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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Featured Holiday Homes in North Windham

Our top choices for North Windham holiday homes

Willard Beach–Private Apt Near Portland & Parks
Interior

Willard Beach–Private Apt Near Portland & Parks

10.0 out of 10, Exceptional, (2)
"Excellent in every way."
The price is AU$432
includes taxes & fees
15 Sept - 16 Sept
Willard Beach–Private Apt Near Portland & Parks
30 Acres with Woodland Trails and Playground
Fridge, microwave, oven, stovetop

30 Acres with Woodland Trails and Playground

2.0 star property
10.0 out of 10, Exceptional, (1)
"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. "
The price is AU$875
includes taxes & fees
26 Aug - 27 Aug
30 Acres with Woodland Trails and Playground
Sauna & fire table near Portland's Back Cove
Terrace/patio

Sauna & fire table near Portland's Back Cove

10.0 out of 10, Exceptional, (3)
"Great location, clean property"
The price is AU$585
includes taxes & fees
7 Sept - 8 Sept
Sauna & fire table near Portland's Back Cove
Private Entrance Residential Portland
Fridge, microwave, oven, stovetop

Private Entrance Residential Portland

8.8 out of 10, Excellent, (3)
"Check in was simple. Quaint place. "
The price is AU$280
includes taxes & fees
4 Sept - 5 Sept
Private Entrance Residential Portland
Charming Studio apartment with WiFi, AC in welcoming Portland
Interior

Charming Studio apartment with WiFi, AC in welcoming Portland

9.6 out of 10, Exceptional, (5)
"This was a great stay through and through. Excellent condition, very responsive before and during the stay, and a great location. 10/10 will recommend to anyone staying in Portland! "
The price is AU$360
includes taxes & fees
26 Aug - 27 Aug
Charming Studio apartment with WiFi, AC in welcoming Portland
THE LILLIPAD.Off-grid A frame. Sebago lake region!
Property grounds

THE LILLIPAD.Off-grid A frame. Sebago lake region!

10.0 out of 10, Exceptional, (2)
"Charming cabin. Well maintained. Loved my stay! Highly recommend."
The price is AU$296
includes taxes & fees
9 Sept - 10 Sept
THE LILLIPAD.Off-grid A frame. Sebago lake region!
Studio Unit Walkable Everywhere
1 bedroom, bed sheets

Studio Unit Walkable Everywhere

8.0 out of 10, Very good, (2)
"Great, comfortable place to stay. The location is super walkable. There are several bars/restaurants very close, and other areas are close enlighten to walk to as well (I.e. Congress Street). Commercial is a bit of a walk, but if you’re like us and love to walk a new area. It’s not that far. The bed is comfortable and the place was very clean. Communication was great. We would stay here again!"
The price is AU$290
includes taxes & fees
24 Aug - 25 Aug
Studio Unit Walkable Everywhere
Waterfront, Luxury, Spacious home in Freeport!
Terrace/patio

Waterfront, Luxury, Spacious home in Freeport!

10.0 out of 10, Exceptional, (27)
"We had a great time staying at this property. Very clean, big, and great accommodations for a group of 12 females. The hosts were excellent, and super responsive. We would definitely recommend this house to others! "
The price is AU$2,189
includes taxes & fees
1 Sept - 2 Sept
Waterfront, Luxury, Spacious home in Freeport!
The Barnhouse with hot tub
Microwave, oven, stovetop, dishwasher

The Barnhouse with hot tub

10.0 out of 10, Exceptional, (2)
"Thank you Bethany for a most wonderful stay. What a beautiful property you have here. We really loved the opportunity to enjoy the barn house. Hope you and your family have an awesome summer. "
The price is AU$559
includes taxes & fees
3 Sept - 4 Sept
The Barnhouse with hot tub
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
Interior

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

10.0 out of 10, Exceptional, (5)
"Great trip to celebrate my birthday with friends and family. The rental was perfect for our stay. The hot tub, pool and sauna were great. Everything was a 10 minute ride away. Definitely recommend this rental for Maine visitors!"
The price is AU$1,468
includes taxes & fees
23 Aug - 24 Aug
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
Coastal Escape | Hot Tub Fire Pit Chef Kitchen
Outdoor spa tub

Coastal Escape | Hot Tub Fire Pit Chef Kitchen

9.4 out of 10, Exceptional, (3)
"Really nice place. Beds are comfortable. Had nice hot tub with propane fire. Lovely back patio. "
The price is AU$1,101
includes taxes & fees
8 Sept - 9 Sept
Coastal Escape | Hot Tub Fire Pit Chef Kitchen
Luxury on Back Cove - Three Gables
Fridge, microwave, oven, stovetop

Luxury on Back Cove - Three Gables

10.0 out of 10, Exceptional, (3)
"GoodLocation, very clean. Would stay again "
The price is AU$903
includes taxes & fees
16 Sept - 17 Sept
Luxury on Back Cove - Three Gables
Mint Ocean Promenade Condo, Steps to Old Port
Private kitchen

Mint Ocean Promenade Condo, Steps to Old Port

10.0 out of 10, Exceptional, (1)
The price is AU$536
includes taxes & fees
1 Sept - 2 Sept
Mint Ocean Promenade Condo, Steps to Old Port
Waterfront Spacious Luxury Home, 5 min to LL Bean!
Exterior

Waterfront Spacious Luxury Home, 5 min to LL Bean!

9.8 out of 10, Exceptional, (20)
"Great place. Gracious hosts. Warm and cozy space with plenty of room for everyone. "
The price is AU$1,418
includes taxes & fees
2 Sept - 3 Sept
Waterfront Spacious Luxury Home, 5 min to LL Bean!
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Property grounds

1200 sq ft ♦ West End Townhouse ♦ Perfect Location

8.6 out of 10, Excellent, (56)
"Quiet neighborhood. Nice place"
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Walkable near downtown 1 Bedroom
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils

Walkable near downtown 1 Bedroom

The price is AU$318
includes taxes & fees
10 Sept - 11 Sept
Walkable near downtown 1 Bedroom
Adorable Beach House Across the Street From Beach!
Exterior

Adorable Beach House Across the Street From Beach!

9.8 out of 10, Exceptional, (14)
"Lovely home. Clean and inviting. Great location. Wished there were more options for parking when family members are coming from other places."
Adorable Beach House Across the Street From Beach!
Entire Modern Chic Home in Windham
Fridge, microwave, oven, stovetop

Entire Modern Chic Home in Windham

10.0 out of 10, Exceptional, (12)
"Everything was great for our family's vacation!"
The price is AU$728
includes taxes & fees
4 Sept - 5 Sept
Entire Modern Chic Home in Windham
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (61)
"Very clean, lots of room for gathering. Perfect location on a quiet street with great views of the lake. Plenty of towels, bedding, water, etc. Would come back!"
The price is AU$2,045
includes taxes & fees
2 Sept - 3 Sept
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Luxury King Room with Parlor and Balcony
Property grounds

Luxury King Room with Parlor and Balcony

The price is AU$1,106
includes taxes & fees
7 Sept - 8 Sept
Luxury King Room with Parlor and Balcony
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 North Windham Hotel Reviews

Hilton Garden Inn Portland Downtown Waterfront

Hilton Garden Inn Portland Downtown Waterfront

10/10 Excellent
"Everything was great! The staff were very friendly and accommodating. The property was very clean and well maintained. Great location."
Nancy 4-night trip
Posted 4 hours ago
Hilton Garden Inn Portland Downtown Waterfront