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Stockbridge, MA Vacation Rentals

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Our Favorite Vacation Rentals in Stockbridge

  • Family-friendly Cottage Near Lake, Tanglewood
    Family-friendly Cottage Near Lake, Tanglewood
    Excellent3br Cottage
    HolidayLettingsFrom $436
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  • Tanglewood / Berkshires - 2 Bed 2 Bath Apartment
    Tanglewood / Berkshires - 2 Bed 2 Bath Apartment
     2br Home/Apartment
    HolidayLettingsFrom $480
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  • Gartner House, a charming home in Lenox
    Gartner House, a charming home in Lenox
    Excellent4br Home/Apartment
    HolidayLettingsFrom $307
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  • Berkshire Getaway ~ Romantic Tower Suite on Storybook Estate
    Berkshire Getaway ~ Romantic Tower Suite on Storybook Estate
     1br Home/Apartment
    HolidayLettingsFrom $303
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  • RiverSong Suite In The Berkshires
    RiverSong Suite In The Berkshires
    Excellent1br Home/Apartment
    HolidayLettingsFrom $256
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  • INTERIOR DESIGNERS BOTANICAL COTTAGE
    INTERIOR DESIGNERS BOTANICAL COTTAGE
    Excellent1br Cottage
    HolidayLettingsFrom $281
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  • NEW! Monterey Home w/Porch by Beach & State Parks!
    NEW! Monterey Home w/Porch by Beach & State Parks!
     3br Home/Apartment
    HolidayLettingsFrom $453
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  • Renovated 2 bedroom in Heart of Lenox
    Renovated 2 bedroom in Heart of Lenox
     2br Home/Apartment
    HolidayLettingsFrom $464
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See all 225 deals in Stockbridge

Stockbridge Vacation Rentals with a Pool

  • Berkshires Rustic Retreat (close to everything!)
    Berkshires Rustic Retreat (close to everything!)
    Excellent1br Home/Apartment
    AirbnbFrom $158
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  • Berkshire Retreat with Pool and Views
    Berkshire Retreat with Pool and Views
    Excellent7br Retreat
    AirbnbFrom $1181
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  • Idyllic Berkshires Retreat With Pond Views & Pool
    Idyllic Berkshires Retreat With Pond Views & Pool
    Excellent2br Home/Apartment
    AirbnbFrom $386
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  • The East Street Cabin
    The East Street Cabin
    ExcellentHome/Apartment
    AirbnbFrom $226
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See all deals in Stockbridge with a pool

Stockbridge Vacation Rentals with Wi-Fi

  • Elegant country French stone house in Stockbridge
    Elegant country French stone house in Stockbridge
     3br Home/Apartment
    AirbnbFrom $1695
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  • Brooklyn in the Berkshires 2
    Brooklyn in the Berkshires 2
     2br Bedroom
    AirbnbFrom $381
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  • ..BSO Tanglewood Suite. 2Queen+Sofa.full priv bath
    ..BSO Tanglewood Suite. 2Queen+Sofa.full priv bath
    Good1br Studio
    AirbnbFrom $471
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  • Farmhouse at Pixley Hill
    Farmhouse at Pixley Hill
     4br Home/Apartment
    AirbnbFrom $5650
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See all deals in Stockbridge with WiFis

Stockbridge Pet-Friendly Vacation Rentals

  • Stockbridge Carriage House
    Stockbridge Carriage House
    Good3br Home/Apartment
    AirbnbFrom $537
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  • Serene Home Around the Corner From Chesterwood
    Serene Home Around the Corner From Chesterwood
     4br Home/Apartment
    AirbnbFrom $720
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  • Cozy&Modern Near Tanglewood Kripalu
    Cozy&Modern Near Tanglewood Kripalu
    Good2br Home/Apartment
    AirbnbFrom $311
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  • Location! Beautiful Victorian home in Berkshires
    Location! Beautiful Victorian home in Berkshires
    Excellent5br Home/Apartment
    AirbnbFrom $540
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See all deals in Stockbridge that allow pets

Stockbridge, Massachusetts Travel Guide

Stockbridge, Massachusetts is a town in the western part of the state that has ample history, historical monuments and stunning nature.

Things to Do in Stockbridge, Massachusetts

The famous American author Norman Rockwell was from Stockbridge, Massachusetts, giving the town a worthy claim to fame. His former home has been converted into a living museum that contains artwork and memorabilia to celebrate his life. Naumkeag is another interesting historic site located here and is a 19th-century vacation home that can now be toured. The home has retained its original furnishings and character.

The Berkshire Botanical Garden is a pleasant place to enjoy an afternoon stroll and take in the fragrant scent of the various colorful plants and flowers growing here.

Best Time to Visit Stockbridge, Massachusetts

Stockbridge, Massachusetts is best visited in the summer months.

Price and Availability in Stockbridge

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The most expensive month to stay in a vacation rental in Stockbridge is in September, while the cheapest month is in April. The most popular time to book a vacation rental in Stockbridge is in the high season in August. Stockbridge has its low season in April, when less people are visiting and the vacation home occupancy rate drops.
The cheapest day to stay at a vacation rental in Stockbridge tends to be Wednesday, while the most expensive day tends to be Friday. Vacation homes in Stockbridge tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.

The Weather in Stockbridge

93º 46º
4.68
90º 51º
8.25
89º 40º
6.89
79º 27º
2.84
64º 0º
6.39
59º 9º
3.94
61º -10º
4.66
73º -3º
4.09
55º 7º
2.35
67º 18º
3.63
86º 40º
2.56
91º 42º
3.42
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Rainy days
This climate histogram shows you the weather patterns in Stockbridge. The warmest months in Stockbridge are June and July, when temperatures reach 93 ˚F. The coolest month is January, when temperatures drop to -10 ˚F. The wettest month in Stockbridge is August with 8.25 inches of rain, while the driest month is March with 2.35 inches of rain.

What Expert Travelers Think

Vacation Rentals in Stockbridge

At AllTheRooms.com we have rentals from all of the best providers - Airbnb, Bed and Breakfast, Priceline and more. AllTheRooms has 224 rentals, hotels and other great places to stay while you enjoy Stockbridge, with everything from cheap hostels and homestays to extravagant Airbnbs and hotels. When traveling on a budget, the cheapest place to stay in Stockbridge is available at $89 per night. The average price of an accommodation is generally $585 per night.

If you need to stay connected during your vacation, then you can choose from over 115 accommodations in Stockbridge that have WiFi. 9 of our accommodations come with breakfast in the price. Fitness fanatics can get a workout in during their stay by choosing from 10 accommodations that have gym facilities. If you're planning on getting to Stockbridge by car, be sure to choose from 108 accommodations that provide parking. 11 vacation rentals come with a pool or jacuzzi

Those traveling with a dog, cat or some other animal can stay in any of 35 accommodations that are designated as pet-friendly.

139 accommodations in Stockbridge have been reviewed; 72% are rated excellent or good. You can instantly book any of 51 places to stay right now.

Destinations near Stockbridge