Holiday Homes in Windham

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Windham holiday homes

Terrace/patio

•Peaceful Private Freeport 2 BR Home on the Ocean•

•Peaceful Private Freeport 2 BR Home on the Ocean•
Freeport
The price is NZ$1,144
includes taxes & fees
10 June - 11 June
•Peaceful Private Freeport 2 BR Home on the Ocean•
Fridge, microwave, oven, stovetop

Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
The price is NZ$837
includes taxes & fees
9 June - 10 June
Fully Updated Airy Historic Home in South Freeport
Fridge, microwave, oven, stovetop

Two Beautiful apartment

Two Beautiful apartment
Back Cove
10.0 out of 10, Exceptional, (28 reviews)
"Such an amazing property and host in an incredible location! "
United States
Devin M.
The price is NZ$1,775
includes taxes & fees
15 June - 16 June
Two Beautiful apartment
3 bedrooms, desk, iron/ironing board, travel cot

⚓ Cozy 3BR Coastal Retreat • Private Yard & Fire Pit • 5 Min to Beach!

⚓ Cozy 3BR Coastal Retreat • Private Yard & Fire Pit • 5 Min to Beach!
Old Orchard Beach
10.0 out of 10, Exceptional, (7 reviews)
"The host was extremely responsive, the house perfectly accommodated our needs, and the beds were super comfortable. Highly recommend!"
United States
Tina B.
The price is NZ$789
includes taxes & fees
8 June - 9 June
⚓ Cozy 3BR Coastal Retreat • Private Yard & Fire Pit • 5 Min to Beach!
Interior

Seas the Day by Bayley Vacation Rentals

Seas the Day by Bayley Vacation Rentals
Pine Point
10.0 out of 10, Exceptional, (3 reviews)
"If you are beach lovers this is the place for you. Pine Point is a dog friendly beach(look for rules and hours) and bike beach. Low tide offers hard packed sand. Great for running and walking!Lots of restaurants nearby and the cutest place just across the street, Salty Bay with a tavern only if you order food from Salty Bay so not a big bar scene just a few people and last call is 8:30! So perfect!It's great for a couple or a couple with young children. "
United States
emie b.
Seas the Day by Bayley Vacation Rentals
Interior

The Gregory House in Southern Maine close to many beaches & popular destinations

The Gregory House in Southern Maine close to many beaches & popular destinations
Downtown Saco
9.6 out of 10, Exceptional, (19 reviews)
"Lots to do. Great location"
United States
Bob Z.
The price is NZ$1,526
includes taxes & fees
7 June - 8 June
The Gregory House in Southern Maine close to many beaches & popular destinations
1 bedroom, Internet, bed sheets

Charming 1-bedroom ADU in wonderful Portland neighborhood

Charming 1-bedroom ADU in wonderful Portland neighborhood
Back Cove
The price is NZ$475
includes taxes & fees
7 June - 8 June
Charming 1-bedroom ADU in wonderful Portland neighborhood
Property grounds

South Portland Beach area rental

South Portland Beach area rental
Willard Beach
10.0 out of 10, Exceptional, (1 review)
"Great place, just like pictures "
United States
Evan M.
The price is NZ$580
includes taxes & fees
9 June - 10 June
South Portland Beach area rental
Terrace/patio

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (52 reviews)
"Wonderful stay!"
United States
Erika T.
The price is NZ$625
includes taxes & fees
15 June - 16 June
Full sized home
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 NZ$1,678
includes taxes & fees
7 June - 8 June
A historic treasure in Southern Maine, very unique and spacious
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
The price is NZ$563
includes taxes & fees
9 June - 10 June
Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
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 NZ$4,271
includes taxes & fees
10 June - 11 June
The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury
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 NZ$1,043
includes taxes & fees
8 June - 9 June
Huge New Townhome 10mins from the Beach
Interior

Luxe Coastal Retreat with Hot Tub & Fire Pit

Luxe Coastal Retreat with Hot Tub & Fire Pit
North Deering
9.4 out of 10, Exceptional, (8 reviews)
"Very nice! Would stay again and would highly recommend."
United States
Peter H.
The price is NZ$1,595
includes taxes & fees
9 June - 10 June
Luxe Coastal Retreat with Hot Tub & Fire Pit
Fridge, oven, stovetop, dishwasher

Luxe 5BR/3BA Cape: Game Room & 20min to Portland

Luxe 5BR/3BA Cape: Game Room & 20min to Portland
Yarmouth
The price is NZ$1,387
includes taxes & fees
9 June - 10 June
Luxe 5BR/3BA Cape: Game Room & 20min to Portland
Property grounds

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Westbrook
9.6 out of 10, Exceptional, (43 reviews)
"Host was excellent, even thinking of bug spray, yoga mats, binoculars, and extra blankets. We loved our stay!"
United States
Genevieve W.
The price is NZ$1,056
includes taxes & fees
10 June - 11 June
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
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 NZ$818
includes taxes & fees
15 June - 16 June
Beautiful 3BR Home with Office in Town of Brunswick with King beds
Exterior detail

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
East Deering
10.0 out of 10, Exceptional, (73 reviews)
"Had a really nice stay. "
United States
John F.
The price is NZ$2,209
includes taxes & fees
7 June - 8 June
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Fridge, microwave, oven, stovetop

Upscale Spacious OOB Beach House - Seasonal Heated Pool

Upscale Spacious OOB Beach House - Seasonal Heated Pool
Old Orchard Beach
10.0 out of 10, Exceptional, (14 reviews)
"The place was great, lot's of room for everyone. It was easy to drive around to where we were going. We would definitely recommend this place. "
United States
Robin T.
The price is NZ$1,417
includes taxes & fees
1 July - 2 July
Upscale Spacious OOB Beach House - Seasonal Heated Pool
Beach nearby

Charming Victorian beach house 5 bedrooms. 50 steps to the beach

Charming Victorian beach house 5 bedrooms. 50 steps to the beach
Old Orchard Beach
9.6 out of 10, Exceptional, (18 reviews)
"We had a great time and it’s an awesome place. Can’t wait to rebook for next year. "
United States
Robert D.
The price is NZ$2,068
includes taxes & fees
8 June - 9 June
Charming Victorian beach house 5 bedrooms. 50 steps to the beach
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.
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Top Windham Hotel Reviews

Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

8/10 Good
"The staff were all very good. The in-house restaurant was surprisingly good, and the breakfast was excellent. The one thing that didn't work was the surprise $13. parking fee that was not included in the hotel cost. This is a hotel with its own parking lot. I have never paid a parking fee when staying at such a place and don't intend to again. It's not about the money, but the sleazy way they extracted another fee."
Bruce 1-night trip
Posted 2 hours ago
Embassy Suites by Hilton Portland Maine

Find out more about Windham

Windham Holiday Homes information

Number of reviews
300
Accommodation
918 Holiday Homes
Lowest Price
NZ$475
Highest Price
NZ$4,271