Lodging Image

Search Guest Houses in Chebeague Island from CA $194

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18
In one month
Oct 30 - Nov 1
In two months
Nov 27 - Nov 29

Our top choices for Chebeague Island guest houses

A view from a window overlooking a body of water with a distant shoreline, a vase with flowers, and a glass on a table.

1. The McKernan Inn

The McKernan Inn
3.0 star property
South Portland
9.2 out of 10, Wonderful, (149 reviews)
"Enjoyed our stay"
United States
Kathy
The price is CA $286
CA $311 total
includes taxes & fees
Oct 15 - Oct 16
The McKernan Inn
A wooden deck with picnic tables and umbrellas overlooking a lake.

2. Spinneys Guesthouse & Beach Cottages

Spinneys Guesthouse & Beach Cottages
3.0 star property
Phippsburg
9.2 out of 10, Wonderful, (78 reviews)
"I loved Spinneys and wish we could have stayed longer. It is such a great spot, right on the water, super cute and quaint. I recommend 100 percent. Staff is very friendly and you have breakfast and coffee as well."
United States
Shari
The price is CA $238
CA $305 total
includes taxes & fees
Oct 12 - Oct 13
Spinneys Guesthouse & Beach Cottages
A spacious room with large windows overlooking a beach, furnished with blue and white patterned chairs and a wooden table.

3. The Breakers Inn

The Breakers Inn
3.0 star property
Higgins Beach
9.8 out of 10, Exceptional, (30 reviews)
"Stunning Vistas & Superb Staff!"
United States
Deborah
The price is CA $356
CA $388 total
includes taxes & fees
Oct 25 - Oct 26
The Breakers Inn
A spacious living room with a wooden dining table, dark leather sofa, and a flat-screen TV.

4. The Woodland Loft at Falmouth

The Woodland Loft at Falmouth
Falmouth
10.0 out of 10, Exceptional, (2 reviews)
"Excellent communication. Host checked in to make sure we didn’t need anything. Property and unit were beautiful, clean and well stocked."
United States
Deborah M.
The price is CA $215
CA $574 total
includes taxes & fees
Oct 27 - Oct 28
The Woodland Loft at Falmouth
A balcony with a view of the beach and ocean. There is a table and a chair with a blue cushion.

5. The Rebekah Inn

The Rebekah Inn
2.5 star property
Old Orchard Beach
9.0 out of 10, Wonderful, (94 reviews)
"Great location friendly staff"
United States
Dan
The price is CA $178
CA $194 total
includes taxes & fees
Oct 4 - Oct 5
The Rebekah Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chebeague Island Hotel Reviews

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

10/10 Excellent
"Visited Portland for the first time, the Regency is in the perfect location. It’s a great food town, do your homework before you go and make reservations."
Joseph 2-night trip
Posted less than an hour ago
Portland Regency Hotel & Spa

Find out more about Chebeague Island

Chebeague Island Guest Houses information

Number of reviews
353
Accommodation
6 Guest Houses
Lowest Price
CA $194
Highest Price
CA $574

Explore a world of travel with Expedia