House vacation rentals in Chebeague Island

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Top-rated house rentals in Chebeague Island

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Top guest favorite

A bright bedroom features a spacious bed dressed in a floral quilt with decorative pillows. Large windows are adorned with sheer curtains, allowing natural light to fill the room. Two bedside tables with lamps complement the cozy atmosphere.

Home in Portland

4.96 out of 5 average rating, 170 reviews

Quiet Comfy Victorian Escape

Spend your vacation, work-trip, or weekend getaway in this lovely renovated cozy 2 bedroom unit. Apartment 2 is located on the second floor of a three family house where you have access to all the modern appliances: refrigerator, W/D, microwave and TV in the living room. A brand new queen bed each bedroom, with seat in cozy seating in the living room. Located in the very central Oakdale neighborhood, this unit is steps from Deering Park, Sea Dogs stadium, USM Law School and Portland's Old Port.

Guest favorite

The cabin's exterior is captured through a flickering flame, showcasing large glass windows that invite natural light. Surrounded by lush trees, the cozy structure features a modern design, blending seamlessly with the serene outdoors.

Home in Naples

4.99 out of 5 average rating, 122 reviews

LUX Designer Private Waterfront

Waterfront GLASS cabin with privacy professionally designed, escape to somewhere really special. Crooked river acres surrounding the house with the river wrapping around the property. Dock with direct access to Sebago lake and state park just minutes away, Outdoor shower, hot tub, hammocks, BIG walk-in shower w/ window. Heated bath floors, ac. See through Fireplace. The property has its own sandy swimming beach, pets are welcome. Come enjoy privacy and the space to run around seconds to Sebago.

Guest favorite

The welcoming living area includes a wooden dining table adorned with a vibrant flower arrangement. A cozy seating area features a patterned armchair and a large window allowing natural light. Exposed wooden beams enhance the warm character of the space.

Home in Falmouth

4.88 out of 5 average rating, 251 reviews

Amazing Bay View Home with Hot Tub

This enchanting 2-bedroom home is a coastal dream come true! Luxurious and well-appointed, Casco Bay House sleeps up to six, provides a five-star stay, offers all of the comforts of home AND a relaxing hot tub spa. With stunning views of the water, the house also has easy access to dining, shopping, and sightseeing in Portland's lively Old Port district (just 5 minutes away). Whether you seek quiet tranquility or want to hit the town, this waterside house is the perfect home away from home!

Top guest favorite

A modern beach house is positioned along a serene shoreline, featuring large windows that reflect the colorful sunset. The exterior showcases a blend of natural materials and white accents, with a deck that offers expansive ocean views. Rocky shores frame the property, enhancing the coastal setting.

Home in Saco

5 out of 5 average rating, 175 reviews

Oceanfront w/ Stunning views and Private Deck☀️🏖

Welcome to the Beach House on the Rocks, your very own oceanfront retreat! This beautiful, 1350 sq ft house is nestled right next to the ocean. With panoramic views and the ocean just steps away, you won’t forget this one of a kind experience. Tucked away in the hidden gem of Camp Ellis, you’ll enjoy a lively beach scene in the summer and a tranquil retreat in the off season. Just a short trip away to Old Orchard Beach and 30 min to Portland you’ll never be in need of fun activities.

Superhost

Four wooden lounge chairs are arranged around a small table on a grassy lawn, overlooking a rocky shoreline. The calm ocean stretches into the distance, framed by a clear sky with soft clouds.

Home in Harpswell

4.94 out of 5 average rating, 120 reviews

Brand new Scandinavian cottage: dock & kayaks!

Brand new architectural cottage and detached 'boathouse' with sweeping elevated ocean views both east and west, private waterfront lawns and deep water dock with kayaks. This property was built in 2020 so expect a fresh and clean experience on one of Harpswell's most private peninsulas. Watch the sunrise from the cantilevered 2nd floor deck, sit by the campfire on your private lawn oceanside, or walk down to the dock for a paddle in the west facing protected cove. The best of coastal Maine!

Superhost

An aerial view captures a serene point surrounded by calm water, with lush green trees lining the rocky shore. The rocky outcrop extends into the water, providing direct access to the tidal area. The tranquil setting highlights the natural beauty of the landscape.

