Hillsdale Rentals

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

156 Houses

(1) Excellent 

18

Hillhouse Log Cabin

New York / Hillsdale

Hillsdale log cabin

3 13 2 nights min

  • 3 bedrooms
  • sleeps 13
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning
“rest,relax,recharge” It's a Beautiful home that has all the modern conveniences. It's quiet, quaint and had just what I needed to get away from it all. I enjoyed morning coffee on the back deck among the trees and afternoon walks in the woods. A perfe
…see more

Price per night from

$425

Price per night from

$425

(17) Excellent 

31

Beautifully decorated & immaculate log chalet

New York / Hillsdale

Hillsdale log cabin

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$175

Price per night from

$175

48

Total Privacy! Tanglewood Retreat With Berkshire Views!

New York / Hillsdale

Hillsdale house

5 14 2 nights min

  • 5 bedrooms
  • sleeps 14
  • 2 nights min
  • Ask about children

Price per night from

$600

Price per night from

$600

(3) Excellent 

11

Overnight at Althouse -Higgins

New York / Hillsdale

Hillsdale apartment

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$175

Price per night from

$175

Great rentals within 20 miles that match your search

Distance approx 14.3 km from Hillsdale

24

3BR Lee House w/ Easy Access to Main Street!

Berkshires / Lee

Lee house

1 10 min stay varies

  • 1 bedroom
  • sleeps 10
  • min stay varies
  • Ski
  • Child Friendly

Price per night from

$239

Responds fast!
avg. 46 minutes

Price per night from

$239

Distance approx 10.63 km from Hillsdale

(1) Excellent 

17

Restored 1886 Eyebrow Colonial

Berkshires / Stockbridge

Stockbridge house

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$214

Price per night from

$214

Distance approx 10.27 km from Hillsdale

13

Designer Loft Style Residence

Berkshires / Sheffield

Sheffield house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$448

Price per night from

$448

Distance approx 15.98 km from Hillsdale

31

Lakefront house , great lake and mountain views

Catskill Region / Athens

Athens house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$313

Price per night from

$313

Distance approx 18.9 km from Hillsdale

7

Secluded House in the Woods w/ Year Round Hot Tub

New York / Red Hook

Red Hook house

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$200

Price per night from

$200

Distance approx 10.17 km from Hillsdale

(4) Excellent 

10

Comfortable Farmhouse in the Berkshires

Berkshires / West Stockbridge

West Stockbridge farmhouse

5 12 2 nights min

  • 5 bedrooms
  • sleeps 12
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$325

Price per night from

$325

Distance approx 10.82 km from Hillsdale

(7) Excellent 

18

Plan your holidays in the Berkshires. Forecasting plenty of snow and mild temps.

Berkshires / West Stockbridge

West Stockbridge house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Pet Friendly
“A memorable weekend getaway includes the most perfect house..” My husband and I had the pleasure to rent out this house last summer with another married couple and their son. Although our daughter and their son truly enjoyed Tanglewood and our visits
…see more

Price per night from

$274

Price per night from

$274

Distance approx 14.5 km from Hillsdale

24

NEW! Cozy Lenox Home 1.5 Mi. to Tanglewood Music!

Berkshires / Lenox

Lenox house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly

Price per night from

$375

Responds fast!
avg. 2 hours 0 minutes

Price per night from

$375

Distance approx 12.94 km from Hillsdale

(1) Excellent 

20

Renovated Barn

Connecticut / Taconic

Taconic house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$349

Responds fast!
avg. 32 minutes

Price per night from

$349

Distance approx 14.01 km from Hillsdale

(1) Excellent 

21

Berkshire Country Estate - The Library Suite

New York / Old Chatham

Old Chatham house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly

Price per night from

$150

Price per night from

$150

Distance approx 14.6 km from Hillsdale

18

Gracious 3-BR Garden Apt. in the Heart of Hudson

New York / Hudson

Hudson apartment

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$249

Price per night from

$249

Distance approx 12.9 km from Hillsdale

30

Evergreen Pines Country Estate Villa

New York / Ancram

Ancram house

4 8 1 night min

  • 4 bedrooms
  • sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$1,999

Price per night from

$1,999

Distance approx 16.22 km from Hillsdale

24

Beautiful Lakefront Berkshire Rental

Berkshires / Monterey

Monterey house

5 6 7 nights min

  • 5 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$420

Responds fast!
avg. 3 hours 51 minutes

Price per night from

$420

Distance approx 13.73 km from Hillsdale

(2) Excellent 

18

Mussmacher Porch

New York / Hudson

Hudson apartment

3 9 1 night min

  • 3 bedrooms
  • sleeps 9
  • 1 night min
  • Ski
  • Child Friendly

Price per night from

$125

Responds fast!
avg. 47 minutes

Price per night from

$125

Distance approx 11.53 km from Hillsdale

26

3BD Newly Rennovated Contempoary Near Stockbridge

Berkshires / Stockbridge

Stockbridge house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$299

Price per night from

$299

Distance approx 10.61 km from Hillsdale

16

Olde York Farm Distillery Suite

New York / Claverack

Claverack farmhouse

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$250

Price per night from

$250

Distance approx 14.05 km from Hillsdale

16

Roaring Rapids Cottage

New York / Columbiaville

Columbiaville house

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Nearest beach 3 mi
  • Ask about children
  • Air conditioning

