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HomeAway.co.uk, the home of Holiday-Rentals®, is part of the HomeAway family. As the world leader in holiday rentals, we offer the largest selection of properties for any travel occasion and every budget. We’re committed to helping families and friends find the perfect holiday rental to create unforgettable travel experiences together.

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Any priceavg/night

AnyBedrooms

Use exact match for bedrooms

AnyBathrooms

Instant Confirmation

Book without waiting for owner approval

Location

Lake

Waterfront

City centre

Mountains

Beach

Beachfront

Town

Ski-in/ski-out

Beach view

Oceanfront

Ocean

Rural

Village

Golf course

Properties good for

Families

Luxury

House rules

Pets allowed

Children welcome

Smoking allowed

Events allowed

Nearby activities

Golfing

Skiing/snowboarding

Hiking

Fishing

Horse riding

Amusement/theme parks

Cycling

Tennis

Shopping & relaxation

Winery/brewery tours

Museums & galleries

Rock/mountain climbing

Scuba diving/snorkelling

Water sports

Booking Options

24-Hour Confirmation

Property type

House

Cottage

Apartment/condo

Cabin

Farmhouse

Bungalow

Chalet

Barn

Estate

Chateau/country house

Mobile home/caravan

Lodge

Studio

Castle

Resort

Tower

Townhouse

Villa

Boat

Yacht

Guest house

Mill

Hotel

Bed & breakfast

Houseboat

Features & amenities

Pool

Air conditioning

Internet/WiFi

Hot tub

TV

Washing machines

Fireplace

Outdoor grill/BBQ

Parking available

Garden

Dishwasher

Balcony

Heated/indoor pool

Bed linen provided

Patio or deck

Oven/stove

Cot

Microwave

DVD player

Kids' high chair

Iron & ironing board

Heating

King-size bed

Gym/fitness equipment

Private pool

Property reviews

★★★★☆ 4+ stars

★★★☆☆ 3+ stars

Safety & accessibility

Low-allergen environment

Wheelchair accessible

Lift

Services

Housekeeping

about HomeAway Sort

1 - 50 of 300+

HomeAway Sort
Price: Low to High
Price: High to Low
Guest Rating
Availability Last Updated
Bedrooms: Fewest to Most
Bedrooms: Most to Fewest
Instant Confirmation
Number of Reviews

Viewed 7 times in the last 48 hours

Garfield Guest House in the Office Complex

6.2 km to Stockbridge centre

Excellent! 4.6/5

Premier Partner

Viewed 7 times in the last 48 hours

Large home w/ beautiful gardens on pond in Berkshires. Walking distance to town.

6.6 km to Stockbridge centre

Excellent! 4.7/5

Viewed 10 times in the last 48 hours

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

6.2 km to Stockbridge centre

Excellent! 4.6/5

Premier Partner

Viewed 2 times in the last 48 hours

Charming Private Guest Suite-Historic New England Village

19.9 km to Stockbridge centre

Excellent! 4.4/5

Viewed 7 times in the last 48 hours

Stockbridge Cape Near Tanglewood & Kripalu - Heart Of The Berkshires!

4.1 km to Stockbridge centre

Exceptional! 5/5

Premier Partner

Viewed 16 times in the last 48 hours

Cozy Stockbridge Home - Walk To Golf Course!

