Hinsdale Rentals

Close

Enter dates for more accurate prices

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

149 Houses

8

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Berkshires / Hinsdale

Hinsdale house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Ask about pets
  • Private garden

Price per night from

$167

Price per night from

$167

Great rentals within 20 miles that match your search

Distance approx 13.09 km from Hinsdale

5

Cozy Modern Condo for the Berkshires

Berkshires / West Stockbridge

West Stockbridge condo

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$251

Responds fast!
avg. 2 hours 34 minutes

Price per night from

$251

Distance approx 11.15 km from Hinsdale

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

$276

Responds fast!
avg. 7 minutes

Price per night from

$276

Distance approx 12.09 km from Hinsdale

(4) Excellent 

20

Escape to the Berkshires!

Berkshires / Becket

Becket house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$316

Price per night from

$316

Distance approx 7.89 km from Hinsdale

31

Big Beautiful 7 bedroom 3 bath hot tub pool table

Berkshires / Pittsfield

Pittsfield house

7 18 2 nights min

  • 7 bedrooms
  • sleeps 18
  • 2 nights min
  • Child Friendly
  • Ask about pets

Price per night from

$345

Price per night from

$345

Distance approx 13.89 km from Hinsdale

4

The Meadow House 4 bdrm 4 bath house

New York / Stephentown

Stephentown house

4 12 2 nights min

  • 4 bedrooms
  • sleeps 12
  • 2 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$724

Price per night from

$724

Distance approx 12.18 km from Hinsdale

14

Christmas in The Berkshires

Berkshires / Hancock

Hancock condo

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child Friendly

Price per night from

$259

Price per night from

$259

Distance approx 13.76 km from Hinsdale

(13) Very Good 

13

Quiet Comfortable Cabin 5 Min. Walk to Lake

Berkshires / Becket

Becket house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Ask about pets
“Great winter getaway spot” My girlfriend and I spent new years at this awesome cabin tucked away in Becket, ma. It was quiet, clean, spacious and just about everything we could have asked for. The property was great, there was lots to do in nearby are
…see more

Price per night from

$172

Price per night from

$172

Distance approx 10.61 km from Hinsdale

12

Idyllic Berkshire Home perfect for families or friends with pool and gardens

Berkshires / Richmond

Richmond house

4 10 3 nights min

  • 4 bedrooms
  • sleeps 10
  • 3 nights min
  • Child Friendly

Price per night from

$575

Price per night from

$575

Distance approx 14.04 km from Hinsdale

(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

$277

Price per night from

$277

Distance approx 9.74 km from Hinsdale

(30) Excellent 

21

Gartner House, a charming home in Lenox

Berkshires / Lenox

Lenox apartment

4 7 2 nights min

  • 4 bedrooms
  • sleeps 7
  • 2 nights min
  • Child Friendly
  • Car not necessary
  • Ask about pets
“Great Location In Lenox” My family, friends, & I had a wonderful 2 weeks at Gartner House. It is within easy walking distance of nice shops, terrific restaurants, & a friendly library. Not far are Chesterwood, Tanglewood, Jacob's Pillow, Mass MoCa,
…see more

Price per night from

$230

Price per night from

$230

Distance approx 18.8 km from Hinsdale

(2) Excellent 

24

Country Elegance in the Berkshires

Berkshires / Great Barrington

Great Barrington house

4 12 2 nights min

  • 4 bedrooms
  • sleeps 12
  • 2 nights min
  • Nearest beach 0 mi
  • Child Friendly
  • Air conditioning

Price per night from

$747

Responds fast!
avg. 2 hours 36 minutes

Price per night from

$747

Distance approx 17.61 km from Hinsdale

23

Spacious Lakeside Berkshire Home

Berkshires / Monterey

Monterey house

4 10 3 nights min

  • 4 bedrooms
  • sleeps 10
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$460

Responds fast!
avg. 3 hours 48 minutes

Price per night from

$460

Distance approx 6.95 km from Hinsdale

(1) Excellent 

34

INTERIOR DESIGNERS BOTANICAL GARDENS

Berkshires / Lenox

Lenox cottage

1 5 min stay varies

  • 1 bedroom
  • sleeps 5
  • min stay varies
  • Nearest beach 3 mi
  • Child Friendly
  • Air conditioning

Price per night from

$121

Responds fast!
avg. 3 hours 59 minutes

Price per night from

$121

Distance approx 9.84 km from Hinsdale

(2) Very Good 

12

Berkshires Spacious Comfortable Charming Farmhouse

Berkshires / Lee

Lee apartment

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning
“lovely stay” The house is comfortable, clean, and convenient to Lenox, Stockbridge, and the rest of the Berkshires. Traffic from the street can be a bit loud at times, but it quiets down at night.
…see more

Price per night from

$302

Responds fast!
avg. 1 hour 42 minutes

Price per night from

$302

Distance approx 18.8 km from Hinsdale

(4) Very Good 

18

Lakefront Berkshires Ski/Summer House, Great Views

Berkshires / Great Barrington

Great Barrington house

4 10 min stay varies

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

Price per night from

$213

Price per night from

$213

Distance approx 13.17 km from Hinsdale

(6) Excellent 

6

Retreat in the Woods

Berkshires / Savoy

Savoy house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Suitable for children age 5+

Price per night from

$230

Price per night from

$230

Distance approx 12.66 km from Hinsdale

6

Berkshires on the Pond

Berkshires / Becket

Becket house

2 2 4 nights min

  • 2 bedrooms
  • sleeps 2
  • 4 nights min
  • Nearest beach 16 mi
  • Ask about children
  • Private garden

Price per night from

$144

Price per night from

$144

Distance approx 11.02 km from Hinsdale

(2) Very Good 

12

Heart of the Berkshires!

