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Holiday homes in West Stockbridge You’ll Love

Top-Rated West Stockbridge Holiday homes for Every Budget and Style!

Looking for a holiday home in West Stockbridge (Massachusetts)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $51.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of West Stockbridge.

We found 22 Holiday-homes in West Stockbridge and the surrounding area (within 30 miles)

Great Barrington Lakeside Getaway with Kayak and Grill in Great Barrington, USA

Great Barrington Lakeside Getaway with K...

Holiday home in Great Barrington near West Stockbridge, Massachusetts
Great Barrington Lakeside Getaway with Kayak and Grill is located in Great Barrington, just 10 miles from Tanglewood Musical Center and 10 miles from ...
  • Parking

Superb 3 Reviews 9.3

from $388.34 Show details »

Lakefront Berkshires Retreat with Deck, Dock and Boat! in Great Barrington, USA

Lakefront Berkshires Retreat with Deck,...

Holiday home in Great Barrington near West Stockbridge, Massachusetts
Lakefront Berkshires Retreat with Deck, Dock and Boat! is located in Great Barrington, just 5.2 miles from Norman Rockwell Museum and 10 miles from Ta...
  • Parking
  • Pets allowed

Good 4 Reviews 7.5

from $351.06 Show details »

Woodland Zen by AvantStay Modern Design Patio in Stockbridge, USA

Woodland Zen by AvantStay Modern Design...

Holiday home in Stockbridge near West Stockbridge, Massachusetts
Woodland Zen by AvantStay Modern Design Patio is located in Stockbridge, just 3.2 miles from Norman Rockwell Museum and 7.7 miles from Tanglewood Musi...
  • Parking

no reviews

from $346.65 Show details »

Berkshire Vacation Rentals: Spacious & Serene Berkshires Retreat In The Woods in West Stockbridge, USA

Berkshire Vacation Rentals: Spacious & S...

Holiday home in West Stockbridge, Massachusetts , Robin Road 4
Berkshire Vacation Rentals: Spacious & Serene Berkshires Retreat In The Woods offers accommodations in West Stockbridge, 3.2 miles from Norman Rockwel...
  • Parking
  • Pets allowed

no reviews

from $82.00 Show details »

Berkshire Vacation Rental: Stockbridge Home Come Experience The Berkshires in Stockbridge, USA

Berkshire Vacation Rental: Stockbridge H...

Holiday home in Stockbridge near West Stockbridge, Massachusetts , Goodrich Street 22
Berkshire Vacation Rental: Stockbridge Home Come Experience The Berkshires offers accommodations in Stockbridge, 3.7 miles from Norman Rockwell Museum...
  • Parking
  • Pets allowed

Exceptional 3 Reviews 10.0

from $462.25 Show details »

Stockbridge Retreat with Pool and Hot Tub! in Stockbridge, USA

Stockbridge Retreat with Pool and Hot Tu...

Holiday home in Stockbridge near West Stockbridge, Massachusetts
Stockbridge Retreat with Pool and Hot Tub! is located in Stockbridge, just 3.8 miles from Norman Rockwell Museum and 6.8 miles from Cranwell Spa & Gol...
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $1.677.89 Show details »

Too Good AKA 2 Goodrich St in Stockbridge, USA

Too Good AKA 2 Goodrich St

Holiday home in Stockbridge near West Stockbridge, Massachusetts , 2 Goodrich Street
Too Good AKA 2 Goodrich St offers accommodations in Stockbridge, 6.9 miles from Tanglewood and 19 miles from Great Falls.
  • Family rooms

Exceptional 2 Reviews 10.0

from $403.19 Show details »

Classic Stockbridge Cottage in Stockbridge, USA

Classic Stockbridge Cottage

Holiday home in Stockbridge near West Stockbridge, Massachusetts , Christian Hill Road 15
Classic Stockbridge Cottage is located in Stockbridge, just a 19-minute walk from Norman Rockwell Museum and 5.6 miles from Tanglewood Musical Center.
  • Parking
  • Pets allowed

no reviews

from $473.45 Show details »

Berkshire Vacation Rentals: Loft Style Cabin In West Stockbridge Book Now in West Stockbridge, USA

Berkshire Vacation Rentals: Loft Style C...

Holiday home in West Stockbridge, Massachusetts , Pixley Hill Road 9
Berkshire Vacation Rentals: Loft Style Cabin In West Stockbridge Book Now is located in West Stockbridge, just 2.7 miles from Norman Rockwell Museum a...
  • Parking
  • Pets allowed

no reviews

from $80.00 Show details »

Tranquil 3 BR Stockbridge House with Private Deck! in Stockbridge, USA

Tranquil 3 BR Stockbridge House with Pri...

Holiday home in Stockbridge near West Stockbridge, Massachusetts
Tranquil 3 BR Stockbridge House with Private Deck! offers accommodations in Stockbridge, 5.7 miles from Tanglewood and 8.7 miles from Cranwell Spa & G...
  • Parking
  • Pets allowed
  • Spa and wellness centre

Exceptional 2 Reviews 9.5

from $354.41 Show details »

Cordelia by AvantStay Amazing Backyard 10mins from Stockbridge in Lee, USA

Cordelia by AvantStay Amazing Backyard 1...

Holiday home in Lee near West Stockbridge, Massachusetts
Cordelia by AvantStay Amazing Backyard 10mins from Stockbridge is located in Lee, just 3.2 miles from Cranwell Spa & Golf Club and 5.7 miles from Tang...
  • Parking
  • Pets allowed

Very good 3 Reviews 8.3

from $307.34 Show details »

Berkshire Vacation Home in Lee - Pool is Open! in Lee, USA

Berkshire Vacation Home in Lee - Pool is...