1 km to Stockbridge centre

Wonderful! 4.8/5

Premier Partner

Viewed 14 times in the last 48 hours

Modern And Spacious Berkshires Retreat 5 bdrm 3 bath

5.9 km to Stockbridge centre

Exceptional! 5/5

Premier Partner

Viewed 18 times in the last 48 hours

Escape To | Stockbridge | TANGLEWOOD | Red Lion | Berkshires |Rockwell |SKIING

2.6 km to Stockbridge centre

Excellent! 4.5/5

Viewed 21 times in the last 48 hours

Gorgeous, Private, Family-Friendly, Organic Home with a Great Location in Lee

7.1 km to Stockbridge centre

Wonderful! 4.8/5

Premier Partner

Viewed 25 times in the last 48 hours

Fall Special Rate September, October, November, Chic Berkshire Carriage House

11.4 km to Stockbridge centre

Wonderful! 4.9/5

Premier Partner

Viewed 9 times in the last 48 hours

Tranquil 3BR Stockbridge House w/Private Deck

2.5 km to Stockbridge centre

Exceptional! 5/5

Premier Partner

Viewed 78 times in the last 48 hours

The Playhouse: 7,000 Square Feet of Berkshires Modern Luxury and History

5.2 km to Stockbridge centre

Wonderful! 4.9/5

Premier Partner

Viewed 16 times in the last 48 hours

Elegant Newly Renovated 19th Century New England 2BR Vacation Rental

6.2 km to Stockbridge centre

Wonderful! 4.9/5

Premier Partner

Viewed 8 times in the last 48 hours

Modern cottage in the heart of the Berkshires!

1.9 km to Stockbridge centre

Exceptional! 5/5

Premier Partner

Viewed 6 times in the last 48 hours

Unique Condo, Quiet Neighborhood, Walk to Town.

8.9 km to Stockbridge centre

Wonderful! 4.9/5

Viewed 8 times in the last 48 hours

Stunning Post & Beam home minutes from Butternut, Great Barrington & Lenox!

5.1 km to Stockbridge centre

Exceptional! 5/5

Premier Partner

Viewed 10 times in the last 48 hours

Restored 1940s Cabin 30 Mile Views

16.7 km to Stockbridge centre

Wonderful! 4.8/5

Premier Partner

Viewed 23 times in the last 48 hours

Private rustic cottage with lake access

13.7 km to Stockbridge centre

Exceptional! 5/5

Viewed 13 times in the last 48 hours

Berkshire retreat in the Heart of West Stockbridge

7 km to Stockbridge centre

Wonderful! 4.9/5

Premier Partner

Viewed 14 times in the last 48 hours

Waterfront Lake Buel Cottage - Open Year-Round!

13.6 km to Stockbridge centre

Exceptional! 5/5

Premier Partner

Viewed 3 times in the last 48 hours

Stockbridge! 1/2 mile from Red Lion inn. Great Barrington, Lenox, Lee close by.

1.2 km to Stockbridge centre

Wonderful! 4.9/5

Premier Partner

Viewed 8 times in the last 48 hours

Charming Farmhouse Steps from Downtown West Stockbridge

6.4 km to Stockbridge centre

Exceptional! 5/5

Viewed 12 times in the last 48 hours

Come Relax and Enjoy the Berkshires!

9.8 km to Stockbridge centre

Wonderful! 4.8/5

Premier Partner

Viewed 16 times in the last 48 hours

Peace And Quiet On The Lake

21.4 km to Stockbridge centre

Wonderful! 4.8/5

Viewed 11 times in the last 48 hours

Cozy Cottage In Berkshire Woods, 3 Min. Walk to Lake Buel; Close to Butternut.

13.8 km to Stockbridge centre

Wonderful! 4.8/5

Sophisticated and Comfortable Stockbridge Retreat - A+ Location!

