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

Search Holiday Homes in Windham

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Windham holiday homes

TV, offices

Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
The price is £389
includes taxes & fees
1 Jul - 2 Jul
Fully Updated Airy Historic Home in South Freeport
Terrace/patio

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (53 reviews)
"Wonderful stay!"
United States
Erika T.
The price is £277
includes taxes & fees
1 Jul - 2 Jul
Full sized home
Dining

Seaglass Cottage by Bayley Vacation Rentals

Seaglass Cottage by Bayley Vacation Rentals
Old Orchard Beach
The price is £1,041
includes taxes & fees
25 Jul - 26 Jul
Seaglass Cottage by Bayley Vacation Rentals
Interior

Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is £267
includes taxes & fees
5 Jul - 6 Jul
Tranquility between the Lakes & Sea
Terrace/patio

•Peaceful Private Freeport 2 BR Home on the Ocean•

•Peaceful Private Freeport 2 BR Home on the Ocean•
Freeport
The price is £586
includes taxes & fees
8 Jul - 9 Jul
•Peaceful Private Freeport 2 BR Home on the Ocean•
Smart TV

Huge New Townhome 10mins from the Beach

Huge New Townhome 10mins from the Beach
Saco
8.0 out of 10, Very good, (1 review)
"The only big issue was that the VRBO listing gave us the wrong address. It sent us to Scarborough instead of Saco. Luckily we were familiar with the area and I knew that Saco was close to Old Orchard Beach, which was mentioned in the listing, so I did a google map search of the same address in Saco and it looked like the pictures. My elderly parents were relieved that we didn’t get scammed. Lol. The place was clean and large and easy to get on the highway. It’s 2 and a half baths, not 3 full...
United States
Stacy H.
The price is £438
includes taxes & fees
1 Jul - 2 Jul
Huge New Townhome 10mins from the Beach
Property grounds

Maine Oceanfront Retreat

Maine Oceanfront Retreat
Brunswick
9.4 out of 10, Exceptional, (3 reviews)
"Gorgeous views house is extremely well equipped "
United States
Cary C.
The price is £861
includes taxes & fees
22 Jul - 23 Jul
Maine Oceanfront Retreat
Fridge, microwave, oven, dishwasher

NEW! Gray Woodland Escape | Golf, Pool & Cinema

NEW! Gray Woodland Escape | Golf, Pool & Cinema
Gray
10.0 out of 10, Exceptional, (1 review)
The price is £987
includes taxes & fees
1 Jul - 2 Jul
NEW! Gray Woodland Escape | Golf, Pool & Cinema
Fridge, microwave, oven, stovetop

The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury

The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury
Harpswell
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful property, well equipped, lots of amenities, plenty of space for our large group."
United States
Edwin M.
The price is £2,414
includes taxes & fees
13 Jul - 14 Jul
The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury
Exterior detail

30 Acres with Woodland Trails and Playground

30 Acres with Woodland Trails and Playground
Freeport
10.0 out of 10, Exceptional, (1 review)
"Spent a week with my family at this lovely property in Freeport, ME. The location is ideal to visit various attractions nearby. Including the pinturesque dowtown. The house was clean and had everything needed to have a pleasant stay away from home. "
United States
Zoraida
The price is £550
includes taxes & fees
14 Jul - 15 Jul
30 Acres with Woodland Trails and Playground
Smart TV

Beautiful 3BR Home with Office in Town of Brunswick with King beds

Beautiful 3BR Home with Office in Town of Brunswick with King beds
Brunswick
9.2 out of 10, Wonderful, (5 reviews)
"Great place for our family to stay while visiting the Maine coast."
United States
Craig C.
The price is £367
includes taxes & fees
2 Jul - 3 Jul
Beautiful 3BR Home with Office in Town of Brunswick with King beds
Exterior

