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Stockbridge Vacation Rentals

Find 143 available offers from 14 partners
Stockbridge
Anytime
Guests
Stockbridge
Anytime
Guests

Popular Filters to find the Perfect Home Rental in Stockbridge

2 Adults
1 Bedroom
Pool
House
Pets allowed
4 Adults
Cabin

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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Vacation Houses With Pools

Make a splash on your next vacation! Over 51% of in Stockbridge vacation rentals have a swimming pool.

House  Stockbridge
May 6 - May 13
$599 per night
House ∙ 8 guests ∙ 4 bedrooms

Family Friendly Pleasant Vacation Home in Stockbridge with Botanical Garden

4.8
Outstanding (30 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Pool
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Bed and breakfast  Stockbridge
Aug 10 - Aug 17
$479 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed And Breakfast in Glendale with Yard, Grill & Pool

4.6
Excellent (75 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Pool
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Bed and breakfast  Stockbridge
Jul 20 - Jul 27
$549 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & Breakfast in Glendale with Pool, Grill & Yard

4.6
Excellent (75 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
May 18 - May 25
-39%
$439
$269 per night
House ∙ 6 guests ∙ 3 bedrooms

Rental House in Stockbridge

4.9
Outstanding (172 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Pet-friendly
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House  Stockbridge
May 6 - May 13
-68%
$533
$170 per night
House ∙ 8 guests ∙ 4 bedrooms

House in Glendale with Botanical Garden

4.9
Outstanding (11 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Pet-friendly
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House  Stockbridge
Jun 3 - Jun 10
$270 per night
House ∙ 8 guests ∙ 3 bedrooms

Wonderful Vacation Home in Stockbridge with Botanical Garden + Mountain Views

4.9
Outstanding (71 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
Jun 3 - Jun 10
$298 per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Stockbridge with Botanical Garden

5.0
Outstanding (62 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Balcony
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Bed and breakfast  Stockbridge
Apr 20 - Apr 27
-24%
$289
$219 per night
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

Wonderful B&B in Stockbridge with Yard, Grill & Patio

5.0
Outstanding (1 rating)
Stockbridge, Berkshire County, Massachusetts, United States
Balcony
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House  Stockbridge
Jun 13 - Jun 20
$585 per night
House ∙ 10 guests ∙ 4 bedrooms

House in Stockbridge with Botanical Garden

5.0
Outstanding (3 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Balcony
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Best Vacation Home Deals in Stockbridge

Save up to 50%

House Stockbridge
May 4 - May 11
-50%
$447
$225 per night
House ∙ 6 guests ∙ 3 bedrooms

Rental House in Stockbridge

4.9
Outstanding (172 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
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House Stockbridge
May 6 - May 13
-38%
$418
$259 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Stockbridge with Grill

5.0
Outstanding (6 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
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Cabin Stockbridge
May 6 - May 13
-17%
$376
$313 per night
Cabin ∙ 4 guests ∙ 2 bedrooms

Cabin in Stockbridge with Grill & Patio

4.8
Outstanding (19 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 14 providers in Stockbridge. Using HomeToGo you can directly compare the offers of each listed property to discover the best price and save up to 48%.

Recommended Vacation Rentals in Stockbridge

Find your perfect vacation rental in Stockbridge: from $155 per night

Cabin Stockbridge
Jun 1 - Jun 8
$238 per night
Cabin ∙ 4 guests ∙ 2 bedrooms

Cabin in Stockbridge with Botanical Garden

5.0
Outstanding (23 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
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House Stockbridge
Jun 1 - Jun 8
$421 per night
House ∙ 5 guests ∙ 3 bedrooms

Vacation Home in Stockbridge with Outside Terrace

5.0
Outstanding (1 rating)
Stockbridge, Berkshire County, Massachusetts, United States
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House Stockbridge
Jun 13 - Jun 20
$277 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
May 6 - May 13
$449 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Stockbridge with Grill & Yard

5.0
Outstanding (74 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
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House Stockbridge
Jun 13 - Jun 20
$525 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
Jun 22 - Jun 29
$999 per night
House ∙ 12 guests ∙ 6 bedrooms

