Windham Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Holiday Rentals in Windham

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (68)
"Absolutely beautiful place to stay. "
The price is NZ$775
includes taxes & fees
14 Aug - 15 Aug
The Weldon Hotel

68 East Grand Ave

3.0 star property
8.0 out of 10, Very good, (6)
"Great location. "
68 East Grand Ave

Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

9.8 out of 10, Exceptional, (213)
"We stayed off season to just get away. The beach view is really nice. We went to the restaurant downstairs for food and live music. Very convenient! Place was clean. "
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

Studio Unit Walkable Everywhere

The price is NZ$354
includes taxes & fees
10 Aug - 11 Aug
Studio Unit Walkable Everywhere

Gorgeous ocean-front home with stunning beach views

9.4 out of 10, Exceptional, (115)
"This property worked well for us. Ocean view was fantastic, beds were comfy, garage was handy for our car. Good in shoulder season, would like to come back and try it in the summer."
Gorgeous ocean-front home with stunning beach views

New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location

9.0 out of 10, Wonderful, (6)
The price is NZ$522
includes taxes & fees
12 Aug - 13 Aug
New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location

Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property was as described, clean, and in a quiet neighborhood. Conveniently located to many local attractions. Check in and check out process was smooth. Overall enjoyed my stay very much. "
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

Sensational Beachfront Property Old Orchard Beach, with indoor elevator

9.6 out of 10, Exceptional, (62)
"Beautiful location even in the offseason, gorgeous house with plenty of room for guests. Very close to Portland for a nice dinner and some drinks. We also went and played some golf at summit in OOB and had a blast. Outdoor grill was perfect and overall we had a great time! Excellent host excellent location and perfect for what we needed. Would recommend highly."
Sensational Beachfront Property Old Orchard Beach, with indoor elevator

4-bedroom vacation home steps to Old Orchard Beach Pier

10.0 out of 10, Exceptional, (11)
"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

Little Miss Cottages

2.5 star property
8.4 out of 10, Very good, (86)
"Cute and tidy cottage, easy walk to beautiful beach."
Little Miss Cottages

Bright and airy condo with beachfront access and walkable entertainment nearby

8.0 out of 10, Very good, (1)
"Not a bad spot. Just don't expect too much in the way of frills and be prepared to be flexible with sleeping/parking arrangements."
Bright and airy condo with beachfront access and walkable entertainment nearby

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

9.8 out of 10, Exceptional, (50)
"We enjoyed ourselves very much! Close to everything we wanted to do. Would stay again."
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

10.0 out of 10, Exceptional, (1)
"We enjoyed our stay there .the cottage was clean loved the charm of the place. Host was very helpful. Will return again. "
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

350 Yards to the beach. Pet friendly!

8.2 out of 10, Very good, (30)
"Clean, easy access to everything! Fantastic stay will come again! Thank you!"
350 Yards to the beach. Pet friendly!

Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC

10.0 out of 10, Exceptional, (2)
"Cute cabin in small quiet campground close to pool and short walk to downtown. The cabin itself was clean, cozy, and had everything we needed for a comfortable stay. Perfect for a small family getaway or a relaxing weekend."
Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC

Rustic-Modern Barn Retreat Near OOB Beach & Pier

10.0 out of 10, Exceptional, (1)
"Place was great. We had some issues with tv but host was helpful and super responsive! The small one in bedroom never worked but I didn’t reach back out for help as we didn’t need it. Walkable to OOB but little far without a wagon if you require lots of beach gear (we had surf and boogie boards so we just drive down which is fine.) Also, I thought there was a sleep sofa but it was a sofa with a chaise but we made it work for my son! I can’t say enough about the host, so accommodating and...
The price is NZ$950
includes taxes & fees
24 Aug - 25 Aug
Rustic-Modern Barn Retreat Near OOB Beach & Pier

Beach House ∆ Prime Location ∆ Steps to the Ocean

10.0 out of 10, Exceptional, (44)
"The house is in a wonderful location with great views of the ocean from several rooms. The listing photos really do tell the story of this beautiful home. The beach is just a few steps away from the property. Attention to detail was obviously put in to ensure a wonderful guest experience. The home is very clean, there are practical amenities throughout (4 smart TV’s), and our host was super communicative and accommodating. Portland & Saco being a short drive away is just icing on the cake. Can’t...
Beach House ∆ Prime Location ∆ Steps to the Ocean

2 bedroom cottage

9.2 out of 10, Wonderful, (5)
"quiet, clean, short walk to beach"
2 bedroom cottage

Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location

10.0 out of 10, Exceptional, (15)
"Stunning property and great location! "
The price is NZ$1,164
includes taxes & fees
2 Sept - 3 Sept
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location

Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !

10.0 out of 10, Exceptional, (36)
"The view is beautiful and has everything you need "
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Windham Hotel Reviews

Frequently asked questions

Are there holiday rentals in Windham?

Yes, there are holiday rentals in Windham close to Maine Wildlife Park, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Windham speak positively about the lakeside and restaurants in this destination. Make sure you have time to check out the shopping and coffee shops during your trip.

What are some of the best holiday rentals that Windham has to offer?

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach: This holiday home rental outside of Windham offers a garden, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Windham?

Expedia has 31 holiday rentals for your stay in Windham.

What can I see and do in Windham?

Family-friendly attractions include Maine Wildlife Park and Seacoast Adventure, whereas Little Sebago Lake and Sebago Lake are a couple of great spots to enjoy the outdoors. Other places in town to visit include Sebago Lake Basin and Jordan Bay.

What are holiday rentals like in Windham?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windham. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.