Vacation Rentals in Stockbridge

Vacation Rentals in Stockbridge

Start comparing over 45 rentals in Stockbridge and book at the best price!

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Best Vacation Rentals in Stockbridge

Guests agree: these stays are highly rated for location, cleanliness, and more.
Vacation Rental for 4 Guests in Stockbridge, Berkshire County
Vacation Rental for 4 Guests in Stockbridge, Berkshire County, Picture 1
Vacation Rental for 4 Guests in Stockbridge, Berkshire County, Picture 2
Vacation Rental for 4 Guests in Stockbridge, Berkshire County, Picture 3
Vacation Rental for 4 Guests in Stockbridge, Berkshire County, Picture 4
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Stockbridge, Berkshire County
Vacation Rental • 4 Guests • 4 Bedrooms
10.0
(23 reviews)
Transform yourself in to the middle of a Norman Rockwell painting. It is easy to see how so many of his paintings were inspired by homes like these and the Stockbridge locals. Cherry Hill at Farley's Crossing has been owned by the same family for over 150 years. A three minute drive from the famous Red Lion Inn in downtown Stockbridge brings you over Farley's Crossing and right up to 13 Cherry Street. Whether you are in town to enjoy the Boston Symphony Orchestra at Tanglewood, or a day at the Stockbridge Bowl beach you have all the best activities near by. Winter sports are all around you ...
from $301 / night
Vacation Rental for 6 Guests in Stockbridge, Berkshire County
Vacation Rental for 6 Guests in Stockbridge, Berkshire County, Picture 1
Vacation Rental for 6 Guests in Stockbridge, Berkshire County, Picture 2
Vacation Rental for 6 Guests in Stockbridge, Berkshire County, Picture 3
Vacation Rental for 6 Guests in Stockbridge, Berkshire County, Picture 4
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Stockbridge, Berkshire County
Vacation Rental • 6 Guests • 2 Bedrooms
8.9
(15 reviews)
We want renters to be comfortable, so we have been particularly careful during the pandemic regarding cleaning and by placing limitations on large gatherings and parties. We hope you understand.This Cozy rustic Berkshire Home offers lots of charm with modern amenities for a wonderful stay in the Berkshire Mountains. Summer: We are centrally located less than two miles from Tanglewood and a mile and a half from Kripalu. The house is a stone's throw from the Stockbridge bowl. Fishing in season, many walking and climbing trails, and lake swimming at the nearby Stockbridge Town beach. The Lake ...
from $183 / night
Vacation Rental for 8 Guests in Stockbridge, Berkshire County
Vacation Rental for 8 Guests in Stockbridge, Berkshire County, Picture 1
Vacation Rental for 8 Guests in Stockbridge, Berkshire County, Picture 2
Vacation Rental for 8 Guests in Stockbridge, Berkshire County, Picture 3
Vacation Rental for 8 Guests in Stockbridge, Berkshire County, Picture 4
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Stockbridge, Berkshire County
Vacation Rental • 1399 ft² • 3 Bedrooms
9.8
(29 reviews)
The Residence is a beautiful, secluded home in the Berkshire foothills. The 14-acre property includes hiking trails through the woods, a meadow, and a lovely babbling brook. Despite its secluded feel, the house just a short drive from many of the area's favorite attractions. The Residence provides a wonderful for base for enjoying all that the Berkshires have to offer, though guests may decide to spend much of their stay exploring the rustic beauty of the property itself.The house gets beautiful sunlight and has a fireplace and a deck overlooking the woods. The property includes a separate ...
from $268 / night

Prices and availability

Current Vacation rental prices Stockbridge

$681for 22 Jun - 29 Jun
$639 annual average
Jul
Aug
Sep
Oct
Nov
Dec
Feb
Average price per week

Current vacation rental availability Stockbridge

5%for 22 Jun - 29 Jun
37% annual average
Jul
Aug
Sep
Oct
Nov
Dec
Feb
Percentage of available rentals

FAQs: Vacation Rentals in Stockbridge

On average, how much do vacation rentals in Stockbridge cost?

With an average cost of $664 per night, Stockbridge lies at the upper end of the price range for vacation rentals in the USA.

Which months allow you to save the most on vacation rentals?

Travelers who want to save as much as possible travel to Stockbridge in May, March, or July, the cheapest months of the year, with average prices of $529, $606, and $607 per night, respectively, based on the previous year.

In which months is it more expensive to rent a vacation rental in Stockbridge?

Last year, the month that offered the highest average prices in Stockbridge was November, with an average price of $867 per night. This was followed by October, with an average of $813, and then January, with $745.

Is Stockbridge a good location for a last-minute getaway?

When visiting Stockbridge, we recommend you to be proactive as 86% of rentals are usually booked, according to last year's data.

What time of the year can I find more available vacation rentals?

The most available months are, on average, September (with an availability of 50%), October (31%), and January (21%), according to the trends observed in the prior year.

Are there many vacation rentals in Stockbridge?

In Stockbridge we work with 2 different providers to give you a choice of 130 properties, so you will not be short of options!

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