Stockbridge Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Stockbridge, Massachusetts, USA

The Inn at Stockbridge
FromUS $280 per night
|
9.8 (99 Reviews)
1 Bedroom 2 Guests
Stockbridge pied-à-terre
10.0 (15 Reviews)
1 Bedroom 3 Guests
Too Good AKA 2 Goodrich St
|
10.0 (1 Review)
8 Bedrooms 8 Guests
The Red Lion Inn
FromUS $211 per night
|
8.8 (1005 Reviews)
1 Bedroom 2 Guests
Fabulous Tanglewood Getaway!
10.0 (14 Reviews)
1 Bedroom 4 Guests
Cozy Stockbridge Cabin - Walk to Beach and Lake!
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9.0 (2 Reviews)
2 Bedrooms 4 Guests
Tanglewood Suites
FromUS $219 per night
6.4 (22 Reviews)
1 Bedroom 2 Guests
Light-filled Carpenter's Cottage w/EV charger!
9.8 (8 Reviews)
1 Bedroom 2 Guests
Steps to Downtown Stockbridge Home with Patio!
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8.0 (1 Review)
2 Bedrooms 5 Guests
Artist's Camp on Lake Mahkeenac
9.6 (20 Reviews)
2 Bedrooms 4 Guests
2 Mi to Norman Rockwell Museum Stockbridge Apt!
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8.0 (1 Review)
1 Bedroom 2 Guests
Cozy Stockbridge Cabin - Walk to Beach & Lake!
9.2 (12 Reviews)
2 Bedrooms 4 Guests
The Cottage
FromUS $259 per night
|
5.4 (63 Reviews)
2 Bedrooms 6 Guests
Stockbridge Village in Summer
9.0 (20 Reviews)
2 Bedrooms 4 Guests
Stockbridge Retreat with Pool and Hot Tub!
|
New
4 Bedrooms 10 Guests
Hearth House | Prime Location!
New
2 Bedrooms 5 Guests
The Red Lion Inn
FromUS $307 per night
|
7.9 (297 Reviews)
108 Bedrooms 58 Guests
A Grand property in Historic Stockbridge
10.0 (105 Reviews)
6 Bedrooms 12 Guests
Just a min from Downtown Stockbridge on 11 Acres
10.0 (78 Reviews)
4 Bedrooms 8 Guests
Stockbridge Home, Come Experience The Berkshires!
10.0 (31 Reviews)
3 Bedrooms 6 Guests
Historic Stockbridge Villa on 25 acres sleeps 23
10.0 (18 Reviews)
11 Bedrooms 23 Guests
Brand New Barn House w/EV charger
10.0 (3 Reviews)
3 Bedrooms 6 Guests
General Williams Estate House Lenox/Stockbridge
9.8 (115 Reviews)
6 Bedrooms 16 Guests
Historic Stockbridge, On Main Street, 3 Bedroom!
4.8 (6 Reviews)
3 Bedrooms 7 Guests
Historic Two Bedroom, Downtown Stockbridge
4.0 (4 Reviews)
2 Bedrooms 5 Guests
Holmes Suite PRIME Downtown Stockbridge
4.0 (1 Review)
1 Bedroom 3 Guests

About Stockbridge Vacation Rentals

With more than 70 Stockbridge vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Stockbridge.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Stockbridge, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Stockbridge. Places to stay near Stockbridge are 1662.45 ft² on average, with prices averaging US $509 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in Stockbridge with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Frequently Asked Questions About Stockbridge?

What are the top vacation rentals in Stockbridge?

How many Rentbyowner vacation rentals are available in Stockbridge?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 70 in the Stockbridge area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Stockbridge.