Price per night from

$250

Price per night from

$250

Distance approx 16.24 km from Hillsdale

(1) Excellent 

8

Writer's Room at Chestnut Lodge

Berkshires / Lee

Lee b and b

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 8 mi
  • Ask about children
  • Air conditioning

Price per night from

$175

Responds fast!
avg. 1 hour 45 minutes

Price per night from

$175

Distance approx 16.24 km from Hillsdale

7

the BIG room at chestnut lodge

Berkshires / Lee

Lee b and b

1 6 2 nights min

  • 1 bedroom
  • sleeps 6
  • 2 nights min
  • Ask about children
  • Pet Friendly

Price per night from

$200

Responds fast!
avg. 1 hour 45 minutes

Price per night from

$200

Distance approx 10.4 km from Hillsdale

22

Vacation Home on 10 Acres with Pool and Spa

Berkshires / Stockbridge

Stockbridge house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Ask about pets

Price per night from

$750

Price per night from

$750

Distance approx 7.61 km from Hillsdale

(1) Very Good 

4

Cozy Copake Lake Cottage

New York / Copake

Copake house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Ask about pets

Price per night from

$107

Price per night from

$107

Distance approx 14.31 km from Hillsdale

15

House share/room for rent

Berkshires / Lee

Lee room

1 1 1 night min

  • 1 bedroom
  • sleeps 1
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 3 mi

Price per night from

$67

Price per night from

$67

Distance approx 9.95 km from Hillsdale

4

Horse Room

Berkshires / Stockbridge

Stockbridge farmhouse

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$150

Price per night from

$150

Distance approx 9.78 km from Hillsdale

24

Cozy Stockbridge Home - Walk To Golf Course!

Berkshires / Stockbridge

Stockbridge house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$209

Responds fast!
avg. 55 minutes

Price per night from

$209

Distance approx 18.78 km from Hillsdale

24

Historic Catskill Village Suite w/Breakfast & Pool

Catskill Region / Catskill

Catskill apartment

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$155

Responds fast!
avg. 2 hours 21 minutes

Price per night from

$155

Distance approx 14.16 km from Hillsdale

13

Garfield House

Maine / Lee

Lee apartment

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$175

Price per night from

$175

Distance approx 14.19 km from Hillsdale

25

NEW! Restored Hudson Home w/ Views-Walk Downtown!

New York / Hudson

Hudson house

4 7 min stay varies

  • 4 bedrooms
  • sleeps 7
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$200

Responds fast!
avg. 1 hour 39 minutes

Price per night from

$200

Distance approx 14.01 km from Hillsdale

19

Berkshire Country Estate - Rose Suite

New York / Old Chatham

Old Chatham villa

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly

Price per night from

$170

Price per night from

$170

Distance approx 6.63 km from Hillsdale Show on Map

(1) Very Good 

14

Cozy and clean in Gt Barrington- available for October

Berkshires / Great Barrington

Great Barrington house

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Nearest beach 2 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$150

Responds fast!
avg. 3 hours 28 minutes

Price per night from

$150

Distance approx 14.6 km from Hillsdale

20

Blue SKies

New York / Hudson

Hudson apartment

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Child Friendly

Price per night from

$249

Price per night from

$249

Distance approx 13.09 km from Hillsdale

17

Picturesque 19th century home on 3 private acres

Berkshires / New Marlborough

New Marlborough house

4 7 min stay varies

  • 4 bedrooms
  • sleeps 7
  • min stay varies
  • Child Friendly
  • Private garden

Price per night from

$150

Price per night from

$150

Distance approx 10.27 km from Hillsdale

18

1 Bedroom Hudson Valley Farm House

New York / Craryville

Craryville guest house

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Child Friendly

Price per night from

$320

Price per night from

$320

Distance approx 14.48 km from Hillsdale

30

Palazzo Hudson: a light filled home BR2

New York / Hudson

Hudson house

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min

Price per night from

$240

Price per night from

$240

Distance approx 10.27 km from Hillsdale

18

Hudson Valley Farm House

New York / Craryville

Craryville house

5 12 2 nights min

  • 5 bedrooms
  • sleeps 12
  • 2 nights min
  • Child Friendly

Price per night from

$320

Price per night from

$320