Vacation Home in Stockbridge with Botanical Garden

5.0
Outstanding (94 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
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Apartment Stockbridge
May 25 - Jun 1
$211 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Rental Apartment in Stockbridge with Botanical Garden

5.0
Outstanding (20 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
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House Stockbridge
Jun 3 - Jun 10
$395 per night
House ∙ 7 guests ∙ 4 bedrooms

House in Stockbridge with Botanical Garden

4.9
Outstanding (20 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
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Cottage Stockbridge
May 6 - May 13
-38%
$520
$323 per night
Cottage ∙ 8 guests ∙ 1 bedroom

Cottage in Stockbridge with Grill

Stockbridge, Berkshire County, Massachusetts, United States
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Budget-friendly Vacation Rentals in Stockbridge

Find Fantastic yet Inexpensive Offers

House Stockbridge
Jun 13 - Jun 20
$426 per night
House ∙ 10 guests ∙ 5 bedrooms

House in Stockbridge with Patio & Yard

5.0
Outstanding (1 rating)
Stockbridge, Berkshire County, Massachusetts, United States
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Cottage Stockbridge
May 6 - May 13
$391 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage in Stockbridge with Grill

Stockbridge, Berkshire County, Massachusetts, United States
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House Stockbridge
Jun 22 - Jun 29
$253 per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation Home in Stockbridge with Botanical Garden + Backyard Views

4.5
Excellent (26 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
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Top-Rated Rentals and Accommodations in Stockbridge

Book Vacation Rental Offers with the Highest User Rating

House Stockbridge
Jun 1 - Jun 8
$275 per night
House ∙ 5 guests ∙ 3 bedrooms

House in Stockbridge with Botanical Garden

4.9
Outstanding (31 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
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Condo Stockbridge
Jun 22 - Jun 29
$204 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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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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Popular Rental Amenities in Stockbridge

  • Pet-friendly (27)
  • Pool (71)
  • WiFi (140)
  • Kitchen (76)
  • Air conditioning (116)
  • TV (132)
  • No smoking (135)
  • Grill (66)
  • Parking (7)
  • Washing machine (68)
  • Balcony/patio (66)
  • Microwave (84)

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 travel with your pet or you want a rental with a pool. Not as many vacation rentals in Stockbridge are available if you want a rental with 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

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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
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68°
46°
14 days 14
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73°
54°
15 days 15
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81°
59°
14 days 14
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77°
55°
11 days 11
max.
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72°
48°
11 days 11
max.
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59°
39°
16 days 16
max.
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46°
28°
14 days 14
max.
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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

Thu, 18 Apr
42°
41°

50%

1 h

6 mi/h

Fri, 19 Apr
53°
50°

0%

0 h

11 mi/h

Sat, 20 Apr
55°
46°

15%

0 h

9 mi/h

Sun, 21 Apr
51°
50°

15%

1 h

11 mi/h

Mon, 22 Apr
53°
53°

0%

6 h

11 mi/h

Tue, 23 Apr
60°
59°

5%

2 h

4 mi/h

Wed, 24 Apr
41°
41°

15%

0 h

2 mi/h

Accommodations for your vacation in Stockbridge

Nearly half of the offers (48.19%) in Stockbridge are house rental. They are the most typical accommodations in this destination. Additionally, the median size of house rental in Stockbridge is 242 m² and they cost, on average, $610 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 27 listed accommodations. Our data reveals that the standard price of bed and breakfast rental is $464 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 143 rentals
💳 Possible discounts up to 48%
🌙 Nightly prices starting at $155
⭐ Popular amenities Pets allowed, Pool and Internet
🐾 Pet friendly homes 27 homes
🏊 Vacation rentals with pools 73 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 $155. If you’re interested in a house rental, the average price is $610 per night. A bed and breakfast rental Stockbridge will cost on average $464 per night.

How many vacation homes are available to book in Stockbridge?

There are 143 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 73 vacation rentals available in Stockbridge.

Are dogs allowed in vacation homes in Stockbridge?

In case if you are traveling with a pet in Stockbridge - 19% 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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