Holiday home in Lee near West Stockbridge, Massachusetts , 150 Theresa Terrace
Berkshire Vacation Home in Lee - Pool is Open! is located in Lee, just 2.4 miles from Cranwell Spa & Golf Club and 4.7 miles from Tanglewood.
  • Parking
  • Family rooms
  • Outdoor pool
  • Swimming Pool

no reviews

from $76.00 Show details »

Cozy Stockbridge Cabin - Walk to Beach and Lake! in Stockbridge, USA

Cozy Stockbridge Cabin - Walk to Beach a...

Holiday home in Stockbridge near West Stockbridge, Massachusetts
Cozy Stockbridge Cabin - Walk to Beach and Lake! is located in Stockbridge, just 3.2 miles from Norman Rockwell Museum and 3.3 miles from Tanglewood.
  • Parking
  • Spa and wellness centre

Fabulous 2 Reviews 9.0

from $288.51 Show details »

The Gatehouse on Golden Hill in Lee, USA

The Gatehouse on Golden Hill

Holiday home in Lee near West Stockbridge, Massachusetts , 117 Golden Hill Road
The Gatehouse on Golden Hill is located in Lee, just 7.9 miles from Norman Rockwell Museum and 25 miles from Great Falls.
  • Family rooms

no reviews

from $467.41 Show details »

Stockbridge Home Walk to Town Beach! in Stockbridge, USA

Stockbridge Home Walk to Town Beach!

Holiday home in Stockbridge near West Stockbridge, Massachusetts
Stockbridge Home Walk to Town Beach! is located in Stockbridge, just 2.4 miles from Tanglewood and 3.6 miles from Cranwell Spa & Golf Club.
  • Parking
  • Spa and wellness centre

Very good 4 Reviews 8.5

from $245.26 Show details »

Wellspring by AvantStay Indoor Pool Views in Richmond, USA

Wellspring by AvantStay Indoor Pool View...

Holiday home in Richmond near West Stockbridge, Massachusetts
Wellspring by AvantStay Indoor Pool Views offers accommodations in Richmond, 2.4 miles from Tanglewood Musical Center and 2.8 miles from Tanglewood.
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Exceptional 1 Reviews 10.0

from $1.101.83 Show details »

Private Guest House in Dtwn Lenox, Walk to Dining! in Lenox, USA

Private Guest House in Dtwn Lenox, Walk...

Holiday home in Lenox near West Stockbridge, Massachusetts
Private Guest House in Dtwn Lenox, Walk to Dining! offers accommodations in Lenox, 1.6 miles from Cranwell Spa & Golf Club and 1.6 miles from Tanglewo...
  • Parking

Exceptional 11 Reviews 9.5

from $331.27 Show details »

Restored 1881 Farm House in Lenox, USA

Restored 1881 Farm House

Holiday home in Lenox near West Stockbridge, Massachusetts , 76 East Dugway Road
Restored 1881 Farm House offers accommodations in Lenox, 8.6 miles from Norman Rockwell Museum and 26 miles from The Clark Art Institute.
  • Pets allowed
  • Family rooms

Exceptional 5 Reviews 9.8

from $326.15 Show details »

Beautiful Lenox Home, 3 Mi to Shakespeare and Co! in Lenox, USA

Beautiful Lenox Home, 3 Mi to Shakespear...

Holiday home in Lenox near West Stockbridge, Massachusetts
Beautiful Lenox Home, 3 Mi to Shakespeare and Co! offers accommodations in Lenox, 3.7 miles from Cranwell Spa & Golf Club and 3.7 miles from Tanglewoo...
  • Parking
  • Spa and wellness centre

Very good 4 Reviews 8.0

from $409.57 Show details »

Berkshire Vacation Rentals: Private Cottage Come Enjoy Nature in Canaan, USA

Berkshire Vacation Rentals: Private Cott...

Holiday home in Canaan near West Stockbridge, Massachusetts , Tremper Association Road 13
Berkshire Vacation Rentals: Private Cottage Come Enjoy Nature offers accommodations in Canaan, 8.9 miles from Tanglewood Musical Center and 9.3 miles ...
  • Parking

Superb 3 Reviews 9.3

from $281.67 Show details »

Richmond Cottage with Fire Pit and Furnished Deck! in Richmond, USA

Richmond Cottage with Fire Pit and Furni...

Holiday home in Richmond near West Stockbridge, Massachusetts
Richmond Cottage with Fire Pit and Furnished Deck! is located in Richmond, just 6.8 miles from Tanglewood and 10 miles from Norman Rockwell Museum.
  • Parking

no reviews

from $82.00 Show details »

Family-Friendly Richmond Cottage with Private Yard in Pittsfield, USA

Family-Friendly Richmond Cottage with Pr...

Holiday home in Pittsfield near West Stockbridge, Massachusetts
Family-Friendly Richmond Cottage with Private Yard is located in Pittsfield, just 6.7 miles from Tanglewood Musical Center and 7.1 miles from Tanglewo...
  • Parking
  • Pets allowed

Fabulous 1 Reviews 9.0

from $88.00 Show details »

Number of Holiday homes in West Stockbridge 22
Number of guest ratings 216
Average price per night $342.00
Lowest price per night $51,00
Highest price per night $4.626,94

Top 10 Cheapest Holiday-homes in West Stockbridge

Discover the Cheapest Holiday-homes in West Stockbridge – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in West Stockbridge

Check out the Most Booked Holiday-homes in West Stockbridge – Based on Guest Popularity.

Holiday homes in West Stockbridge (Massachusetts), comfortable and familiar

Staying in a holiday or vacation home in West Stockbridge can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in West Stockbridge for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in West Stockbridge should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com