Top Lanesborough Venues

• Spaces for 175 Guests
• 1 Hotel
• 1 Ballroom

A hidden gem nestled between the towns of Lee and Lenox, Massachusetts, in the Berkshire Mountains. This tiny four-season boutique hotel is noted for its warm, friendly hospitality as well as its great position in the heart of downtown. Tanglewood, Kripalu, Jacobs Pillow, Barrington Stage, The Mount, and Monument Mountain Reservation are all excellent places to spend your time during your visit. The LakeHouse is one of the most popular wedding venues in the Berkshires, as well as a popular corporate retreat and relaxation destination. Pull into our driveway, take a look around, and you'll quickly realize that you've discovered a hidden gem in the Berkshire Mountains. Take advantage of the LakeHouse sunset views across Laurel Lake by sitting on the back cliff with a glass of wine at the start of your stay. Save some time to explore the lake, whether it's with a kayak or a paddle board, which are both available to our guests at no extra price. Our goal is for you to feel completely at ease while on your Berkshire getaway with us. The Lakehouse Inn, which is centrally placed, offers a variety of lake activities as well as a tranquil atmosphere that is known to relax the mind. Away from the site, the Berkshires are home to some of the best food and culture in the region. “There aren’t enough superlatives to describe this gorgeous Inn! Fully renovated to such elegant beauty. The rooms are beautiful, comfortable with the best views of Laurel lake… Every detail of this Inn is so well and lovingly thought out.” - Yuki C.

• Spaces for 150-200 Guests
• 2 Museums
• 1 Outdoor
• 2 Total Spaces

Set on 140 acres in the Berkshires of Williamstown, Massachusetts, The Clark Art Institute offers a striking blend of world-class art, modern architecture, and natural landscape. The campus features a collection of thoughtfully designed buildings, including the glass-walled Clark Center and the tranquil Stone Hill, surrounded by rolling meadows, walking trails, and a reflecting pool that shifts beautifully with the seasons. Ideal for weddings, corporate gatherings, and cultural events, the venue offers a range of indoor and outdoor spaces with sweeping mountain views and refined gallery settings, creating a distinctive and elevated backdrop for memorable occasions.

• Spaces for 8-100 Guests
• 1 Restaurant
• 7 Hotels
• 7 Total Spaces

The Red Lion Inn has stood at the corner of Main Street in Stockbridge, Massachusetts since 1773, making it one of New England's longest-continuously operating inns. The property occupies the heart of the village immortalized in Norman Rockwell's painting "Stockbridge Main Street at Christmas" and is managed by Mainstream Hospitality Group. For private events, the inn offers a range of dedicated gathering spaces suited to meetings, dinners, and celebrations of varying scale. The Hitchcock Room, the largest of the private meeting spaces, accommodates up to 96 seated dinner guests and includes an entrance foyer for registration. Smaller rooms — including the Townsend Room, the intimate Plumb Room overlooking the Courtyard, the historically appointed Treadway Room, and the Side Parlor just off the lobby — serve groups from 8 to 48 guests. The flower-filled Courtyard opens seasonally from June through October for outdoor receptions and dining, and the Side Piazza provides a charming porch setting for cocktail receptions. All on-site events are served by the inn's in-house culinary team, whose farm-to-table menus emphasize local Berkshires ingredients. A dedicated Director of Sales guides event planning from first inquiry through the day itself.

• Spaces for 70-250 Guests
• 1 Outdoor
• 1 Historic Space
• 1 Estate

Chesterwood is the former summer estate of sculptor Daniel Chester French — creator of the Lincoln Memorial's seated Abraham Lincoln and Concord's Minute Man — preserved by the National Trust for Historic Preservation on 122 wooded acres in Stockbridge, Massachusetts. The property is an entirely outdoor venue, offering ceremony, cocktail, and reception settings across formal perennial gardens and sweeping lawns with panoramic views of Monument Mountain. During cocktail hour, guests are invited into French's working studio and onto its broad porch, a rare encounter with one of American sculpture's most significant sites. Chesterwood is currently booking private events for 2026 and 2027. Events typically begin at 5pm when the property closes to day visitors, allowing the estate to transition into an exclusive private setting for the evening.

• Spaces for 200 Guests

Bellavista Country Estate is a 12,000-square-foot brick Georgian mansion set on 60 private acres in Columbia County, New York, positioned between the Hudson River Valley and the Berkshires — roughly 2.5 hours from both New York City and Boston. Built originally as a private family gathering home, the estate now hosts weddings, milestone celebrations, corporate retreats, and reunion weekends throughout the year. The property includes 8 bedrooms, 5 full bathrooms, 3 deluxe guest suites, 5 fireplaces, an in-ground pool, full gym, library, and game room, alongside a 3-story party barn and a sweeping 10-acre front lawn. Miles of horseback riding and hiking trails wind through the surrounding acreage. Bellavista does not offer set package plans — organizers may bring their own vendors or draw on the estate's expert planner network to build a fully custom event.

