
Vacation rentals with outdoor seating in Chebeague Island
Find and book unique outdoor seating rentals on Airbnb
Quick stats about vacation rentals with outdoor seating in Chebeague Island

Total vacation rentals
Explore 110 vacation rentals in Chebeague Island

Nightly prices starting at
Chebeague Island vacation rentals start at G$10,458 GYD per night before taxes and fees

Verified guest reviews
Over 3,410 verified reviews to help you choose

Family-friendly vacation rentals
90 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
110 of Chebeague Island vacation rentals include wi-fi access

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

4.8 Average rating
Chebeague Island stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated outdoor seating rentals in Chebeague Island
Guests agree: these outdoor seating rentals 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

Luxury Year-round Hobbit House w/ private hot tub
Fern Hollow 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.

Portland + Cape Elizabeth + Beaches + luxurious!
Permit210780 •Luxurious 3 rm apt with 1322 5* reviews! Only a mi to the beach & 4.4 mi to Portlnd - Location! •1st flr Great Rm to dine & relax: microwave, fridge, toaster, Keurig, TV, cooktop •2nd flr huge bathrm & bedrm for 2 w/ another sitting rm + a 2nd bdrm w/ 1 Q & 2 twins •More than 2 people? Alter reservation #’s for additional cost •2 people wanting 2 bedrms? Only add a $50 cleaning fee for 2nd bdrm •luxurious furnishings & superior bedding! •I am known for thinking of EvErYtHiNg ;-l

Yurt on Chebeague Island
Imagine staying in a yurt in the woods of Chebeague Island, nestled in a private clearing in the woods. Explore island beaches and hidden trails. This yurt is “glampy” inside with leather chairs and a substantial log bed. The yurt has a rusticator kitchen with all of the basics for cooking: fridge, stovetop, sink, water, firepit & firewood. Outdoor shower. WiFi . Cozy heater for cool spring nights. Ferry options on Casco Bay Lines or CTC Ferry. Host provides transport to/from ferry to the yurt.

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.

Sauna+Near Beach+Pond+Outdoor Shower+Fire Pit
Relax at your own private forest retreat! * Private Cedar Glass Sauna * Minutes Reid State Park Beach & 5 Island🦞 * Private Outdoor Shower * Private Fire Pit w/S'mores * 100% Cotton sheets/towels * Rain Shower & Heated Bathroom Floor * AC/Heat * SmartTV & Record Player w/Vinyl * Fast Broadband Wifi *Pine Cabin is one of two cabins on 8 acres right down the road from one of the best beaches in Maine! The cabins are 150ft. apart and separated by a privacy screen and natural landscaping.

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!

BREEZE, in a tree The Appleton Retreat
BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE does not have a hot tub but guests may reserve the sauna, which is close by and private. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

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.

Beach, Parks, Trails, Tranquil, Quiet, Peaceful
The Kettle Cove neighborhood is beautiful, relaxing, safe, quiet. Kettle Cove and Crescent beaches are a stroll away. We live in a 200 year-old farmhouse, and we love to host guests at our guesthouse, which is separate and private. The wide lawn, fire-pit, and BBQ are open for our guests. We are quiet, friendly, inviting, and respectful of our guests' space and privacy. ***WEKND STAY REQUIRED FRIDAY/SATURDAY/SUNDAY NIGHTS***
Popular amenities for Chebeague Island outdoor seating rentals
House rentals with outdoor seating

Seacoast Escape with a View

Stone Isle. 8 acres next 2 little john preserve.

Close to Breweries, Outlets, and Portland Food!

Historic, pastoral home in charming Yarmouth, ME!

LUX Designer Private Waterfront Hot Tub - Secluded

Renovated home with amazing waterfront views

Modern & Sunny East End House. Private Parking!

Higgins Beach *New* Beach Home & Private Offices
Apartment rentals with outdoor seating

Cape Elizabeth Garden Apt+Beach+Close to Portland!

25 Middle: Two floor loft w. water view -sleeps 5

Welcome to our BoHo Treehouse! Beaches/Portland

Chic 1-Bedroom at the Heart of Boothbay Harbor

Crescent Beach Gardens

Beekeeper's Cottage- Peaceful,Quiet - Ocean Front

Thompson's Point Studio

Falmouth Waterfront Carriage House Apt
Condo rentals with outdoor seating

Beach Breeze

Charming, newly remodeled space atop Munjoy Hill.

Modern Industrial Beach Cottage

Cozy condo with North Conway at your finger tips!

Penthouse, Walk To The Old Port & The Beach!

Cozy condo by the beach!

Top Of The Line Stay!

Attractive 1 bedroom cabin only 50 ft from beach#1
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$50,407 GYD | G$50,407 GYD | G$41,832 GYD | G$37,230 GYD | G$52,917 GYD | G$56,473 GYD | G$63,793 GYD | G$60,447 GYD | G$56,473 GYD | G$51,035 GYD | G$48,106 GYD | G$54,172 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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- House rentals Chebeague Island
- Rentals with a fire pit Chebeague Island
- Rentals with a fireplace Chebeague Island
- Cottage rentals Chebeague Island
- Rentals with beach access Chebeague Island
- Rentals with a washer and dryer Chebeague Island
- Rentals with a patio Chebeague Island
- Pet-friendly rentals Chebeague Island
- Family-friendly rentals Chebeague Island
- Waterfront rentals Chebeague Island
- Beachfront rentals Chebeague Island
- Rentals with outdoor seating Cumberland County
- Rentals with outdoor seating Maine
- Rentals with outdoor seating United States
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Long Sands Beach
- Popham Beach, Phippsburg
- York Harbor Beach
- Willard Beach
- Short Sands Beach
- Scarborough Beach
- Pemaquid Beach
- East End Beach
- Pemaquid Point Lighthouse
- Footbridge Beach
- Popham Beach State Park
- Cape Neddick Beach
- Coastal Maine Botanical Gardens
- Gooch's Beach
- King Pine Ski Area
- Hills Beach
- Crescent Beach State Park
- Wolfe's Neck Woods State Park
- Pleasant Mountain Ski Area
- Fortunes Rocks Beach
- Funtown Splashtown USA





