Stockbridge Vacation Rentals

Compare 499 available properties from 15 providers
Stockbridge
Save up to 44%

Best vacation home deals in Stockbridge

$116
from $65
-44%
400 ft² Apartment
2 1
Lee, Berkshire County, Massachusetts, United States
Found on
HomeAway
$294
from $243
-17%
1250 ft² House
6 3
Stockbridge, Berkshire County, Massachusetts, United States
Found on
HomeAway
$291
from $211
-27%
House
6 3
Stockbridge, Berkshire County, Massachusetts, United States
Found on
HomeAway

Compare and find a vacation rental meeting your needs among the 499 beautiful options from 15 providers in Stockbridge. Using HomeToGo you can directly compare the offers of each listed property to discover the best price and save up to 44%.

Recommended vacation rentals in Stockbridge

Rent a vacation accommodation in Stockbridge: from $52 per night

$116
from $65
-44%
400 ft² Apartment
2 1
Lee, Berkshire County, Massachusetts, United States
4.6
"Excellent" 5 reviews
Found on HomeAway
from $122
540 ft² Apartment
3
Stockbridge, Berkshire County, Massachusetts, United States
5.0
"Excellent" 7 reviews
Found on HomeAway
from $129
890 ft² Apartment
5 3
Stockbridge, Berkshire County, Massachusetts, United States
5.0
"Excellent" 6 reviews
Found on HomeAway
from $200
1190 ft² House
4 2
West Stockbridge, Berkshire County, Massachusetts, United States
5.0
"Excellent" 3 reviews
Found on HomeAway
from $500
House
6 3
Stockbridge, Berkshire County, Massachusetts, United States
4.7
"Excellent" 19 reviews
Found on HomeAway
from $362
2500 ft² House
6 3
Housatonic, Great Barrington, Massachusetts, United States
4.9
"Excellent" 6 reviews
Found on HomeAway
$291
from $211
-27%
House
6 3
Stockbridge, Berkshire County, Massachusetts, United States
4.6
"Excellent" 18 reviews
Found on HomeAway
$165
from $126
-24%
1000 ft² House
6 2
Lee, Berkshire County, Massachusetts, United States
4.9
"Excellent" 8 reviews
Found on HomeAway
See all offers

  Vacation homes with fishing spots nearby

from $315
1100 ft² House
6 2
Stockbridge, Berkshire County, Massachusetts, United States
4.8
"Excellent" 10 reviews
Found on HomeAway
from $236
1590 ft² House
6 3
Stockbridge, Berkshire County, Massachusetts, United States
5.0
"Excellent" 25 reviews
Found on HomeAway
$334
from $247
-26%
1250 ft² House
7 4
Stockbridge, Berkshire County, Massachusetts, United States
4.9
"Excellent" 12 reviews
Found on HomeAway
$134
from $100
-25%
590 ft² Apartment
4 1
Lee, Berkshire County, Massachusetts, United States
4.7
"Excellent" 26 reviews
Found on HomeAway
See all offers

  Vacation rentals with a fireplace

$310
from $253
-18%
790 ft² House
4 2
Stockbridge, Berkshire County, Massachusetts, United States
4.8
"Excellent" 10 reviews
Found on HomeAway
$290
from $102
-65%
740 ft² Apartment
6 2
Stockbridge, Berkshire County, Massachusetts, United States
4.7
"Excellent" 30 reviews
Found on HomeAway
from $143
1500 ft² House
6 2
Lee, Berkshire County, Massachusetts, United States
4.9
"Excellent" 30 reviews
Found on HomeAway
from $264
1190 ft² House
4 2
Stockbridge, Berkshire County, Massachusetts, United States
4.0
"Very good" 1 review
Found on HomeAway
See all offers

