Opting for a vacation home in Stockbridge, Massachusetts, will place you strategically at the westernmost edge of the state, just south of Green Mountain National Forest. This Eden-like woodland stretches for miles, encompassing waterfalls, cliffs, and extensive trails through peaceful backcountry – all yours to discover.

Choose the perfect vacation rental
Best Vacation Home Deals in Stockbridge
Compare and find a vacation rental meeting your needs among the 187 beautiful options from 6 providers in Stockbridge. Using HomeToGo you can directly compare the offers of each listed property to discover the best price and save up to 78%.
Top-Rated Rentals and Accommodations in Stockbridge
Recommended Vacation Rentals in Stockbridge
Find your perfect vacation rental in Stockbridge: from $147 per night
Budget-friendly Vacation Rentals in Stockbridge
Vacation Houses With Pools
Make a splash on your next vacation! Over 49% of in Stockbridge vacation rentals have a swimming pool.
Dog-Friendly Vacation Rentals
Bring Fido on your next trip and book a stay in one of these pet-friendly rentals in Stockbridge!
Apartments With Balconies or Patios
Looking for a home with a balcony? Check out these vacation homes in Stockbridge with their own private patios and balconies.
Popular Rental Amenities in Stockbridge
The Weather in Stockbridge
This is the climate diagram in Stockbridge. The highest average temperatures are in the month of July. On the contrary, the coolest month is January. The rainiest month is December while the driest month is August.
7-Day Weather Forecast in Stockbridge
Accommodations for your vacation in Stockbridge
Information about vacation rentals in Stockbridge
🏡 Vacation rentals | 187 properties |
---|---|
💳 Possible discounts | up to 51% |
🌙 Nightly prices starting at | $147 |
⭐ Popular amenities | Internet, TV and Air conditioning |
🐾 Pet friendly accommodations | 31 properties |
🏊 Vacation rentals with pools | 95 properties |
Frequently Asked Questions
What is the price per night for a vacation rental in Stockbridge?
The price of a night's stay in Stockbridge starts at $147. If you’re interested in a house rental, the average price is $649 per night. A bed & breakfast Stockbridge will cost on average $439 per night.
How many vacation rentals are available for booking in Stockbridge?
Currently there are 187 vacation homes from 6 providers in Stockbridge.
What amenities are most popular for vacation homes in Stockbridge?
The most popular amenities for home rentals in Stockbridge include accommodations that have: Internet, TV, and Air conditioning.
Are dogs allowed in vacation rentals in Stockbridge?
If traveling with a pet in Stockbridge, 16% of rentals are pet-friendly.
What's the best time to travel to Stockbridge?
July and August are typically the warmest months in Stockbridge with temperatures around 81 °F. January and February in Stockbridge are the coldest, with 16 °F on average.
We list offers from thousands of providers, including:











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