Home in Harpswell

4.89 out of 5 average rating, 114 reviews

Rising Tide Times - quintessential Maine cottage

Out of State guests please read the Maine State COVID-19 restrictions currently in affect. Classic Maine cottage on the end of a point, surrounded by water on 3 sides provides stunning views. The perfect backdrop for the quintessential cottage vacation. Features spacious decks, direct tidal access for kayaking, and outdoor firepit. 15 min to downtown Brunswick/45 min to Portland. We even have Kayaks onsite for guests to paddle around Cards Cove. Perfect for couples and families!

Guest favorite

A rustic cottage with dark wood siding is surrounded by greenery. Two adirondack chairs are positioned on the grassy lawn in front of the house, which features large windows and a spacious deck. Trees provide shade on a bright, sunny day.

Home in Yarmouth

4.81 out of 5 average rating, 136 reviews

Kelley's Ocean View Cottage

PLEASE READ CAREFULLY!! Rustic Quaint cottage that's been in my family since 1893.Bathroom pre dates indoor plumbing. The Bathroom is very tight and small, not the best for larger folks...This is not a 5 star resort! if that is your thing this is not for you! History and Nature it is! Ocean views on a mile around Island with spectacular night views of Portland and the stars with no light pollution and preserve is right down the street. 20 min to Freeport 20 min to Portland

Top guest favorite

The Birch Ledge Guest House is a two-story structure nestled among trees, featuring a rustic exterior with a metal roof. A small patio with two chairs is positioned at the entrance, and a staircase leads to the loft area. Lush greenery surrounds the home.

Home in Hollis

4.99 out of 5 average rating, 422 reviews

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.

Superhost

A sunlit sunroom features three woven chairs adorned with soft cushions in varying shades of blue. A low wooden table with a vintage checkers board is situated in the center. Sheer white curtains gently drape around the windows, allowing natural light to enter.

Home in Falmouth

4.86 out of 5 average rating, 177 reviews

Beautiful +Nostalgic + Coastal Maine Cottage

Conveniently located 15 minutes from Portland Jetport and 10 minutes from Old Port in downtown Portland, this newly renovated, charming, and sunny historic home is perfect for your Maine getaway. It is a fantastic home-base for exploring Southern and Midcoastal Maine while enjoying close proximity to Portland's award-winning restaurants and attractions as well as beautiful beaches, islands, museums, lighthouses, and much more.

Guest favorite

A private balcony offers views of tranquil waters and nearby trees. A white chair is positioned against the railing, inviting relaxation while taking in the natural scenery. The landscape includes subtle reflections on the water's surface, enhancing the coastal surroundings.

Home in Yarmouth

4.95 out of 5 average rating, 119 reviews

Stone Isle. 8 acres next 2 little john preserve.

Nestled on 8 acres overlooking Casco Bay, the Stone Isle guest house has 2 bedrooms, 1 bathroom and amazing water views. The guest house includes an open plan layout with a full kitchen, living room (with sleeper sofa) and a dining table for 4. Last but not least the guest house is a 5-minute walk from a 23-acre preserve that has numerous scenic viewpoints, tide pools and ledges, and picnic tables. Coastal Maine at its best!

Top guest favorite

A well-maintained cottage is positioned beside a tranquil body of water, surrounded by lush greenery. A spacious lawn is visible in the foreground, showcasing an outdoor seating area with a patio umbrella. The scenic view of the water complements the serene setting.

Home in Harpswell

4.98 out of 5 average rating, 200 reviews

Waterfront Cottage On Basin Cove - Amazing Sunsets

Bright, airy cottage right on Basin Cove,a tidal cove in Harpswell Maine. Cool breezes with pristine views, especially for the sunsets over the cove. At the end of Harpswell Neck, so it feels like you're far away, but still only an hour from Portland, 1/2 hour from Freeport & 15 minutes from Brunswick. Use it as your hub to explore Midcoast Maine or hunker down and enjoy the screened in porch after a swim in the cove.

Guest favorite

A bright living space features large windows that invite natural light. A light-colored sofa is positioned next to a minimalist table. An open kitchen with modern seating is visible, with light wood accents and a clean design on display.

Home in Freeport

4.95 out of 5 average rating, 148 reviews

Spacious costal home in Freeport, ME

Come enjoy Freeport, Maine in this beautiful home. One mile from the downtown shopping district and the L.L. Bean flagship store. This two family home is being rented as a single family home, giving you the benefit of two kitchens and two living rooms. Perfect for families and groups of friends. The two sides are connected via a door similar to adjoining hotel rooms.