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.

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Best Vacation Home Deals in Stockbridge
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Compare and find a vacation rental meeting your needs among the 143 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 80%.
Top-Rated Rentals and Accommodations in Stockbridge
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Recommended Vacation Rentals in Stockbridge
Find your perfect vacation rental in Stockbridge: from $190 per night
Budget-friendly Vacation Rentals in Stockbridge
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Vacation Houses With Pools
Make a splash on your next vacation! Over 56% 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!
Best vacation rentals with a balcony
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
Filters are available so you can tailor your search and find the ideal accommodation in Stockbridge. Most of the accommodations in Stockbridge offer "Pets allowed" or "Pool," which makes it a wonderful destination if you are looking for a pet-friendly rental or you're dreaming of days spent poolside. Not as many vacation rentals in Stockbridge are available if you want to sweat it out in a sauna or if you need a crib for your baby as "Crib" and "Sauna" are not often provided in this destination.
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
Walk in the footprints of dinosaurs
Don't miss the dinosaur footprints on the west bank of the Connecticut River. These 134 footprints belonging to carnivorous two-legged dinosaurs date back to 190 million years ago. In nearby Amherst, you can visit the museum dedicated to one of America's greatest and most reclusive poets, Emily Dickinson. Tours of the house where she lived and worked, largely in secret, let you peep through the keyhole into the world of this pivotal poet.
Delve into the wonky world of Dr. Seuss
Dr. Seuss is beloved among children around the world. What could be more exciting than a trip to the Dr. Seuss National Memorial Sculpture Garden? Dedicated to the wacky creations of the famous children's book writer, this park is full of life-size sculptures of the Cat in the Hat and other Seuss favorites – make sure to bring your camera! The museum dedicated to the author is also worth a look. Also, at the George Walter Vincent Smith Art Museum in Springfield, kids can engage with costumes and armor in the exciting Hasbro Games Art Discovery Center.
Discovering Northampton and surroundings
Pioneer Valley is less than an hour from your comfortable vacation home in Stockbridge. Amid its softly undulating countryside and picturesque farmland, you’ll find the attractive city of Northampton, with its high-class cuisine and exceptional museums. Wander through its winding streets past red brick college buildings and independent bookstores. Cafés and club culture are prevalent in this charming and offbeat town.
Information about vacation rentals in Stockbridge
🏡 Vacation rentals available | 142 homes |
---|---|
💳 Possible discounts | up to 58% |
🌙 Nightly prices starting at | $190 |
⭐ Popular amenities | Pets allowed, Pool and Internet |
🐾 Pet friendly homes | 23 homes |
🏊 Vacation rentals with pools | 80 homes |
Frequently Asked Questions
What is the typical nightly price for a vacation home in Stockbridge?
The nightly price of accommodations in Stockbridge starts at $190. If you’re interested in a house rental, the average price is $681 per night. A bed and breakfast rental Stockbridge will cost on average $409 per night.
How many vacation homes are available to book in Stockbridge?
There are 142 vacation homes available for booking for your vacation.
What are the most popular amenities for vacation rentals in Stockbridge?
If you're looking to book a vacation rental in Stockbridge, the most popular amenities are: Pool, Pets allowed and Internet.
How many vacation rentals with pools are there in Stockbridge?
Discover 80 vacation rentals available in Stockbridge.
Are dogs allowed in vacation homes in Stockbridge?
In case if you are traveling with a pet in Stockbridge - 16% of vacation homes allow pets.
What's the best month to travel to Stockbridge?
July and August are typically the warmest months in Stockbridge with temperatures around 81 °F. The coldest months in Stockbridge are January and February, with 16 °F on average.
Find the perfect Stockbridge home to match your style
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