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Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 894 Vacation Homes in Windham with updated reviews, rates, and availability.

Rent a room in the gorgeous Holt House
Exterior

Rent a room in the gorgeous Holt House

8.0 out of 10, Very Good, (25)
"This was a perfect place, close to everything in Portland! "
Rent a room in the gorgeous Holt House
Dog-friendly cottage with deck & porch - walk to the beach, pier & town
Beach nearby

Dog-friendly cottage with deck & porch - walk to the beach, pier & town

8.2 out of 10, Very Good, (13)
"Dog friendly."
Dog-friendly cottage with deck & porch - walk to the beach, pier & town
Why rent a Hotel when you can have a whole House!!
Fridge, microwave, oven, stovetop

Why rent a Hotel when you can have a whole House!!

10.0 out of 10, Exceptional, (57)
"this place is a hidden gem located on a little slice of heaven! We can NOT wait to book our next trip there!"
Why rent a Hotel when you can have a whole House!!
Cozy Waterfront cottage with Private dock- dog friendly!
Miscellaneous

Cozy Waterfront cottage with Private dock- dog friendly!

10.0 out of 10, Exceptional, (20)
"We loved our stay! The property is beautiful, and you can’t beat waking up to the view of the lake right outside your window. Would absolutely book again! "
Cozy Waterfront cottage with Private dock- dog friendly!
Convenient Portland home 3 miles from Downtown
Fridge, microwave, oven, stovetop

Convenient Portland home 3 miles from Downtown

10.0 out of 10, Exceptional, (22)
"The reclining furniture was our favorite after running around all day! Very comfortable beds! Great place to stay!"
The price is AED 1,377
AED 3,111 total
includes taxes & fees
3 Jul - 4 Jul
Convenient Portland home 3 miles from Downtown
Beachfront | Just steps and you're on the beach!
On the beach

Beachfront | Just steps and you're on the beach!

Beachfront | Just steps and you're on the beach!
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!
Smart TV, video games, table tennis, books

Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

8.2 out of 10, Very Good, (50)
"We had a large group and had more than enough beds and plenty of space to hang out. Would recommend for a big group or a family looking to spread out!"
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!
4-bedroom vacation home steps to Old Orchard Beach Pier
Sun loungers, beach towels

4-bedroom vacation home steps to Old Orchard Beach Pier

9.8 out of 10, Exceptional, (6)
"Mitchells home was PERFECT.Always quick to communicate and very accommodating. If you are looking for a great place to stay I cant say enough good things. Well stocked he has thought of everything people need when away. He even has games to play which was a nice surprise. You wont regret staying bere! Thanks again so much Mitchell!!!"
4-bedroom vacation home steps to Old Orchard Beach Pier
Spacious 5BR Family Dream with Private Beach Access
Private kitchen

Spacious 5BR Family Dream with Private Beach Access

The price is AED 868
AED 2,199 total
includes taxes & fees
3 Jun - 4 Jun
Spacious 5BR Family Dream with Private Beach Access
Fantastic lakefront escape with large deck, private dock, fast WiFi, & gas grill
Aerial view

Fantastic lakefront escape with large deck, private dock, fast WiFi, & gas grill

8.8 out of 10, Excellent, (16)
"Beautiful views, modern amenities, comfortable beds, well stocked, reasonably priced."
Fantastic lakefront escape with large deck, private dock, fast WiFi, & gas grill
Five miles from the beach, newly remodeled home with lots of privacy.
Fridge, microwave, oven, stovetop

Five miles from the beach, newly remodeled home with lots of privacy.

10.0 out of 10, Exceptional, (48)
"This is a lovely place for us to stay, it is always clean and the owners are really wonderful. It is the place for us to stay while visiting"
Five miles from the beach, newly remodeled home with lots of privacy.
Entire Home in Sunny Saco + Gym
Fridge, microwave, oven, dishwasher

Entire Home in Sunny Saco + Gym

10.0 out of 10, Exceptional, (9)
"The home was very clean and comfortable. Location was great. Property manager gave us some recommendations for things to visit"
Entire Home in Sunny Saco + Gym
East Grand Ave Fabulous Cottage
Beach

East Grand Ave Fabulous Cottage

9.2 out of 10, Wonderful, (132)
"The cottage was very comfortable, clean, well equipped and near to the beach, close to all amenities. Host was very responsive to our needs. Lovely visit!!"
East Grand Ave Fabulous Cottage
Maine Cottage
Property grounds

Maine Cottage

9.8 out of 10, Exceptional, (77)
"Second time staying at this property and will definitely stay again !!! "
Maine Cottage
The Moonglow! A beautiful ocean view house in Biddeford!
Terrace/patio

The Moonglow! A beautiful ocean view house in Biddeford!

9.8 out of 10, Exceptional, (109)
"Stayed here for a week in February. Excellent location for walking on the beach every day."
The Moonglow! A beautiful ocean view house in Biddeford!
Cute House -2 Blocks from Beach
Sun loungers, beach towels

Cute House -2 Blocks from Beach

9.4 out of 10, Exceptional, (24)
"Nice place with two bedrooms and a full kitchen. While it looks small from the outside, it’s is nicely roomy inside. "
Cute House -2 Blocks from Beach
Old Orchard Beach, Surfside 3 Bedroom End Unit Townhouse- 4 houses from beach
Beach

Old Orchard Beach, Surfside 3 Bedroom End Unit Townhouse- 4 houses from beach

Old Orchard Beach, Surfside 3 Bedroom End Unit Townhouse- 4 houses from beach
Walk to Beach: Maine Home w/ Hot Tub & Deck!
Fridge, microwave, stovetop, dishwasher

Walk to Beach: Maine Home w/ Hot Tub & Deck!

9.4 out of 10, Exceptional, (33)
"We had a great time. We’d like to book late July next year if possible "
Walk to Beach: Maine Home w/ Hot Tub & Deck!
Charming, comfortable 2 Bedroom, One Bath, home, gorgeous views of Lowell's Cove--A great homeba...
Property grounds

Charming, comfortable 2 Bedroom, One Bath, home, gorgeous views of Lowell's Cove--A great homeba...

10.0 out of 10, Exceptional, (1)
"Cottage is Bristol. Owners are extremely hospitable. Peaceful and quiet. "
Charming, comfortable 2 Bedroom, One Bath, home, gorgeous views of Lowell's Cove--A great homeba...
Walk to the Beach - 3 bedroom house with outdoor fire pit
Beach nearby

Walk to the Beach - 3 bedroom house with outdoor fire pit

9.8 out of 10, Exceptional, (19)
"Had a great time and lovely property!"
Walk to the Beach - 3 bedroom house with outdoor fire pit
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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