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West Stockbridge House Rentals

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    Don't let other travellers get your favourite West Stockbridge area holiday rental. You're so close to securing your perfect getaway. Book today.
    19 Matching Rentals in the West Stockbridge AreaView all 32 rentals
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    Berkshire Farmhouse Vacation1 / 20
    (36)Excellent
    West Stockbridge
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Two weeks in July !!!  Last minute cancellation  WOW1 / 18
    (6)Excellent
    West Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    West Stockbridge
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    The following rentals are within 10 kilometres of West Stockbridge.
    Beautiful Vacation Home1 / 32
    (5)Excellent
    Stockbridge
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Mountain Views
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Patio
    • Sauna
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 February 2017
    Our 4 families stayed here for a long ski weekend and had the best time! The home is beautiful-- and had plenty of space for all of us! The home was fully stocked with...
    Reviewed 10 November 2016
    Excellent experience. Very spacious and beautiful. Amazing backyard woods. Beautiful scenery within and around the town. Very attentive owners.
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    About this property
    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 floors, custom white pine trim and...
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Restored 1886 Eyebrow Colonial1 / 17
    (1)Excellent
    Stockbridge
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Mountain Views
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Washer
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 January 2017
    Our family of four absolutely loved our stay in Melanie and Henry's home. After communicating with Melanie before our arrival, we felt welcome before we stepped into the house...
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    About this property
    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 Stockbridge and the Norman Rockwell...
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    Location Information
    Stockbridge, Berkshires 01262
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Heart of the Berkshires!1 / 12
    (2)Very good
    Lenox
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2017
    A friend and I rented this charming home for 3 nights. It was immaculate, the kitchen was well stocked, furniture/beds comfortable. The bedrooms had window a/c units. What...
    Reviewed 30 June 2017
    I was looking for a place for two couples for a weekend in the Berkshires, and stayed at this house. It was a perfect fit for my needs. The house is on a road that has very...
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    About this property
    This sophisticated ranch is privately sited on a premier road in Stockbridge. Less than a mile to Tanglewood, Stockbridge Bowl, and local theatre companies. Nestled between Lenox and Stockbridge, this is perfect location for your vacation. 3 bedroom and 1 bath, an open floor plan with the guest...
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    Lenox, Berkshires 01240
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Great Vacation House in the Berkshires on Richmond Pond1 / 10
    (3)Excellent
    Richmond
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Grill
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 August 2017
    This comfortable, breezy house was perfect! We loved being able to walk to the lake and canoe, play frisbee on the lawn, walk in the woods, eat on the deck, and gaze at the...
    Reviewed 29 July 2017
    This house is well quipped with everything you need. It is conveniently located close to beaches with sandy bottoms. Both supermarkets are restaurants are nearby.There are many...
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    About this property
    Beautiful two bedroom house sits just steps from Richmond Pond. Enjoy a day on the water swimming and fishing followed by an evening enjoying the symphony at Tanglewood (ten scenic minutes away). Yoga enthusiasts will love the proximity to Kripalu (again, ten minutes away). Leaf peepers and skiers...
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    Location Information
    Richmond, Berkshires 01254
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Heart of Lenox1 / 10
    (1)Excellent
    Lenox
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Private Garden
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 May 2017
    Title sums it up! Excellent choice for our recent visit to Lenox. The house is very clean and comfortable and the owners are very accommodating. Location is great, just steps...
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    About this property
    Just rated Best Small Town in the Northeast by USA Today, our home is located in the heart of Lenox MA! Come relax in our lovely home, situated in a quiet neighborhood just steps from downtown. Walk to Zagat rated restaurants, shop unique boutique shops, hike in Kennedy Park. Whether you love the...
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    Location Information
    Lenox, Berkshires 01240
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Richmond
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Porch
    • Internet Access
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly furnished 3 bedroom (with AC) & 2 1/2 bath single family home with stunning deck and in ground pool nestled in the quiet countryside opposite a horse farm. Situated minutes from West Stockbridge convenience stores and restaurants. Property is on 2 quiet tree lined acres with an enclosed...
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    Richmond, Berkshires 01254
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 woods. Central air...
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    Location Information
    Stockbridge, Berkshires 01262
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Patio
    • Grill
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 bedroom has king bed and master...
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    Location Information
    Stockbridge, Berkshires 01238
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Tranquil 3BR Stockbridge House w/Private Deck1 / 30
    (2)Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2017
    The degree of care of the owners to assure a pleasant experience was incredible! There was a many page guide to the house, the property and the surrounding area. It...
    Reviewed 24 October 2016
    Awesome setting and a great outside porch complete with herb gardens(2). The forest around the property just invites a hike. Every possible thing was thought of by these...
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    About this property
    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 retreat. THE PROPERTY...
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    Location Information
    Stockbridge, Berkshires 01262
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lenox
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Parking
    • Internet Access
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great little house in a very convenient location. Set nicely back from the street with a spacious back and side yard. 8 minutes drive to tanglewood. All rooms are furnished. Living room with bay window and fireplace, hardwood floors throughout. Almost an acre of land with large trees and garden....
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    Location Information
    Lenox, Berkshires 01240
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Stockbridge
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Parking
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THE ESCAPE at Stockbridge. Enjoy our Open & Spacious Newly built house in the Berkshires, Complete Privacy! No Visible Neighbors. -1 1/2 miles to downtown Stockbridge, -just minutes to Norman Rockwell museum, Chesterwood, Naumkeag, Tanglewood & Kripalu. -Housatonic River just across the street,...
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    Location Information
    Stockbridge, Berkshires 01262
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    Newly Renovated Colonial on the River! Sleeps 5-61 / 20
    (1)Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Internet Access
    • Patio
    • Waterfront
    • Central Heating
    • Cable/satellite TV
    • Porch
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Blue House on the Bend Newly renovated historic eyebrow colonial located on an idyllic bend of the Housatonic river comfortably accommodates 5 or 6 people. Built around 1820, the Blue House on the Bend has been updated and outfitted for modern day convenience but retains its charm and unique...
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    Location Information
    Stockbridge, Berkshires 01236
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Stockbridge
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Private Garden
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    **1 week minimum July & August** Just 1 1/2 to the Red Lion Inn in Downtown Stockbridge, Tanglewood, Norman Rockwell Museum, Private country setting just across from the Housaitonic River. Our newly built home pairs a traditional shingle style exterior with an open & slightly modern interior. The...
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    Location Information
    Stockbridge, Berkshires 01262
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Stockbridge
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Mountain Views
    • Air Conditioning
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 plan kitchen, dining room, and...
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    Location Information
    Stockbridge, Berkshires 01262
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Lenox
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    No matter the season, you'll find the getaway you crave while staying at this 3-bed, 2.5-bath house in Lenox! This welcoming vacation rental features room for 6, numerous amenities, and an incredible location just minutes from the Tanglewood Music Center. In addition, enjoy easy access to the...
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    Location Information
    Lenox, Berkshires 01240
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Stockbridge
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Mountain Views
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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'll be central to all the...
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    Location Information
    Stockbridge, Berkshires 01262
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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