WATERSIDE RETREAT - City of Rockland

LOCATION: Rockland, Rockland Harbor - Well Appointed And Steps To Downtown

  6 guests
  3 bedrooms
  3 full bathrooms
  1500 sq. ft.

Instant Quote

Sleeping Arrangement

Bedroom 1- 2nd Floor
1 Queen
Bedroom 2- 2nd Floor
1 Queen
Bedroom 3- Main Level
1 Queen, 1 Twin

Property Info


1st Floor- Kitchen with Dining Area (the table has a leaf to expand and accommodate seating 6 comfortably), Living Room, Bedroom with Queen bed and 1 Twin bed with en suite tub-shower bathroom, Shared Laundry
2nd Floor- 2 Bedrooms each with a Queen bed and en suite tub-shower bathroom

DOGS PERMITTED? Sorry, Dogs are NOT permitted at this property.

Waterside Retreat boasts comfortable furnishings and is perfect for couples wanting their own bed & breakfast feel in a private property with Rockland Harbor views. The unit is shared property with a long term tenant on the otherside of the house. 

Just a few hundred feet from the Rockland Public Landing, this property is perfect for those coming to experience the North Atlantic Blues Festival or the Lobster Festival held in July and August. Restaurants, art galleries, and shops are also just steps away.

A sandy beach on Rockland Harbor is located 300 yards from the property.

2023 Rockland City Permit: STR24-12


Boats Available?: Sorry, boat rentals are not offered at this property as it has no direct water access or place to store them.

LINENS & TOWELS: The rental of this property includes all bed linens and towels.  Beds will be made up upon arrival and there will be one bath towel and wash cloth per listed occupancy, two hand towels per bathroom, one bath mat per full bathroom, and two kitchen towels in the kitchen.  Additional bath towels can be rented.

SECURITY DEPOSIT: No, the owner of this property does not require a security deposit, however, guests are still financially responsible for non-accidental damages at the property.

Cleaning: The property will be professionally cleaned before and after the rental. Above normal cleaning charges will be billed to guest at the current hourly rate
Washer & Dryer: Yes, shared with a neighboring long-term lease apartment
Dishwasher: Yes
Coffee Maker: Yes, combination standard automatic drip with filters and K-Cup
Air Conditioning: Yes, the entire unit has central air-conditioned and there are fans in all bedrooms.
Usable Fireplace: No
Outdoor Fire Pit: No
Internet Access: Yes, with WiFi
TV: Yes, with Smart TV with Netflix access (account required) and cable service
Grill: Propane gas grill
Trash Removal Service : Included with rental
Water Source : City Water
Closest Shopping Village: Rockland – the property is right on the edge of the city center
Number of Restaurants within 10 Miles: 30 Plus
Water Frontage: No
Beach Access: Yes – Public Nearby
Dock/Pier Access: Yes - Public Nearby
Property Good For Fisherman: No
Additional Amenities: Minimum Standards List

Exploring Area



Jul - 2024
  1 2 3 4 5 6
7 8 9 10 11 12 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
28 29 30 31
Aug - 2024
        1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
Sep - 2024
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30
Oct - 2024
    1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30 31
Nov - 2024
          1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27 28 29 30
Dec - 2024
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30 31
Jan - 2025
      1 2 3 4
5 6 7 8 9 10 11
12 13 14 15 16 17 18
19 20 21 22 23 24 25
26 27 28 29 30 31
Feb - 2025
2 3 4 5 6 7 8
9 10 11 12 13 14 15
16 17 18 19 20 21 22
23 24 25 26 27 28


