Monthly Rentals in Stockbridge Bowl

Discover long-term rentals that feel like home, for stays of a month or longer.

Nearby monthly rentals

Superhost
Condo in Lenox
4.63 out of 5 average rating, 8 reviews

Peaceful 1BR Condo with Pond View

VeraRating, 5 stars5 months ago
Very nice and clean 1-bedroom apartment with a great view and everything you need for cooking meals. Wonderful location and very kind hosts
Guest favourite
Cabin in Stockbridge
4.96 out of 5 average rating, 26 reviews

Stockbridge Snug- cabin luxury just steps to lake!

JenRating, 5 stars5 days ago
What a treat to stay at McCaela's magical, cozy, home! Everything – from the surroundings, to the furnishings, to the amenities – were just perfect. Entry into the house was no problem, and inside we found a delightfully thoughtful and intentional home that was extremely comfortable and spotlessly clean. Just as key, the bed in the primary bedroom was supremely comfortable! We had no reason to ask any questions, and we had no issues at all; still, McCaela reached out to make sure we were settled and to see if we needed anything. We SO appreciated her generosity, kindness, and insight into (and commitment to) the local community. It's clear that a great deal of thought and care has gone into this house, and we would stay there again in a heartbeat. The location is perfect – off the beaten path and extremely private, yet close to everything we wanted in the Berkshires. I highly recommend staying here, ideally for longer than the two nights we did. We can't wait to return!
Guest favourite
Cottage in Stockbridge
4.94 out of 5 average rating, 34 reviews

Quiet 2 BR cottage in the heart of the Berkshires

CatherineRating, 5 stars9 months ago
Perfect spot for a peaceful, relaxing Berkshires weekend and/or visit to Tanglewood. Beautiful location of the cabin among the trees, super convenient to lots of hiking, cute towns to wander with great food, and town beach for swimming. And, couldn't be better situated for catching a show at Tanglewood. Sonia was also helpful, responsive, and friendly about all of the preparation details and made the logistics of the trip simple.
Guest favourite
Guesthouse in Lenox
4.93 out of 5 average rating, 376 reviews

The Granary at House on Golden Hill

CedricRating, 5 stars5 days ago
We had a great time! Beautiful, cozy and unique place. Perfectly located to explore the area.

Amenities and perks for longer stays

Furnished rentals

Fully furnished rentals include a kitchen and the amenities you need to live comfortably for a month or longer. It’s the perfect alternative to a sublet.

Flexibility you need

Choose your exact move-in and move-out dates and easily book online, without any additional commitment or paperwork.*

Simple monthly prices

Special rates for long-term holiday rentals and a single monthly payment without additional charges.*

Book with confidence

Reviewed by our trusted community of guests and 24/7 support during your extended stay.

Work-friendly spaces for digital nomads

Travelling professional? Find a long-term stay with high-speed Wi-Fi and dedicated working spaces.

Looking for corporate housing?

Airbnb has fully furnished apartment homes ideal for staffing, corporate housing and relocation needs.
*Some exclusions may apply in certain geographies and for some properties.