Holiday rentals in Waterboro

Luxury Year-round Treehouse with private hot tub

The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

Retro Camper on farm property in Lakes Region, NH

Come experience this beautifully restored 1969 retro camper in a rural wooded setting. Located in the lakes region, it is close to hiking, swimming, apple orchards, as well as popular restaurants. Only 1 hr from Portland and 1.5 hrs from Boston. The camper is on a private and quiet 7-acre farm. Solar powered with backup. The camper has a toilet, very small shower, sink, cooktop, fridge, and small microwave. The camper is very small w a tiny bathroom but cozy and comfortable. LGBTQ+ friendly.

The Cottage at Lake Arrowhead

Welcome to our brand new cottage built in 2024 in the beautiful Lake Arrowhead Community. Lake Arrowhead is one of the largest lakes in Southern Maine, with 14 private beaches and excellent fishing spots for you to enjoy. The cottage is across the street from the water, offering peaceful water views, calming lake breezes and a short 4 min walk to the beach. Enjoy the lake, hiking, fishing, restaurants and craft breweries - everything that the waters and woods of Southern Maine has to offer!

The LOTUS welcomes you, stay a while

The Lotus is your zen home away from home. Enjoy peace and tranquility on your private back deck, the amazing salt water hot tub (exclusively use) new sauna (extra $88 per day) heated outdoor shower, deep bathtub (showering is tricky for people taller then 5'5)with bluetooth speaker.Comfortable king size bed with European bedding will let you get some much needed rest. Enjoy walks on our 12 ac property or any of the lakes near by for any kind of year round outdoor experience. Welcome :)

Guest Suite

Kick back and relax in this calm, stylish space. 5 mins from Little Ossipee Lake. Just 45 min from Portland, ME. 35 from Old Orchard Beach and other beaches. Just 12 mins from renowned Woodland Valley Disc golf course. Also, just over an hour away from the beautiful White Mountains in NH! We are in beautiful rural location. With a scenic drive past lakes and farms. The grocery store is 11 mins away and there is a dollar store conveniently located just 4 minutes away for essentials.

1BR cozy, luxurious getaway @ Krista's Guesthouse

Newly built guesthouse above owner's garage with insane sunrises & great view. Property is located on 36 acres, owner lives on site in a separate house with her 3 dogs, 1 exceptionally lazy cat and 4 rogue chickens (they may all come visit you!). Grounds have ancient apple trees, loads of perennial gardens with more in progress, berries and an organic vegetable garden that we would love to share from if desired. Please do not hesitate to ask any questions! We hope to meet you soon!

Romantic A-Frame cabin in the woods

Modern cabin tucked privately in the forest. Loaded with modern amenities make it perfect for a romantic getaway. Unwind in the hot tub looking up at the sky full of stars. Take a Sauna while being surrounded by nature all around. Relax by the fire pit. Located in the majestic forest of mount agamenticus, the extensive trail system is off our road. Short drive to the Ogunquit/ york beaches, outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

Birch Ledge Guesthouse--Four Season Maine Getaway

Both rustic and elegant, the Birch Ledge Guest House offers a cozy place to relax and recharge, whatever the season. The first floor features a spacious living room (with queen sized pull-out-couch), dining area, and small kitchen. The bathroom has a walk-in shower. The second floor is a loft accessible by a spiral staircase and has a comfy queen and two twin sized beds. The guesthouse is surrounded by quiet forest and is an easy 30 minute drive to Portland.

Maine Guest House

Relax with your spouse and children at this pet and family-friendly home. This restored Old England farmhouse is our "home away from home". We hope you will be at ease in our home that has evidence of our personalized touches. It is a peaceful home nestled in a woodland setting with a rippling stream. Enjoy wandering through the trails in the woods across the bridge over the creek. Song birds and wild life such as wild turkeys sited in the back yard.