Windham Vacation Rentals

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Our top choices for Windham vacation homes

Windham Lakefront: Fire Pit and Modern Comforts

Windham Lakefront: Fire Pit and Modern Comforts
Windham
10.0 out of 10, Exceptional, (2 reviews)
"This is an exceptional property. It was quiet and comfortable, and we all slept well. The location was ideal for our plans and the host answered every question promptly.I highly recommend this rental, and I plan to return."
United States
Richard G.
The price is CA $583
CA $1,413 total
includes taxes & fees
Jul 10 - Jul 11
Windham Lakefront: Fire Pit and Modern Comforts

Manor Suite,cozy newly renovated,downtown & beach

Manor Suite,cozy newly renovated,downtown & beach
Bridgton
10.0 out of 10, Exceptional, (1 review)
"Property was very clean! it had everything you needed right there! "
United States
Lisa
The price is CA $147
CA $261 total
includes taxes & fees
Jun 24 - Jun 25
Manor Suite,cozy newly renovated,downtown & beach

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 CA $649
CA $1,837 total
includes taxes & fees
Jun 24 - Jun 25
NEW! Gray Woodland Escape | Golf, Pool & Cinema

Cozy Family Home w/ Beach Access

Cozy Family Home w/ Beach Access
Raymond
The price is CA $188
CA $656 total
includes taxes & fees
Jun 24 - Jun 25
Cozy Family Home w/ Beach Access

Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is CA $222
CA $541 total
includes taxes & fees
Jul 1 - Jul 2
Tranquility between the Lakes & Sea

⚓ 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, (8 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 CA $471
CA $872 total
includes taxes & fees
Jun 24 - Jun 25
⚓ Cozy 3BR Coastal Retreat • Private Yard & Fire Pit • 5 Min to Beach!

Serenity between the lakes and seashore

Serenity between the lakes and seashore
Westbrook
9.8 out of 10, Exceptional, (26 reviews)
"Lovely apartment in a great location!David was a wonderful host, very friendly, accommodating, communicative, and quick to assist when needed. He even put up some Christmas decorations!Clean and comfortable, nicely stocked kitchen for spices, coffee, and staples. I cannot recommend enough - we will stay here again."
United States
Darcy G.
The price is CA $282
CA $578 total
includes taxes & fees
Jun 26 - Jun 27
Serenity between the lakes and seashore

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 CA $1,465
CA $2,352 total
includes taxes & fees
Jul 6 - Jul 7
Sunny Beachfront Cottage with Spectacular Ocean Views

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 CA $1,129
CA $1,927 total
includes taxes & fees
Jul 1 - Jul 2
A historic treasure in Southern Maine, very unique and spacious

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (53 reviews)
"Wonderful stay!"
United States
Erika T.
The price is CA $287
CA $524 total
includes taxes & fees
Jul 1 - Jul 2
Full sized home

Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport

Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
Freeport
10.0 out of 10, Exceptional, (8 reviews)
"Incredible location right in downtown Freeport, and an even better host. We will definitely be staying with Jared again."
United States
Jake P.
The price is CA $395
CA $1,032 total
includes taxes & fees
Jun 25 - Jun 26
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport

•Peaceful Private Freeport 2 BR Home on the Ocean•

•Peaceful Private Freeport 2 BR Home on the Ocean•
Freeport
The price is CA $544
CA $1,119 total
includes taxes & fees
Jul 2 - Jul 3
•Peaceful Private Freeport 2 BR Home on the Ocean•

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)
"We had a wonderful stay! "
United States
Ashma B.
The price is CA $1,061
CA $2,902 total
includes taxes & fees
Jun 24 - Jun 25
Classic New England Waterfront House Big Lawn Beautiful Sunrise

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 CA $2,268
CA $5,432 total
includes taxes & fees
Jul 22 - Jul 23
Family Tides by Bayley Vacation Rentals

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 CA $446
CA $1,040 total
includes taxes & fees
Jul 14 - Jul 15
30 Acres with Woodland Trails and Playground

Cozy Library Tiny Home *Private Hot Tub* King Bed *Minutes to Lakes & Hiking

Cozy Library Tiny Home *Private Hot Tub* King Bed *Minutes to Lakes & Hiking
Bridgton
10.0 out of 10, Exceptional, (15 reviews)
"Very quaint and quiet, we enjoyed our staying very much would heavily recommend"
United States
Jacob B.
The price is CA $256
CA $512 total
includes taxes & fees
Jun 30 - Jul 1
Cozy Library Tiny Home *Private Hot Tub* King Bed *Minutes to Lakes & Hiking

Luxe 5 Bed/ 3 Bath with Game Room & AC

Luxe 5 Bed/ 3 Bath with Game Room & AC
Yarmouth
10.0 out of 10, Exceptional, (1 review)
"What a beautiful home! Everything about our stay was perfect. The home has everything you could possibly need and more. My family stayed for a long weekend and everyone was so happy with the accommodations. Hoping to go back!"
United States
Lisa L.
The price is CA $666
CA $1,534 total
includes taxes & fees
Jun 28 - Jun 29
Luxe 5 Bed/ 3 Bath with Game Room & AC

Hank's Hideaway by Bayley Vacation Rentals

Hank's Hideaway by Bayley Vacation Rentals
Grand Beach
9.4 out of 10, Exceptional, (11 reviews)
"It was an easy walk to the beach and there are some good walkable restaurants and bars. Easy to park at municipal parking lot and access everything at old orchard beach"
United States
Debra C.
The price is CA $318
CA $2,035 total
includes taxes & fees
Jun 28 - Jun 29
Hank's Hideaway by Bayley Vacation Rentals

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 CA $414
CA $1,001 total
includes taxes & fees
Jun 30 - Jul 1
Huge New Townhome 10mins from the Beach

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)
"This is such a great house and it was perfect for our group! We would definitely stay there again "
United States
Catherine T.
The price is CA $1,546
CA $2,211 total
includes taxes & fees
Jun 24 - Jun 25
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
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

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Windham Vacation Homes information

Number of reviews
292
Accommodation
953 Vacation Homes
Lowest Price
CA $261
Highest Price
CA $5,432

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