Peaks Island Rentals USA Maine Portland Peaks Island

Waterfront Island Getaway w/two cottages perfect for Multiple or Large Families | Cottage in Peaks Island

9.8 (44 Reviews) |   5 Bedrooms  2 Bathrooms  14 Guests  Stay&Play
Peaks Island Cottage | Waterfront Island Getaway w/two cottages perfect for Multiple or Large Families

5 Bedroom Cottage in Peaks Island

Cindy's Place is a hidden gem located on the rocky shoreline of Peaks Island overlooking the Casco Bay and the Portland skyline, House Island, and Fort Gorges. The property is located a quarter mile from the passenger ferry, the Inn on Peaks, the Downfront ice cream shop, and two restaurants. Within a half mile is the Post Office, Hannigan's Market, a third restaurant, and other Island businesses, including outfitters for renting bikes, golf carts, kayaks, and paddleboards. On the property you will find the Main Cottage located 12 feet from the water; the Captain's Quarters, a separate cottage with 2 bedrooms, a large sleeping loft, and a full bathroom and kitchenette; two patios with tables, chairs, and umbrellas overlooking the water; access to the rocky shoreline; and a beautifully landscaped yard. The Main Cottage was fully renovated in 2015 and includes a full kitchen, a full bath upstairs, a main-level half bath, a laundry area, a coffee and wine bar, and an airy open-concept main level. Upstairs are 2 bedrooms, each featuring a queen bed, chest of drawers, and television, and 1 bedroom containing a twin over full bunk bed with storage drawers underneath. Each of the queen bedrooms has access to a large furnished deck overlooking Casco Bay. The Captain's Quarters is an open-concept space with a kitchenette (including a sink, refrigerator, and Keurig coffee machine), a full bath, one queen bedroom, one king bedroom, and a sleeping loft with two queen beds.
The Island offers an array of activities, from walking or jogging the three-mile seashore perimeter to biking, kayaking, paddle boarding and sailing to visiting the historic Fifth Maine Regiment Museum. If your plans include the mainland, the restaurants, shops, tour operators and landmarks of Portland's lively waterfront district are only a 15 minute ferry ride away.
Casco Bay Lines operates passenger and car ferries all day from Monday through Sunday, along with narrated tours of the Bay and it's Islands. Visit for more information on the ferry schedule.
All Cindy's Place rentals include the Captain's Quarters unless otherwise stipulated. The rental price will not be adjusted for groups who choose not to use the Captain's Quarters.

Waterfront Island Getaway w/two cottages perfect for Multiple or Large Families is located in Peaks Island. Waterfront Island Getaway w/two cottages perfect for Multiple or Large Families provides accommodation, featuring Internet, View, Ocean View, among other amenities. This Cottage features Internet, View, Ocean View, to make your stay a comfortable one.

Waterfront Island Getaway w/two cottages perfect for Multiple or Large Families has 5 Bedrooms , 2 Bathrooms, and max occupancy of 14 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated Cottage because of the excellent services rendered by the owner or manager of this Cottage, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. Cottage has a friendly neighborhood, and the Peaks Island has interesting places to visit. If you want to learn more about the Cottage in Peaks Island, such as places to visit and things to do nearby, you can check below to learn more.

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Unique Amenities

  • Air Conditioner
  • Parking
  • TV
  • View
  • Ocean View
  • Balcony/Terrace
  • Oceanfront
  • Security/Safety
  • Sports/Activities
  • Bedding/Linens
  • Wellness Facilities
  • Fireplace/Heating
  • Entertainment
  • Barbecue/Outdoor Cooking
  • Child Friendly
  • Internet
  • Kitchen
  • Laundry
 
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Policies

Event Policy No events allowed
Check-in Check-in time starts at 4:00 pm minimum check-in age: 25
Check-out Check-out before 10:00 am
Child Policy Children are welcome.
Pet Policy Pets not allowed
Smoking Policy Smoking is not permitted
Other Policy Extra-person charges may apply and vary depending on property policy government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property onsite parties or group events are strictly prohibited safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed this property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation
 
