
Holiday houses in Casco Bay
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Top-rated holiday rentals in Casco Bay
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Moss House: A Modern Waterfront Cabin in the Woods
Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

Lobstermen's ocean-front cottage
Be our guests & experience the life & beauty of Midcoast Maine. Relax & enjoy the views, warm up in the sauna or go for a refreshing dip. The cottage is part of an over 100 year old working lobstering, and now oyster farming property we call, Gurnet Village. Located right on historic Route 24, we are conveniently situated between Brunswick & the islands of Harpswell. All rooms have ocean views. The tidal beach & the floating dock (May-Dec) is ideal for seasonal fishing, lounging & swimming.

Dreamy Post&Beam Hideaway Near Portland & Freeport
Escape to a dreamy timber-frame cottage tucked in Maine’s woods! Soaring beams, radiant-heated floors, a king loft bed, and a crackling fire pit await. Sip coffee on one of the two decks, hike Bradbury Mountain (3 minutes away), shop Freeport (10 minutes away), or dine in Portland (20 minutes away)—then return to your cozy hideaway under the stars. Full kitchen, vaulted ceilings, radiant heat floors, private driveway, fire pit and peaceful forest views make it the perfect year-round retreat.

Higgins Beach *New* Beach Home & Private Offices
Custom designed contemporary at the beach. Perfect for a relaxing getaway, visiting family and friends or working remotely. Chef's kitchen w/ high end appliances, granite countertops, enclosed porch grill area. 3 bedrooms and 2 private offices Huge windows and amazing views from all of the rooms highlight the natural beauty of high tides, sun rises and sun sets. Wonderful beachfront walks and beautiful surroundings inside and out. Easy proximity to Portland's Old Port.

Cozy log cabin on private pond, near Reid St Park!
Winter or summer, the Little River Retreat will help you step away from the world - but still be minutes from Reid State Park, Five Islands Lobster, the Georgetown General Store, and the rugged beauty of Midcoast Maine. This is our family camp, with our own books, games, and “vibe”. It is not a hotel, and some things may not be “industry standard”. We love the unique charm of this space and place, and many repeat guests do too. We hope you will treasure (and care for it) as we do!

The Maine Frame | Modern A-Frame Cabin in Freeport
• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

Classic Maine Cottage - dock, sauna & kayaks
The Perfect Maine Cottage! On the edge of the ocean, carefully preserved with traditional details. Charming, open floor plan, with a wall of windows to the ocean. Sunny large wrap-around deck and screen porch creates beautiful outside spaces to enjoy. Perfect for listening to waves and watch lobstermen pull up their traps. Cathedral ceilings and Scandinavian design gives the cottage an exclusive feeling. Gentle stairs lead to the private deep water dock for all kinds of boating.

Peaks Island Master Bedroom Suite
Enjoy your stay at this conveniently located, light-filled, modern, chic living space--only a 4-minute walk from ferry, great sunsets, close to market and restaurants with a private entrance and deck. Walking distance to the best island beaches. Located on a quiet, dead end road off the main street. The space is found at the rear of one of Peaks Island's most beautiful, original Cape homes. Guests can enjoy a comfy queen size bed, organic cotton sheets, and a pull-out sofa bed.

Modern Treehouse with hottub + Water Views
Experience the airiness of life up among the pines. This unique tree dwelling, with its own private attached wood-fired cedar hot tub, is perched atop a 21-acre wooded hillside sloping to beautiful water views. Enjoy the view from the wood-fired cedar hot-tub or the king size bed--through a wall of windows. This treehouse is cozy all year round, especially in winter. Located in a classic coastal Maine village with Reid State Park's beaches and the famed Five Islands Lobster Co.

Cape Elizabeth Garden Apt+Beach+Close to Portland!
Bright, airy, two-story, 1000 sf apartment, with view of gardens. Off-street parking and private entrance. First floor living area with kitchenette, and sofa-bed, for additional guests. Second floor king bedroom with full bath. Ideally located a short walk to Kettle Cove Beach, and just minutes from Two Lights State Park, Crescent Beach, Higgins Beach and Robinson Woods Trail. Portland - voted the best restaurant city in the US - is a 10 minute drive. STR Permit #210701.

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.

Gorgeous Studio 2 Blocks from Eastern Prom!
Located in Portland's trendy East End and within walking distance to the Old Port and Downtown, this beautiful studio is only 2 blocks from the Eastern Promenade and Casco Bay! You will have the Unit entirely to yourself with its own entrance, air conditioning, kitchenette, queen sized bed and an additional pull out single. Easily walk to all of the cool breweries, great restaurants, coffee shops, and night life! Welcome to Portland!
Popular amenities for Casco Bay holiday rentals
Other great holiday rentals in Casco Bay

Ocean Paradise Sunrise/Sunset Peaks Portland

Modern Brunswick Tiny Home near Bowdoin & Downtown

Private Guesthouse in the Woods

Oceanside Modern Victorian 2BR- East End/ Downtown

Historic Schoolhouse c1866 / Sauna + Hot Tub + Gym

Cozy Cottage-Near Harbor & Park

Cottage Under a Crabapple Tree

"Periwinkle" ~ a Charming Oceanfront Cottage
Destinations to explore
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- Waterfront rentals Casco Bay
- Family-friendly rentals Casco Bay
- Pet-friendly rentals Casco Bay
- Rentals with a patio Casco Bay
- Beachfront rentals Casco Bay
- Rentals with outdoor seating Casco Bay
- Condo rentals Casco Bay
- Rentals with beach access Casco Bay
- Rentals with a fire pit Casco Bay
- Cottage rentals Casco Bay
- Rentals with a fireplace Casco Bay
- Rentals with a washing machine and dryer Casco Bay
- House rentals Casco Bay
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Scarborough Beach
- Long Sands Beach
- Popham Beach, Phippsburg
- Popham Beach State Park
- Pemaquid Beach
- Willard Beach
- East End Beach
- Short Sands Beach
- Pemaquid Point Lighthouse
- Gooch's Beach
- Cape Neddick Beach
- Funtown Splashtown USA
- Coastal Maine Botanical Gardens
- Crescent Beach State Park
- Wolfe's Neck Woods State Park
- Palace Playland
- Footbridge Beach
- Pleasant Mountain Ski Area
- Maine Maritime Museum
- Ogunquit Playhouse
- Bradbury Mountain State Park




