Windward House Monhegan

05/22/2026

We have a special guest at Windward House. They didn’t have a reservation but we were able to accommodate them. 😊 We still have open dates in June if you need accommodations as well!

05/17/2026

A beautiful day on Monhegan today! We hiked out Red Ribbon trail and headed to 1A and back via Cathedral Woods. Come out and see for yourself. It’s worth the trip!

05/01/2026

May 1st means we are back on the island and ready to get the house prepared for our first visitors on May 16th! We still have some availability in June, August and September in Westerly and limited availability in June in Easterly. So it’s not too late to reserve your Monhegan vacation. 😊 Specific dates can be found at brackettrentals.com

03/09/2026

Spring is coming and we can’t wait to get back on Monhegan and begin readying Windward House for the upcoming season! Reservations are being taken and we are filling in quickly. There are still multiple availabilities in Westerly but only a few openings in Easterly. Check out the calendar on brackettrentals.com. The bold dates are the available ones. Bring on spring! 😊

Brackett Rentals -

10/27/2025

Fall morning sky. Windward is all ready for its winter tenants. See you on May 1st, Monhegan. ❤️

08/29/2025

The pic doesn’t do it justice but the clouds are pretty cool!

05/08/2025

A beautiful day on Monhegan!

04/15/2025

May is almost here and we can’t wait to get back to Windward House and start to ready the rentals for our guests! We still have some availability in both Easterly and Westerly. Contact brackettrentals.com and click on the calendar. The dates still in bold are available. Happy Spring! 🌼

Brackett Rentals -

02/19/2025

It’s not too late to book your stay with us on Monhegan. We have some available dates in June and July in both Easterly and Westerly. Westerly has most of September available as well. Go to brackettrentals.com and click on Windward House to check on availability. The bold dates are the ones that are open.

01/16/2025

Happy New Year! Our calendar is starting to fill in. Looking forward to seeing those familiar faces that continue to come year after year! If you are looking to book for this coming season, don't delay. Go to brackettrentals.com to book. Things fill up quickly! Can't wait until May!

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