Discover a selection of 500 vacation rentals in Stockbridge, MA that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $247 per night, and houses and cottages are popular options for a stay in Stockbridge. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Stockbridge
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Destination guide

The historic city of Stockbridge awaits you

Enjoy the area's museums, history and architecture and make a vacation rental your home during your stay in Stockbridge. Well-liked for its gardens, camping and hiking, this city is both romantic and relaxing. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Things to do

Activities and attractions in and around Stockbridge

Are you looking for top things to see and do while you're in the area? Venture out of your vacation home and experience everything that makes Stockbridge a one-of-a-kind vacation spot. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Cranwell Golf Club (4.7 mi / 7.6 km)
  • Ski Butternut (7.6 mi / 12.2 km)
  • Furnace Brook Winery at Hilltop Orchards (8.1 mi / 13 km)
  • Bousquet Ski Area (9.1 mi / 14.6 km)
  • Catamount Ski Area (11.6 mi / 18.7 km)
  • Jiminy Peak Mountain Resort (18.6 mi / 29.9 km)
Natural features

Exploring the natural features in Stockbridge

Whether you're looking for adventure or just want to appreciate the scenery, you'll be sure to find the perfect setting for your vacation in Stockbridge. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Naumkeag (0.3 mi / 0.4 km)
  • The Mount (3.8 mi / 6.2 km)
  • Housatonic River Walk (6.6 mi / 10.6 km)
  • October Mountain State Forest (8.9 mi / 14.3 km)
  • Bash Bish Falls State Park (15.1 mi / 24.3 km)
  • Taconic State Park (18.1 mi / 29.1 km)
How to get there

Transportation options to and around Stockbridge

Fly into Albany Intl. Airport (ALB), the closest airport, located 40.3 mi (64.8 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is 9.6 mi (15.5 km) away.

What are the top vacation rentals in or near Stockbridge?

Whatever you're seeking in a vacation, you'll find a rental property in or around Stockbridge that fits you like a glove. These are some of our favorites:

  • "Close To Skiing Beautiful +family Friendly" is a favorite with guests. Around 14 miles from Stockbridge, it has 4 bedrooms and plenty of amenities to help you feel at home, including books and a washing machine.
  • Another great option is "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi", which is around 17 miles from Stockbridge. With 4 bedrooms, beach towels and a stereo, it has everything you need to make your visit comfortable.

For even more great options, use the search bar at the top of the page to find the perfect Stockbridge vacation rental for you.

Can I find log cabins to rent in or near Stockbridge?

You most certainly can! From simple retreats to luxurious escapes, we've got an impressive range of log cabins to rent in or near Stockbridge. If the great outdoors is calling, you'll love these options:

  • "Water Front Log Cabin Next To Tanglewood": This fabulous cabin is an ideal base if you're an outdoorsy type. Snowboarding and kayaking are a couple of activities you can do in the area when you're not chilling in your comfy cabin.
  • "Cozy Log Cabin Adjacent To Beartown Forest": Stay in and enjoy the peaceful atmosphere or try some of the fun activities nearby, including tennis and skiing. The choice is all yours around here.

What are the top-rated vacation rentals for weekend getaways in or near Stockbridge?

Those chores can wait, because weekends were made for fun. Take time out at one of these weekend getaways in and around Stockbridge and make the most of all the incredible things to do close by:

  • Located 12 miles to the south of central Stockbridge, "Elterwater - - Your Lakefront Oasis" is popular among adventurous types and nature buffs. Find your way to nearby attractions, such as Lake Mansfield Park and Otis Ridge. Then, try some activities like cycling or snowmobiling.
  • "Swiss Chalet Style Timber Frame Home In Berkshires With All Modern Conveniences" is another great property where you can escape the everyday. Around 17 miles northeast of Stockbridge, use it as a base to try some fishing or cycling. Skyline Country Club and Great Falls Discovery Center also have to be on your to-do list if you stay here.

Can I find studio apartments for rent in and around Stockbridge?

Studio apartments are a hard act to beat when it comes to location, convenience and affordability. Check out these studio apartments for rent in or near Stockbridge and discover the local energy and vibe:

  • Make "The Clearing - Quiet - Close To Nature" your home for a few days or more. This great vacation rental features amenities including a hair dryer and a boat.
  • Another appealing option is "Cabin - A - Frame In Sherwood Forest". Make use of a hair dryer, a kitchen and other convenient amenities during your stay.

With the moolah you save on your studio apartment, you'll be able to discover more of Stockbridge. Cultural sights like Jose Mateo Ballet Theatre and Outpost 186 will help you understand the character of this destination.

Can I find short term rentals in or near Stockbridge?

