Meghan Ottolini


Cole Boskey


Chatham Highlander

946 Main St, Chatham, MA
An economically-friendly option with direct access to main street. Room block available - Please mention Ottolini/Boskey wedding. Standard room $199 (2 night min); apartment & 2 room suites also available.
Expense level: $

Pleasant Bay Village Resort

1191 Orleans Rd, Chatham, MA 02633
Another economic option, set farther away from the action of downtown but with more amenities than the Highlander. Room block available, please mention Ottolini/Boskey wedding. Standard rooms $175- $225 (2 night min); 1bd & 2 bd suites $295 - $375, (2 night min).
Block expires June 29th.
Expense level: $$

**See note from mgmt regarding reservations**
Since we are closed from November 6th to April 19th, guests calling to make their reservations should leave a message if no one answers the phone, and they will receive a return call usually within 24 hours. The best number to call for reservations during the winter is (508) 945-6061.

If guests prefer to make their reservations online using our website, they should enter “Ottolini/Boskey Wedding” under Special Instructions, when filling out the online reservation form. The following link will take you directly to the online booking engine on our website,

Chatham Wayside Inn

This charming inn has recently undergone a major renovation. It is ideally located on Main Street and features a variety of room sizes available to book. It also has a swimming pool, bar, and restaurant.
No room block
Expense level: $$$

Chatham Bars Inn

One of the Cape's most luxurious vacation offerings. We will be having our welcome party on the grounds of this resort, and it is just a short walk from our wedding venue and town. If you're interested in really living it up, this is the place to book.
No room block
Expense level: $$$$


AirBnB offers various homes and apartments for rent in Chatham. If you choose to stay in one of these properties, please send us a note about where you'll be so we can best coordinate our centralized shuttle stops.
Expense level: $-$$$$


VRBO offers numerous houses for rent in Chatham. We recommend booking near town (Main Street) or the Chatham lighthouse. If you choose to rent a house, please send us a note regarding its location so we can best coordinate our centralized shuttle stops.
Expense level: $$-$$$$
Alston Wise