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The Chatham Wayside Inn

4.4(215)
Hotel

About

The Chatham Wayside Inn blends historic charm with modern comfort in a polished 1860 mansion located steps from downtown Chatham. Its heated seasonal pool, fitness center, and private balconies offer a relaxed coastal retreat ideal for small corporate gatherings or executive stays.

The inn's on-site Wild Goose Tavern serves elevated New England fare in a warm dining room, perfect for client dinners or team meals. With attentive service and a prime location near shops, parks, and the lighthouse, it’s a refined setting for business events with a local touch.

Best for

  • Executive retreats with historic charm
  • Client dinners in a refined mansion setting
  • Small group stays near downtown shops & dining

Request a Package

Tell the venue what you're planning and they'll respond with a custom proposal within 1–2 business days.

Group Meeting

Custom request

Professional meeting space for your team — whether it's a meeting, training, workshop, or multi-day offsite. Half-day, full-day, or multi-day — with the option to request AV, catering, and your preferred room layout.

What's typically included

  • Meeting room & layout
  • Food & beverage
  • AV & technology

Room Block

Custom request

Reserve a block of rooms for your group — ideal for multi-day conferences, offsites, or any event where attendees are traveling from out of town.

What's typically included

  • Reserved guest rooms for your group
  • Flexible check-in & check-out dates
  • Negotiated group rates

Meeting + Room Block

Custom request

Bundle your meeting space and guest rooms in one request — perfect for multi-day offsites and conferences where the team meets by day and stays overnight.

What's typically included

  • Meeting room & layout
  • Food & beverage
  • AV & technology
  • Reserved guest rooms for your group

Venue Details

Standout features

Historic Architecture
Polished mansion dating from 1860
The hotel is set in a beautifully restored mansion from 1860, blending historic Cape Cod character with contemporary boutique comfort. This setting offers a distinctive, elegant backdrop for business events.
Outdoor Amenities
Seasonal heated outdoor pool and patio
A seasonal outdoor pool heated just enough for comfort in cooler weather, complemented by a patio space ideal for casual gatherings or breaks during events.
Location
Central downtown setting near park and lighthouse
Located in the heart of Chatham’s historic downtown, the inn offers walkable access to shops, restaurants, a small town park hosting music and theater, and views of the nearby lighthouse flag-raising ceremony.

At a glance

Rated 4.4 on Google · 215 reviews