Monthly Rentals in Simmons Pond

Great place to stay even in the winter. The loft was so warm & well insulated you’d have no idea it was 20 degrees outside! Cozy place

We really enjoyed our stay at Matthew’s house. The peaceful, quiet neighborhood was a great beginning and end to our day after the sights. Perfect area for walking the dogs too. The beds were comfortable, the ocean decor interesting, the bathroom was big enough to share. Just a very comfortable space that we appreciated.

I was lucky to stay here for months and loved it! Cried when I had to leave even though I just moved a couple towns over. Westport is an amazing town and this place is tucked away in a great location, it really felt like home. I worked here remotely doing video calls all day and had no issues with the internet. There are so many places to explore nearby even in the off season - all the Westport land trust properties, the Westporter, and I'll miss Lee's Market dearly. Emily has a ton of great info & recommendations in the guest book at the house, enjoy!

Steven is a very welcoming host. He is always responsive, and makes you feel at home. He is honest about the amenities provided and gives you plenty of privacy.