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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

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

Quiet rustic cottage with shared lake access
Fridge, microwave, oven, stovetop

Quiet rustic cottage with shared lake access

10.0 out of 10, Exceptional, (105)
"Great hosts who made our stay enjoyable. Very peaceful location. "
Quiet rustic cottage with shared lake access
Two Bedroom Cottage Close To Town
Fridge, microwave, oven, stovetop

Two Bedroom Cottage Close To Town

9.0 out of 10, Wonderful, (20)
"Wonderful time..beautiful location. "
Two Bedroom Cottage Close To Town
Reset and Relax in Luxury Cottage
Property grounds

Reset and Relax in Luxury Cottage

10.0 out of 10, Exceptional, (32)
"Amazing floors, bathroom showers (wow!), and an awesome kitchen."
Reset and Relax in Luxury Cottage
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!
Charming Artist's Retreat
Fridge, microwave, oven, stovetop

Charming Artist's Retreat

10.0 out of 10, Exceptional, (134)
"Enjoyed our stay!"
Charming Artist's Retreat
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)
"Very nice and cozy and comfortable! "
Charming Cottage in Private Lake Community (Pet-Friendly!)
Family-Friendly Richmond Cottage w/ Private Yard
Property grounds

Family-Friendly Richmond Cottage w/ Private Yard

2.0 star property
10.0 out of 10, Exceptional, (4)
"Excellent property: would have liked to stay longer. "
Family-Friendly Richmond Cottage w/ Private Yard
Loblolly Cottage - Enchanting Retreat set among towering pines.
1 bedroom, desk, free WiFi, bed sheets

Loblolly Cottage - Enchanting Retreat set among towering pines.

10.0 out of 10, Exceptional, (37)
"My wife and I had a wonderful stay. Super cozy, romantic and accommodating. We had a wonderful time and William was very responsive. Would highly recommend and stay again. "
Loblolly Cottage - Enchanting Retreat set among towering pines.
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Miscellaneous

Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

10.0 out of 10, Exceptional, (3)
"Nestled among luxe lakefront properties, this tidy cabin was perfectly suited to relaxing in kayaks and family dinners. Near Great Barrington and lovely hikes. Exceeded all expectations for a last minute getaway."
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Hits Adjacent | Pet Friendly | Caraway Cottage
TV, fireplace, offices

Hits Adjacent | Pet Friendly | Caraway Cottage

10.0 out of 10, Exceptional, (5)
"We had a lovely stay, and wish we had stayed longer. The house was warm, spacious, clean, comfortable. Will definitely be back!"
The price is AED 738
AED 1,534 total
includes taxes & fees
18 May - 19 May
Hits Adjacent | Pet Friendly | Caraway Cottage
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, (9)
"Great spot!"
The price is AED 404
AED 699 total
includes taxes & fees
19 May - 20 May
Country Cottage with beautiful views and easy access to Catskills activities.
Rose Cottage
Outdoor dining

Rose Cottage

9.6 out of 10, Exceptional, (5)
"It was a beautiful location which gave me a chance to reset and decompress I had access to all the nearby attractions such as Wyndham Hunter and castigger falls"
Rose Cottage
The Blue Elm - A Historic Berkshire Cottage
Exterior

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (7)
"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 AED 735
AED 1,485 total
includes taxes & fees
12 May - 13 May
The Blue Elm - A Historic Berkshire 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
Charming Cottage in the Heart of Catskill & Pet Friendly
Beach

Charming Cottage in the Heart of Catskill & Pet Friendly

10.0 out of 10, Exceptional, (12)
"Really enjoyed my stay! Very thoughtful host. "
Charming Cottage in the Heart of Catskill & Pet Friendly
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, (4)
"This stay was exactly what we needed—quiet, cozy, and super relaxing. The house was well stocked for a comfortable visit, and the outdoor space was amazing for both us and our pup to explore. Bridget was so easy to communicate with, which made everything stress-free, and we loved the thoughtful honey gift—it made for the best tea moments. Highly recommend. "
The price is AED 511
AED 1,289 total
includes taxes & fees
12 May - 13 May
Experience Peace in this Beautiful country cottage nestled beneath the mountains
4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!
Fridge, microwave, stovetop, dishwasher

4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!

2.0 star property
10.0 out of 10, Exceptional, (1)
"This property was exactly as advertised and was in a safe and private location. The hosts perfectly accommodated our stay and we cannot be more thankful to them for a fully-functional house that was suitable for the adults and children. It was truly a pleasure to stay at this home."
4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!
Lake Views & Dock Access - Pittsfield Cottage!
Outdoor dining

Lake Views & Dock Access - Pittsfield Cottage!

10.0 out of 10, Exceptional, (1)
"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!
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!
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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Other property types in Hillsdale

Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
Fridge, oven, stovetop, dishwasher

Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!

10.0 out of 10, Exceptional, (11)
"Very comfortable, clean home with all the amenities. We really enjoyed our stay in the beautiful area. Big yard for outdoor fun. Close to many attractions."
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
Postcard Cabins Eastern Catskills
Exterior

Postcard Cabins Eastern Catskills

2.0 star property
8.8 out of 10, Excellent, (11)
"We always live these cabins & we've been coming for years!"
The price is AED 643
AED 833 total
includes taxes & fees
28 May - 29 May
Postcard Cabins Eastern Catskills
Micosta Leisure Inn
Balcony

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (96)
"Third or fourth time staying. Always a pleasure "
The price is AED 477
AED 515 total
includes taxes & fees
27 May - 28 May
Micosta Leisure Inn
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.