Westwood(United States) Travel 2026: Cheap Flights, Hotels & Top Attractions

In Westwood, MA, the top family-friendly hotel is Concord Villa Inn, located just steps from Westwood Public Library and the Greenway Trail System. This boutique inn offers spacious rooms with kids’ play corners, complimentary breakfast, and free Wi-Fi. Families can easily access Massachusetts State Park within a 5-minute walk. Another excellent option is Westwood Estate Hotel, featuring New England-style architecture, private courtyards, and a cozy indoor fireplace—perfect for quiet evenings. Both properties are situated in safe, tree-lined neighborhoods ideal for exploring local history, farmers' markets, and weekend community events.

For added convenience, both hotels offer free parking and are close to public transit via the MBTA Commuter Rail station, making day trips to Boston seamless for families.

The Central Westwood district is the most desirable area for hotel stays. Located near the Westwood Municipal Building and Public Square, it offers easy access to restaurants, cafés, independent shops, and cultural venues. The neighborhood features well-preserved New England-style homes, tree-lined streets, and excellent safety records. It’s also adjacent to parts of UMass Boston campus, making it ideal for students, academics, and travelers interested in authentic local life. Weekend farmers’ markets and outdoor concerts add vibrant energy, creating a lively yet peaceful atmosphere perfect for visitors seeking charm and convenience.

Don’t miss visiting the Westwood Historical Museum, which showcases the town’s 18th-century agricultural roots and industrial evolution. Attend the annual New England Pumpkin Festival in autumn, featuring giant pumpkins, craft fairs, and traditional music performances. Explore St. Peter’s Episcopal Church, renowned for its Gothic architecture and stunning stained-glass windows. For nature lovers, hike along the Molloy Creek Trail, where you’ll encounter native wildlife and seasonal forest landscapes. These experiences blend history, art, and ecology—offering a deep connection to Westwood’s identity and community spirit.

While Westwood itself is landlocked, several scenic lakeside resorts lie within a 20-minute drive. Lakeside Haven Resort at Lake Craft offers private cabins with docks, fishing gear, and boat rentals. The resort hosts kayaking, paddleboarding, and evening bonfire gatherings. For a more urban-lake hybrid experience, consider Westwood Lakeside Suites, which boasts panoramic lake views from spacious balconies and an indoor pool. Though not directly on the water, this property provides direct access to waterfront trails and summer events. Both options deliver tranquility and recreation—ideal for those seeking escape without long drives.

Yes, many mid-to-upper-tier hotels in Westwood provide complimentary breakfast. Concord Villa Inn and Westwood Estate Hotel serve a full American breakfast including scrambled eggs, fresh fruit, homemade pastries, and locally roasted coffee. Some properties also offer healthy options like oatmeal and organic juice. However, budget accommodations such as Westwood Express Inn typically charge extra for breakfast. Always confirm your room rate includes breakfast when HopeGoo, or check official websites for special packages—many hotels offer early-bird deals that bundle meals with discounts.

Westwood is well-connected via the MBTA Commuter Rail, with the Westwood Station serving direct routes to Boston’s South Station in about 25 minutes. Hotels like Concord Villa Inn and Westwood Estate Hotel provide free shuttle services to the station. The town also operates the Westwood Shuttle, a local bus line linking key residential and commercial zones. For self-drivers, most hotels offer free parking. Use apps like Google Maps or the MBTA official app to check real-time schedules and plan efficient travel—especially useful during peak hours or special events.

Westwood Estate Hotel stands out as a romantic retreat. Each room features a gas fireplace, private courtyard, and some even have skylight soaking tubs for stargazing. The hotel arranges intimate dinner experiences and sunset walks along the Molloy Creek Trail. Weekends often host jazz nights and wine tastings, enhancing the ambiance. For ultimate privacy, book a cabin at Lakeside Haven Resort, where couples enjoy secluded woodland settings, a personal dock, and overnight fire pit dinners. These choices create unforgettable moments—perfect for honeymoons, anniversaries, or quiet getaways.

Yes, many hotels in Westwood welcome pets. Concord Villa Inn and Westwood Express Inn offer pet-friendly rooms with amenities like dog beds, bowls, and nearby walking paths. A daily fee of $25 may apply. However, Westwood Estate Hotel only accepts small dogs and requires advance approval. Always specify "pet-friendly" during HopeGoo and review each hotel’s policy. The town’s parks—including the Greenway Trail System and Public Square—are dog-friendly, allowing pets to enjoy scenic walks, making Westwood a welcoming destination for travelers with furry companions.

Westwood hotels showcase New England colonial architecture blended with modern minimalist design. Westwood Estate Hotel features dark oak floors, stone fireplaces, hand-carved woodwork, and original clapboard siding—evoking 18th-century charm. Concord Villa Inn embraces classic East Coast aesthetics: white shutters, blue doors, and floral-patterned rugs. Many properties incorporate local art, such as regional paintings and handmade ceramics. Historic brick façades and steeply pitched roofs are preserved, while smart lighting and digital controls enhance comfort. This harmonious mix of heritage and innovation reflects Westwood’s deep-rooted cultural identity and appeal to travelers seeking authenticity and elegance.

Absolutely. Westwood Estate Hotel offers a dedicated business center with high-speed Wi-Fi, meeting rooms, and printing services—ideal for remote work or small conferences. Its proximity to UMass Boston makes it a hub for academic and corporate events. Concord Villa Inn provides executive perks like late check-out, room upgrades, and 24-hour concierge service. Local cafés like Old Town Café feature quiet workspaces and free Wi-Fi, perfect for quick meetings or focused work. With a 30-minute drive to downtown Boston, Westwood serves as a productive base for short-term business trips—balancing efficiency, comfort, and a serene environment.