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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Windham vacation homes

TV, offices

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.
Windham Lakefront: Fire Pit and Modern Comforts
Property grounds

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 AED 370
AED 663 total
includes taxes & fees
28 Jun - 29 Jun
Manor Suite,cozy newly renovated,downtown & beach
Fridge, microwave, oven, dishwasher

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 AED 2,241
AED 5,547 total
includes taxes & fees
6 Jul - 7 Jul
NEW! Gray Woodland Escape | Golf, Pool & Cinema
Beach nearby

Cozy Family Home w/ Beach Access

Cozy Family Home w/ Beach Access
Raymond
The price is AED 591
AED 1,810 total
includes taxes & fees
30 Jun - 1 Jul
Cozy Family Home w/ Beach Access
Interior

Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is AED 569
AED 1,389 total
includes taxes & fees
30 Jun - 1 Jul
Tranquility between the Lakes & Sea
3 bedrooms, desk, iron/ironing board, travel crib

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

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 AED 562
AED 1,277 total
includes taxes & fees
26 Jun - 27 Jun
Serenity between the lakes and seashore
Exterior

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 AED 3,802
AED 6,106 total
includes taxes & fees
6 Jul - 7 Jul
Sunny Beachfront Cottage with Spectacular Ocean Views
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 AED 2,891
AED 4,949 total
includes taxes & fees
1 Jul - 2 Jul
A historic treasure in Southern Maine, very unique and spacious
Terrace/patio

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (53 reviews)
"Wonderful stay!"
United States
Erika T.
The price is AED 744
AED 1,363 total
includes taxes & fees
1 Jul - 2 Jul
Full sized home
Fridge, microwave, oven, stovetop

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, (10 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 AED 1,117
AED 2,794 total
includes taxes & fees
9 Jul - 10 Jul
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
Terrace/patio

•Peaceful Private Freeport 2 BR Home on the Ocean•

•Peaceful Private Freeport 2 BR Home on the Ocean•
Freeport
The price is AED 1,340
AED 2,814 total
includes taxes & fees
13 Jul - 14 Jul
•Peaceful Private Freeport 2 BR Home on the Ocean•
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)
"We had a wonderful stay! "
United States
Ashma B.
The price is AED 2,388
AED 7,022 total
includes taxes & fees
29 Jun - 30 Jun
Classic New England Waterfront House Big Lawn Beautiful Sunrise
Dining

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 AED 5,887
AED 13,597 total
includes taxes & fees
22 Jul - 23 Jul
Family Tides by Bayley Vacation Rentals
Exterior detail

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
30 Acres with Woodland Trails and Playground
Smart TV, fireplace, books

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 AED 661
AED 1,321 total
includes taxes & fees
30 Jun - 1 Jul
Cozy Library Tiny Home *Private Hot Tub* King Bed *Minutes to Lakes & Hiking
Smart TV

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 AED 1,872
AED 4,082 total
includes taxes & fees
28 Jun - 29 Jun
Luxe 5 Bed/ 3 Bath with Game Room & AC
Fridge, microwave, oven, stovetop

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 AED 824
AED 5,250 total
includes taxes & fees
28 Jun - 29 Jun
Hank's Hideaway by Bayley Vacation Rentals
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 AED 964
AED 2,408 total
includes taxes & fees
30 Jun - 1 Jul
Huge New Townhome 10mins from the Beach
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)
"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 AED 4,545
AED 6,416 total
includes taxes & fees
29 Jun - 30 Jun
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

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

8/10 Good
"The room was very clean along with the bedding. We were on the first floor and the individual in the room above us never stopped walking back and forth. Most of the night also. Breakfast was good. Sausage and eggs as well as yogurt. Waffles. Serial etc. Staff was polite and the air conditioning worked well. The less than optimal sound deadening is a small gripe that is likely shared with most hotels. There is one small gripe. The bathroom while clean had no rods to hang your used towels or your clothing. Overall it was a good experience."
David 1-night trip
Posted less than an hour ago
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

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