Stockbridge vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Stockbridge
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Stockbridge vacation rentals
Other great vacation rentals in Stockbridge
Guest suite in East Chatham
4.89 out of 5 average rating, 119 reviewsPrivate guest suite without the high price.
Farm stay in Pittsfield
4.99 out of 5 average rating, 112 reviewsPrivate 2nd-floor studio on a working produce farm
Apartment in Lee
4.79 out of 5 average rating, 109 reviewsCozy Berkshire Cottage Style Apartment
Home in Canaan
5.0 out of 5 average rating, 138 reviewsCountry Cottage
Guest suite in Lenox
4.96 out of 5 average rating, 171 reviewsT’Other House
Home in Great Barrington
4.96 out of 5 average rating, 217 reviewsJaw dropping mountain & lake views
Loft in Great Barrington
4.99 out of 5 average rating, 299 reviewsThe Old Red Barn
Cabin in Chatham
4.98 out of 5 average rating, 105 reviewsThe Upstate Cabin: A secluded getaway in the woods
Other great vacation rentals in Stockbridge
Home in Stockbridge
4.95 out of 5 average rating, 104 reviewsSun-filled, Charming Stockbridge Classic- In Town!
Home in Stockbridge
4.94 out of 5 average rating, 97 reviewsBright Stockbridge country home, near everything!
Home in Becket
4.95 out of 5 average rating, 41 reviewsNerd Preservation Sanctuary
Apartment in Canaan
5.0 out of 5 average rating, 94 reviewsMountain View Getaway
Guest suite in Great Barrington
5.0 out of 5 average rating, 49 reviewsSweet 1-bedroom with salt water pool
Apartment in Stockbridge
4.97 out of 5 average rating, 86 reviewsHistoric,Famous,Iconic, Unforgettable Berks Escape
Home in Lee
5.0 out of 5 average rating, 40 reviewsGreenHouse
Home in Stockbridge
4.98 out of 5 average rating, 87 reviewsGreek Revival Farmhouse
Quick stats about vacation rentals in Stockbridge
Total rentals
130 properties
Rentals with a pool
30 properties have a pool
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
80 properties are a good fit for families
Total number of reviews
3.6K reviews
Nightly prices starting at
$100 before taxes and fees
Frequently Asked Questions
Are there pet-friendly vacation rentals in Stockbridge?
Four-legged friends are welcome in Stockbridge. Choose from more than 30 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Stockbridge?
Yes! Work meets play with ease at over 60 vacation rentals in Stockbridge featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Stockbridge vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 30 vacation homes with pools in Stockbridge, available on Airbnb. Make a splash and soak up the sun in style!
Do boutique hotel rentals in Stockbridge have air conditioning?
Absolutely! We offer over 10 boutique hotel rentals with air conditioning in Stockbridge. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Stockbridge?
Stockbridge has more than 50 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in hotel rentals in Stockbridge?
Experience the best of Stockbridge with our hotel rentals, starting at about $150 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do boutique hotel rentals in Stockbridge have wifi?
Absolutely! We offer over 10 boutique hotel rentals with wifi in Stockbridge. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Stockbridge have a gym?
Absolutely! We offer over 10 house rentals with a gym in Stockbridge. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Stockbridge have a bbq area?
Absolutely! We offer over 10 cabin rentals with a bbq area in Stockbridge. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Hotel Rentals in Stockbridge?
Enhance your stay in our Hotel Rentals with the most popular amenities: over 20 homes with wifi, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
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