Compare Windham Vacation Rentals

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Windham Rentals

Classic Maine Cabin, Private Waterfront Easy Access to Nearby Amenities

Classic Maine Cabin, Private Waterfront Easy Access to Nearby Amenities

2 out of 5
6.92 mi from city center
At this cabin, guests have access to features like laundry facilities.
Refurbished waterfront 1950s cabin with sauna, firepit, grill & kayaks - dogs ok

Refurbished waterfront 1950s cabin with sauna, firepit, grill & kayaks - dogs ok

11.83 mi from city center
This apartment features a sauna and barbecue grills.
In-town no frills 2 bedroom apt

In-town no frills 2 bedroom apt

9.67 mi from city center
$233 nightly
The price is $235 total per night
$235 total
Jul 13 - Jul 14
Total includes taxes and fees
This apartment is a smoke-free apartment building.
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
54 York St, Portland, ME
Free Cancellation
10.18 mi from city center
$458 nightly
The price is $492 total per night
$492 total
Jul 20 - Jul 21
Total includes taxes and fees
A 24-hour gym and free WiFi in public areas are features at The Weldon Hotel. Self parking is available for USD 40 per night. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls.
AmongstTheAspens - Tiny House in a serene location

AmongstTheAspens - Tiny House in a serene location

15.06 mi from city center
$295 nightly
The price is $322 total per night
$322 total
Jul 8 - Jul 9
Total includes taxes and fees
Guests of New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location enjoy access to a water park, laundry facilities, and barbecue grills.
100 feet from the ocean 3 bedroom cottage 420 friendly

100 feet from the ocean 3 bedroom cottage 420 friendly

16.51 mi from city center
Guests of this cottage enjoy access to a water park, laundry facilities, and a garden. This cottage also has barbecue grills.
68 East Grand Ave

68 East Grand Ave

3 out of 5
68 E Grand Ave, Old Orchard Beach, ME
16.52 mi from city center
A stay here includes free parking.
Gorgeous ocean-front home with stunning beach views

Gorgeous ocean-front home with stunning beach views

16.63 mi from city center
Guests of this condo enjoy features like a water park and laundry facilities.
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

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

17.04 mi from city center
$239 nightly
The price is $260 total per night
$260 total
Jul 8 - Jul 9
Total includes taxes and fees
Guests of this vacation home enjoy access to a water park, laundry facilities, and a garden. This smoke-free vacation home also has barbecue grills.
Kitchen
Washer
2 bedroom cottage

2 bedroom cottage

17.3 mi from city center
At this cottage, guests have access to barbecue grills.
Air conditioning
Parking available
Come enjoy 7 miles of beaches in Sunny OOB in this 2 bedroom condo.

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

17.38 mi from city center
$609 nightly
The price is $664 total per night
$664 total
Jul 7 - Jul 8
Total includes taxes and fees
Guests of this condo enjoy access to a water park, laundry facilities, and a garden. This smoke-free condo building also has barbecue grills.
Lakefront Cottage: Boat Dock, Patio & Kayaks!

Lakefront Cottage: Boat Dock, Patio & Kayaks!

3 out of 5
25.5 mi from city center
This cottage features free WiFi in public areas and barbecue grills. You can put free parking to good use if you drive. This smoke-free cottage also has a garden.
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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.

Windham Large Group Rentals

How to Book Vacation Rentals in Windham



🏠 What is the best price for Windham vacation rentals?

Windham vacation rentals range in price, starting at $235 per night.


🏠 What types of vacation rentals in Windham can I rent?

Orbitz offers a wide range of Windham rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Windham condo rentals.


🏠 Is it free to cancel my Windham vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Windham vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Windham. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Windham?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Windham apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Windham?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Windham package deals will get you even more savings.

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