Luxury Cottage
Property grounds

Reset and Relax in Luxury Cottage

10.0 out of 10, Exceptional, (35)
"Amazing floors, bathroom showers (wow!), and an awesome kitchen."
Reset and Relax in Luxury Cottage
Cozy Berkshire cottage with fireplace.
Fridge, microwave, oven, stovetop

Cozy Berkshire cottage with fireplace.

10.0 out of 10, Exceptional, (24)
"Very nice house. Owners very helpful."
Cozy Berkshire cottage with fireplace.
Charming Cottage in Private Lake Community (Pet-Friendly!)
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (27)
"We enjoyed ourselves,relaxed,visited had a very enjoyable bisit"
Charming Cottage in Private Lake Community (Pet-Friendly!)
Perfect Vacation Get Away - Historical New Marlborough
Property grounds

Perfect Vacation Get Away - Historical New Marlborough

9.4 out of 10, Exceptional, (54)
"2nd time here so I give it excellent review."
The price is AED 496
AED 951 total
includes taxes & fees
12 Jun - 13 Jun
Perfect Vacation Get Away - Historical New Marlborough
Charming loft cottage in tranquil Germantown with WiFi, AC
Outdoor dining

Charming loft cottage in tranquil Germantown with WiFi, AC

10.0 out of 10, Exceptional, (2)
"My husband and I said “WOW” when we walked in the door. The space is absolutely gorgeous with plenty of room to spread out and a beautiful sleeping loft. The bed was super comfy and the apartment was so clean! It was decorated thoughtfully and had everything you could think of that you might need. Terri was a gracious host and let us check in early. Everything about this unit was exceptional!"
The price is AED 507
AED 881 total
includes taxes & fees
11 Jun - 12 Jun
Charming loft cottage in tranquil Germantown with WiFi, AC
Lake Views & Dock Access - Pittsfield Cottage!
Outdoor dining

Lake Views & Dock Access - Pittsfield Cottage!

10.0 out of 10, Exceptional, (2)
"This house was more than we could ask for it’s right on the water and has everything you could possibly forget handy! A all around, great place to enjoy nature and spend time with family and friends. Super straightforward didn’t need to ask the host any questions Will be booking here again! "
Lake Views & Dock Access - Pittsfield Cottage!
Beachwood Cottage
Beach nearby

Beachwood Cottage

10.0 out of 10, Exceptional, (3)
"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."
Beachwood Cottage
LAKE FRONT COTTAGE - YEAR ROUND HOT TUB
Terrace/patio

LAKE FRONT COTTAGE - YEAR ROUND HOT TUB

9.6 out of 10, Exceptional, (41)
"Great amenities, relaxing and extra touches were lovely"
LAKE FRONT COTTAGE - YEAR ROUND HOT TUB
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, (6)
"Very clean, cute house right on the lake. We enjoyed our time there. "
Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake
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
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
Heaven Cant Wait, On Beautiful Kinderhook
Property grounds

Heaven Cant Wait, On Beautiful Kinderhook

9.8 out of 10, Exceptional, (83)
"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 Cant Wait, On Beautiful Kinderhook
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, (9)
"Great spot!"
The price is AED 476
AED 784 total
includes taxes & fees
8 Jun - 9 Jun
Country Cottage with beautiful views and easy access to Catskills activities.
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Golf

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

9.0 out of 10, Wonderful, (37)
"My husband, dog and I enjoyed a long weekend here to celebrate our 8th wedding anniversary- the property was beautiful and quaint! Perfect for exploring on walks, or nearby to the Norman Rockwell museum. Would stay here again."
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
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, (5)
"Nice house, well stocked and nice outdoor area/deck."
The price is AED 459
AED 1,230 total
includes taxes & fees
9 Jun - 10 Jun
Experience Peace in this Beautiful country cottage nestled beneath the mountains
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
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

Why book your cottage in Hillsdale with Expedia?
We think that vacations should be easy, so if you’re looking for cottages in Hillsdale at an affordable rate, Expedia has got your back. Keep the budget under control and check in to an inexpensive option far away from the city rush, or splurge on a 5-star cottage to treat your loved ones.
How can I find cheap cottages in Hillsdale?
The quickest way to score cheap cottages in Hillsdale is with Expedia’s user-friendly filter tool. Refine your search results by star rating, budget and amenities to take advantage of awesome rates with only a few clicks.