Berkshires / Lenox

Lenox house

3 6 2 nights min

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

Price per night from

$259

Price per night from

$259

Distance approx 19.24 km from Hinsdale

6

Stunning Home! 120 Acres! Amazing!

Berkshires / Great Barrington

Great Barrington house

9 16 3 nights min

  • 9 bedrooms
  • sleeps 16
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$4,138

Price per night from

$4,138

Distance approx 15.4 km from Hinsdale

(37) Excellent 

20

Berkshire Farmhouse Vacation

Berkshires / West Stockbridge

West Stockbridge house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Child Friendly
  • Pet Friendly
  • Private garden
“Quaint Getaway” We were 2 families with 5 kids staying for the weekend. We had plenty of space to spread out, cook & dine together and lots of bedroom options to meet everyone's needs. The house had a lot of antique charm like exposed beams in the l
…see more

Price per night from

$299

Price per night from

$299

Distance approx 10.14 km from Hinsdale

10

ground floor garden room

Berkshires / Lee

Lee b and b

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 5 mi
  • Ask about children
  • Ask about pets

Price per night from

$91

Responds fast!
avg. 1 hour 45 minutes

Price per night from

$91

Distance approx 12.57 km from Hinsdale

(2) Excellent 

16

PanoramicView1000 sq ft Guest Quarters Berkshires

Berkshires / Hancock

Hancock cottage

1 6 2 nights min

  • 1 bedroom
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Ask about pets

Price per night from

$167

Price per night from

$167

Distance approx 16.63 km from Hinsdale

(4) Excellent 

16

Lakefront Summer Vacation Cottages

Hampshire County / Goshen

Goshen cottage

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Pet Friendly

Price per night from

$196

Price per night from

$196

Distance approx 10.29 km from Hinsdale

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

$230

Responds fast!
avg. 1 hour 45 minutes

Price per night from

$230

Distance approx 12.92 km from Hinsdale

20

New Pristine Berkshire Vacation Rental with Pool (5 miles Tanglewood)

Berkshires / Richmond

Richmond house

3 6 7 nights min

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

Price per night from

$575

Price per night from

$575

Distance approx 11.8 km from Hinsdale

(1) Excellent 

10

Wyndham Bentley Brook Resort Rents-Hancock,MA -Jiminy Peak

Berkshires / Hancock

Hancock hotel apartment

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$523

Price per night from

$523

Distance approx 14.38 km from Hinsdale

(6) Excellent 

23

Berkshire Blueberry Lodge LLC - Near Jiminy Peak

New York / Stephentown

Stephentown lodge

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Child Friendly
  • Private garden

Price per night from

$431

Responds fast!
avg. 1 hour 50 minutes

Price per night from

$431

Distance approx 11.67 km from Hinsdale

6

Rustic Rivers end room in the barn at chestnut lodge

Berkshires / Lee

Lee barn

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Ask about pets
  • Private garden

Price per night from

$179

Responds fast!
avg. 1 hour 45 minutes

Price per night from

$179

Distance approx 10.86 km from Hinsdale

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

$77

Price per night from

$77

Distance approx 19.21 km from Hinsdale

(1) Excellent 

22

Berkshire Getaway at 'Tofu'S Retreat'

Berkshires / Alford

Alford chateau

3 6 7 nights min

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

Price per night from

$247

Responds fast!
avg. 1 hour 10 minutes

Price per night from

$247

Distance approx 18.04 km from Hinsdale

14

ROOM walking distance to Mass MoCa

Berkshires / North Adams

North Adams apartment

1 8 min stay varies

  • 1 bedroom
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$115

Price per night from

$115

Distance approx 14.44 km from Hinsdale

4

Iris Room

Berkshires / Stockbridge

Stockbridge farmhouse

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$173

Price per night from

$173

Distance approx 12.18 km from Hinsdale

10

Vacation Village in the Berkshires Available July 22-29

Berkshires / Hancock

Hancock condo

2 8 7 nights min

  • 2 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$158

Price per night from

$158

Distance approx 11.8 km from Hinsdale

8

7 night Christmas week Wyndham Bentley Brook 2 bdr condo Slopeside

Berkshires / Hancock

Hancock condo

2 8 7 nights min

  • 2 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$230

Price per night from

$230

Distance approx 12.85 km from Hinsdale

(13) Excellent 

17

Serene Lakefront Cottage

Berkshires / Becket

Becket house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly
“Peaceful country escape” Really enjoyed the stay here. Very complete driving and house directions provided by the owners, and checking in - even at a late hour - was a breeze. The house was very clean, woods and lake were beautiful. Many of the hou
…see more

Price per night from

$167

Price per night from

$167

Distance approx 8.38 km from Hinsdale

19

Charming Berkshires lakefront house, great views

Berkshires / Cheshire

Cheshire house

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Beach / lakeside relaxation
  • Ask about children
  • Car not necessary

Price per night from

$229

Price per night from

$229

Distance approx 9.78 km from Hinsdale

12

Beautiful Berkshire Mtn. Condo with Mountain Views, near Tanglewood, Lakes et al

Berkshires / Lee

Lee condo

3 8 30 nights min

  • 3 bedrooms
  • sleeps 8
  • 30 nights min
  • Child Friendly

Price per night from

$250

Price per night from

$250