Just because you only have two or three days up your sleeve doesn't mean you need to spend it in a characterless hotel. Take off on vacation but still have the home comforts you love at one of these short-term rentals in or around Stockbridge:

  • "Swiss Chalet Style Timber Frame Home In Berkshires With All Modern Conveniences" is near the heart of Stockbridge, so you'll have loads of things to keep you busy. Tick off cool sights like Walden Pond and Louisa May Alcott's Orchard House when you're not chilling in your cozy digs.
  • Hop out of bed, make some breakfast and then start planning what to see around "Unique People And Pet - Welcoming Country Haven". Old Manse and Concord Visitors Center should be on your itinerary if you choose to stay at this short-term rental.

What are the best romantic weekend getaways in or near Stockbridge?

Whether spent in a cabin, an apartment or a lodge, a romantic weekend getaway is one of the best ways to add some zing to your relationship. Whisk your sweetie off for a couple of relaxing days at one of these enticing escapes in or near Stockbridge:

  • Sneak off on Friday for a couple of passion-filled evenings at "Close To Skiing Beautiful +family Friendly". Located roughly 14 miles from Stockbridge, this property comes with lots of nice touches, including a fireplace and skiing facilities.
  • Another place where you can spend a few precious days together is "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi". Located 17 miles from Stockbridge, outdoor furniture and a dining table add to the atmosphere here.

What are the best houses for rent with a pool in or near Stockbridge?

Nothing says fun times like a pool does. Dust off your unicorn floatie and check out these rental houses in or near Stockbridge that feature this vacation perk:

  • Pack your swimsuit and book a few days or more at "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi". There are also lots of other appealing amenities here, including beach sun loungers and a dishwasher.
  • Alternatively, unpack your bags at "General Williams Estate House Lenox". In addition to its inviting pool, make use of a separate dining area and towels.

Not sure how to pack for your Stockbridge escape? This leading destination has a humid continental climate. In summer, expect average temperatures of between 55 ºF and 75 ºF. Check out our selection of Stockbridge vacation rentals by using the search bar at the top of the page. Simply adjust the filters to get more inspiration on where to stay.

What are the best large family vacation rentals in or near Stockbridge?

It's always more fun when you share wonderful times with the ones you care about the most. Whether you're planning a family catch-up or getting away with close friends, we'll have a large vacation rental that's just right for you. Here are two of our best in and around Stockbridge:

  • Get everyone under the same roof at "88 Acres Of Beauty In The Berkshires", which has 4 bedrooms sleeping up to 9 guests. This getaway is around 14 miles to the south of Stockbridge and comes with amenities such as childrens activities and cable/satellite TV services.
  • Another great option is "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi". This large rental is 17 miles southeast of Stockbridge and features nearby birdwatching activities, a barbecue grill and more. With 4 bedrooms accommodating up to 10 people, you won't need to leave anyone off your invitation list.

When you're ready to explore your surroundings, there are lots of family-friendly attractions nearby to keep everyone entertained. New England Aquarium, Newbury Street and CoCo Key Water Resort - Boston should be top of your itinerary.

Can I find family cabin rentals in or near Stockbridge?

Escape the busyness of life and treat the ones you love to a different type of vacation. Stay in one of these family cabin rentals in or near Stockbridge and get the camping experience — but with all the comforts of home!

  • "Cabin - A - Frame In Sherwood Forest" - Enjoy fun times with your nearest and dearest at this escape, which is around 12 miles east of the center of Stockbridge. Free toiletries and a fridge are among its family-friendly amenities.
  • "Quiet Comfortable Cabin 5 Min. Walk To Swimming And Boating" - Another fabulous choice, this property comes with a separate dining area, free toiletries and more. You'll find it around 14 miles to the east of Stockbridge.

For more options, use the search bar at the top of the page and adjust the filters to find the Stockbridge vacation rental that's perfect for your needs.

What are the best large houses to rent with indoor pools in or near Stockbridge?

Nothing says "glamorous getaway" like having a pool right inside your house. Pack your favorite bikini and enjoy a dip in the comfort and privacy of one of these spacious houses in or near Stockbridge:

  • Book a stay at "Equipped Villa With Access To Pools" and spend your days stretched out poolside. This roomy rental has 3 bedrooms that sleep up to 8 guests along with many other amenities. A nearby waterfront and a sauna are among them.
  • Alternatively, escape to "Monument Mountain Lodge", which has 6 bedrooms and accommodates up to 12 guests. Along with that swish pool waiting for you inside, a fireplace and a firepit will help keep everyone comfortable and content.

If you're curious about other options, use the search bar at the top of the page and adjust the filters to find the Stockbridge vacation rental that's perfect for your needs.