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Holiday homes in Stockbridge You’ll Love

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

Looking for a holiday home in 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 Stockbridge.

We found 21 Holiday-homes in Stockbridge and the surrounding area (within 30 miles)

Magical Country Retreat in the Berkshires in Great Barrington, USA

Magical Country Retreat in the Berkshire...

Holiday home in Great Barrington near Stockbridge, Massachusetts , 250 Long Pond Road
Providing a garden, Magical Country Retreat in the Berkshires offers accommodations in Great Barrington.
  • Parking
  • Bar
  • Family rooms
  • Outdoor pool
  • Swimming Pool

no reviews

from $4.626.94 Show details »

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

Great Barrington Lakeside Getaway with K...

Holiday home in Great Barrington near 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 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, 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 near 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, 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, 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 »

Berkshire Vacation Rentals: Stonebridge Cabin: Modern Amenities Enjoy Nature in Lee, USA

Berkshire Vacation Rentals: Stonebridge...

Holiday home in Lee near Stockbridge, Massachusetts , Stonebridge Way 11
Berkshire Vacation Rentals: Stonebridge Cabin: Modern Amenities Enjoy Nature is located in Lee, just 6.5 miles from Cranwell Spa & Golf Club and 9 mil...
  • Parking
  • Pets allowed

Exceptional 1 Reviews 10.0

from $464.41 Show details »

Holiday Inn Oak n Spruce Resort -1BD Sleep up to 4 in Lee, USA

Holiday Inn Oak n Spruce Resort -1BD Sle...

Holiday home in Lee near Stockbridge, Massachusetts , 190 Meadow St, Lee, MA 01238, USA
Holiday Inn Oak n Spruce Resort -1BD Sleep up to 4 is located in Lee, just 6.9 miles from Cranwell Spa & Golf Club and 8.4 miles from Tanglewood Music...
  • Fitness centre
  • Indoor pool
  • Swimming Pool

no reviews

from $99.00 Show details »

Too Good AKA 2 Goodrich St in Stockbridge, USA

Too Good AKA 2 Goodrich St

Holiday home in 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, 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 near 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, 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 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 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, 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 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, 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 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 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 »

Econo Lodge Lee - Great Barrington in Lee, USA

Econo Lodge Lee - Great Barrington

Lodge in Lee near Stockbridge, Massachusetts , 980 Pleasant Street
Located in Lee, Econo Lodge Lee - Great Barrington has mountain views and free WiFi, 5.4 miles from Norman Rockwell Museum and 5.7 miles from Cranwell...
  • Parking
  • Pets allowed

Pleasant 235 Reviews 6.5

from $56.97 Show details »

Number of Holiday homes in Stockbridge 21
Number of guest ratings 372
Average price per night $361.00
Lowest price per night $51,00
Highest price per night $4.626,94

Top 10 Cheapest Holiday-homes in Stockbridge

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

Top 10 Most Booked Holiday-homes in Stockbridge

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

Holiday homes in Stockbridge (Massachusetts), comfortable and familiar

Staying in a holiday or vacation home in 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 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 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