Vacation rentals in Stockbridge - HomeToGo base64Hash Vacation rentals in Stockbridge - HomeToGo

Vacation rentals in Stockbridge

Browse 163 available vacation homes and compared across 11 trusted partners
Anytime
Guests
Anytime
Guests

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • House
    • Apartment
    • Bed and breakfast

  • Distance to center

    • 2 mi
    • 3 mi
    • Any

  • Rating

    • 4.5+
    • 4+

  • Services

    • Pool
    • WiFi
    • Kitchen
    • Air conditioning
    • TV
    • Parking
    • Washing machine
    • Balcony/patio
    • Microwave
    • Dishwasher
    • Hot tub
    • Fireplace
    • Sauna
    • Crib
    • Yard
    Show more

  • Accommodation type

    • Pet-friendly
    • No smoking
    • No pets
    • Wheelchair access

  • Activities

    • Grill
    • Fishing

Top 15 most Recommended Vacation Rentals in Stockbridge

Discover your ideal Stockbridge vacation rental with real-time comparisons of 163 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Condo Stockbridge
Condo ∙ 7 guests ∙ 3 bedrooms

Children-friendly condo with jacuzzi | Mountain view | Perfect for remote work | Pets allowed

Stockbridge, Berkshire County, Massachusetts, United States
This Stockbridge condo offers mountain views, a hot tub, and a waterfront location, perfect for families and pets alike.
from $135
per night
Outstanding(7 ratings)
from $135
per night
View deal
House Stockbridge
House ∙ 6 guests ∙ 4 bedrooms

House with terrace, barbeque & garden | Lake view

Stockbridge, Berkshire County, Massachusetts, United States
This waterfront house rental in Stockbridge features a cozy fireplace, a full kitchen, and a yard, perfect for family fun.
from $413
per night
Outstanding(21 ratings)
from $413
per night
View deal
House Stockbridge
House ∙ 8 guests ∙ 3 bedrooms

Family-oriented ample vacation home with yard, patio & BBQ | Nature view | Pet-friendly

Stockbridge, Berkshire County, Massachusetts, United States
This house rental in Glendale features a kitchen, fireplace, balcony, and a yard, perfect for gatherings of up to 8 guests.
from $410
per night
Outstanding(112 ratings)
from $410
per night
View deal
Cabin Stockbridge
Cabin ∙ 6 guests ∙ 2 bedrooms

Cottage with patio | Lake view

Stockbridge, Berkshire County, Massachusetts, United States
This Stockbridge cabin offers a kitchen, parking, and waterfront views, accommodating up to six for an unforgettable getaway.
from $174
per night
Outstanding(39 ratings)
from $174
per night
View deal
House Stockbridge
House ∙ 6 guests ∙ 4 bedrooms

Fully equipped wonderful vacation home with yard, grill & terrace | Nature view | Suitable for remote work

Stockbridge, Berkshire County, Massachusetts, United States
This waterfront house rental in Stockbridge features a fireplace, kitchen, yard, mountain view, and parking for six guests.
from $351
per night
Outstanding(44 ratings)
from $351
per night
View deal
House Stockbridge
House ∙ 8 guests ∙ 4 bedrooms

House with barbecue, patio & yard | Nature view

Stockbridge, Berkshire County, Massachusetts, United States
This house rental in Stockbridge offers a fireplace, a kitchen, and a yard, perfect for families seeking a memorable getaway.
from $350
per night
Outstanding(11 ratings)
from $350
per night
View deal
House Stockbridge
House ∙ 6 guests ∙ 3 bedrooms

Child-friendly spacious house with barbecue, yard & patio | City view | Perfect for remote work

Stockbridge, Berkshire County, Massachusetts, United States
This welcoming Stockbridge house rental features a fireplace, kitchen, yard, and mountain views, perfect for family getaways.
from $363
per night
Outstanding(46 ratings)
from $363
per night
View deal
Cabin Stockbridge
Cabin ∙ 6 guests ∙ 3 bedrooms

