Stockbridge houses
We found 650 houses — enter your dates for availability
Explore Stockbridge house rentals
A Grand property in Historic Stockbridge
Sleeps 12 · 6 bedrooms · 6+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
99 reviews(99 reviews)
In-Town Victorian 5 Bd Front House &/or 6 Bd Back House w/Beach Rights, Skiing
Sleeps 24 · 12 bedrooms · 7+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
53 reviews(53 reviews)
Historic Rectory Retreat in Stockbridge – Getaway for 8-12 Guests
Sleeps 12 · 5 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Sleeps 8 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
127 reviews(127 reviews)
Stylish 5 bed/5 bath Hilltop Manor + Cottage - Amazing location!! 4mi Tanglewood
Sleeps 11 · 5 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Fabulous In-town Stockbridge Pied-á-Terre, pet friendly!
Sleeps 3 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
Are there any vacation home rentals in Stockbridge?
Browse our 650 vacation home rentals in Stockbridge that provide that home-away-from-home charm. Consider staying in the well-known neighborhood of Richmond and then discover the city just like a local.
How much does it cost to stay in a vacation rental house in Stockbridge?
Prices vary depending on season, length of stay and exact property location, so enter your trip details to find out what's available. Whatever your style or budget, Vrbo has vacation home rentals in Stockbridge for guests of all types.
When is the best time to rent a vacation house in Stockbridge?
April is when the majority of guests book a vacation home rental in Stockbridge, which is in The Berkshires. Average temperatures range from 2ºC (36ºF) to 12ºC (54ºF) during this month.
Where can I rent a Stockbridge vacation house with great views?
Vrbo has some superb vacation home rentals in Stockbridge, including houses with views of historic areas. When you aren't seeing the sights, unwind and gaze at vistas that are an attraction in themselves.
Does Stockbridge have any weekend house rentals?
You'll discover a range of quality houses that are available for weekend rental. Simply key in your dates of travel and prepare for a spontaneous few days of fun. If you don't find the ideal vacation home rental in Stockbridge straight away, just play around with your dates and search again.
Are there any pet-friendly house rentals in Stockbridge?
Spend your next adventure with your four-legged friend at one of the nine pet-friendly vacation home rentals in Stockbridge. These stays come with perks that'll make your dog feel welcome, such as a backyard to play in. Just select the "Pets allowed" filter to book a house that has space for every precious member of your family.
What are the top things to do in Stockbridge?
There's plenty to do with the family in Stockbridge besides just enjoying the amenities and comforts of your vacation home rental. Don't miss awesome attractions like Tanglewood Music Center and National Shrine of the Divine Mercy. Looking for more inspiration? Norman Rockwell Museum deserves a spot on your Stockbridge must-see list.
Why should I book my vacation rental house with Vrbo?
No sharing your space, no awkward small talk with strangers. When you book a Vrbo vacation home rental, you'll get the entire place for your use only. Need to cancel or alter your travel plans? Our flexible cancellation policies mean you can book your rental house with total peace of mind.