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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 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)
"Such a beautiful home and peaceful location. We loved our stay and the host was responsive and helpful with any questions we had!"
United States
Diana H.
The price is HK$1,578
HK$3,587 total
includes taxes & fees
28 Apr - 29 Apr
Mere Point Sunrise Views at Eastern Shore!
3 bedrooms, desk, iron/ironing board, travel cot

3BR Coastal Gem with a 5 Min Drive to Ocean Fun

3BR Coastal Gem with a 5 Min Drive to Ocean Fun
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 HK$1,448
HK$3,469 total
includes taxes & fees
19 Apr - 20 Apr
3BR Coastal Gem with a 5 Min Drive to Ocean Fun
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 HK$2,348
HK$4,010 total
includes taxes & fees
20 Apr - 21 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 HK$5,956
HK$8,761 total
includes taxes & fees
20 Apr - 21 Apr
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
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 HK$4,028
HK$7,888 total
includes taxes & fees
19 Apr - 20 Apr
A historic treasure in Southern Maine, very unique and spacious
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 HK$1,369
HK$2,158 total
includes taxes & fees
19 Apr - 20 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 HK$1,565
HK$5,880 total
includes taxes & fees
19 Apr - 20 Apr
Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
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 HK$2,233
HK$4,389 total
includes taxes & fees
21 Apr - 22 Apr
Modern Cottage with Peeks of 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
Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
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 HK$1,614
HK$4,523 total
includes taxes & fees
19 Apr - 20 Apr
Huge New Townhome 10mins from the Beach
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 HK$3,615
HK$7,378 total
includes taxes & fees
20 Apr - 21 Apr
The Gregory House in Southern Maine close to many beaches & popular destinations
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, (14 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 HK$2,108
HK$4,970 total
includes taxes & fees
19 Apr - 20 Apr
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
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 HK$1,956
HK$3,344 total
includes taxes & fees
14 May - 15 May
Full sized home
Exterior

Lake Front Cabin on Desirable Highland Lake

Lake Front Cabin on Desirable Highland Lake
Bridgton
9.8 out of 10, Exceptional, (9 reviews)
"Beautiful place to stay with all the amenities."
United States
Paul J.
The price is HK$1,465
HK$3,227 total
includes taxes & fees
18 Apr - 19 Apr
Lake Front Cabin on Desirable Highland Lake
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 HK$1,542
HK$2,994 total
includes taxes & fees
20 Apr - 21 Apr
Modern & Sunny House Steps from the Promenade. Private Parking!
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 HK$1,479
HK$2,772 total
includes taxes & fees
19 Apr - 20 Apr
The Barnhouse with hot tub
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 HK$1,914
HK$5,635 total
includes taxes & fees
19 Apr - 20 Apr
Spacious Home Close to Beaches! 3BR, Dog & Family Friendly, 30 Mins to Portland
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 HK$3,913
HK$8,368 total
includes taxes & fees
5 May - 6 May
Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!
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.
The price is HK$2,247
HK$10,346 total
includes taxes & fees
30 Apr - 1 May
On Par for the Beach
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 HK$3,913
HK$9,255 total
includes taxes & fees
5 May - 6 May
Classic New England Waterfront House Big Lawn Beautiful Sunrise
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

The Westin Portland Harborview

The Westin Portland Harborview

10/10 Excellent
"A fine location with nice rooms and helpful staff. The bar on the 15th floor has a nice view of the harbor and pretty good draft beer. Don't order food - or at least the tots as the serving size is meager and quality very low. Not to mention the high cost. Like many cities, Portland does struggle with issues of housing and, sometimes associated, drug use. The Westin area of town does has abundance of both of these issues. We NEVER felt threatened but some might be uncomfortable in this area."
Matthew 4-night trip
Posted 4 hours ago
The Westin Portland Harborview

Find out more about Windham

Windham Vacation Homes information

Number of reviews
262
Accommodation
767 Vacation Homes
Lowest Price
HK$2,158
Highest Price
HK$10,346

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