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Stockbridge Vacation Rentals

Find 143 available offers from 6 partners
Stockbridge
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Apartment
Bed and breakfast
Distance to center
1 km
2 km
5 km
Rating
4.5+
4+

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.

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Best Vacation Home Deals in Stockbridge

Save up to 80%

House Stockbridge
Mar 2 - Mar 9
-58%
$695
$295 per night
House ∙ 6 guests ∙ 2 bedrooms

Beautiful House in Stockbridge with Botanical Garden

4.9
Outstanding (20 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
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House Stockbridge
Dec 9 - Dec 16
-80%
$1,185
$239 per night
House ∙ 14 guests ∙ 6 bedrooms

House in Stockbridge with Botanical Garden

4.0
Very good (9 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
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Condo Stockbridge
Dec 9 - Dec 16
-39%
$240
$147 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Stockbridge with Botanical Garden

4.6
Excellent (41 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
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Compare and find a vacation rental meeting your needs among the 143 beautiful options from 6 providers in Stockbridge. Using HomeToGo you can directly compare the offers of each listed property to discover the best price and save up to 80%.

Top-Rated Rentals and Accommodations in Stockbridge

Book Vacation Rental Offers with the Highest User Rating

House Stockbridge
Dec 9 - Dec 16
$315 per night
House ∙ 8 guests ∙ 4 bedrooms

House in Stockbridge with Botanical Garden

4.9
Outstanding (126 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
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House Stockbridge
Mar 2 - Mar 9
-18%
$850
$700 per night
House ∙ 24 guests ∙ 12 bedrooms

House in Stockbridge with Botanical Garden

4.9
Outstanding (61 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
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House Stockbridge
Mar 2 - Mar 9
-62%
$598
$226 per night
House ∙ 8 guests ∙ 4 bedrooms

House in Glendale with Botanical Garden

4.9
Outstanding (8 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
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Recommended Vacation Rentals in Stockbridge

Find your perfect vacation rental in Stockbridge: from $190 per night

House Stockbridge
Mar 2 - Mar 9
$572 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Stockbridge with Botanical Garden

Stockbridge, Berkshire County, Massachusetts, United States
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House Stockbridge
Apr 6 - Apr 13
-26%
$687
$510 per night
House ∙ 6 guests ∙ 3 bedrooms

Charming House in Stockbridge with Botanical Garden

5.0
Outstanding (23 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
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House Stockbridge
Dec 9 - Dec 16
-71%
$660
$192 per night
House ∙ 6 guests ∙ 3 bedrooms

Pleasant Vacation Home in Stockbridge with Botanical Garden

5.0
Outstanding (14 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
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House Stockbridge
Jan 20 - Jan 27
$999 per night
House ∙ 12 guests ∙ 6 bedrooms

Vacation Home in Stockbridge with Botanical Garden

5.0
Outstanding (91 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
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Condo Stockbridge
Dec 19 - Dec 26
$225 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Stockbridge with Botanical Garden

4.6
Excellent (61 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
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Cabin Stockbridge
Nov 21 - Nov 28
-19%
$386
$313 per night
Cabin ∙ 4 guests ∙ 2 bedrooms

Cabin in Stockbridge with Grill

4.7
Excellent (12 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
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House Stockbridge
Dec 9 - Dec 16
-54%
$532
$244 per night
House ∙ 6 guests ∙ 3 bedrooms

Rental House in Stockbridge with Patio

4.9
Outstanding (90 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
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House Stockbridge
Mar 2 - Mar 9
$234 per night
House ∙ 7 guests ∙ 4 bedrooms

Entire Vacation Home in Stockbridge with Botanical Garden

5.0
Outstanding (69 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
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House Stockbridge
Jun 22 - Jun 29
$300 per night
House ∙ 4 guests ∙ 4 bedrooms

Wonderful Vacation Home in Stockbridge with Botanical Garden

5.0
Outstanding (36 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
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Budget-friendly Vacation Rentals in Stockbridge

Find Fantastic yet Inexpensive Offers

House Stockbridge
Nov 16 - Nov 23
$495 per night
House ∙ 10 guests ∙ 4 bedrooms

House in Stockbridge with Botanical Garden

Stockbridge, Berkshire County, Massachusetts, United States
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Apartment Stockbridge
Feb 3 - Feb 10
-30%
$315
$220 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Rental Apartment in Stockbridge with Botanical Garden

5.0
Outstanding (18 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
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House Stockbridge
Feb 3 - Feb 10
$665 per night
House ∙ 8 guests ∙ 3 bedrooms

House in Stockbridge with Botanical Garden

5.0
Outstanding (25 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
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Vacation Houses With Pools

Make a splash on your next vacation! Over 56% of in Stockbridge vacation rentals have a swimming pool.

Bed and breakfast  Stockbridge
Mar 2 - Mar 9
$294 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B in Stockbridge with Yard, Patio & Pool

4.8
Outstanding (90 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Pool
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Bed and breakfast  Stockbridge
Apr 20 - Apr 27
$327 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B in Stockbridge with Pool, Yard & Patio

4.8
Outstanding (90 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Pool
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Bed and breakfast  Stockbridge
Jan 6 - Jan 13
$282 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed And Breakfast in Stockbridge with Pool, Yard & Patio

4.8
Outstanding (90 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Pool
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Dog-Friendly Vacation Rentals

Bring Fido on your next trip and book a stay in one of these pet-friendly rentals in Stockbridge!

