Holiday houses in Stockbridge (Massachusetts) and its surroundings

Tranquil 3 BR Stockbridge House with Private Deck!

Stockbridge
Holiday home, 149 m² 6 people, 3 bedrooms, 2 bathrooms

1.5 km
from center

9.7/10
Outstanding

Cozy Stockbridge Cabin - Walk to beach and Lake!

Stockbridge
Holiday home, 65 m² 4 people, 2 bedrooms, 2 bathrooms

2.3 km
from center

9.3/10
Outstanding

Classic Stockbridge Cottage

Stockbridge
Holiday home, 257 m² 8 people, 4 bedrooms, 3 bathrooms

2.5 km
from center

Stockbridge House Walk to Town beach!

Stockbridge
Holiday home, 97 m² 6 people, 3 bedrooms, 1 bathroom

3.4 km
from center

7.5/10
Good

Too Good Aka 2 Goodrich St

Stockbridge
Holiday home, 279 m² 8 people, 4 bedrooms, 3 bathrooms

3.5 km
from center

Berkshire Vacation Rentals: Loft Style Cabin In West Stockbridge Book Now

West Stockbridge
Holiday home, 184 m² 8 people, 4 bedrooms, 2 bathrooms

3.9 km
from Stockbridge

Berkshire Vacation Rental: Stockbridge House Come Experience The Berkshires

Stockbridge
Holiday home, 107 m² 6 people, 3 bedrooms, 2 bathrooms

3.9 km
from center

Berkshire Retreat- A stone's throw to downtown Lenox

Stockbridge
Holiday home, 130 m² 6 people, 3 bedrooms, 2 bathrooms

4.6 km
from center

Private Berkshire Escape Special April Pricing select your dates for discount Monthly Pricing

Lee
Holiday home, 177 m² 10 people, 4 bedrooms, 2 bathrooms

4.9 km
from Stockbridge

Wellspring by AvantStay Indoor swimming-pool Views

Richmond
Holiday home 12 people, 1 bedroom, 4 bathrooms

4.9 km
from Stockbridge

The Ponds at Foxhollow by Capital Vacations

Lenox

5.1 km
from Stockbridge

8.2/10
Very good

Berkshire Vacation Rentals: & Serene Berkshires Retreat In The Woods

West Stockbridge
Holiday home, 263 m² 14 people, 6 bedrooms, 3 bathrooms

5.3 km
from Stockbridge

Woodland Zen by AvantStay Modern Design Patio

Stockbridge
Holiday home, 196 m² 8 people, 1 bedroom, 2 bathrooms

5.4 km
from center

Berkshire Vacation House in Lee - swimming-pool is Open!

Lee
Holiday home, 237 m² 12 people, 5 bedrooms, 2 bathrooms

6.2 km
from Stockbridge

Holiday Inn Oak n Spruce Resort -1BD Sleep up to 4

Lee
Holiday home, 68 m² 4 people, 1 bedroom, 1 bathroom

6.3 km
from Stockbridge

Cordelia by AvantStay Backyard 10mins from Stockbridge

Lee
Holiday home, 189 m² 12 people, 1 bedroom, 3 bathrooms

6.7 km
from Stockbridge

7.5/10
Good

Berkshire's Manor for Lasting Memories

Lee
Holiday home, 214 m² 10 people, 5 bedrooms, 5 bathrooms

6.7 km
from Stockbridge

The GateHouse on Golden Hill

Lee
Holiday home, 279 m² 10 people, 4 bedrooms, 3 bathrooms

6.9 km
from Stockbridge

Built for a US Secretary of State 13K SF

Lenox
Villa, 1394 m² 37 people, 14 bedrooms, 13 bathrooms

6.9 km
from Stockbridge

House In The Woods Huge Yard spa

Great Barrington
Holiday home, 281 m² 8 people, 4 bedrooms, 3 bathrooms

7 km
from Stockbridge

Lakefront Berkshires Retreat with Deck, Dock and Boat!

Great Barrington
Holiday home, 186 m² 10 people, 4 bedrooms, 2 bathrooms

7.5 km
from Stockbridge

7.7/10
Good

Great Barrington Lakeside Getaway with Kayak and Grill

Great Barrington
Holiday home, 204 m² 10 people, 4 bedrooms, 4 bathrooms

7.8 km
from Stockbridge

Magical Country Retreat in the Berkshires

Great Barrington
Holiday home, 1000 m² 1 person, 1 bedroom, 1 bathroom

8.5 km
from Stockbridge

Restored 1881 Farm House

Lenox
Holiday home, 120 m² 4 people, 2 bedrooms, 2 bathrooms

9 km
from Stockbridge

Berkshire Beauty-Full House

Richmond
Holiday home, 1000 m² 8 people, 3 bedrooms, 2 bathrooms

9.9 km
from Stockbridge

Lenox House, 3 Mi to Shakespeare and Co!

Lenox
Holiday home, 228 m² 6 people, 3 bedrooms, 2 bathrooms

10.5 km
from Stockbridge

9/10
Outstanding

Family-Friendly Richmond Cottage with Private Yard

Pittsfield
Holiday home, 163 m² 8 people, 2 bedrooms, 2 bathrooms

11.6 km
from Stockbridge

Berkshire Vacation Rentals: Private Cottage Come Enjoy Nature

Canaan
Holiday home, 72 m² 6 people, 2 bedrooms, 1 bathroom

12 km
from Stockbridge

Holiday houses Stockbridge