Vacation Rentals in Stockbridge

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

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Vacation housesBarnsPoolPets allowed

8.0

Vacation Rentals in Stockbridge

Vacation rental for 4 people, with terrace and yard

2 bedrooms

9.4

(7 reviews)

from $242 / nightFREE cancellation

Vacation rental for 4 people, with yard, with pets

2 bedrooms

9.0

(14 reviews)

from $256 / nightFREE cancellation

Vacation rental for 4 people, with yard and terrace

2 bedrooms

10.0

(11 reviews)

from $300 / nightFREE cancellation

Vacation rental for 4 people, with terrace and yard

2 bedrooms

9.8

(13 reviews)

from $245 / nightFREE cancellation

Vacation rentals with free cancellation

Vacation rental for 4 people, with yard

4 bedrooms

10.0

(23 reviews)

from $303 / nightFREE cancellation

Vacation rental for 5 people, with yard, with pets

3 bedrooms

9.6

(19 reviews)

from $279 / nightFREE cancellation

Vacation rental for 6 people, with yard and terrace

3 bedrooms

10.0

(14 reviews)

from $444 / nightFREE cancellation

Vacation rental for 6 people

2 bedrooms

10.0

from $242 / nightFREE cancellation

Vacation rentals with pets allowed

Pets allowed

Vacation rental for 6 people, with yard, with pets

2 bedrooms

8.8

(24 reviews)

from $207 / nightFREE cancellation

Pets allowed

Vacation rental for 6 people, with balcony and hot tub as well as yard

2 bedrooms

8.9

(15 reviews)

from $184 / night

Pets allowed

Vacation rental for 6 people

3 bedrooms

9.6

(31 reviews)

from $298 / night

Pets allowed

Vacation rental for 8 people, with hot tub and yard, with pets

4 bedrooms

9.8

(65 reviews)

from $357 / nightFREE cancellation

Vacation rentals with hot tub

Hot tub

Vacation rental for 6 people, with hot tub and yard as well as terrace

3 bedrooms

9.8

(10 reviews)

from $304 / nightFREE cancellation

Hot tub

Vacation rental for 7 people, with hot tub

3 bedrooms

10.0

(6 reviews)

from $496 / nightFREE cancellation

Hot tub

Vacation rental for 7 people, with balcony and hot tub

3 bedrooms

9.0

(2 reviews)

from $148 / nightFREE cancellation

Hot tub

Vacation rental for 6 people, with yard and hot tub, with pets

3 bedrooms

from $578 / nightFREE cancellation

Vacation Rentals with Yard

Yard

Vacation rental for 5 people, with yard

3 bedrooms

9.8

(24 reviews)

from $338 / night

Yard

Vacation rental for 6 people, with yard

2 bedrooms

9.8

(10 reviews)

from $515 / night

Yard

Vacation rental for 7 people, with yard and terrace

4 bedrooms

10.0

(29 reviews)

from $280 / nightFREE cancellation

Yard

Vacation rental for 7 people, with terrace and yard

4 bedrooms

9.8

(10 reviews)

from $401 / nightFREE cancellation

Find Vacation Rentals in Stockbridge

Best Vacation Rentals in Stockbridge

Guests agree: these stays are highly rated for location, cleanliness, and more.

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

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Stockbridge, Berkshire County

Vacation Rental • 6 Guests • 2 Bedrooms

Stockbridge, Berkshire County

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 $184 / night

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Vacation Rental for 5 Guests in Stockbridge, Berkshire County

Vacation Rental for 5 Guests in Stockbridge, Berkshire County, Picture 1

Vacation Rental for 5 Guests in Stockbridge, Berkshire County, Picture 2

Vacation Rental for 5 Guests in Stockbridge, Berkshire County, Picture 3

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Stockbridge, Berkshire County

Vacation Rental • 2594 ft² • 3 Bedrooms

Stockbridge, Berkshire County

With soaring cathedral ceilings and light filled tranquility, off a quiet cul de sac road, this is the perfect place for your Berkshire retreat.For the past 25 years, the BSO has rented this house as a summer residence for their guest conductors and soloists. (Hence, there is only one review from the general public.) They chose this home because of it's lovely, quiet and spacious ambiance. The whole house is on one level for your ultimate comfort and convenience, Located only 3 miles from Tanglewood and midway between Lenox and Stockbridge, in a private setting on over three acres, this art...

from $586 / night

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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

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Stockbridge, Berkshire County

Vacation Rental • 4 Guests • 4 Bedrooms

Stockbridge, Berkshire County

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 $303 / night

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Prices and availability

Current Vacation rental prices Stockbridge

$186for 27 Apr - 4 May

$566 annual average

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Average price per week

Current vacation rental availability Stockbridge

45%for 27 Apr - 4 May

38% annual average

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

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.