A white church with a steeple and red accents, surrounded by autumn trees.

Windham Vacation Rentals

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Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Windham vacation rentals

House (2 Bedrooms) | Interior

1 Mi to Maine Street! Mcm-style Home in Brunswick

1 Mi to Maine Street! Mcm-style Home in Brunswick
3.0 star property
Brunswick
$282 nightly
The price is $307
Jul 16 - Jul 17
Total with taxes and fees
1 Mi to Maine Street! Mcm-style Home in Brunswick
Terrace/patio

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (53 reviews)
"Wonderful stay!"
United States
Erika T.
$336 nightly
The price is $366
Jul 1 - Jul 2
Total with taxes and fees
Full sized home
Outdoor dining

'Osprey Cottage' South Freeport Home on Casco Bay!

'Osprey Cottage' South Freeport Home on Casco Bay!
Freeport
8.8 out of 10, Excellent, (22 reviews)
"This was an adorable cottage in a picturesque location. The cottage was clean and comfortable, right on the water. Additional friends stayed in the adjacent Heron cottage, and we joined them on the patio for a fire one evening as summer faded to autumn."
United States
John J.
$593 nightly
The price is $644
Jul 19 - Jul 20
Total with taxes and fees
'Osprey Cottage' South Freeport Home on Casco Bay!
Interior

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (27 reviews)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
$368 nightly
The price is $401
Jul 6 - Jul 7
Total with taxes and fees
Sunny Spot with Private Parking.
Smart TV

Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (35 reviews)
"Absolutely wonderful little place to stay in Scarborough! "
United States
Eric S.
$332 nightly
The price is $362
Jul 1 - Jul 2
Total with taxes and fees
Pine Point Beach private, quaint, charming studio.
Interior

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Old Orchard Beach
9.8 out of 10, Exceptional, (75 reviews)
"Place was great and fenced in backyard for our dog. "
United States
Billy N.
$236 nightly
The price is $258
Jul 1 - Jul 2
Total with taxes and fees
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Honeymoon Studio | Egyptian cotton sheets, premium bedding, down comforters, bed sheets

Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
$457 nightly
The price is $498
Jul 2 - Jul 3
Total with taxes and fees
Fortland Island Campground
Beach nearby, sun loungers, beach towels

Charming Pine Point OOB Beach Cottage Tiny House, Steps away from the beach

Charming Pine Point OOB Beach Cottage Tiny House, Steps away from the beach
Grand Beach
9.8 out of 10, Exceptional, (47 reviews)
"Stay was good. It was clean well decorated and equipped with everything you need"
United States
Tom K.
$306 nightly
The price is $334
Jul 21 - Jul 22
Total with taxes and fees
Charming Pine Point OOB Beach Cottage Tiny House, Steps away from the beach
Beach nearby, sun loungers, beach towels

Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland

Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland
Pine Point
9.6 out of 10, Exceptional, (43 reviews)
"Beautiful, clean place to stay and dogs welcome "
United States
Anonymous traveler
$331 nightly
The price is $361
Jul 1 - Jul 2
Total with taxes and fees
Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland
Sun loungers

The Saco Suite - Downtown, Dog Friendly, Sleeps 4, Walk to Bars & Restaurants!

The Saco Suite - Downtown, Dog Friendly, Sleeps 4, Walk to Bars & Restaurants!
Downtown Saco
10.0 out of 10, Exceptional, (24 reviews)
"Great space, responsive host, great location!"
United States
Reed C.
The Saco Suite - Downtown, Dog Friendly, Sleeps 4, Walk to Bars & Restaurants!
Beach

City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (130 reviews)
"Wonderful place! Owner very responsible! Would stay again! Great choice for place to stay away from home."
United States
Arlene L.
$464 nightly
The price is $505
Jul 5 - Jul 6
Total with taxes and fees
City Amenities, Casco Bay Sunrises and Natural Beauty
Terrace/patio

