15 Best Stockbridge Apartments on Holiday Lettings - Flats

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15 Vacation rentals

(5) Excellent 

16

Cottage accommodation in Stockbridge

Berkshires / Stockbridge

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
Located a short walk to the town beach on the Stockbridge Bowl, and 1.5 miles from Tanglewood's Hawthorn entrance, this casual summer cottage is a great get away for the whole family. The master bedroom is equipped with a queen bed; two twins in the 2nd bedroom, and a …see more

from $285 / night

$1800 - $2450 / week

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from $285 / night

26

Vacation home rental

Berkshires / Stockbridge

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Newly renovated contemporary house on 2 acres in Stockbridge. Great space surrounding house for outdoor sports and sitting around the fire at night. 3 bedrooms, 3 bathrooms, indoor fireplace, wood floors, many windows and closets. Large kitchen. WiFi. Master bed …see more

from $300 / night

$2000 - $2700 / week

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from $300 / night

(5) Excellent 

32

Vacation home in Stockbridge

Berkshires / Stockbridge

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
We call this house ‘South Sedgwick’ because of its location on a piece of land formerly used by the Sedgwick family for picnicking–an ideal spot for relaxation with stunning views of Monument Mountain and Ice Glen. The house is newly constructed with ash hardwood floor …see more

from $499 / night

$2499 - $3805 / week

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Responds fast!
avg. 2 hours 37 minutes

from $499 / night

(1) Excellent 

25

Vacation cottage accommodation

Berkshires / Stockbridge

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Child friendly
This 1600 sq. ft. cottage boasts everything you would need for your visit to the Berkshires whether it be for a full summer / winter season to explore this beautiful area or a quick getaway to Tanglewood, The recently added master suite features a queen size bed, en- …see more

from $300 / night

$1500 - $2350 / week

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from $300 / night

(1) Excellent 

21

Vacation home in Stockbridge

Berkshires / Stockbridge

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Our cottage is situated in a private lake community. Short walk to lake and private beach. Minutes from Tanglewood, Kripalu, Stockbridge town center and Lenox town center. Convenient to many cultural institutions, hiking, skiing. Our cottage has plenty of outdoor space …see more

from $200 / night

$1200 / week

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Responds fast!
avg. 2 hours 56 minutes

from $200 / night

22

Vacation home in Stockbridge

Berkshires / Stockbridge

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Ask about pets
Completely renovated vacation home with state of the art kitchen and marble baths, centrally located in the Berkshires 3 miles from Tanglewood, on 10 acres on a quiet country road. New in-ground pool surrounded by patio and expansive deck and pool house nestled in the …see more

from $500 / night

$3301 / week

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from $500 / night

4

Vacation farmhouse in Stockbridge

Berkshires / Stockbridge

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
The 1762 farmhouse has 3 bedrooms available to bring your family and friends enjoy the close proximity to Tanglewood, Norman Rockwell Museum, and several lakes, many hiking areas, great restaurants. Larry makes a fresh egg breakfast which is included in your stay. You …see more

from $150 / night

$900 / week

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from $150 / night

(1) Excellent 

30

Vacation home rental

Berkshires / Stockbridge

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Elevate your Stockbridge experience by staying at this 3-bedroom, 1.5-bath vacation rental house, which sleeps 6 and boasts a private deck. Nestled within the serene forests of the Berkshires, ‘The Redway House’ is the quintessential setting for your next Massachusetts …see more

from $215 / night

$1290 - $2094 / week

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from $215 / night

4

Vacation farmhouse in Stockbridge

Berkshires / Stockbridge

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
This farmhouse has 3 bedrooms available so guests may bring their family, several friends, or overlap with new ones. The Iris Room is bright and airy with 4 windows; the Nasturtium Room has a Full bed with a half bath and the Horse room has a full and single bed acros …see more

from $150 / night

$900 / week

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from $150 / night

4

Vacation farmhouse in Stockbridge

Berkshires / Stockbridge

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
This 1762 farmhouse features wide board floors, kitchen, dining and living room areas along with a spacious front porch. Agritour gardens, horseback riding, and close proximity to Tanglewood and the Norman Rockwell Museum make for an adventure filled visit. Larry prepa …see more

from $150 / night

$900 / week

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from $150 / night

(1) Excellent 

17

Vacation home in Stockbridge

Berkshires / Stockbridge

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Explore the culture and natural beauty of the Berkshires while vacationing in a completely restored colonial home with modern amenities. You will be central to all the wonderful cultural attractions and outdoor activities in the area. Walk to the quaint town of Stockbri …see more

from $215 / night

$1500 / week

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from $215 / night

(4) Good 

11

Stockbridge Vacation home rental

Berkshires / Stockbridge

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
3-bedroom home on lake, near Tanglewood. 2 baths, den, screened porch, large yard. …see more

from $225 / night

$1500 / week

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from $225 / night

39

Stockbridge Vacation home rental

Berkshires / Stockbridge

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Explore the culture and natural beauty of the Berkshires while vacationing in a completely restored colonial home with modern amenities in Stockbridge. This quaint vacation rental home features 2 bedrooms and 2 bathrooms, accommodating 6 guests. From this property, you' …see more

from $210 / night

$1470 - $2205 / week

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from $210 / night

35

Vacation b&b in Stockbridge

Berkshires / Stockbridge

8 17 3 nights min

  • 8 bedrooms
  • Sleeps 17
  • 3 nights min
  • Swimming pool
  • Air conditioning
  • Private garden
Our Stockbridge MA Bed & Breakfast is the closest Inn and within walking distance to the Norman Rockwell and Chesterwood Museums. Nestled on 4 private acres of Berkshires landscape, we offer top quality B&B lodging accommodations that is centrally located to all major a …see more

from $970 / night

$4900 / week

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from $970 / night

17

Stockbridge Vacation home rental

Berkshires / Stockbridge

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
THIS CUSTOM BUILT HOME is a one-of-a-kind, must see getaway retreat that is beautifully furnished, and meticulously maintained. The entire first floor 'guest suite' was designed to accommodate friends or extended family. The upper level is the main floor with an open p …see more

from $500 / night

$2450 - $4130 / week

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from $500 / night