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Book Online or call VRBO Booking Assistance: 888-829-7076
Book Online or call VRBO Booking Assistance: 888-829-7076

Stunning views and comfort complete your ultimate Maine island vacation getaway.

Bedrooms 2
Space 1,400 sq ft
Property type house
Minimum Stay 3 nights


About the property

Unwind in style in a homey yet stylish and unique family vacation place.

Upper House is a beautiful modern summer house with post Frank Lloyd Wright design aesthetic. This comfortable and well appointed vacation house sits up on a hill, and boasts some of the best views on Casco Bay. Cook your lobsters in a well designed kitchen, melt your butter in a vintage cast iron pan, and enjoy your drinks on any of the 3 porches looking out over dozens of islands in the sparkling bay.

Luke Rothschild
Member since: 2016
Speaks: english
Response time:
Within a day
Response rate:
Calendar last updated:
August 10, 2018

About Luke Rothschild

I'm a music professional that ended up in the Los Angeles area. I enjoy music, fine art, reading, and surfing. I LOVE our house on Chebeague island. Since it sits empty for some months of the year, I'm now listing it on VRBO and will be the point person for the rentals for the rest of my family.

Luke Rothschild purchased this house in 1954

Why Luke Rothschild chose Chebeague Island

My grandfather and grandmother bought the property in the 1950's. This house was originally built as a study and writing room for my grandfather. It then underwent multiple additions and grew into a really special 3 season home on the island. My grandmother was an interior designer in New York in the 50s and 60s, and she brought her substantial design aesthetic to bear on this special space. It sits tucked into the hill, with the stunning views expanding outward towards the bay.

What makes this house unique

Wake up to sun bathed wood and glass, and see the bay spread out before you. Soothe yourself with the balm of the salt air. The view is worth staying in for... But go exploring! When's that last time you walked the paths of an island retreat? The Upper House is situated uniquely to provide privacy, and yet is just a few hundred yards from The Boatyard, The Niblic, and multiple beaches just below. Biking and fishing and swimming are favorite activities. As are reading eating and sleeping. Its pretty much impossible to get a fresher lobster than the ones that come right out of Casco Bay and can be brought to you by the lobstermen themselves. There's also Second Wind Farms that has delicious fresh produce at the farm stand.


Chebeague Island House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
Floor Area:
  • 1400 sq ft
House Rules:
  • Check-in: Noon / Check-out: 2:00 PM
  • Max. occupancy: 5
  • pets considered ...
  • children welcome
  • non smoking only
Location Type:
  • Ocean View
  • Away From It All
  • Family
  • Romantic
  • Clothes Dryer
  • Fireplace
  • Heating
  • Internet
  • Linens Provided
  • Living Room
  • Telephone
  • Towels Provided
  • Washing Machine
  • Coffee Maker
  • Dishes & Utensils
  • Kitchen
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator
  • Stove
  • Toaster
  • Dining Area
  • 1 Bathroom
  • Bathroom 1 - toilet , combination tub/shower , tub , shower
  • 2 Bedrooms, Sleeps 5
  • Bedroom 1 - 2 twin/ single , 1 baby crib
    Master Bedroom - 1 queen
  • Books ...
  • Stereo ...
  • Bicycles
  • Deck / Patio ...
  • Golf ...
  • Lawn / Garden
  • Tennis ...
  • 6 bicycles
  • wheelchair accessible
  • library
  • museums
  • restaurants
Leisure Activities:
  • beachcombing
  • bird watching
  • photography
  • shelling
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • groceries
Sports & Adventure Activities:
  • cycling
  • fishing
  • golf
  • golf privileges optional
  • pier fishing
  • swimming


5/5 -
(2 traveler reviews)

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Stunning views and comfort complete your ultimate Maine island vacation getaway.
average rating of 5.0 based on 2 reviews

Pure Heaven

  • 5 of 5

The house was lovely, comfortable and well-appointed. We felt at home within moments of arriving. The owner and our "island hosts" made certain that any questions we had about the island and/or home were answered in a timely and thorough manner. We would love to spend another week in this wonderful home again!

  • Submitted: Jul 18, 2017
  • Stayed: July 2017
  • Source: VRBO, from HomeAway
Owner's Response: Dominique and her family were wonderful guests! Kind, conscientious and communicative. We would love for them to come back next year :)
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Nice home, beautiful views, and great location!

  • 5 of 5

We loved our stay at the upper house. The location is close to everything Including the beaches, restaurants, pier , etc. you can pretty much bike everywhere. We would recommend this home to anyone!

  • Submitted: Sep 16, 2016
  • Stayed: August 2016
  • Source: HomeAway
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Nearest Airport
15 Miles
Nearest Ferry
1.5 Miles
Car: not necessary


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning $100
Property Damage Protection $59

Upper House is in easy walking distance of boatyard, and beaches. The Niblic shop with coffee, pastries, soup & sandwiches, beer and wine is right down the hill. Six bikes live on the property and allow access to the rest of the island. Six simple spincasting outfits are accessible for fishing for mackerel off pier at Chandlers Cove. Doughty's Island Market has many necessities, and it is also possible to put in an order at Whole Foods Portland, and they'll shop for you and put it on the ferry that delivers at 4pm every weekday.

Owner's Cancellation Policy

  • 50% refund if canceled at least 30 days before arrival date.
  • 100% refund if canceled at least 60 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

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