Cottage with terrace & BBQ

Stockbridge, Berkshire County, Massachusetts, United States
This cozy cabin in Stockbridge features a fireplace, kitchen, and parking, perfect for a getaway with family or friends.
from $344
per night
from $344
per night
View deal
House Stockbridge
House ∙ 7 guests ∙ 4 bedrooms

Child-friendly charming vacation home with barbeque, yard & patio | Nature view | Perfect for remote work

Stockbridge, Berkshire County, Massachusetts, United States
This waterfront house in Stockbridge features a cozy fireplace, spacious yard, and a full kitchen, perfect for family gatherings.
from $249
per night
Outstanding(81 ratings)
from $249
per night
View deal
House Stockbridge
House ∙ 8 guests ∙ 3 bedrooms

Child-friendly vacation home with garden, terrace & grill | Mountain view | Pets allowed

Stockbridge, Berkshire County, Massachusetts, United States
This house rental in Glendale features a balcony with mountain views, a yard, and a fireplace, perfect for family getaways.
from $294
per night
Outstanding(61 ratings)
from $294
per night
View deal
House Stockbridge
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped pleasant house with terrace, grill & yard | Mountain view

Stockbridge, Berkshire County, Massachusetts, United States
This house rental in Stockbridge features a kitchen, yard, hot tub, mountain view, and parking for a memorable getaway.
from $337
per night
Outstanding(22 ratings)
from $337
per night
View deal
House Stockbridge
House ∙ 7 guests ∙ 3 bedrooms

House with terrace, jacuzzi & grill

Stockbridge, Berkshire County, Massachusetts, United States
This Stockbridge house rental features a fireplace, kitchen, hot tub, and parking, perfect for family gatherings of up to 7.
from $448
per night
Outstanding(16 ratings)
from $448
per night
View deal
House Stockbridge
House ∙ 5 guests ∙ 2 bedrooms

Vacation home with grill & yard | Mountain view

Stockbridge, Berkshire County, Massachusetts, United States
This Stockbridge house rental features a kitchen, fireplace, and yard with mountain views, perfect for a family getaway with pets.
from $179
per night
from $179
per night
View deal
House Stockbridge
House ∙ 8 guests ∙ 4 bedrooms

House with terrace & grill

Stockbridge, Berkshire County, Massachusetts, United States
This Stockbridge house rental features a cozy fireplace, a full kitchen, and ample parking for an unforgettable getaway with friends.
from $268
per night
Outstanding(2 ratings)
from $268
per night
View deal
House Stockbridge
House ∙ 6 guests ∙ 3 bedrooms

House with barbeque, garden & patio

Stockbridge, Berkshire County, Massachusetts, United States
This Stockbridge house rental features a fireplace, kitchen, yard, and parking, perfect for a getaway with up to six guests.
from $179
per night
Outstanding(31 ratings)
from $179
per night
View deal

Vacation Houses With Pools

House Stockbridge
from $428
per night
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped vacation home with pool | Mountain view

Stockbridge, Berkshire County, Massachusetts, United States
Pool
View deal
Condo Stockbridge
from $226
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Fully equipped spacious condo with pool & patio

Stockbridge, Berkshire County, Massachusetts, United States
Pool
View deal
House Stockbridge
from $1,234
per night
House ∙ 16 guests ∙ 6 bedrooms

Family-friendly wonderful house with garden, patio & private pool

4.9
Outstanding(125 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Pool
View deal
See all offers

Dog-Friendly Vacation Rentals

Apartment Stockbridge
from $160
per night
Apartment ∙ 2 guests ∙ 1 bedroom

Family-oriented wonderful holiday apartment | Pet-friendly

Stockbridge, Berkshire County, Massachusetts, United States
Pet-friendly
View deal
House Stockbridge
from $285
per night
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped spacious house with BBQ & terrace | Pets allowed

5.0
Outstanding(112 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Pet-friendly
View deal
House Stockbridge
from $327
per night
House ∙ 5 guests ∙ 3 bedrooms

