Verified Review icon check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit Default Owner Icon heart-filled Family icon
Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Sunny Hilltop House next to Tennis, Golf and Beaches on Chebeague Island

Bedrooms 3
Half Baths1
Space 1,800 sq. ft.
Property type house
Minimum Stay 2 - 6 nights


About the property

3 bedroom home with bunk house, 1-1/2 baths plus outdoor shower, sleeps 6-8

The Island House is located on Chebeague Island, the largest island in Casco Bay. There is convenient ferry service out of both Yarmouth and Portland, Maine. The Island House, built in the 1890s, is a sunny, light-filled home situated on a private 1-1/2 acre hilltop lot, with broad views of the tennis courts, the Great Chebeague Golf Club and distant views of Casco Bay. The house is conveniently located within walking distance to the ferry, Hamilton beach, the Chebeague Inn, library, island grocery, bakery, restaurants, museum, with golf and tennis located right across the street.

The main house has 3 bedrooms upstairs that will comfortably sleep 6 people (one king bed, one queen bed, one twin over full bunk bed). There is a 1/2 bath upstairs, a full bath downstairs and a lovely, private outdoor shower behind the bunkhouse. The detached bunkhouse has two daybeds that can accommodate 2 people. There is no bathroom in the bunkhouse. The main house has an eat-in kitchen (seats 4), dining room (seats 8), living room, great room, enclosed sun porch, front porch and stone patio area. There is a large lawn with a picnic table for outside dining.

Enjoy your morning coffee on the front porch before playing tennis and/or golf, walking to the beach, exploring the island on bikes, or simply relaxing with a good book.

The Islander Ferry (through the Chebeague Transportation Company) makes frequent trips to and from Yarmouth and the Casco Bay Lines ferry travels to Portland and the surrounding islands, perfect for exploring Casco Bay and for fine dining and shopping in Portland's Old Port. Groceries can be ordered by calling or emailing area markets, including Whole Foods and Rosemont Market, to be delivered to the island weekdays via the Casco Bay Lines ferry. Fresh seafood is also available daily right on the island.

More Details

Property Manager
Member since: 2014
Speaks: english
Response time:
Within a few days
Response rate:
Calendar last updated:
February 12, 2018

About Owner

We live on the mainland in Yarmouth.

Why Owner chose Chebeague Island

If you are looking for an authentic Maine coast vacation, close to the Portland area, this is it! Chebeague is charming, unpretentious, and beautiful. It is a fun, safe place for kids to explore. Look for the many "Right of Way to Shore" signs as you explore the island and you will be rewarded with quintessential Maine sandy beaches and rocky outcrops for a private picnic, swimming or relaxing on the beach. Step back in time and truly disconnect, slow your pace and enjoy the island life.