Write a Review
Katy, US
Reviewed: Oct 12, 2023
Property Manager
Very easy. No issues or concerns
Was our second stay at Waterside Retreat, so far. Very nice place - nice living space layout, roomy. Good location for us. Convenient to Rockland city center / Main St amenities.
Orlando, US
Reviewed: Sep 6, 2023
Property Manager
They were great as they are always are. Kim was especially helpful!
We have stayed at the Waterside Retreat seven or eight times and are always very pleased. There's nothing fancy about it. It's really very simple. But it works and works perfectly. It's immaculately clean, well furnished, with good central air conditioning and wonderful beds. We've stayed at much more lavish and expensive properties over the years, but we will continue to come back to Waterside when we return to Maine.
Bloomingburg, US
Reviewed: Jan 8, 2022
Property Manager
Excellent! Paige was very thorough and helpful.
Our stay exceeded our expectations. We were very pleased to be only 800 feet from the water and within walking distance to downtown and other conveniences.
Philadelphia, US
Reviewed: Sep 26, 2021
Property Manager
Newburyport, US
Reviewed: Sep 12, 2021
Property Manager
Working with On the Water in Maine was seamless.
Favorite feature of the property was the front porch
West Rockport, US
Reviewed: Aug 18, 2021
Property Manager
Easy and responsive
Very comfortable and liked having the picnic table so we could be outside, front porch area was lovely too
Allison park, US
Reviewed: Aug 17, 2021
Property Manager
Alexandria, US
Reviewed: Aug 10, 2021
Property Manager
We have rented with On the Water in Maine for several years and have been consistently very pleased with every aspect of our rental experience. They have truly done everything to try to make your vacation outstanding.
Great stay, as always! Favorite features of property - location, clean, enough space, starter supplies provided, washer/dryer
Winchester, US
Reviewed: Jul 19, 2021
Property Manager
The process was easy, and we had no difficulties.
Our stay was marvelous! The house was perfect for two seniors, two adults, and two teens that stayed there. The home was well laid out for our family, and well furnished. The view was beautiful! And the walking access to town was a definite plus. We were able to walk to the shops and restaurants with ease.
Reviewed: Sep 9, 2019
Property Manager
We've worked with On the Water since it's first year of business and we've never been disappointed in their service, their professionalism, and the manner in which they insure that their properties are ready for occupancy. They're available if you need them and they don't bug you if you don't. Tiffany, Paige and the crew and simply wonderful.
We've stayed at the Waterside Retreat for several years and we're always very pleased with the property. The home is not overly fancy, but it is extremely functional - from a wonderful air conditioning system to the three large bedrooms, the wonderful equipped kitchen, and it incredibly wonderful location two or three blocks from everything to see, do and eat in Rockland.
Upper Darby, US
Reviewed: Aug 11, 2019
Property Manager
Saylorsburg , US
Reviewed: Aug 4, 2019
Property Manager
Your team is awesome! As I stated above Paige was a great help and so friendly. Jack came to our rescue with a bedroom door key because the door became inadvertently locked. He was super nice. Meg helped with all of that as well, and couldn't have been nicer. Fantastic team. Each and everyone of you. Everyone was kind and accommodating. Paige was especially helpful and provided tips on local restaurants and things to do.
Reviewed: Sep 4, 2018
Property Manager
We've worked with On the Water since the agency opened about a decade ago. We've always been completed satisfied with their service, and this year was no exception. Paige was a pleasure to work with - from the day we booked our stay until we left Maine. Forget Home Away and VBRO. Stick with On the Water!
The Waterside Retreat is a terrific value for those wanting to spend time in wonderful Rockland. We're stayed there in the past, but were thrilled to find a host of upgrades to the house that enhanced every aspect of our visit. There's nothing fancy about the Retreat - but for sheer comfort, a perfect location, and if one wants a home where everything just works perfectly, it cannot be beat. Our only regret is that we could only stay one week. We'll not make that mistake next year.
Pecos, US
Reviewed: Oct 18, 2017
Property Manager
I have used On the Water in Maine several times. I have been very pleased.
The house had been updated since my stay a year ago. Very nice!
Nashville, US
Reviewed: Oct 3, 2017
Property Manager
On the Water in Maine was Straightforward; responsive; cordial.
