Chill Vacation Rentals

05/25/2026

🐦 Did you know Maine is the ONLY place in the US to see Atlantic Puffins in the wild?! 🐦 Hop aboard a Cap’n Fish boat right out of beautiful Boothbay Harbor for an experience you’ll never forget! 🌊⚓

The puffins have been incredible so far this season! 🤩
Join us on an Audubon Puffin and Scenic Cruise and learn about puffins and the other seabirds of Eastern Egg Rock from Audubon naturalists!

📸: Passenger, Walter Brooks

05/02/2026

Looking for that special Maine getaway for your family and pup? We've gotcha covered! 🐶👀

03/25/2026

Summer, we’re ready for you! Check out this amazing sunset at Seaglass Cottage in East Boothbay. It won’t be long now… 😍🌅

12/06/2025

🌊 Our 2026 booking calendar is open!
Summer weeks always disappear fast, so if you’re thinking about a Maine getaway, now’s the time to snag your spot. Can’t wait to see everyone back in Boothbay!

10/14/2025

Just had to share one of our favorite spots — Water Street Kitchen and Bar 😍 Super cozy atmosphere and tons of gluten-free options (even celiac safe 🙌). Highly recommend if you’re looking for a place that’s both tasty and comfy! 💯

Unwind in our cozy lounge and enjoy the warmth of a welcoming ambiance. ✨

09/02/2025

🎉 Bit of a milestone moment—we just hit our 100th review of 2025, and guess what? Every single one has been 5 stars! ⭐️⭐️⭐️⭐️⭐️

We couldn’t do this without our amazing community:

🏡 Our wonderful homeowners who trust us with their beautiful properties
🧼 The hardworking cleaners and contractors who keep everything looking its best
🧳 And of course, our awesome guests who treat our homes like their own and take the time to leave such kind words

We’re so grateful for all the support, and we truly hope our work is making a positive impact for our community and everyone involved. Thanks all! Here’s to keeping the streak alive! 🙌🤞🍀

08/22/2025

The Boothbay Region is VERY welcoming to your pups. In addition to the many trails, several restaurants with outdoor seating also welcome them. Check out our dog-friendly properties, On a Whim and Morning View. Oh, and by the way, they both have availability the first week in September at a discounted rate.

08/17/2025

Want a last-minute getaway? Early September is one of our favorite times to visit. The crowds have thinned, everything is open, the weather is still warm, and the rates have dropped. We have availability at several incredible cottages, all with a 3-night minimum and reduced rates. Check ‘em out at the link in the comments!

08/01/2025

It’s a gorgeous day to stroll downtown and check out our wonderful galleries during the First Friday Art Tour this afternoon, Aug 1, from 5 to 7.

07/26/2025

We’ve got a few great last-minute deals for August!

-Ship’s Wheel: Aug 15-22 & Aug 29-Sept 5th

SW, a very popular 2 BR/1BA rustic cottage in Ocean Point, had a few cancellations in August. If you know Ocean Point, you know this is rare! It's right across the street from the ocean, with a gorgeous water view and one of the best screened-in porches in the area.

- Lobstercliff Cottage: Aug 22-31

Lobstercliff is a waterfront 2BR/1BA in East Boothbay with a huge deck and some of the most stunning water views in the area. It's on a cliff-like setting on one of the area’s favorite roads for ocean vistas.

-Appalachee Ocean View: Aug 17-23

AOV is a 2BR/2BA in Boothbay Harbor, with beautiful bay views and a lake beach across the street. This cabin is excellent for families who like lakes for recreational use, but also has that coastal feel and is only 2 miles from downtown.










Links in comments

07/12/2025

Nothin better than homemade pretzels and local beer! 😋🍻🥨

What makes our beer even better? Dan's (no longer) ugly pretzel! He got wicked peeved with the quality of the store bought variety so he set out to make his own. They weren't always this beautiful but they were and are delicious! They come with Ray's Old World or Sweet and Spicy mustard, or add Footbridge Brewery's very own beer cheese! Can I get a "yum!"

We are open noon to 9pm. Come see us.