Find Vacation Rentals in Stockbridge

We have 215 properties to choose from
Anytime
Guests
Anytime
Guests

Popular Stockbridge Vacation Rentals

Find the perfect Stockbridge vacation rental

House Stockbridge
from $410 per night
House ∙ 4 guests ∙ 2 bedrooms

65 m² House

4.8
Outstanding(22 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
HomeToGo
Details
Cabin Stockbridge
from $363 per night
Cabin ∙ 4 guests ∙ 4 bedrooms

65 m² Cabin

4.8
Outstanding(22 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Vrbo
Details
House Stockbridge
from $293 per night
House ∙ 6 guests ∙ 3 bedrooms

149 m² House

5.0
Outstanding(184 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Vrbo
Details
House Stockbridge
from $383 per night
8 guests ∙ 5 bedrooms

House

5.0
Outstanding(79 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Vrbo
Details
House Stockbridge
from $366 per night
House ∙ 6 guests ∙ 3 bedrooms

107 m² House

5.0
Outstanding(37 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Vrbo
Details
House Stockbridge
from $950 per night
House ∙ 24 guests ∙ 12 bedrooms

539 m² House

4.9
Outstanding(63 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Vrbo
Details
House Stockbridge
from $312 per night
House ∙ 6 guests ∙ 3 bedrooms

158 m² House

5.0
Outstanding(80 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Vrbo
Details
Apartment Stockbridge
from $358 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

70 m² Apartment

5.0
Outstanding(40 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Vrbo
Details
House Stockbridge
from $465 per night
4 guests ∙ 2 bedrooms

House

5.0
Outstanding(23 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Vrbo
Details
Show more

Cabins and Homes With Fireplaces

House  Stockbridge
from $310 per night
House ∙ 8 guests ∙ 4 bedrooms

257 m² House

5.0
Outstanding(20 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Fireplace
Vrbo
Details
House  Stockbridge
from $377 per night
House ∙ 6 guests ∙ 3 bedrooms

84 m² House

4.8
Outstanding(22 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Fireplace
Vrbo
Details
Condo  Stockbridge
from $188 per night
7 guests ∙ 3 bedrooms

Condo

4.7
Excellent(6 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Fireplace
Vrbo
Details
Show more

Recommended Rentals With Pools

House  Stockbridge
from $1,349 per night
House ∙ 10 guests ∙ 4 bedrooms

362 m² House

5.0
Outstanding(3 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Pool
HomeToGo
Details
House  Stockbridge
from $732 per night
House ∙ 6 guests ∙ 3 bedrooms

195 m² House

Stockbridge, Berkshire County, Massachusetts, United States
Pool
Vrbo
Details
House  Stockbridge
from $1,085 per night
House ∙ 16 guests ∙ 6 bedrooms

511 m² House

4.9
Outstanding(110 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Pool
Vrbo
Details
Show more

Pet-Friendly Homes and Apartments

House  Stockbridge
from $328 per night
House ∙ 6 guests ∙ 3 bedrooms

148 m² House

5.0
Outstanding(187 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Pet-friendly
HomeToGo
Details
House  Stockbridge
from $342 per night
House ∙ 8 guests ∙ 4 bedrooms

130 m² House

4.9
Outstanding(57 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Pet-friendly
Vrbo
Details
House  Stockbridge
from $501 per night
House ∙ 8 guests ∙ 3 bedrooms

209 m² House

5.0
Outstanding(30 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Pet-friendly
Vrbo
Details
Show more

Frequently Asked Questions

How much does it cost to book a vacation rental in Stockbridge?

Usually, a stay in Stockbridge starts at $181 per night.

Are there any vacation rentals available to book in Stockbridge?

Tripping.com offers great selection on vacation rentals with 215 offers currently available in Stockbridge.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Stockbridge

Looking for a vacation rental in Stockbridge? Tripping.com has 52 vacation rental homes available in Stockbridge. You'll find 0 studios, 13 1-bedroom, 6 2-bedroom and 33 rentals with 3 or more bedrooms ranging from $102 a night. For extra convenience, many of these vacation homes can be booked directly online. The average price of a nightly rental in Stockbridge is $385 while the average price of a weekly rental is $25. For those looking for more than a short term rental such as corporate rentals, extended stays or long term rentals, the average monthly price of a Stockbridge home is $25. Wondering if you can bring your dog or cat along with you? There are 12 pet-friendly vacation rentals available in Stockbridge. In addition to accommodating pets, Stockbridge rentals offer a variety of amenities. In particular, 41 rentals have Internet and WiFi, 41 have TV and/or cable and 5 have a pool or hot tub. Search properties from 5 vacation rental sites in Stockbridge where the top providers in that area are HomeAway, TripAdvisor, and HRS Holidays. There are 32 HomeAway rentals, 6 TripAdvisor short term rentals and 6 HRS Holidays vacation rentals.

What are the trendiest neighborhoods in Stockbridge?

Popular Day Trips Near Stockbridge

image-tag