Vacation Homes in Stockbridge
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Featured Vacation Homes in Stockbridge

Cozy Riverside Berkshires Retreat

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

120-Acre Private Estate: Heated Pool, Fire Pit, Apple Orchard, Catskills Views

Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!

The Meadows House @ Otis Ridge w/ 7-person hot tub

Large Barn styled vacation home that fits groups with space to spare.

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay

Spacious Living, Covered Porch & Forest Setting | Beaver Creek by AvantStay

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Top trending hotels in Stockbridge

The Yankee Inn
Vacation Rentals in Stockbridge
What kind of vacation do you want in Stockbridge? The answer to that question will help you choose the right lodging for your stay. The wise wanderer knows that a vacation rental is an essential part of the traveling experience. It’s more than just a place to crash at night—it’s where you wake up in the morning, where you lounge when you’re not exploring, and it’s the starting point for all your adventures. No matter what type of vacation homes strike your fancy, Travelocity has something in Stockbridge that will speak to you.
Do you want a fully equipped kitchen so you can exercise your culinary mastery and impress your travel buddies? How about a romantic terrace for your anniversary trip? Have you always wished to fall asleep to the sound of waves crashing on the shore? One of our vacation home rentals is bound to add that extra magic to your trip. In fact, we’ve got plenty of options lined up just for you in Stockbridge, including luxury vacation rentals. On a budget? We can work with your funds and still give you a great place to sleep at night.
Take a look at what we have on offer. You’ll find rentals close to the big tourist draws, as well as rentals that keep you away from the crowd. Consider vacation rentals a little off the beaten path where you can live like a local and discover hidden gems that never make it to the tourist sites. Book through Travelocity and start your getaway today.
Stockbridge Vacation Homes essential information
Accommodation | 430 Vacation Homes |
|---|---|
Lowest Price | CA $147 |
Highest Price | CA $559 |
Popular accommodation | Cozy Riverside Berkshires Retreat, Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight., 120-Acre Private Estate: Heated Pool, Fire Pit, Apple Orchard, Catskills Views, Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires! , The Meadows House @ Otis Ridge w/ 7-person hot tub, Large Barn styled vacation home that fits groups with space to spare. , The Great Escape Ski Cottage w/HOT TUB @ Great Barrington , Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay, Spacious Living, Covered Porch & Forest Setting | Beaver Creek by AvantStay, Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets. , Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!, Imagine Being Lakeside, Kayaks/Fishing/EV Charger |






