
House holiday rentals in Chebeague Island
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Quick stats about house rentals in Chebeague Island

Total holiday rentals
Explore 120 holiday rentals in Chebeague Island

Nightly prices starting at
Chebeague Island holiday rentals start at $103 NZD per night before taxes and fees

Verified guest reviews
Over 2,320 verified reviews to help you choose

Family-friendly holiday rentals
100 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
120 of Chebeague Island holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chebeague Island rentals

4.9 Average rating
Chebeague Island stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated house rentals in Chebeague Island
Guests agree: These houses are highly rated for location, cleanliness and more.

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
You will be close to everything when you stay at this centrally-located place with a pool and spacious yard! Enjoy the home and it is a quick 10 minute uber to downtown Portland to the most popular shops and restaurants. This home is located perfectly to explore greater Portland from beautiful parks/trials to the shopping outlets not far away. This is a family neighborhood and out of respect for my neighbor’s, quiet hours after 10 pm. No parties. City of Portland License #: STHR-004465-2022

Large Historic 7 Bedroom home with Pool & Hot Tub
Very Unique, large historial home in beautiful Falmouth, Maine. Originally built in 1725, this nearly Three-Hundred-Year old Federal-style farmhouse still retains some original features. In the early 1900's, this home served as a bootleg hard cider mill, and more recently, an oriental rug business. Great place for families with kids to stay while enjoying coastal Maine and Portland. Less than a mile from Portland and 4 miles from the historic Old Port district. (Hot tub open year-round)!

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.

The Outlet Studio, Rustic Comfort w Fireplace
Conveniently and perfectly located! Our studio is in a private building on a quiet dead end street yet walking distance to L.L. Bean, Bow Street Market, Leon Gorman Park, restaurants, breweries, live music, outlet shops, Freeport Farmers Market, the Amtrak station and all that downtown Freeport has to offer. A short drive to Wolfe's Neck State Park, Bradbury Mountain State Park, Mast Landing Audubon Sanctuary, the Desert of Maine, Winslow Park, farm stands and the beautiful mid-coast coast.

The Modern Lakehouse
This modern lakehouse is situated on Hogan Pond in Oxford Maine. Here you can stay with all the comforts of a beautiful lakehouse built in 2020 while being feet from the water. This is a great place to vacation whether you prefer the private sandy beach, the A/C inside complete with Smart TV cable and Wifi, or the hottub! Sip a drink at the bar while watching the game or use the grill on the deck but be sure to use the built in sound system to play your music throughout the house and deck.

LUX Designer Private Waterfront Hot Tub - Secluded
Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

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.

Wren Cabin + Wood fired Sauna
We built the Wren Cabin to be a serene space filled with light and art and with lots of cozy details. Lofted ceilings, a spiral staircase and large open concept with lofted bedroom. The cabin also has a gorgeous wood-fired sauna for those colder days. Wren cabin has a large wraparound deck for relaxing and an outdoor fire pit, as well as shared access to Adams Pond. The space is modern Scandinavian, light and aery, and filled with thoughtful details.

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.

Private Oceanfront Home 🔆2 min to Popham ✔️Hot Tub
Experience authentic Midcoast Maine at this private and secluded waterfront home on Atkins Bay with unobstructed views of Popham Beach State Park’s unique flood plains, rocky coast, and 12-foot tides. The house is a recently renovated 3-bed, 2-bath with a large open living space, wrap-around screened porch, hot tub, and seating area overlooking Atkins Bay. Located two minutes driving from Popham Beach, Maine’s most beautiful beach!

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!

Beautiful Designer's Hideaway on the Maine coast!
Welcome to our chic & cozy rental cottage located in Harpswell, Maine, a tranquil coastal town known for its picturesque harbors, pristine beaches, and rich maritime history. Our charming cottage is the perfect retreat for families, couples, or anyone seeking a peaceful getaway amidst the beauty of nature. You won't find anything like it on the Maine Coast! Wake up to seals, geese, eagles and more right outside your window.
Popular amenities for Chebeague Island house rentals
House rentals with a pool

Faith Lane with community pool

Bubbles & Pines - Pool, HotTub, Lg Deck, ME Coast

The Lodge at Hidden Pines

Cottage on 50 Acres | Lakeside + Pool + Hot Tub

Unique Church Stay • Sebago Lake • Pool • Fire Pit

Spacious 5BR Cottage w/Pool, Water & Resort Access

There's No Place Like Home

The Hurkle Durkle House
Weekly house rentals

On Tondreau's Point of Quahog Bay.

Oceanfront Cottage w/ Wharf & Kayaks – Harpswell

Whole house on a great island in Casco Bay!

Water views, privacy, decks, minutes to Portland

The Beach Pea - Waterfront cottage, Pet Friendly!

Five Islands Waterfront Retreat

Cozy Lakefront Cabin-Private Dock-Kayaks-Firepit

Tide & Timber - Surf Cottage
Private house rentals

Waterfront Cottage in Freeport

Maine Vacation Home on the Water

Maine Coastal Retreat

Classic NewEngland Waterfront

Sunset Stunner w/summer dock

Mainelandia! Stunning New Waterfront Home!

Island home w/fireplace, balcony, and water access

Stunning Views from Spacious Oceanfront Home
When is the best time to visit Chebeague Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $549 NZD | $470 NZD | $427 NZD | $477 NZD | $481 NZD | $592 NZD | $676 NZD | $678 NZD | $599 NZD | $481 NZD | $484 NZD | $577 NZD |
| Avg. temp | -4°C | -3°C | 1°C | 7°C | 13°C | 18°C | 21°C | 21°C | 16°C | 10°C | 4°C | -1°C |
Destinations to explore
- New York City Holiday rentals
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- Portland Holiday rentals
- Mont-Tremblant Holiday rentals
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- York County Holiday rentals
- Cambridge Holiday rentals
- Rentals with beach access Chebeague Island
- Rentals with a washing machine and dryer Chebeague Island
- Waterfront rentals Chebeague Island
- Beachfront rentals Chebeague Island
- Rentals with outdoor seating Chebeague Island
- Rentals with a fire pit Chebeague Island
- Family-friendly rentals Chebeague Island
- Rentals with a patio Chebeague Island
- Pet-friendly rentals Chebeague Island
- Rentals with a fireplace Chebeague Island
- Cottage rentals Chebeague Island
- House rentals Cumberland County
- House rentals Maine
- House rentals United States
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Long Sands Beach
- Popham Beach, Phippsburg
- Willard Beach
- York Harbor Beach
- Short Sands Beach
- Scarborough Beach
- Pemaquid Beach
- Footbridge Beach
- Cape Neddick Beach
- Pemaquid Point Lighthouse
- East End Beach
- Gooch's Beach
- Coastal Maine Botanical Gardens
- King Pine Ski Area
- Popham Beach State Park
- Hills Beach
- Wolfe's Neck Woods State Park
- Crescent Beach State Park
- Pleasant Mountain Ski Area
- Fortunes Rocks Beach
- Funtown Splashtown USA