Chebeague Island House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
Floor Area:
  • 1800 sq. ft.
House Rules:
  • Check-in: Noon / Check-out: 10:00 AM
  • Max. occupancy: 8
  • children welcome
  • pets not allowed
  • non smoking only
Location Type:
  • Golf Course View ...
  • Near The Ocean
  • Away From It All
  • Family
  • Clothes Dryer ...
  • Hair Dryer
  • Internet ...
  • Linens Provided
  • Living Room
  • Towels Provided ...
  • Washing Machine ...
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher ...
  • Kitchen ...
  • Microwave
  • Oven
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Toaster
  • Dining
  • Dining Room
  • seating for 8 people
  • 1 Bathroom
  • 1 Half Bath
  • Bathroom 1 - toilet , combination tub/shower
    Bathroom 2 - toilet
    Bathroom 3 - outdoor shower
  • Full bath is located downstairs, half bath upstairs
  • 3 Bedrooms, Sleeps 8
  • Bedroom 1 - 1 king
    Bedroom 2 - 1 queen
    Bedroom 3 - 1 double , 1 twin/ single , Bunk bed with twin over full
    Bunk House - 2 twin/ single , Two daybeds
  • Books
  • Games ...
  • Deck / Patio ...
  • Golf ...
  • Lawn / Garden ...
  • Outdoor Grill ...
  • Tennis ...
  • wheelchair inaccessible
Pool / Spa:
  • Communal Pool ...
  • autumn foliage
  • bay/sound
  • churches
  • forests
  • library
  • marina
  • museums
  • playground
  • recreation center
  • restaurants
Leisure Activities:
  • beachcombing
  • bird watching
  • photography
  • walking
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • massage therapist
Sports & Adventure Activities:
  • cycling
  • fishing
  • golf
  • golf privileges optional
  • sailing
  • sound/bay fishing
  • swimming
  • tennis
Chebeague is the largest island in Casco Bay, stretching 4 miles long. It is the perfect place to get away while having room to explore. Chebeague has a relaxed and friendly vibe with kids on bikes and golf carts on the roads. Beautiful Hamilton beach is within walking distance with many more beaches and coves to explore within biking distance. Bike to the Niblic (at the Chebeague Island Boat Yard) for coffee or a gourmet lunch on the second floor seaside deck. The boat yard also has an ATM and post office. Within walking distance, enjoy breakfast or lunch at the Ebb & Thyme Bakery and Cafe or a pub-style dinner and live music at the Slow Bell. Enjoy the sunsets by strolling up the hill to the Chebeague Island Inn for cocktails on the porch or make reservations ahead of time for an upscale dinner at the Inn. For the more adventurous, hop on a Casco Bay Lines ferry from Chandler's Wharf to Portland where you'll find great dining, movies and shopping in the Old Port


Wonderful! 4.8/5 -
(8 traveler reviews)

75% Complete
25% Complete
0% Complete
0% Complete
0% Complete
Sunny Hilltop House next to Tennis, Golf and Beaches on Chebeague Island
average rating of 4.75 based on 8 reviews

Island Away

  • 5 of 5

Had a fabulous week in this beautifully appointed, cozy home. Each room has been decorated with care, evoking ocean blues, grays and greens, with relaxation in mind! Every room has someplace to nestle in for a nap or a good read. Loved the ocean breezes through the windows and the view of the ocean out over the golf course. Super convenient to tennis, golf, the ferry from Yarmouth... and ice cream! The island store is a five-minute bike ride away. Gardens are beautiful and the outdoor shower is a communing-with-nature experience not to be missed. Even in the rain!

  • Submitted: Aug 23, 2017
  • Stayed: August 2017
  • Source: HomeAway
Owner's Response: We love it when we hear that a guest's experience of our home is just like our experience. You touched on all the aspects that we love about the house and since we renovated it ourselves it is very satisfying to hear how much you enjoyed each room including the outdoor shower. You, of course, are welcome back anytime. Best,
Did you find this review helpful?
0 0

One of our best family vacations!

  • 5 of 5

We were two families attending a wedding on Chebeague Island and were lucky enough to find this fabulous home to rent for the week. There were 9 of us in all. Even though the pictures of the Sunny Hilltop House are amazing, the house is even more impressive in person. The main floor was much larger than we expected with two large living areas and a dining room that easily seats a crowd. Kitchen had everything you could imagine you would need. Beds were super comfortable. And bathrooms were spotless. The bunkhouse out back was just right for sleeping our teenage boys and they loved the outdoor shower! The location on the island is perfect -within walking distance to the ferry and to the hotel. Would love to go back one day and enjoy going back in time to simple island living. Our two families couldn't have asked for more in a rental home!!

  • Submitted: Sep 22, 2017
  • Stayed: June 2017
  • Source: HomeAway
Did you find this review helpful?
0 0

Enjoyable vacation home

  • 4 of 5

Pleasant house, well-appointed and well-located. Owners are attentive.

