
House vacation rentals in Chebeague Island
Find and book unique houses on Airbnb
Quick stats about house rentals in Chebeague Island

Total vacation rentals
Explore 120 vacation rentals in Chebeague Island

Nightly prices starting at
Chebeague Island vacation rentals start at G$12,551 GYD per night before taxes and fees

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

Family-friendly vacation rentals
100 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
120 of Chebeague Island vacation 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.

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.

Cozy Maine Cottage • Near Jetport & Coast
Cozy Cottage Retreat w/ Loft near Portland Welcome to your Maine escape. Reno barn offers a warm, cottage-inspired atmosphere with character, an open loft, and inviting spaces for rest and connection. Located mins from the airport and within walking distance to Allagash Brewing Company and other local favorites. A quick drive to downtown Portland, beaches, lighthouses, and live music. End your evenings on the private back deck — wine in hand, stars overhead, and nothing but quiet around you.

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.

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.

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.

Waterfront 5BR Home on Casco Bay in Freeport
Spacious waterfront 5BR coastal retreat on Harraseeket Cove and South Freeport Harbor, perfect for kayaking, wildlife, and relaxing coastal Maine getaways. Set on 3.5 private wooded acres, the home features fast WiFi, smart TVs, outdoor dining, grills, firepit, kayaks, and peaceful water views throughout the property. Enjoy the tranquility of Maine’s coast while being only 3 minutes from Freeport’s shops, restaurants, breweries, and LLBean, with Wolfe’s Neck Woods State Park nearby.

Mary J. Eastburn House-Eastburn Suite
City of Portland Reg. No. : STHR-002888-2021 Perched on a quiet street corner on Portland's Western Promenade, this historic residence enjoys what Longfellow called the "rarefied air of this little town by the sea," spectacular sunsets, and commanding views of the White Mountains. Built in 1891, the Mary J. Eastburn House now offers 3 private and exclusive guest suites for those who enjoy the grandeur of the past, updated with the luxuries and technology of the present.

The Barnhouse with hot tub
Get away with your whole family at this peaceful home in the country. Hear the frogs chirping in the pond, birds tweeting in the treetops and watch chickens roam around. Enjoy the clear, starry nights while relaxing in the hot tub or cozying up by the fire. Centrally located between coast and mountains. Head a hour north to take the family hiking or on the slopes to enjoy the mountains. Head 40 minutes south to take in the coast and see the iconic Maine lighthouse.

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!
Popular amenities for Chebeague Island house rentals
House rentals with a pool

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

OOB Oasis: 6BR Home w/ Private Pool Near Beach

Large private area, close to Rockland

Faith Lane with community pool

There's No Place Like Home

Beach House w/ Pool · Fire Pit · Dual Kitchens

Moose Pond Mountain Escape

Cottage on 50 Acres | Lakeside + Pool + Hot Tub
Weekly house rentals

Perched atop the Coast of the Atlantic Ocean

Oceanfront Escape • Walk to Beach • Sleeps 14

Rustic charm close to Portland

The Modern Lakehouse

Amazing Bay View Home with Hot Tub

Mermaid's Chair | Private Beach | Hot Tub

The Beach Pea - Waterfront cottage, Pet Friendly!

Cozy Lakefront Cabin-Private Dock-Kayaks-Firepit
Private house rentals

Oceanfront Cottage w/ Wharf & Kayaks – Harpswell

Island home w/fireplace, balcony, and water access

Sunset Stunner w/summer dock

Water views, privacy, decks, minutes to Portland

Stunning Views from Spacious Oceanfront Home

Mainelandia! Stunning New Waterfront Home!

Maine Vacation Home on the Water

Maine Coastal Retreat
When is the best time to visit Chebeague Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$66,936 GYD | G$57,314 GYD | G$52,085 GYD | G$58,151 GYD | G$58,569 GYD | G$72,166 GYD | G$82,415 GYD | G$82,625 GYD | G$73,002 GYD | G$58,569 GYD | G$58,988 GYD | G$70,283 GYD |
| 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 |
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- Rentals with a fire pit Chebeague Island
- Family-friendly rentals Chebeague Island
- Rentals with a fireplace Chebeague Island
- Rentals with outdoor seating Chebeague Island
- Beachfront rentals Chebeague Island
- Waterfront rentals Chebeague Island
- Rentals with beach access Chebeague Island
- Rentals with a washer and dryer Chebeague Island
- Cottage rentals Chebeague Island
- Rentals with a patio Chebeague Island
- Pet-friendly 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