4.6 km to Stockbridge centre

Viewed 13 times in the last 48 hours

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

6.4 km to Stockbridge centre

Wonderful! 4.9/5

Premier Partner

Viewed 15 times in the last 48 hours

Craftsman Home In The Berkshire Forest

21 km to Stockbridge centre

Wonderful! 4.9/5

Premier Partner

Viewed 11 times in the last 48 hours

General Williams Estate House Lenox/Stockbridge

2.9 km to Stockbridge centre

Wonderful! 4.8/5

Premier Partner

Viewed 11 times in the last 48 hours

Berkshires Pontoosuc Lake Beauty - Beautifully renovated lakefront home

24.5 km to Stockbridge centre

Wonderful! 4.8/5

Premier Partner

Viewed 16 times in the last 48 hours

Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow

14.2 km to Stockbridge centre

Excellent! 4.7/5

Premier Partner

Viewed 5 times in the last 48 hours

2 Bedroom newly renovated townehouse, beautifully decorated at Garfield House

6.2 km to Stockbridge centre

Wonderful! 4.9/5

Viewed 34 times in the last 48 hours

BEAUTIFULLY RENOVATED LAKE BUEL COTTAGE

13.8 km to Stockbridge centre

Excellent! 4.6/5

Premier Partner

Viewed 10 times in the last 48 hours

Eviva!!!!! Location Location Location!!!!!! 20% DISCOUNT WEEKLY RATE

7.2 km to Stockbridge centre

Excellent! 4.4/5

Viewed 6 times in the last 48 hours

A Small Oasis in the Heart of Lenox

8.6 km to Stockbridge centre

Wonderful! 4.9/5

Premier Partner

Viewed 9 times in the last 48 hours

Newly Renovated Farm House!

10.2 km to Stockbridge centre

Excellent! 4.4/5

Premier Partner

Viewed 5 times in the last 48 hours

Beautiful Berkshire family home

15.5 km to Stockbridge centre

Wonderful! 4.9/5

Premier Partner

Viewed 3 times in the last 48 hours

Quiet Renovated Barn

21.6 km to Stockbridge centre

Exceptional! 5/5

Viewed 11 times in the last 48 hours

Greek Revival Style Farmhouse Circa 1820

2 km to Stockbridge centre

Exceptional! 5/5

Viewed 14 times in the last 48 hours

Hudson River Valley/Berkshires Rural Retreat

19.2 km to Stockbridge centre

Wonderful! 4.8/5

Premier Partner

Viewed 2 times in the last 48 hours

Spacious four bedroom, bright contemporary home, tennis, lake, gym, pool.

22 km to Stockbridge centre

Viewed 2 times in the last 48 hours

Country Cottage On Quiet Street!!

10.1 km to Stockbridge centre

Viewed 17 times in the last 48 hours

5BR Great Barrington House w/Mountain Views!

3.8 km to Stockbridge centre

Premier Partner

Viewed 9 times in the last 48 hours

Location, location! Old world charm with updates. Victorian beauty in Lee

5.8 km to Stockbridge centre

Wonderful! 4.9/5

Premier Partner

Viewed 32 times in the last 48 hours

Spacious 6 BR Country Retreat With Secluded Tree Top Mountain Views

23.5 km to Stockbridge centre

Exceptional! 5/5

Premier Partner

Viewed 8 times in the last 48 hours

Berkshire Octoganal Glass Tree House near Tanglewood, Great Barrington

20.2 km to Stockbridge centre

Excellent! 4.7/5

Viewed 3 times in the last 48 hours

Studio Apt. In Quiet Country Setting, 3 Miles From Downtown Great Barrington

13.9 km to Stockbridge centre

Wonderful! 4.9/5

Viewed 20 times in the last 48 hours

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

22.2 km to Stockbridge centre

Excellent! 4.5/5

Premier Partner

Viewed 8 times in the last 48 hours

Great Barrington Perfect WINTER Retreat! Minutes to Butternut!

9.6 km to Stockbridge centre

Wonderful! 4.9/5

Premier Partner

Viewed 25 times in the last 48 hours

Ideal location for summer and winter activities with plenty of outdoor space.

21.4 km to Stockbridge centre

Wonderful! 4.9/5

1 - 50 of 300+

Additional taxes and fees may apply.

Stockbridge Holiday

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Berkshire County
Stockbridge

United States
Massachusetts
Berkshire County
Stockbridge

Berkshire Theatre Festival
Naumkeag
Norman Rockwell Museum
Chesterwood
Mission House
Berkshire Botanical Garden
National Shrine of the Divine Mercy
Hancock Shaker Village

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