Offers & Packages

At Chatham Wayside Inn, we believe in creating memorable experiences for all our guests. Our thoughtfully curated packages and special offers are designed to cater to a variety of preferences and needs, ensuring every stay is unique and unforgettable. Whether you're seeking a romantic getaway, a family adventure, or a rejuvenating retreat, our exclusive packages provide exceptional value and unparalleled comfort.

Chatham Wayside Inn

Book Direct & Save!

10% discount on new reservations

Book directly through our website and save 10% off your stay!

Boats and small yachts rest in a calm harbor beside a sandy beach under a clear blue sky.

August Breeze Getaway

Make the most of summer before it slips away! Enjoy up to 18% off stays Sunday through Thursday nights throughout August.

Whether you're planning a midweek getaway, a relaxing staycation, or a last-minute escape, this exclusive offer lets you enjoy all the comforts of our hotel at our best weekday rates. Skip the weekend crowds, unwind in style, and soak up the final days of summer for less.

Valid for stays Sunday–Thursday nights in August. Applicable to new reservations only. Cannot be combined with any other offers, packages, or group rates. Blackout dates and other restrictions apply. Subject to availability at time of booking. Discount applied to room rate only.

A blue bicycle with red rims stands on a sandy path by a wooden fence, leading toward a bright sky and distant dunes.

Cruise the Cape Package

The Cruise the Cape package includes a Wayside Inn tote bag stuffed with delicious snacks, drinks, and a map of the local area. Hop on our complimentary beach cruiser bikes to explore the scenic town and beaches.

Available May through September of 2026, enhance your stay and enjoy the beauty of Chatham in peak season!

The image shows two hands holding each other, with one hand wearing a diamond engagement ring.

Proposal Package

USD 450.00 / stay

Chilled bottle of Veuve Clicquot Champagne, Chatham Candy Manor Truffles, Engraved Chatham Wayside Inn Keepsake flutes, Floral Bouquet & festive balloons, Dinner for Two at The Wild Goose Tavern, Daily a la carte breakfast. Please call to add the package to your reservation.

A couple stands near water with sunlight in the background, the man touches the woman's belly as they both smile.

Babymoon Package

$400 plus tax and lodging

This “Babymoon” package is designed for expecting parents to get away on a relaxing vacation before the new baby arrives. A baby will change your lives forever (for the good of course!), but there will be less time for quiet dinner dates and romantic vacations. So, seize the moment and enjoy each other at The Chatham Wayside Inn.

  • Sparkling Cider
  • Chocolate Covered Strawberries
  • Dinner for Two at the Wild Goose tavern, the evening of your choice (Advanced Reservations)
  • Daily Continental Breakfast
  • A Floral Bouquet upon arrival
  • A $200 gift certficate for the La Petite Day Spa

Please call to add package to reservation

GIFT CARDS

Gift Card can be used at both the Hotel and Restaurant!

BUY GIFT CARDS

Answers You Need

Have a question? Whether you're planning your next visit, curious about our amenities, or need assistance with a booking.
Visit FAQs page