top of page

Waterfront &
Water View

in the 
Boothbay Region

Chill Vacation Rentals

Search our Listings

Our Cottage Locations

Abstract Man on Beach
Abstract Man on Beach

About Us

Welcome to Chill Vacation Rentals, your go-to source for high-end waterfront and water view vacation rentals in the Boothbay Harbor Region. Our locally owned company takes pride in offering comfortable and charming cottages, as well as elegant estates, all with a little coastal flair. With our portfolio of top-quality properties, you're sure to find the perfect vacation rental for your needs. Browse our selection today and experience the best that Boothbay has to offer!

Read More

Exceptional Properties

High End Linens

Great linens are essential! Your vacation rental will have crisp, high quality sheets, duvets with duvet covers and fluffy, soft towels.

We are Fussy

Your vacation rental will be meticulously cleaned and cared for. No dust bunnies here!

Tip Top Shape

Your vacation rental will be in great shape and will have comfortable, clean furnishings and high quality mattresses. 

All the Right Stuff

Your vacation rental will have a fully stocked kitchen, high speed WiFi, flat-screen television, outdoor grill and much more...


Excellent Service

On Call - 24/7

In the unusual event that something needs our attention, we are here to help 24/7.


We are happy to give you insider tips, schedule a private charter fishing excursion or help to get a table at one of the best restaurants in town. 


We have ALL 4 & 5 star reviews. We will let you know what expect, so there are no surprises and you can focus on enjoying your vacation in Boothbay Harbor.

Easy Online Booking

We accept all major credit cards and provide a seamless online booking experience. 

Abstract Man on Beach

Renowned for it's natural beauty, there's no better place to have a vacation rental than the Boothbay Region. The region is made up of the charming villages of Boothbay, Boothbay Harbor, East Boothbay and Southport that are each unique in their history and character. Though our peninsula is only some 10 miles long, the area boasts over 100 miles of rugged and scenic coastline, and provides the opportunity for all kinds of water activities and many scenic destinations. In addition to the numerous restaurants, shops and galleries that you will find here, the area is also home to The Boothbay Botanical Gardens, which was recently rated as the #1 public garden in the nation by Tripadvisor, The Maine State Aquarium and a large fleet of tour boats. Plan your Boothbay Harbor vacation here!

Boothbay Harbor

The charming seaside village of Boothbay Harbor is one of the most popular vacation destinations in Maine. With over 25 restaurants, from fine dining to lobster shacks, and numerous shops and galleries, there aren't many places anywhere that offer so much to do in such a picturesque setting. Boothbay Harbor also has all kinds of boat tours, kayak rentals and even a world renowned live music venue, The Boothbay Opera House. 

KPT Road.jpg
East Boothbay

East Boothbay is nestled between Linekin Bay and the Damariscotta River, only a few miles east of downtown Boothbay Harbor. It's renowned for its absolutely stunning natural beauty. Whether you enjoy the scenery from a hike on a waterfront trail, or a beach chair on the rocks at Ocean Point, you will quickly understand why East Boothbay has been a favorite vacation rental spot for decades. ​



"This house was first rate in every way. It was so pleasant and quiet. It is a nice house if you need at least three bedrooms each with a bath and the location is centrally located in the state of Maine. It was ideal for our situation."

- Bob C Oct 2018


"This is a beautiful cottage right on the water with an awesome dock for coffee, reading, cocktails and fun. The cottage is well equipped for everything. The towels and linens are first class. Bed we slept in was awesome. The views are incredible and the cottage is beautifully decorated for the area. We totally enjoyed our stay."

-Sharon M

VRBO.COM Oct 2018


We came up to Boothbay not knowing what to expect. The place was terrific! The views were amazing, the place was clean, well kept and safe. Pam was thoughtful, communicative and just a great host!

-David S

AirBnB Oct 2018

bottom of page