Peaks Island, 04108, USA

What Our Guests say 500 + Reviews

Jun 6, 2025 01:31:36 AM
Summary: This property is gorgeous! The location and set up was perfect for our family of 8. Greg the host was welcoming and accommodating, going as far as making recommendations for our stay. We will be visiting the island again!
Kassie S. Kassie S.
Jun 3, 2025 06:12:17 PM
Summary: The house is absolutely beautiful and the location can’t be beat. Perfect place to spend the weekend!
Marlena L. Marlena L.
Sep 10, 2024 02:44:09 AM
Summary: My husband, daughter and her friend, along with my sisters in law and brother in law stayed at Cindy's place for 3 nights. It was more beautiful than the pictures showed and very well appointed with everything you need. We loved the privacy and convenience of the location and also having two houses. My daughter and friend loved the loft and stayed in the Captains quarters with the extended family while my husband and I enjoyed the main house. I slept with the slider and window open to hear the ocean waves and smell the salty air; I slept like a baby. We were able to walk along the beach/rocks and make our way to picnic point to explore that sweet little island too. Greg was easy to communicate with and we hope to get back to Cindy's place again in the coming years. Greg, well done preserving your family's home and thank you for sharing it with us.
Rhonda Y. Rhonda Y.
Sep 3, 2024 05:50:17 AM
Summary: 5-star property with room for 14 adults and children. Right on the water, all amenities, and a 5 minute walk from the Ferry. You cannot do better than to select Cindy's Place for your next family vacation.
John H. John H.
Sep 1, 2024 05:37:50 AM
Summary: What a fantastic property for an extended family, 70yo grands, 2 couples, 7, 8, 9 yo kids. 2 houses made it easy to have get-away space, plus a place to gather and cook together. Beautiful views with constantly changing bay. Kids especially loved exploring the adjacent beach during low tide. Everyone was able to climb down to it. Nice short walk into town. Everyone said they wished we had a second week. Things to know: live, loud, band in town Saturday til 10:30 and Sunday til 8. Not terrible but glad it wasn’t 6 days. After that it was a very quiet and peaceful location. A sloped hill leads from parking lot to main house but there is a little red wagon to load and pull your stuff. The main house was comfortable for 2 couples and one kid. The 3rd bedroom is small and would be tight for a couple. Owner is very responsive with info and addressing issues. We all wished for more time here.
Nancy R. Nancy R.
May 28, 2024 02:04:51 AM
Summary: We celebrated our wedding on Peaks Island Inn and the house was perfectly located for us. We were able to walk into town. Our friends and family could stop by and sit by the water. Could’ve been better!
Brian B. Brian B.
Nov 1, 2023 11:01:05 AM
Summary: We were up for our son's wedding in October at Peaks Island Inn. This was the absolute perfect VRBO rental for the occasion. Plenty of open concept room with beautiful views out over the bay. The outdoor decks are inviting and comfortable, the indoor spaces are warm and open. Distance to the Inn is about 1/4 mile, so an easy walk for those that wish, but there is also plenty of parking at both the inn and the VRBO if needed. Kitchen is well stocked, bathrooms are clean, washer and dryer on premise. We had plenty of wedding guests on the Island, many of whom came over for "day after" wedding brunch. I guess that is when you realize you have the nicest VRBO on the island... because everyone at a different place says so when they visit :) You will not go wrong with this VRBO, and if you are trying to figure which one to rent, this is it. The pictures on line are nice, the actual experience is better. Some VRBO's post nice pictures, and when you get there the unit does not hold up to the online presentation. This is the opposite, even better than you anticipate. Owner is very nice, receptive to all questions, and clearly takes great pride in both the home and your positive experience.
paul m. paul m.
Sep 23, 2023 12:00:10 PM
Summary: This was a great property for our group. The views from the house are stunning and the whole property is very well maintained. We appreciated the comfortable seating in both houses and the beds were also comfortable. The location is easily walkable from the ferry. We had no need for a car while there. A few quirks—none of the bedrooms in the main house have closets or any place for hanging clothes so pack accordingly. Check in/out instructions were a bit more arduous than what is typical, You do have to make the beds when you arrive and they ask that you wash and dry sheets, towels if possible. We did the best we could. Overall a wonderful property.
Liz and Joe G. Liz and Joe G.
Sep 2, 2023 08:51:20 AM
Summary: Everyone loved the location! House was perfect!
Martha C. Martha C.
Sep 27, 2022 11:00:33 AM
Summary: Everything at Cindy’s place was absolutely perfect!
Nancy F. Nancy F.

FAQ's

Is this Peaks Island cottage pet-friendly for guests?

No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Peaks Island cottage have a swimming pool?

No, this Peaks Island cottage does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Peaks Island cottage?

Best-rates for the Peaks Island cottage starts from $894 per night with includes Air Conditioner, Wellness Facilities, Internet, View, Ocean View, Oceanfront, Security/Safety, Sports/Activities, Kitchen, Fireplace/Heating, Barbecue/Outdoor Cooking, Child Friendly, Bedding/Linens, Entertainment, Parking, TV, Balcony/Terrace, Laundry StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

Is Peaks Island cottage a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this cottage Good or guests have recommended them suitable for families. As reported by the owner or manager, the cottage has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Peaks Island cottage wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Peaks Island cottage has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Peaks Island cottage?

Based on the information reported by the owner or manager, the Peaks Island cottage indicates 1 day stay policy at this cottage. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Peaks Island cottage?

Based on the information reported by the owner or manager, details for the cancellation policy for the Peaks Island cottage are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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