This is the third time our family has rented this property, and, as on the other years, it did not disappoint. Each room having an en suite was quite nice. We enjoyed the updates to the kitchen. All the rooms are comfortable and spacious. The location works well for us as it is within walking distance of restaurants, shopping, Farnsworth, etc. and right across from the harbor walk. My only suggestion (and I know this is difficult when stocking rental property) is to include a good sharp knife. Even those "disposable" Hinkels are pretty good; better than the assortment currently in the kitchen.
Reviewed: Jul 27, 2017
Property Manager
Pecos, US
Reviewed: Oct 26, 2016
Property Manager
On the Water in Maine is always helpful. I have rented from them several times.
Ideal location. Close to the boardwalk and within easy walking distance of several great restaurants. House is well equipped and very comfortable. Especially liked the in-suite bathrooms.
Warren, US
Reviewed: Sep 12, 2016
Property Manager
This agency is amazing! Everyoneissoniceand they are so responsive. Justin couldn't be more kind and responsive.
We love this house! We rented two years in a row with friends from So. Carolina. This house is solid ,homey, plenty of room ( rarely found 3 beds with 3 bathrooms.). The location is amazing! You an walk to restaurants, pubs, shops and you're a few miles from Camden, Thomaston, Rockport. Easy day trips include Boothbay Harbor, Pemaquid, Wiscasset,Lincolnville among others. You're also close to ferry terminal including Knights dock where you can buy lobsters fresh off the boat! Take those lobsters to Cuzzys in Camden and they'll cook them for $1 each! That's how they support their local fisherman! The house is so convenient yet quiet and serene.
Warren, US
Reviewed: Sep 11, 2015
Property Manager
On the Water in Maine was awesome! Justin was caring and always reachable. When we had a problem his response was so fast and problem was solved. We woke up to no hot water on day after arrival. One call to Justin and problem solved in one hour! Justin originally apologized that it might takes some time to fix until later that day. We received call within an hour from his service man and they had solved the problem!
Our stay couldn't have been better. We loved the house, atmosphere , location and amenities. Homes location was perfect and central . We often walked to dinner.
Lexington, US
Reviewed: Aug 1, 2015
Property Manager
Friendly and accommodating with all the phone calls I had to make from KY.
Location, location! Beautiful place. Beautiful home. Considerate with all the extras, sugar, tea, dishwashing soap, etc.
Pecos, US
Reviewed: Oct 21, 2014
Property Manager
On the Water in Maine's website is simple to navigate. I have rented from this agency 4 or 5 times and have never had a problem.
Lovely, clean property. Bedrooms are very spacious and comfortable. Great house and an easy walk to town, restaurants, etc. Plus the board walk is just across the street.
Oldsmar, US
Reviewed: Aug 29, 2014
Property Manager
Any problems or issues we had were dealt with promptly.
It was important to us that the Waterside Retreat be clean and everything was in working order upon our arrival. On The Water in Maine made this happen. Our stay was perfect!
Maidens, US
Reviewed: Aug 13, 2014
Property Manager
Reviewed: Jul 18, 2014
Property Manager
Boy was the rental process efficient!
Rockland really is a beautiful area. We enjoyed that we could walk to most places we wanted to visit, including the Blues Festival. What a surprise to see that there were 3 en suite bathrooms -- made it very comfortable for our weekend guests. -- we would like to reserve the same week next year!


No Smoking is permitted anywhere on or inside of any of our rental properties nor are those who may partake in tobacco smoking allowed to occupy any of our properties.

Occupancy may not exceed what is posted for each home. Maximum occupancy could include infants and children.

Boat Rentals and other amenities offered through On the Water in Maine Inc. are not available at all the properties we offer for rent. Boat Rentals through Maine Watercraft Rentals Inc. are offered Sunday morning to Friday after 4pm and include free delivery to the property. Check with an agent to find out what boats are available to rent at this property, or, when you process the booking here online, only the boats available for the property will be listed as available to rent.

Please see our Rental Guidelines Page for further questions regarding how to book this property and additional charges and fees. Contact a reservation agent for more details or to ensure you are booking the right property for you.

Town Info - Owls Head / Rockland / South Thomaston

Owls Head / Rockland / South Thomaston
Still rooted in its historic past, Rockland's downtown is a designated National Historic District, with vivid examples of Italianate, Greek Revival, and Colonial architecture. Here you'll find a small city experiencing a renaissance, anchored by the first-class Farnsworth Art Museum and the Wyeth Center. Home to a substantial collection of Wyeth family artworks, the Farnsworth is one of the finest regional art museums in the country, with a spec...
Learn More