Windham Vacation Rentals

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Vacation Rentals in Windham

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (71)
"Absolutely beautiful place to stay. "
The price is CA $557
CA $711 total
includes taxes & fees
Aug 26 - Aug 27
The Weldon Hotel

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

9.8 out of 10, Exceptional, (215)
"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. "
The price is CA $466
CA $753 total
includes taxes & fees
Sep 1 - Sep 2
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

Grand Victorian on the Beach, Summer

9.8 out of 10, Exceptional, (75)
"Wonderful spot with great accommodations! Would definitely stay again!"
Grand Victorian on the Beach, Summer

68 East Grand Ave

3.0 star property
8.0 out of 10, Very good, (7)
"Great location. "
68 East Grand Ave

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

Sensational Beachfront Property Old Orchard Beach, with indoor elevator

9.6 out of 10, Exceptional, (62)
"Our stay was perfect. The house allowed for us to sleep 17 people comfortably, eat together, cook in teams for a progressive dinner and spread out all at the same time. Jason was quick to answer questions, and he provided excellent suggestions for places to eat and shop. We could not be more pleased with our stay. Thank you, Jason!!"
Sensational Beachfront Property Old Orchard Beach, with indoor elevator

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

10.0 out of 10, Exceptional, (16)
"Stunning property and great location! "
The price is CA $545
CA $951 total
includes taxes & fees
Sep 1 - Sep 2
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location

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

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.

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

9.0 out of 10, Wonderful, (6)
The price is CA $342
CA $426 total
includes taxes & fees
Aug 26 - Aug 27
New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location

4-bedroom vacation home steps to Old Orchard Beach Pier

10.0 out of 10, Exceptional, (14)
"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

350 Yards to the beach. Pet friendly!

8.0 out of 10, Very good, (33)
"Clean, easy access to everything! Fantastic stay will come again! Thank you!"
The price is CA $269
CA $474 total
includes taxes & fees
Aug 20 - Aug 21
350 Yards to the beach. Pet friendly!

Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.

7.4 out of 10, Good, (26)
"The cute apartment was clean with super comfy beds and very convenient to everything in OOB."
The price is CA $344
CA $600 total
includes taxes & fees
Sep 1 - Sep 2
Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.

Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)

9.8 out of 10, Exceptional, (126)
"Right on the beach. Beautiful view. Clean and well appointed apartment Would definitely recommend and return "
Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)

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

9.8 out of 10, Exceptional, (53)
"We enjoyed ourselves very much! Close to everything we wanted to do. Would stay again."
The price is CA $249
CA $414 total
includes taxes & fees
Sep 14 - Sep 15
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

2 min walk to the beach. Pet friendly condo

8.2 out of 10, Very good, (36)
"Host was very accommodating and easy to contact & communicate with. I'll definitely stay again! Highly recommended "
The price is CA $207
CA $396 total
includes taxes & fees
Sep 1 - Sep 2
2 min walk to the beach. Pet friendly condo

Little Miss Cottages

2.5 star property
8.4 out of 10, Very good, (87)
"Cute and tidy cottage, easy walk to beautiful beach."
Little Miss Cottages

New 2-bedroom cabin with WiFi, AC in delightful Old Orchard Beach

10.0 out of 10, Exceptional, (2)
"A beautiful home, very clean, and a perfect location for us. Short walking distance to everything we wanted to do. "
New 2-bedroom cabin with WiFi, AC in delightful Old Orchard Beach

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

10.0 out of 10, Exceptional, (5)
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!

9.8 out of 10, Exceptional, (42)
"This place is a real gem. Really clean, well equipped and for our two kids it was perfect (toys inside and playground in the yard. The host is very kind and very quick to fulfill our needs. Thanks again!"
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!
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

Frequently asked questions

Are there vacation rentals in Windham?

Yes, we offer vacation rentals in Windham near Maine Wildlife Park, 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?

4-bedroom vacation home steps to Old Orchard Beach Pier: This vacation home rental near Windham offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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?

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 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.