Rent Stockbridge Condos

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Featured Condo Rentals in Stockbridge

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is NZ$218 per night from 4 Jan to 5 Jan
NZ$218
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff in their ...
Opens in a new windowVacation Village in the Berkshires
Club Wyndham Bentley Brook Resort - 2 Bedroom

Club Wyndham Bentley Brook Resort - 2 Bedroom

Hancock MA
Stay at this ski condo in Hancock. Enjoy laundry facilities, concierge services and ski-in/ski-out access. Popular attractions Jiminy Peak Mountain Resort and ...
Opens in a new windowClub Wyndham Bentley Brook Resort - 2 Bedroom
Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool

Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool

Hancock MA
Stay at this condo in Hancock. Enjoy a fitness centre, laundry facilities and air conditioning. Popular attractions Jiminy Peak Mountain Resort and Mountain ...
Opens in a new windowFamily-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool
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SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!

SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!

Hancock MA
Stay at this ski condo in Hancock. Enjoy free Wi-Fi, breakfast (surcharge) and a fitness centre. Popular attractions Jiminy Peak Mountain Resort and Mountain ...
Opens in a new windowSKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

Hancock MA
The price is NZ$576 per night from 5 Jan to 6 Jan
NZ$576
5 Jan - 6 Jan 2026
includes taxes & fees
Stay at this condo in Hancock. Enjoy a fitness centre, a garden and laundry facilities. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster ...
Opens in a new window2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Tranquil Lakeside Escape in the Berkshires

Tranquil Lakeside Escape in the Berkshires

Lenox MA
Stay at this condo in Lenox. Enjoy free Wi-Fi, a sauna and laundry facilities. Popular attractions The Mount and Wyndhurst Golf & Club are located nearby.
Opens in a new windowTranquil Lakeside Escape in the Berkshires
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2

Hancock MA
Stay at this ski condo in Hancock. Enjoy free Wi-Fi, breakfast (surcharge) and a fitness centre. Popular attractions Jiminy Peak Mountain Resort and Mountain ...
Opens in a new windowSKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1

Hancock MA
Stay at this ski condo in Hancock. Enjoy free Wi-Fi, breakfast (surcharge) and a fitness centre. Popular attractions Jiminy Peak Mountain Resort and Mountain ...
Opens in a new windowSKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths

Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths

Hancock MA
Stay at this condo in Hancock. Enjoy a fitness centre, laundry facilities and air conditioning. Popular attractions Jiminy Peak Mountain Resort and Mountain ...
Opens in a new windowEscape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths
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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.

Stockbridge Condo Rentals essential information

Accommodation
43 Condo Rentals
Lowest Price
NZ$169
Highest Price
NZ$576
Popular accommodation
Vacation Village in the Berkshires, Club Wyndham Bentley Brook Resort - 2 Bedroom, Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool , SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!, 2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7, Tranquil Lakeside Escape in the Berkshires, SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2, SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1, Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths

Top trending hotels in Stockbridge

The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Fully refundableReserve now, pay when you stay
The price is NZ$363 per night from 14 Jan to 15 Jan
NZ$363
14 Jan - 15 Jan 2026
includes taxes & fees
Stay at this historic hotel in Stockbridge. Enjoy free Wi-Fi, 3 restaurants and breakfast (surcharge). Our guests praise the helpful staff in their reviews. ...
Opens in a new windowThe Red Lion Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is NZ$218 per night from 4 Jan to 5 Jan
NZ$218
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff in their ...
Opens in a new windowVacation Village in the Berkshires
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is NZ$177 per night from 4 Jan to 5 Jan
NZ$177
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
Opens in a new windowThe Yankee, Trademark Collection by Wyndham
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Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is NZ$169 per night from 3 Jan to 4 Jan
NZ$169
3 Jan - 4 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Pittsfield. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Opens in a new windowHoliday Inn & Suites Pittsfield-Berkshires by IHG
Don't see what you're looking for?
See all available properties in Stockbridge
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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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^Subject to availability and chosen travel dates.