Sunny Beachfront Cottage with Spectacular Ocean Views

Sunny Beachfront Cottage with Spectacular Ocean Views
Kinney Shores
9.4 out of 10, Exceptional, (26 reviews)
"The home was on the ocean, with views from most of the windows. The beach was aways changing with the tides , beautiful. We all enjoyed our stay"
United States
Kevin C.
The price is £1,246
includes taxes & fees
8 Jul - 9 Jul
Sunny Beachfront Cottage with Spectacular Ocean Views
Beach

Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton

Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
Buxton
6.0 out of 10, (1 review)
"Overall, value property. It's a very old home that was slightly renovated. Pros. 3 bedrooms, washer dryer, good price Cons. Smelled musty, pans not usable for cooking, small living room.Host was great with communication, and the stay was worth the price."
United States
Renee D.
The price is £343
includes taxes & fees
16 Jul - 17 Jul
Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
Beach towels

Spacious Home Close to Beaches! 3BR, Dog & Family Friendly, 30 Mins to Portland

Spacious Home Close to Beaches! 3BR, Dog & Family Friendly, 30 Mins to Portland
Biddeford
9.8 out of 10, Exceptional, (10 reviews)
"We have stayed three times and will be back"
United States
Michael W.
The price is £621
includes taxes & fees
1 Jul - 2 Jul
Spacious Home Close to Beaches! 3BR, Dog & Family Friendly, 30 Mins to Portland
Exterior

A historic treasure in Southern Maine, very unique and spacious

A historic treasure in Southern Maine, very unique and spacious
Biddeford
10.0 out of 10, Exceptional, (44 reviews)
"Loved this house. Perfect for a getting ready spot for family before a wedding. Plently of rooms and space for parking "
United States
Jeanne C.
The price is £841
includes taxes & fees
1 Jul - 2 Jul
A historic treasure in Southern Maine, very unique and spacious
Microwave, oven, stovetop, dishwasher

The Links Lodge - Modern Golf and Beach Retreat

The Links Lodge - Modern Golf and Beach Retreat
Old Orchard Beach
10.0 out of 10, Exceptional, (10 reviews)
"Great home for family!"
United States
Christie B.
The price is £769
includes taxes & fees
13 Jul - 14 Jul
The Links Lodge - Modern Golf and Beach Retreat
Dining

Family Tides by Bayley Vacation Rentals

Family Tides by Bayley Vacation Rentals
Pine Point
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful propertyPerfect gathering space - living room and kitchenEasy walk to the beachEasy access to Portland "
United States
Neena M.
The price is £2,821
includes taxes & fees
15 Jul - 16 Jul
Family Tides by Bayley Vacation Rentals
Property grounds

Long Lake 3BR: Beach Access + Dock

Long Lake 3BR: Beach Access + Dock
Naples
The price is £433
includes taxes & fees
6 Jul - 7 Jul
Long Lake 3BR: Beach Access + Dock
Smart TV

Beachside Retreat on the Hill

Beachside Retreat on the Hill
Old Orchard Beach
The price is £473
includes taxes & fees
5 Jul - 6 Jul
Beachside Retreat on the Hill
Microwave, oven, stovetop, dishwasher

The Barnhouse with hot tub

The Barnhouse with hot tub
New Gloucester
9.8 out of 10, Exceptional, (8 reviews)
"This was the perfect spot for my friends and I who were attending a wedding down the road! Great location, lovely property and very clear instructions from the hosts! "
United States
Jen V.
The price is £308
includes taxes & fees
12 Jul - 13 Jul
The Barnhouse with hot tub
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

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

8/10 Good
"Great hotel for exploring Old Port! Wasn't too far from anything - felt like the perfect location for our long weekend getaway. Beds are SO comfortable, great pillows, nice shower. Everyone at the front desk was very friendly and helpful. We did ask for our room to be cleaned on day 2 of our 4 night stay and it wasn't done (had to ask again the next day), but other than that it was a great experience."
Susan 4-night trip
Posted less than an hour ago
Portland Regency Hotel & Spa

Find out more about Windham

Windham Holiday Homes information

Number of reviews
184
Accommodation
958 Holiday Homes
Lowest Price
£267
Highest Price
£2,821