Holiday houses in Waterboro

Cozy Log Cabin

Experience the ultimate getaway in this enchanting 3-bedroom log cabin with direct lake access! Nestled in a tranquil setting, this cozy retreat boasts a warm living area with a 3 season porch and large windows showcasing stunning lake views. The fully equipped kitchen is perfect for family meals, while the expansive grounds invites you to unwind outdoors. Enjoy swimming, fishing, or kayaking right at the dock. Ideal for families and friends, this cabin promises unforgettable moments in paradise

Location · Family · Comfort

Mountain View Getaway 4Season Maine

Hello there, single traveler! If you are looking for a peaceful place to stay, you are at the right spot. This entire apartment is located on the second floor of the house. The place is situated at the highest point of Ossipee Hill Road, overlooking a grassy field with mountain views and sunsets. It is minutes from Lake Side Market and Ossipee Lake, as well as local restaurants and bars. It’s 6 minutes from Hannaford Supermarket and Pharmacy, and 44 minutes from Portland and other Maine beaches.

Value · Location · Accuracy

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.

Family · Location · Quiet

Charming Limerick Lake House

Direct access to Pickerel Pond! Private beach front and dock! Escape to the peace and beauty of Limerick with this serene lakefront house — perfect for a relaxing weekend, a family vacation, or a remote work retreat. This charming lake house offers stunning views, direct access to the water, and all the comforts of home. Enjoy mornings on the private deck with coffee in hand, afternoons kayaking or swimming in the clear lake, and evenings around the fire pit under the stars. No smoking inside.

Family · Value · Laundry

Glass Wall Waterfront Hot Tub Fireplace Tiny Home

Wake up to rushing waterfalls right outside your glass wall in this romantic waterfront tiny home in Norway, Maine! Private hot tub with river views, see-through gas fireplace, cozy raised queen bed overlooking the water, outdoor shower, hammocks, and direct access to hiking trails. Total privacy—no neighbors in sight. Modern kitchen, heated floors, fast WiFi, and thoughtful touches for couples or solo escapes. Romantic getaway near Sunday River skiing, golf & Maine adventures. Nature's oasis

Location · Family · Check-in

Enchanting Artist Retreat

Enjoy this enchanting cottage set in nature. Only 35 minutes from Portland & close to hiking trails. Listen to the owls & wind while enjoying a fire in the pit. Fresh muffins in the morning, baked by Barb. We offer a queen-sized Tempur-Pedic bed with comfy cotton bedding. Air conditioner for hot days and a NEW gas stove for chilly nights. Our Bathroom Greenhouse has a shower & a green Compostable toilet. ( changed daily) We provide bathrobes, hand soap, body wash, shampoo & conditioner.

Location · Value · Nearby

The Getaway at Lake Arrowhead

The Getaway is a new space, completed in 2025 over our garage with its own entrance and private deck. Located on a quiet cove on Lake Arrowhead, you can enjoy your morning coffee or an afternoon glass of wine on your deck or the deck on the water’s edge. Enjoy fishing, kayaking, walking or a morning run. Shopping at the outlets in either North Conway or Freeport is about an hour away. There are several restaurants nearby and Portland is about an hour away. Getaway and relax on the lake.

Location · Condition · Sleep quality

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!

Value · Family · Bathroom

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.

Value · Family · Decor

The Fish Bowl-Waterfront Tiny House

Escape to a one-of-a-kind lakefront tiny house on a 5-acre peninsula on beautiful Sokokis Lake. This waterfront getaway offers lake views, direct shoreline access and a dome skylight in Maine. * 5 acre peninsula on Sokokis Lake * Shared dock & swim raft & dockside seating * Kayaks & canoes * Fire pit * BBQ grill * Full bathroom * Kitchen * Eating area * Sleeping loft w/memory foam queen mattress * U-shaped couch folds into large bed * A/C * Free parking

Family · Location · Hiking

Waterfront, Wood stove & Private beach, Solo Stove

Welcome to the Luna Lake House, your very own lakefront retreat! Just 2 hrs from Boston and 1 hour from Portland, this is the perfect getaway. You get the entire house to yourself! This 1,810 sq ft house has 100 ft of private waterfront, a wood burning stove, private dock (June-October) and outdoor bonfire pit for your enjoyment. With incredible sunset views and it’s amazing location, you will make lasting memories in this one of a kind experience.

Location · Family · Outdoor spaces

Romantic Mirror cabin in the woods

Stay at Hidden Pines Cabins. The Mirror cabin is Maines only 3 sided floor to ceiling mirrored glass cabin. Unwind in the hot tub while looking up at the sky full of stars. Take a sauna while surrounded by nature all around. Located in the majestic forest of mount Agamenticus, the extensive trail system is off of our road. Short drive to the Ogunquit/York beaches, Outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

Location · Value · Indoor spaces