Stockbridge holiday lettings

Why visit Stockbridge

• Historic charm: Discover the rich history of Stockbridge through its iconic historic houses and charming High Street, filled with quaint shops and delightful eateries.
• Scenic landscapes: Enjoy the natural beauty of serene lakes and nature reserves, perfect for family-friendly outdoor activities.
• Romantic getaways: Experience a tranquil retreat in a picturesque setting, ideal for couples seeking romance.
• Diverse accommodation: Choose from charming holiday homes, stylish condos, and quaint cottages for a cosy stay.
• Community atmosphere: Explore the friendly neighbourhoods that embody a welcoming and family-oriented vibe.

Popular types of accommodation in Stockbridge

Discover the perfect getaway with our selection of Stockbridge vacation rentals, featuring charming private holiday homes, stylish condos, and quaint cottages. Whether you're seeking a cosy retreat or a spacious house for the family, Stockbridge offers diverse options to suit every traveller. Enjoy the beauty of the surrounding Hamptons while experiencing transparent pricing and reassurance in your booking. Explore our holiday lettings for an unforgettable stay in this picturesque destination.

• Houses: The top choice for visitors in Stockbridge, ideal for families or groups seeking ample space and comfort.
• Condos: A popular second option, these offer modern amenities and often stunning views.
• Cottages: Quaint and charming, cottages provide a cosy retreat amidst the scenic beauty of Stockbridge.
• Apartments: Convenient and versatile, perfect for shorter stays in the heart of the area.
• Cabins: Rustic and inviting, cabins offer a unique experience in the surrounding nature.**

Top attractions in and around Stockbridge

Stockbridge, Massachusetts, offers a delightful blend of culture, romance, and entertainment for visitors. With attractions such as historic houses, nature reserves, and serene lakes, the area caters to those seeking family-friendly outdoor experiences. Whether you're exploring the rich history or enjoying the beautiful landscapes, Stockbridge promises a memorable getaway for all types of travellers.

• National Shrine of the Divine Mercy: This serene shrine in Stockbridge offers a tranquil atmosphere, perfect for reflection and spiritual connection, surrounded by beautiful gardens and stunning architecture.
• Norman Rockwell Museum: Dedicated to the iconic American artist, this museum houses an extensive collection of his works, providing insight into his life and the cultural narratives he captured through his art.
• The Mount: Once the home of author Edith Wharton, this historic house features exquisite gardens and scenic views, allowing visitors to explore both her literary legacy and the property’s rich history.

Things to do recommended for couples

If you're seeking a romantic getaway in Stockbridge, enjoy a concert at the enchanting Tanglewood Music Center, just 3.1km away. For a thrilling day, head to Ski Butternut, 4.3km distant, or indulge in a wine tasting at Furnace Brook Winery, 5.0km away, perfect for couples.

Things to do recommended for families

Families visiting Stockbridge can unwind at Lake Mansfield Park, a delightful recreational area 3.7km away, perfect for wellness and relaxation. Alternatively, explore Tyringham Cobble, located 3.1km from Stockbridge, offering a serene environment for family bonding amidst nature.

Things to do recommended for groups

Groups visiting Stockbridge can enjoy a captivating performance at the Berkshire Theatre Festival, indulge in unique finds at the Berkshire Mountain Country Store just 2.5km away, and unwind with a round of golf at Wyndhurst Golf & Club, located 3.1km from the town.

What do I need to keep in mind when booking a vacation in 'Stockbridge

Regardless of whether you’re travelling with a group, as a family, bringing your pets along, or seeking longer stays, it’s essential to filter based on your key priorities. Here are some helpful booking tips for using Vrbo.

• Traveling to Stockbridge with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor space for group gatherings. Luckily, you can easily filter for all these options and more on Vrbo.
• Traveling to Stockbridge with young kids: Travelling with young children can present its challenges. It's essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
• Taking your pets with you to Stockbridge: For many families, a holiday isn’t truly fulfilled without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
• Planning for a long term stay visiting Stockbridge: If you’re seeking holiday rentals with offers for stays of a month or more, you’ve come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don’t forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay near Stockbridge

Stockbridge, Massachusetts, offers a delightful blend of culture and romance, perfect for a relaxing getaway. Explore the charming High Street, lined with quaint shops and eateries, or wander through the scenic neighbourhoods that embody a family-friendly atmosphere. Nearby, you'll find iconic spots like Princes Street, where modern living meets historical charm. Whether you seek a romantic escape or a tranquil retreat, Stockbridge promises an unforgettable experience amidst its picturesque surroundings.

• Lenox: Lenox is a charming town located 3.1km from Stockbridge, renowned for its vibrant cultural scene and romantic atmosphere. It provides an array of entertainment options, from music concerts to theatre performances, making it a delightful destination for families and couples alike. Outdoor enthusiasts can also enjoy its beautiful lakes and scenic mountains. With several event and conference venues, Lenox is perfect for those looking to combine leisure with business. The town's picturesque setting and community events create a welcoming environment for all visitors.
• The Berkshires: Situated 7.5km from Stockbridge, The Berkshires is a haven for outdoor adventurers and nature enthusiasts. Known for its stunning scenery, this region offers numerous skiing opportunities, with access to ski fields and resorts that cater to all skill levels. Whether you’re hitting the slopes in winter or exploring the lush trails in summer, The Berkshires promises an unforgettable experience. The local lakes and mountains provide a picturesque backdrop, and various event venues enhance the area’s appeal for those seeking both adventure and relaxation.
• Great Barrington: Located 4.3km away from Stockbridge, Great Barrington is an energetic town perfect for sports and adventure lovers. The area is particularly popular for skiing, with multiple ski fields and resorts nearby, appealing to both beginners and seasoned skiers. In addition to winter sports, visitors can explore the natural beauty of the surrounding lakes and the nearby national state park. Great Barrington has a vibrant community atmosphere, with unique shops and eateries that add to its charm, making it an ideal spot for an active getaway.

Best time to go to Stockbridge

If you're planning a trip to Stockbridge, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from July to September, while off-peak times, like January to March tend to have fewer bookings and better deals.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	22.8°F (-5.1°C)	Light Rain	Mostly Cloudy	Slightly Low	Average
February	24.6°F (-4.1°C)	Light Rain	Mostly Cloudy	Slightly Low	Average
March	32.5°F (0.3°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly Low
April	44.2°F (6.8°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
May	56.3°F (13.5°C)	Light Rain	Mostly Sunny	Average	Average
June	64.0°F (17.8°C)	Light Rain	Mostly Sunny	Average	Average
July	70.3°F (21.3°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	68.4°F (20.2°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
September	61.3°F (16.3°C)	Light Rain	Mostly Sunny	Slightly High	Average
October	50.0°F (10.0°C)	Light Rain	Mostly Sunny	Average	Slightly Low
November	37.8°F (3.2°C)	Light Rain	Mostly Sunny	Average	Average
December	29.5°F (-1.4°C)	Light Rain	Mostly Cloudy	Average	Slightly High

Booking with Vrbo is simple

Are you hoping to make your next trip more affordable? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, consider booking a longer stay to enjoy substantial savings. To discover a Vrbo property that suits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a handy platform for you to plan new trips, resume your previous arrangements, or review and organise your itineraries. You'll discover your saved or booked properties neatly organised into categories: Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.