Compare Windham Cottage Rentals

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Featured Windham Cottages

Private Contemporary Artist's Tree House on two acres with perennial gardens.

Private Contemporary Artist's Tree House on two acres with perennial gardens.

Guests staying at this cottage enjoy ski-in/ski-out access, a hot tub, and local meal delivery service. Other amenities at this ski cottage include barbecue grills and a garden.
Hot Tub
Kitchen
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

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

This cottage offers a water park, an outdoor pool, and laundry facilities. This smoke-free cottage also has barbecue grills.
Pool
Kitchen
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

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

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
WATERFRONT ON PETTENGILL POND

WATERFRONT ON PETTENGILL POND

Guests of this villa enjoy access to a water park, laundry facilities, and barbecue grills. This smoke-free villa also has a garden.
Kitchen
Washer
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !

Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !

Guests staying at this cottage enjoy a hot tub, laundry facilities, and barbecue grills.
Professionally styled waterfront cottage on Sebago. Cozy and Serene.

Professionally styled waterfront cottage on Sebago. Cozy and Serene.

At Professionally styled waterfront cottage on Sebago. Cozy and Serene., guests have access to features like laundry facilities.
Lakefront Cottage - private dock, large decks, large fire pit

Lakefront Cottage - private dock, large decks, large fire pit

Guests staying at this cottage have access to barbecue grills and a garden.
Lakefront Traditional 4-bedroom cottage in Frye Island

Lakefront Traditional 4-bedroom cottage in Frye Island

2 out of 5
Frye Island, ME
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
Large 2BD cottage 10 min to Pier & Beach Pets ok

Large 2BD cottage 10 min to Pier & Beach Pets ok

$421 nightly
The price is $459 total per night
$459 total
Oct 9 - Oct 10
Total with taxes and fees
This cottage is a smoke-free cottage.
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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.

Hotel Options in Windham

    Dormir

    Dormir

    965 Roosevelt Trail, Windham, ME
    $112 nightly
    The price is $122 total per night from Nov 2 to Nov 3
    $122 total
    Nov 2 - Nov 3
    Total with taxes and fees
    8.8/10 Excellent! (1,008 reviews)
    Clarion Hotel Portland

    Clarion Hotel Portland

    1230 Congress St, Portland, ME
    $93 nightly
    The price is $103 total per night from Nov 2 to Nov 3
    $103 total
    Nov 2 - Nov 3
    Total with taxes and fees
    7.8/10 Good! (1,100 reviews)
    Germaine Inn South Portland

    Germaine Inn South Portland

    675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME
    $90 nightly
    The price is $98 total per night from Oct 13 to Oct 14
    $98 total
    Oct 13 - Oct 14
    Total with taxes and fees
    7.4/10 Good! (286 reviews)

Cottages

Book a cottage in Windham
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Windham. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Windham better.

Cottage apartments in Windham range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Windham
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Windham and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Windham cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Windham. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Windham Cottages essential information

Accommodation
457 Cottages
Lowest Price
$98
Highest Price
$459
Popular accommodation
Private Contemporary Artist's Tree House on two acres with perennial gardens. , Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC, Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach, WATERFRONT ON PETTENGILL POND, Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !, Professionally styled waterfront cottage on Sebago. Cozy and Serene., Lakefront Cottage - private dock, large decks, large fire pit, Lakefront Traditional 4-bedroom cottage in Frye Island, Large 2BD cottage 10 min to Pier & Beach Pets ok

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