House with garden, barbeque & terrace | Lake view

4.9
Outstanding(34 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Pet-friendly
View deal
See all offers

Vacation houses with Balconies or Patios

House Stockbridge
from $407
per night
House ∙ 5 guests ∙ 3 bedrooms

Vacation home with BBQ, terrace & yard

Stockbridge, Berkshire County, Massachusetts, United States
Balcony/Patio
View deal
Cabin Stockbridge
from $260
per night
Cabin ∙ 6 guests ∙ 3 bedrooms

Cottage with patio, garden & grill

4.9
Outstanding(31 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Balcony/Patio
View deal
House Stockbridge
from $432
per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation home with BBQ, garden & patio

5.0
Outstanding(24 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Balcony/Patio
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Stockbridge offering exceptional value for money

Cabin Stockbridge
from $247
per night
Cabin ∙ 4 guests ∙ 2 bedrooms

Cabin with barbeque & patio

4.8
Outstanding(67 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
View deal
Cabin Stockbridge
from $437
per night
Cabin ∙ 8 guests ∙ 4 bedrooms

Cottage with barbeque & terrace

5.0
Outstanding(2 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
View deal
House Stockbridge
-15%
$245
from $209
per night
House ∙ 6 guests ∙ 3 bedrooms

Child-friendly spacious vacation home with barbeque, terrace & yard

4.9
Outstanding(31 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
View deal

Top-Rated Vacation rentals in Stockbridge

Book the highest-rated Stockbridge vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

Condo Stockbridge
from $257
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with garden | Lake view

4.6
Excellent(71 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
View deal
Condo Stockbridge
from $257
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with garden | Nature view

4.6
Excellent(46 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
View deal
House Stockbridge
from $196
per night
House ∙ 6 guests ∙ 3 bedrooms

House with barbecue

5.0
Outstanding(32 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
View deal

Discover real guest reviews to help you choose the perfect stay in Stockbridge

How are reviews collected?
Mary H.
Guest verified by HomeToGo

Beautiful home perfect for a large family gathering. The kitchen was well stocked. We took advantage of the hot tub, piano, puzzle table, and playing games on the large dining table. Cross country skiing was available right outside the door and downhill a short drive away. Thanking you for making such a special time possible.

Reviewed on 1/22/2026 | Family
House Stockbridge
from $766
per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding(7 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
View deal

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Popular Features & Amenities in Stockbridge

  • Pet-friendly (61)
  • Pool (79)
  • WiFi (173)
  • Kitchen (101)
  • Air conditioning (152)
  • TV (152)
  • No smoking (156)
  • Grill (81)
  • Parking (18)
  • Washing machine (90)
  • Balcony/patio (96)
  • Microwave (104)

Nearly half of the rentals include a pool, which makes Stockbridge a perfect destination for people looking to relax pool-side. In addition, more House rental have pools than any other type of accommodation. They are a great choice if you go in a group of 7, as that is the number of people they can welcome on average. Among these rentals, 57 of them are within 2 miles of water.

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.

What are the best activities for families in Stockbridge?

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.

Where are the unique attractions in Stockbridge?

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 163 rentals
🌙 Nightly prices starting at $134
⭐ Popular amenities Pets allowed, Pool and Internet
🐾 Pet friendly homes 61 homes
🏊 Vacation rentals with pools 69 homes
10 reviews
Stockbridge vacation rentals have an average rating of 5/5 on 10 reviews left by travelers.

Frequently Asked Questions

What is the typical price per night for a vacation home in Stockbridge?

On average, vacation rentals in Stockbridge cost around $134 per night. $626 is the average nightly price for house rentals in Stockbridge. Bed and breakfast rentals in Stockbridge cost $583 per night on average.

How many vacation rentals are available for booking in Stockbridge?

There are currently 163 vacation rentals in Stockbridge to browse and book for your next trip.

What amenities are most popular for vacation homes in Stockbridge?

Three most popular amenities for home rentals in Stockbridge include accommodations with: Pets allowed, Pool, and Internet.

How many vacation homes with a pool are in Stockbridge?

Stockbridge offers 69 Hotel room and Cabin options available for renting.

Are dogs allowed in vacation rentals in Stockbridge?

Absolutely, currently there are 61 vacation homes in Stockbridge that allow dogs and the average price is $481 per night.

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