Windward House Monhegan

10/26/2026

Last night we caught our final sunset of 2026 and this morning we get to watch the moon set. The 2026 season is in the books and we are looking forward to the 2027 season already. 😊

09/10/2026

Hard to believe that we became the owners of our house ten years ago today! It’s been a lot of work and we’ve certainly had our challenges but we keep plugging along. We truly appreciate the visitors that choose to stay with us and have a really wonderful group of “regulars” that visit every year. We wouldn’t be here without you all!

08/21/2026

My morning coffee view. Not too shabby! We still have a few open dates in Westerly. It’s not too late for a last minute trip to Monhegan. Go to brackettrentals.com and click on Windward House and look at the calendar for Westerly. Fall is the best time to be here!

07/22/2026

It's not too late to plan a stay in August, September or October. We have some limited dates available in Westerly, our one bedroom apartment. You can find the available dates on brackettrentals.com. Click on Windward house and go to the calendar. The bold dates are the available slots. Summer could slow down just a little...

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06/21/2026

We took a stroll up to the lighthouse tonight to catch the sunset. It was a popular spot! 😊

06/03/2026

Pheasants anyone? Our yard is very popular these days but the two guys hanging out on the deck railing is new. We still have some limited availability if you’d like to come and hangout with the pheasants. 😊 Book through brackettrentals.com

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