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A stone staircase leading up to a blue arched entrance, surrounded by lush greenery and birch trees.

Search Condos Rentals in Stockbridge from CA $448

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    Check prices for these dates, December 15–16, 2026

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    Our top choices for Stockbridge condo rentals

    1. UNIQUE - 1BR Country Condo @ Jiminy Peak

    A Country Inn with a covered entrance, stone foundation, and a white fence.

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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    Learn more about Stockbridge

    Norman Rockwell's Museum showcases the artist's iconic paintings of small-town American life in his former studio. Stroll down Main Street's historic district before hiking Monument Mountain for views that inspired Nathaniel Hawthorne's literary works.

    See all hotels in Stockbridge

    A stone staircase leading up to a blue arched entrance, surrounded by lush greenery and birch trees.

    Top reviews in Stockbridge

    Granville House

    A dining table with pastries, a coffee pot, and a vase of sunflowers.

    Devonfield Inn B&B

    A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

    Inn at Silver Maple Farm

    A spacious kitchen with wooden beams, a dining area with a large table and chairs, and a view of the outdoors through large windows.

    Shaker Mill Inn

    A red building with a sign reading "Shaker Mill Inn".

    Hotel On North

    A multi-story hotel with a classic facade, large windows, and a prominent entrance.

    Chambery Inn

    A vintage turquoise Ford truck parked in front of a building labeled "CHAMBÉRY INN."

    Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

    A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

    The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

    A two-story house with a brick entrance and a white facade.

    The Cornell Inn, Lenox & The Berkshires

    A snow-covered outdoor area with a patio, seating, and a covered dining area.

    The Black Swan Lee - Lenox, an Ascend Collection Hotel

    A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

    Frequently Asked Questions

    How much do condos in Stockbridge cost?

    Expect to pay from CA $448 to CA $448 per night for condos in Stockbridge. No matter your budget, you'll find the perfect stay on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

    Why book your condo in Stockbridge with Expedia?

    Use Expedia to find your dream condo in Stockbridge. After a luxury escape? Try out our filters to search for properties with a 5-star rating. If you have a fixed budget, click on how much you want to spend and then browse our amazing options. We'll help you find the perfect fit whatever your vacation looks like.

    How can I find cheap condos in Stockbridge?

    Expedia can help you locate cheap condos in Stockbridge. To find your dream stay in a couple of clicks, simply use our handy filter tool to tailor your search results by star rating, budget and amenities.

    What is there to do in Stockbridge near my condo?

    Stockbridge has enough sights and experiences to keep you occupied for weeks (or months!), starting with National Shrine of the Divine Mercy. Norman Rockwell Museum, Naumkeag Museum and Berkshire Botanical Garden are other well-known attractions. If you're in town a while, Berkshire Theatre Festival and Mission House are worthwhile additions to your itinerary.

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