House  Stockbridge
Mar 2 - Mar 9
$825 per night
House ∙ 10 guests ∙ 4 bedrooms

Pleasant Vacation Home in Stockbridge with Sauna

5.0
Outstanding (4 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Pet-friendly
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House  Stockbridge
Mar 2 - Mar 9
$250 per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Stockbridge with Botanical Garden

4.9
Outstanding (58 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Pet-friendly
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House  Stockbridge
Dec 9 - Dec 16
-54%
$495
$225 per night
House ∙ 6 guests ∙ 3 bedrooms

Rental House in Stockbridge

4.9
Outstanding (90 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Pet-friendly
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Best vacation rentals with a balcony

Looking for a home with a balcony? Check out these vacation homes in Stockbridge with their own private patios and balconies.

House  Stockbridge
Nov 16 - Nov 23
$778 per night
House ∙ 16 guests ∙ 7 bedrooms

Lovely Vacation Home in Alford with Yard & Grill

5.0
Outstanding (39 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Balcony
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Chalet  Stockbridge
May 3 - May 10
$190 per night
Chalet ∙ 6 guests ∙ 2 bedrooms

Chalet in Monterey with Botanical Garden

5.0
Outstanding (114 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Balcony
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House  Stockbridge
Mar 23 - Mar 30
-58%
$300
$125 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Great Barrington with Botanical Garden

4.7
Excellent (35 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Balcony
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Popular Rental Amenities in Stockbridge

  • Pet-friendly (25)
  • Pool (80)
  • WiFi (143)
  • Kitchen (71)
  • Air conditioning (127)
  • TV (140)
  • No smoking (104)
  • Grill (66)
  • Parking (7)
  • Washing machine (62)
  • Balcony/patio (43)
  • Microwave (82)

Filters are available so you can tailor your search and find the ideal accommodation in Stockbridge. Most of the accommodations in Stockbridge offer "Pets allowed" or "Pool," which makes it a wonderful destination if you are looking for a pet-friendly rental or you're dreaming of days spent poolside. Not as many vacation rentals in Stockbridge are available if you want to sweat it out in a sauna or if you need a crib for your baby as "Crib" and "Sauna" are not often provided in this destination.

The Weather in Stockbridge

max.
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32°
16°
17 days 17
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34°
16°
18 days 18
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41°
23°
16 days 16
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55°
34°
15 days 15
max.
Min.
68°
46°
14 days 14
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Min.
73°
54°
15 days 15
max.
Min.
81°
59°
14 days 14
max.
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77°
55°
11 days 11
max.
Min.
72°
48°
11 days 11
max.
Min.
59°
39°
16 days 16
max.
Min.
46°
28°
14 days 14
max.
Min.
37°
25°
20 days 20
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

This is the climate diagram in Stockbridge. The highest average temperatures are in the month of July. On the contrary, the coolest month is January. The rainiest month is December while the driest month is August.

7-Day Weather Forecast in Stockbridge

Sat, 2 Dec
39°
37°

20%

2 h

1 mi/h

Sun, 3 Dec
37°
35°

65%

0 h

10 mi/h

Mon, 4 Dec
41°
37°

15%

0 h

8 mi/h

Tue, 5 Dec
37°
32°

15%

0 h

4 mi/h

Wed, 6 Dec
35°
33°

15%

0 h

3 mi/h

Thu, 7 Dec
32°
28°

0%

5 h

9 mi/h

Fri, 8 Dec
32°
32°

15%

0 h

9 mi/h

Accommodations for your vacation in Stockbridge

Nearly half of the offers (49.33%) in Stockbridge are house rental. They are the most typical accommodations in this destination. Additionally, the median size of house rental in Stockbridge is 255 m² and they cost, on average, $681 per night. Furthermore, this type of accommodation is an excellent option for large groups, as most of the house rental can host 8 people. You can also consider other accommodation types in Stockbridge. Bed and breakfast rental are, for example, another common accommodation type in this destination, with 24 listed accommodations. Our data reveals that the standard price of bed and breakfast rental is $409 per night for an area of 81 m².
What are the best places to discover the arts and culture of Stockbridge?

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.

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 142 homes
💳 Possible discounts up to 58%
🌙 Nightly prices starting at $190
⭐ Popular amenities Pets allowed, Pool and Internet
🐾 Pet friendly homes 23 homes
🏊 Vacation rentals with pools 80 homes

Frequently Asked Questions

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

The nightly price of accommodations in Stockbridge starts at $190. If you’re interested in a house rental, the average price is $681 per night. A bed and breakfast rental Stockbridge will cost on average $409 per night.

How many vacation homes are available to book in Stockbridge?

There are 142 vacation homes available for booking for your vacation.

What are the most popular amenities for vacation rentals in Stockbridge?

If you're looking to book a vacation rental in Stockbridge, the most popular amenities are: Pool, Pets allowed and Internet.

How many vacation rentals with pools are there in Stockbridge?

Discover 80 vacation rentals available in Stockbridge.

Are dogs allowed in vacation homes in Stockbridge?

In case if you are traveling with a pet in Stockbridge - 16% of vacation homes allow pets.

What's the best month to travel to Stockbridge?

July and August are typically the warmest months in Stockbridge with temperatures around 81 °F. The coldest months in Stockbridge are January and February, with 16 °F on average.

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