The spirit of Winbrooke is tangible. It has a warm and welcoming presence that you feel immediately upon entering the property. We knew we wanted to share this special place with as many people as possible. Three and a half years ago, we began an extensive restoration that brought life back to the property and restored its original beauty. We decided to combine our love for the property, appreciation for world-class service, and attention to detail. With that, we created an intimate Berkshire, Massachusetts wedding venue that is unlike any other. Nick and I have an extensive background in production and event planning and, together, are able to provide next-level service that assures you feel as though Winbrooke is your own private estate while celebrating your special day. We are Berkshire natives and hold the Berkshires near to our hearts. With that comes an inspired passion to make your time with us remarkable. We work closely with you every step of the way to create the Berkshire wedding of your dreams. It's a pleasure to open our property to you and create an unforgettable experience on your wedding day! Sincerely, Amy & Nick

• Spaces for 300 Guests
• 1 Event Space

Barrington Hall is a 4,500-square-foot event venue in Great Barrington, Massachusetts, situated in the heart of the Berkshires. The space accommodates 10 to 300 guests across a flexible combination of an indoor banquet hall, a 30-by-60-foot outdoor lawn, a covered patio, and an A-frame ceremony area suitable for year-round use. Founded by two longtime friends and neighbors with a shared passion for live music and community gathering, the venue hosts weddings, private celebrations, corporate retreats, and live performances. Each booking receives exclusive use of the full grounds, along with tables, chairs, glassware, linens, professional setup and breakdown, and in-house bartending staff. An on-site commercial kitchen is available for outside caterers.

• Spaces for 40-200 Guests
• 1 Barn
• 2 Historic Spaces
• 1 Estate

The Curtis House is an 1850s Dutch Colonial home set on five acres of cut flower gardens, orchards, and open lawn in Ashfield, Massachusetts. The property takes its name from George William Curtis — editor of Harper's Weekly and a prominent 19th-century lecturer and essayist — who summered there with his wife and established the Ashfield Dinners, an annual community gathering that became a New England institution. Today, Gloriosa & Co. operates the Curtis House as an exclusive-use event venue. The restored late 19th-century barn is the heart of the property, accommodating up to 140 guests beneath exposed beams and locally milled hardwood floors, with a stone patio that opens directly onto the cut flower gardens. For winter celebrations, the main house hosts intimate gatherings of up to 40. The venue books one event per weekend, keeping each occasion genuinely exclusive to the couple or group who books it. In-house catering, bar, and floral design services are available on-site, handled by the same team that manages planning and day-of coordination.

• Spaces for 400 Guests

Birch Hill Catering has been a fixture of Hudson Valley hospitality since 1936, bringing more than 80 years and four generations of expertise to weddings, corporate gatherings, and social events throughout the Albany and Capital Region. The company operates two distinct venues — Birch Hill Estate and Stablegate Farm & Vineyard — together offering nine unique indoor and outdoor event spaces suited to celebrations of every scale. Birch Hill Estate features two ballrooms and three covered pavilions set amid manicured grounds, while Stablegate Farm & Vineyard brings a 19th-century Dutch barn, a Lodge for intimate gatherings, and multiple outdoor spaces with views of the Catskill Mountains. Both locations are in Castleton-on-Hudson, NY. The culinary program is built on made-from-scratch cooking with locally inspired ingredients, led by an on-site chef. Each event includes complimentary coordination services, and customizable packages extend to rehearsal dinners, farewell brunches, and off-premise catering across the region.

• Spaces for 500 Guests

Park-McCullough Historic Governor's Mansion is a 35-room Second Empire mansion in North Bennington, Vermont, built between 1864 and 1865 for attorney and entrepreneur Trenor W. Park. The home was later expanded and renovated in 1889-1890 by Park's daughter Eliza and her husband John G. McCullough to host President Benjamin Harrison's 1891 visit for the Bennington Monument dedication. Direct descendants lived in the house for a century until 1965, when it passed to the Park-McCullough House Association, and it is now recognized as one of New England's finest and best-preserved Victorian mansions. The property offers four main event spaces for weddings and private events: the historic mansion itself, formal manicured gardens, a wrap-around veranda for cocktails and touring, and a newly renovated Carriage Barn with a full catering kitchen, restrooms, a hardwood dance floor, heat, air conditioning, and wi-fi. The mansion and grounds host weddings, rehearsal dinners, corporate retreats, nonprofit fundraisers, and celebrations of all kinds throughout the year. No vendor fees are charged, though food must come from a licensed restaurant or caterer and alcohol from a Vermont-licensed vendor.

• Spaces for 350 Guests

Berkshire Outdoor Center is the year-round component of the non-profit Becket-Chimney Corners YMCA, situated on 1,400 acres of prime conservation lands in the Berkshires of Massachusetts. The center hosts more than 14,000 guests each year in Environmental Education, Outdoor Education, Leadership Development, and Adventure Recreation programs. Beyond its core programming, the center also serves conferences and retreats, family events, youth group retreats, and weddings — drawing groups from schools, colleges, corporate organizations, and families across New England and New York.

• Spaces for 165 Guests