  Apartments with a balcony or patio

$203
from $172
-15%
1500 ft² Apartment
4 1
Stockbridge, Berkshire County, Massachusetts, United States
5.0
"Excellent" 4 reviews
Found on HomeAway
$250
from $150
-40%
850 ft² House
6 2
Stockbridge, Berkshire County, Massachusetts, United States
4.4
"Outstanding" 3 reviews
Found on HomeAway
$387
from $316
-18%
House
8 3
Stockbridge, Berkshire County, Massachusetts, United States
5.0
"Excellent" 26 reviews
Found on HomeAway
from $323
2800 ft² House
10 5
Lee, Berkshire County, Massachusetts, United States
5.0
"Excellent" 3 reviews
Found on HomeAway
See all offers

Popular rental amenities in Stockbridge

  • Internet (420)
  • No smoking (376)
  • TV (360)
  • AC (331)
  • Parking (329)
  • Kitchen (303)
  • Yard (285)
  • Microwave (262)
  • Washer (237)
  • Grill (224)
  • Dishwasher (221)
  • Fishing (209)
Filters are available so you can tailor your search and find the ideal accommodation in Stockbridge. Most of the accommodations in Stockbridge offer "internet" or "TVs," which makes it a wonderful destination if you need internet access during your vacation or you want to tune out with some TV time. Not as many vacation rentals in Stockbridge are available if you want a rental with a jacuzzi or if you want to sweat it out in a sauna as "saunas" and "Jacuzzis" are not often provided in this destination.

Price and Availability Index Stockbridge

Vacation Rental Price Information in Stockbridge

The price graph will give you the nightly price average for the upcoming 6 months. $406 is the highest price average in the next six months. Opt for a getaway in December (12/22 - 12/29) for optimal savings when heading to Stockbridge.

Rental Availability Information in Stockbridge

Find out the percentage of available rentals in Stockbridge with the graph above. More people travel to Stockbridge a week in June (6/30 - 7/7). So far, 67% of the rentals are occupied this week. Conversely, 85% of the rentals are still available during a week in December (12/29 - 1/5).

The weather in Stockbridge

32°
16°
34°
16°
41°
23°
55°
34°
68°
46°
73°
54°
81°
59°
77°
55°
72°
48°
59°
39°
46°
28°
37°
25°
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Find the Stockbridge climate diagram. July is the warmest month of the year in Stockbridge with temperatures reaching a maximum average of 80°. On the contrary, the coolest month is January. The wettest month is December with 20 rainy days on average. On the contrary, there is an average of only 11 rainy days in August, which is the driest month.

More than half of the offers (54.14%) in Stockbridge are house rentals. They are the most typical accommodations in this destination. Additionally, the median size of house rentals in Stockbridge is 2,800 ft² and they cost, on average, $450 per night. Furthermore, this type of accommodation is an excellent option for large groups, as most of the house rentals can host 8 people. You can also consider other accommodation types in Stockbridge. Bed & Breakfast rentals are, for example, another common accommodation type in this destination, with 116 listed accommodations. Our data reveals that the standard price of bed & breakfast rentals is $286 per night for an area of 450 ft².

Explore an ancient Eden with a Stockbridge vacation rental

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.

Show all 499 properties
Art & Culture

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.

Family Activities

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.

Local Attractions

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.

We compare more than 250 providers, including:

Booking.com Vacation Rentals in Stockbridge VRBO Vacation Rentals in Stockbridge HomeAway Vacation Rentals in Stockbridge TripAdvisor Vacation Rentals in Stockbridge VacationRentals.com Vacation Rentals in Stockbridge HouseTrip Vacation Rentals in Stockbridge FlipKey Vacation Rentals in Stockbridge Wimdu Vacation Rentals in Stockbridge 9flats.com Vacation Rentals in Stockbridge VaycayHero Vacation Rentals in Stockbridge PerfectPlaces.com Vacation Rentals in Stockbridge Homestay.com Vacation Rentals in Stockbridge only-apartments Vacation Rentals in Stockbridge Interhome Vacation Rentals in Stockbridge Bedycasa Vacation Rentals in Stockbridge Novasol Vacation Rentals in Stockbridge HomeEscape Vacation Rentals in Stockbridge

Vacation destinations near Stockbridge