Windham Vacation Rentals

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Vacation Rentals in Windham

Vacation Home in Windham

9.4 out of 10, Exceptional, (8)
"Great property! So convenient "
United States
Adam B.
The Lookout on Pettingill Pond - waterfront house, 5 min from Sebago Lake!

Aparthotel in Downtown Portland

4.5 star property
9.8 out of 10, Exceptional, (87)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
$238 nightly
The price is $253
Nov 29 - Nov 30
Total with taxes and fees
The Weldon Hotel

Vacation Home in Bailey Island

10.0 out of 10, Exceptional, (233)
"Tremendous stay, great property and host."
United States
Curtis G.
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Vacation Home in Old Orchard Beach

9.8 out of 10, Exceptional, (45)
"Excellent family stay. Backyard is nice and shaded, you can see the ocean from the house and amenities are great. "
United States
Danielle N.
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!

Vacation Home in Old Orchard Beach

9.6 out of 10, Exceptional, (67)
"In one word AMAZING! We rented this property to gather our immediate family, adult children and grandchildren. We had a tragedy in our family as my oldest son was killed, this made our once close family, split apart. This property was so beautiful and such a happy place to be that my prayers were answered my family began the healing process. The location and the views one could not be unhappy. Thank you Jason for helping to make the stay amazing!"
United States
Helen F.
$1,598 nightly
The price is $1,742
Dec 5 - Dec 6
Total with taxes and fees
Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Vacation Home in Old Orchard Beach

9.8 out of 10, Exceptional, (97)
"The location was perfect and the house was exceptional. The host and property manager were very responsive and helpful. Would definitely recommend a stay!"
United States
Kathleen C.
$1,027 nightly
The price is $1,119
Dec 3 - Dec 4
Total with taxes and fees
Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!

Cabin in Raymond

10.0 out of 10, Exceptional, (48)
"We loved this cabin! A stone throw from the lake. Private and quiet. "
United States
Kathy K.
Sebago Lake Cottage on Raymond Cape

Condo in Old Orchard Beach

9.4 out of 10, Exceptional, (126)
"Loved the area. Close to shops and dining. Beach is absolutely beautiful. Perfect place for families."
United States
Victoria H.
Gorgeous ocean-front home with stunning beach views

Vacation Home in Grand Beach

2.0 star property
9.0 out of 10, Wonderful, (17)
"Great location. Beautiful view. Peaceful part of the beach. "
United States
Kristi N.
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

Vacation Home in Poland

9.8 out of 10, Exceptional, (15)
"Great location on Thompson lake! Nice dock and swim platform plus sandy beach area. "
United States
Julie W.
Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views

Apartment in West Bayside

8.6 out of 10, Excellent, (16)
"Host was very accommodating. Apartment worked well for. Description accurate. Would stay again."
United Kingdom
Martha F.
$154 nightly
The price is $156
Nov 24 - Nov 25
Total with taxes and fees
In-town no frills 2 bedroom apt

Vacation Home in Old Orchard Beach

9.2 out of 10, Wonderful, (5)
"Wonderful stay for a small bachelorette party! Right squeeze with 7 girls but great to have the place already decorated. Very close to the pier and lots of stores, restaurants, and places to go around. Host was very friendly and accommodating, answered questions and was flexible with any of our needs!"
United States
Margaret D.
$686 nightly
The price is $748
Nov 23 - Nov 24
Total with taxes and fees
The Dollhouse

Apartment in Deering Center

9.2 out of 10, Wonderful, (5)
"Great location for seeing the Portland Head Lighthouse. Comfortable bed."
United States
Michelle S.
Private Entrance Residential Portland

Apartment in Harpswell

9.6 out of 10, Exceptional, (169)
"Very clean beautiful view we definitely enjoyed ourselves "
United States
Ilona F.
1 room luxury ocean front studio cottage

Vacation Home in Biddeford

9.8 out of 10, Exceptional, (126)
"Beautiful place "
United States
Robert D.
The Moonglow! A beautiful ocean view house in Biddeford!

Apartment in West Bayside

5.8 out of 10, (6)
"We didn't stay there at all. Canceled reservation "
United States
Dianne
$144 nightly
The price is $145
Nov 23 - Nov 24
Total with taxes and fees
Studio Unit Walkable Everywhere

Cabin in Old Orchard Beach

9.8 out of 10, Exceptional, (12)
"Walking distance to the board walk. Clean and just enough space for 4 of us. Had everything we needed plus plenty of towels! "
United States
Natalia R.
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

Cabin in Standish

9.8 out of 10, Exceptional, (6)
"Charming cabin. Well maintained. Loved my stay! Highly recommend."
United States
Danny B.
$165 nightly
The price is $180
Nov 27 - Nov 28
Total with taxes and fees
THE LILLIPAD.Off-grid A frame. Sebago lake region!

Cottage in Old Orchard Beach

9.8 out of 10, Exceptional, (64)
"Place was great and fenced in backyard for our dog. "
United States
Billy N.
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Cabin in Naples

10.0 out of 10, Exceptional, (313)
"Peaceful and relaxing it was the perfect getaway"
United States
melissa d.
Romantic getaway for 2 PEAK fall foliage!!!
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

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 $145 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.

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?

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: This vacation home near Windham is located on the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Windham?

Expedia has 32 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.