  • Submitted: Sep 1, 2017
  • Stayed: August 2017
  • Source: VRBO, from HomeAway
Did you find this review helpful?
0 0

Great location. Very tastefully decorated

  • 5 of 5

The house is an easy walk from the ferry and to the Inn. It sits directly across from two tennis courts and a nine hole golf course with views of the water from every hole. The closest beach is a five minute bike ride as is the market. The house is very comfortable and tastefully decorated. We slept five easily. There is also a bunk house with a mini ping pong table and a fire pit out front with a view of the water. For longer stays I would suggest bringing a car and/or some good bikes. Great family vacation spot

  • Submitted: Aug 27, 2016
  • Stayed: August 2016
  • Source: HomeAway
Did you find this review helpful?
1 0

Looking forward to returning

  • 5 of 5

I don't even know where to start - the house was perfect! It looks straight out of a Coastal Living magazine and has the best cozy but cute nautical decor. The space is incredible for spending time together - big comfy couches in the living room, a nice big living room table, picnic table outside, etc. Beds were SO comfortable. I was a little worried about the bathroom situation but it was no issue - the outdoor shower was definitely a big hit! I was also unsure about the two daybeds in the cabin in the back of the yard, but it's easily one of the coolest parts of the house! The house is very well stocked for a rental - we cooked multiple meals at home and I never felt like we were missing something that we could have used. There are plenty of towels, beach towels, etc.

We used the bikes to explore the island (we rented a few more for $5/hour through the Chebeague Island Inn, a very short walk from the house) and had a blast at "the hook," a beach at the opposite end of the island from the house. I have spent a lot of time in Maine and never have I enjoyed such a sandy beach! We kept joking that it felt like being in the USVI - not Casco Bay! :) We got sandwiches from the Niblic, ice cream from Calder's, and were able to pop down to the market for any last minute needs. The house is perfectly located in that it's close to the ferry (very manageable walk, even with your stuff) and the Chebeague Island Inn (great for a nice dinner or drink on the porch), but it's an easy launch pad to explore from as well. Speaking of exploration, the locals are so incredibly kind and welcoming. People will stop and ask you if you want a ride if you're carrying a bunch of stuff, they'll happily give you directions (there aren't so many street signs, although the Federle's did a great job providing maps), and they are eager to give advice on beaches, bike routes, etc.!

I was traveling with a group of people who have spent time on islands like Martha's Vineyard and Nantucket, so being the organizer I was a bit nervous about what they'd think of a beautiful yet much more rustic experience. Everyone loved it and had a blast, and I owe a lot of that to the Federle's for providing such a beautiful home for our stay!

  • Submitted: Aug 19, 2015
  • Stayed: August 2015
  • Source: HomeAway
Did you find this review helpful?
2 0
Spartanburg, SC

Ideal home for Chebeague Island vacation

  • 5 of 5

It's difficult to do this house justice in a review here, but I'll give it a try. The house is a short hop from the ferry, and sits atop a knoll with superb sunset views over Casco Bay towards Cousins Island. Two tennis courts and the Great Chebeague Golf Course sit immediately across the road. The grounds around the house are well-tended, and there is plenty of room for a friendly (or in our case, highly competitive) game of croquet or cross-country bocce. The interior of the house has been refinished with all the conveniences, and light pours into the living space off the kitchen. The main house has plenty of room for family and friends, with additional space in the bunkhouse for a pile of kids. There is also an extra fridge in the bunkhouse, which takes care of food storage for a week.

Once you've gotten your bearings in the house, throw a leg over your bicycle and roam. The beaches are fabulous on the northeastern edge of the island, and the rocky bluffs overlooking looking south from Deer Point will offer you welcome sanctuary. You can try for catching squid at night off the pier at Casco Bay landing (we caught a sack full), stop in the museum for curiosities, or have a cup of tea on the porch at the Niblic watching sailboats circle around Crow Island. For that matter, sign up for a bit of sailing at the Chebeague Island Sailing School, and be in the sailboat that someone at the Niblic is watching.

There can be no higher recommendation for this house that I can give than this: we will go back next summer, and every other summer we can manage it. I recommend that you rent this house, too. Just please don't try to book it for the week we are there!

  • Submitted: Mar 8, 2015
  • Stayed: August 2014
  • Source: HomeAway
Did you find this review helpful?
1 0


Car: not necessary


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning Fee $200
Damage Deposit $500

Damage deposit will be refunded upon favorable inspection of the house after rental.

Manager's Cancellation Policy

  • Canceled bookings will not receive a refund

You might like these similar properties