Holiday Homes in Windham

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Check prices for these dates

In two weeks
8 May - 10 May
In two months
19 Jun - 21 Jun
In three months
17 Jul - 19 Jul
In four months
14 Aug - 16 Aug

Our top choices for Windham holiday homes

Outdoor dining

Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (8 reviews)
"Lovely location "
United States
Michelle S.
The price is NZ$770
includes taxes & fees
27 Apr - 28 Apr
Mere Point Sunrise Views at Eastern Shore!
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$1,658
includes taxes & fees
21 Apr - 22 Apr
A historic treasure in Southern Maine, very unique and spacious
Interior

Modern Getaway by the Sea

Modern Getaway by the Sea
South Portland
10.0 out of 10, Exceptional, (2 reviews)
"Had a nice stay! House was great."
United States
Karen T.
The price is NZ$858
includes taxes & fees
21 Apr - 22 Apr
Modern Getaway by the Sea
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, (71 reviews)
"Had a really nice stay. "
United States
John F.
The price is NZ$1,883
includes taxes & fees
21 Apr - 22 Apr
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
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$474
includes taxes & fees
21 Apr - 22 Apr
Charming 1-bedroom ADU in wonderful Portland neighborhood
Exterior

Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats

Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
Casco
10.0 out of 10, Exceptional, (14 reviews)
"Our stay at this vacation home was wonderful! We had the best time relaxing and enjoying the fall weather. The property manager was responsive and helpful upon check in and check out. We will most definitely be staying there again!"
United States
Michie K.
The price is NZ$1,225
includes taxes & fees
26 Apr - 27 Apr
Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
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$461
includes taxes & fees
15 May - 16 May
Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
Property grounds

Modern Cottage with Peeks of Ocean Views

Modern Cottage with Peeks of Ocean Views
Cape Elizabeth
10.0 out of 10, Exceptional, (1 review)
"Very cute property, perfect location! Had every amenity we could possibly need. The home was decorated so cutely and the shower was AMAZING! I’m coming back just for the shower! "
United States
Christina S.
The price is NZ$928
includes taxes & fees
21 Apr - 22 Apr
Modern Cottage with Peeks of Ocean Views
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$967
includes taxes & fees
22 Apr - 23 Apr
Huge New Townhome 10mins from the Beach
Interior

Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
Scarborough
10.0 out of 10, Exceptional, (15 reviews)
"It was a lovely stay! Alexa was very responsive and helpful with any questions we had. The house was lovely and clean, and the dogs were so happy to have a yard they could run around in! Hot tub and pool were so needed as well! 10/10 suggest staying here!"
United States
Joe L.
The price is NZ$1,048
includes taxes & fees
26 Apr - 27 Apr
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
Property grounds

Classic New England Waterfront House Big Lawn Beautiful Sunrise

Classic New England Waterfront House Big Lawn Beautiful Sunrise
Harpswell
10.0 out of 10, Exceptional, (2 reviews)
"Great property"
United States
Scott D.
The price is NZ$1,946
includes taxes & fees
4 May - 5 May
Classic New England Waterfront House Big Lawn Beautiful Sunrise
Terrace/patio

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (51 reviews)
"Super clean and lovely place to stay! Highly recommend!"
United States
Evan B.
The price is NZ$724
includes taxes & fees
14 May - 15 May
Full sized home
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$1,497
includes taxes & fees
21 Apr - 22 Apr
The Gregory House in Southern Maine close to many beaches & popular destinations
Beach nearby

On Par for the Beach

On Par for the Beach
Old Orchard Beach
10.0 out of 10, Exceptional, (7 reviews)
"We visited with grandparents-toddlers and had a great stay. Walkable to the golfcourse/restaurant and only 5-10 minute drive to the beach and downtown boardwalk. Beautiful home and bedrooms, very clean and well kept. Easy process and will definitely stay again!"
United States
Rachel C.
On Par for the Beach
Microwave, oven, stovetop, dishwasher

The Barnhouse with hot tub

The Barnhouse with hot tub
New Gloucester
9.8 out of 10, Exceptional, (6 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 NZ$598
includes taxes & fees
23 Apr - 24 Apr
The Barnhouse with hot tub
Outdoor dining

Modern & Sunny House Steps from the Promenade. Private Parking!

Modern & Sunny House Steps from the Promenade. Private Parking!
Munjoy Hill
10.0 out of 10, Exceptional, (39 reviews)
"Great home, great location, very accommodating, clear communication."
United States
Kristi H.
The price is NZ$643
includes taxes & fees
23 Apr - 24 Apr
Modern & Sunny House Steps from the Promenade. Private Parking!
Exterior

Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!

Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!
Portland
9.8 out of 10, Exceptional, (35 reviews)
"Fabulous place. Peaks Island. "
United States
Christopher W.
The price is NZ$1,777
includes taxes & fees
5 May - 6 May
Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!
Dining

Sleeps 16+ | W/D | Parking | 15 mins to Old Port

Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Westbrook
The price is NZ$1,553
includes taxes & fees
27 Apr - 28 Apr
Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Outdoor dining

The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries
Munjoy Hill
10.0 out of 10, Exceptional, (95 reviews)
"Cozy and clean great location "
United States
Michele F.
The price is NZ$949
includes taxes & fees
22 Apr - 23 Apr
The Globe House on Munjoy Hill - Walk to Breweries
Terrace/patio

LUX Designer Private Waterfront Crooked River SEBAGO - GLASS WALLS - Huge Yard

LUX Designer Private Waterfront Crooked River SEBAGO - GLASS WALLS - Huge Yard
Naples
10.0 out of 10, Exceptional, (4 reviews)
"Fantastic home! We had a great time here and look forward to booking again."
United States
Gina P.
The price is NZ$1,323
includes taxes & fees
22 Apr - 23 Apr
LUX Designer Private Waterfront Crooked River SEBAGO - GLASS WALLS - Huge Yard
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

Inn at St John Portland In-Town

Inn at St John Portland In-Town

4/10 Poor
"The room advertised a jetted tub when in fact there was not even hot water to take a shower let alone use the tub. The rooms next to and adjacent also had no hot water. After running the tub I found someone else's used bandaid in there, so looked around other areas of the bathroom and noticed someone else's blood on the rim of the toilet seat."
Haley 1-night trip
Posted 1 hour ago
Inn at St John Portland In-Town

Find out more about Windham

Windham Holiday Homes information

Number of reviews
343
Accommodation
862 Holiday Homes
Lowest Price
NZ$461
Highest Price
NZ$1,946