A white church with a steeple and red accents, surrounded by autumn trees.

Search Guest Houses in Windham from CA $307

  • 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
Nov 6 - Nov 8
In two weeks
Nov 13 - Nov 15
In one month
Nov 27 - Nov 29
In two months
Dec 25 - Dec 27

Our top choices for Windham guest houses

A spacious living room with a wooden dining table, dark leather sofa, and a flat-screen TV.

1. The Woodland Loft at Falmouth by Everrow

The Woodland Loft at Falmouth by Everrow
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 $163
CA $503 total
includes taxes & fees
Oct 29 - Oct 30
The Woodland Loft at Falmouth by Everrow
A brick building with a large bay window, a covered porch, and a staircase leading to the entrance.

2. The McKernan Inn

The McKernan Inn
3.0 star property
South Portland
9.2 out of 10, Wonderful, (167 reviews)
"good size room, convenient location"
United States
Melissa
The price is CA $281
CA $307 total
includes taxes & fees
Nov 8 - Nov 9
The McKernan Inn
A modern interior with a loft bedroom, a sofa, a TV, and a dining area.

3. And.N Lodging

And.N Lodging
2.0 star property
Casco
9.4 out of 10, Exceptional, (3 reviews)
"Such a cute place! The owners were very responsive with our questions. We had a wonderful dinner and games in the screen room. Shower is roomy and the water pressure just right. Only wished there was a firepit. The dock was too unsafe to go out on. Would book with these owners again for sure!"
United States
Gail
The price is CA $253
CA $352 total
includes taxes & fees
Nov 26 - Nov 27
And.N Lodging
A spacious room with large windows overlooking a beach, furnished with blue and white patterned chairs and a wooden table.

4. The Breakers Inn

The Breakers Inn
3.0 star property
Higgins Beach
9.8 out of 10, Exceptional, (43 reviews)
"Stunning Vistas & Superb Staff!"
United States
Deborah
The price is CA $351
CA $383 total
includes taxes & fees
Oct 29 - Oct 30
The Breakers 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 Windham Hotel Reviews

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

10/10 Excellent
"The bed and pillows here were to die for!!!! Felt like sleeping on a cloud! And the man driving our shuttle also checked us in! Wonderfully ran, free standard breakfast in the morning!"
Jamie 1-night trip
Posted 2 hours ago
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Find out more about Windham

Windham Guest Houses information

Number of reviews
215
Accommodation
6 Guest Houses
Lowest Price
CA $307
Highest Price
CA $503

Explore a world of travel with Expedia