Secluded A-Frame Cabin Retreat in Oxford

Secluded A-Frame Cabin Retreat in Oxford
Oxford
10.0 out of 10, Exceptional, (2 reviews)
"Peaceful, beautiful, and everything we wanted ( exception of rain)! Would highly recommend and ca not wait to go back!"
United States
Kelly S.
$369 nightly
The price is $402
Jul 12 - Jul 13
Total with taxes and fees
Secluded A-Frame Cabin Retreat in Oxford
Outdoor dining

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

THE LILLIPAD.Off-grid A frame. Sebago lake region!
Standish
9.8 out of 10, Exceptional, (9 reviews)
"Great view of the pond and nice accommodations for a single guest."
United States
Brian M.
$165 nightly
The price is $180
Jul 7 - Jul 8
Total with taxes and fees
THE LILLIPAD.Off-grid A frame. Sebago lake region!
Outdoor dining

Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.6 out of 10, Exceptional, (10 reviews)
"Apartment was very cute, clean, and just what I was looking for. Jennifer was very accommodating and understanding "
United States
Jolee S.
$399 nightly
The price is $435
Jul 12 - Jul 13
Total with taxes and fees
Peaceful & minutes from the Old Port with private parking
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.
$759 nightly
The price is $827
Jul 1 - Jul 2
Total with taxes and fees
Spacious Home Close to Beaches! 3BR, Dog & Family Friendly, 30 Mins to Portland
Property grounds

Garden Getaway with Hot Tub

Garden Getaway with Hot Tub
Downtown Saco
9.8 out of 10, Exceptional, (8 reviews)
"Great place to stay at a great location! "
United States
Holly W.
$382 nightly
The price is $416
Jul 1 - Jul 2
Total with taxes and fees
Garden Getaway with Hot Tub
Smart TV, fireplace

Sunny Cottage

Sunny Cottage
Biddeford
10.0 out of 10, Exceptional, (54 reviews)
"Exactly as described, close to everything."
United States
Erika J.
$327 nightly
The price is $357
Jul 7 - Jul 8
Total with taxes and fees
Sunny Cottage
Fridge, microwave, oven, stovetop

New Listing! AmongstTheAspens - Off-Grid Tiny Home

New Listing! AmongstTheAspens - Off-Grid Tiny Home
Saco
9.2 out of 10, Wonderful, (15 reviews)
"Had a great stay, very private property. House was very clean and user friendly. Would definitely stay again, thanks"
United States
Doug C.
$304 nightly
The price is $331
Jul 29 - Jul 30
Total with taxes and fees
New Listing! AmongstTheAspens - Off-Grid Tiny Home
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)
$1,185 nightly
The price is $1,291
Jul 1 - Jul 2
Total with taxes and fees
NEW! Gray Woodland Escape | Golf, Pool & Cinema
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.
$3,430 nightly
The price is $3,726
Jul 22 - Jul 23
Total with taxes and fees
Family Tides by Bayley Vacation Rentals
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

Old Orchard Beach Inn

Old Orchard Beach Inn

10/10 Excellent
"Near the main attractions in OO, walking distance Good breakfast for value Friendly staff"
Gaetan 2-night trip
Posted less than an hour ago
Old Orchard Beach Inn

Find out more about Windham

Everything you need to know about Windham vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windham vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windham vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windham vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windham. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windham in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $180 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windham rentals

At Expedia, we put the best Windham vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windham vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Windham?

Yes, we offer vacation rentals in Windham near Seacoast Adventure, or you can go with a more remote option if you're looking for extra privacy while you relax. Visitors to Windham speak positively about the lakeside and restaurants in this destination. Make sure you have time to check out the shopping and coffeehouses during your trip.

What are some of the best vacation rentals in Windham?

Cozy & Quiet Home in Portland Maine. One Bedroom, Private Bathroom “No Kitchen”: This vacation home rental near Windham is located on the beach and offers a fireplace, air-conditioning, and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and an electric kettle.

How many vacation rentals are there in Windham?

Expedia has 35 vacation rentals for your stay in Windham.

What can I see and do in Windham?

Little Sebago Lake and Sebago Lake are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Seacoast Adventure. Other places in town to visit include Sebago Lake Basin and Jordan Bay.

What are vacation rentals like in Windham?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Windham. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from public hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a family getaway.