Book Holiday Homes in Windham

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Featured Holiday Homes in Windham

4-bedroom vacation home steps to Old Orchard Beach Pier

4-bedroom vacation home steps to Old Orchard Beach Pier

Old Orchard Beach ME
Stay at this holiday home in Old Orchard Beach. Enjoy a garden, laundry facilities and patios. Popular attractions Old Orchard Beach and Harmon Historical Museum ...
Opens in a new window4-bedroom vacation home steps to Old Orchard Beach Pier
5 Star Back Cove Apartment with water view!

5 Star Back Cove Apartment with water view!

Portland ME
Stay at this holiday home in Portland. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Thompson's Point and Maine Mall are located ...
Opens in a new window5 Star Back Cove Apartment with water view!
The Lookout by Bayley Vacation Rentals

The Lookout by Bayley Vacation Rentals

Saco ME
Stay at this holiday home in Saco. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Old Orchard Beach and Camp Ellis Beach are located ...
Opens in a new windowThe Lookout by Bayley Vacation Rentals
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Rare West End Home • Walk to Old Port, Harbor View

Rare West End Home • Walk to Old Port, Harbor View

Portland ME
The price is NZ$1,176 per night from 21 May to 22 May
NZ$1,176
21 May - 22 May
includes taxes & fees
Stay at this holiday home in Portland. Enjoy a garden, in-room fireplaces and air conditioning. Popular attractions Thompson's Point and Maine Mall are located ...
Opens in a new windowRare West End Home • Walk to Old Port, Harbor View
Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!

Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!

Saco ME
Stay at this holiday home in Saco. Enjoy free Wi-Fi, a beach locale and laundry facilities. Popular attractions Old Orchard Beach and Ferry Beach are located ...
Opens in a new windowGorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!
Charming Nautical Retreat-3 BR +Fully Equipped+ Short walk to beach!

Charming Nautical Retreat-3 BR +Fully Equipped+ Short walk to beach!

Old Orchard Beach ME
Stay at this holiday home in Old Orchard Beach. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Old Orchard Beach and Harmon Historical ...
Opens in a new windowCharming Nautical Retreat-3 BR +Fully Equipped+ Short walk to beach!
Sun-Kissed Beach Getaway – Family-Friendly, Close to Beach, Private Yard!

Sun-Kissed Beach Getaway – Family-Friendly, Close to Beach, Private Yard!

Saco ME
Stay at this family-friendly holiday home in Saco. Enjoy free Wi-Fi, a water park and a garden. Popular attractions Old Orchard Beach and Ferry Beach State Park ...
Opens in a new windowSun-Kissed Beach Getaway – Family-Friendly, Close to Beach, Private Yard!
Charming  Retreat w/ WiFi, Ping Pong Table & Walking Distance to the Ocean

Charming Retreat w/ WiFi, Ping Pong Table & Walking Distance to the Ocean

Cumberland ME
Stay at this holiday home in Cumberland Foreside. Enjoy a water park, a garden and patios. Popular attractions Twin Brook Recreation Area and Clay Play are located ...
Opens in a new windowCharming Retreat w/ WiFi, Ping Pong Table & Walking Distance to the Ocean
Luxury Lakefront Estate on 155 Acres -  Pickleball, Reunions & Weddings

Luxury Lakefront Estate on 155 Acres - Pickleball, Reunions & Weddings

Otisfield ME
Stay at this family-friendly holiday home in Oxford. Enjoy free Wi-Fi, a fitness centre and laundry facilities. Popular attractions Saturday Pond and Porcupine ...
Opens in a new windowLuxury Lakefront Estate on 155 Acres - Pickleball, Reunions & Weddings
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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 Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Windham vacation homes are the perfect way for you to wing it.

Holiday houses in Windham let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Windham in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Windham adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Windham with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Windham vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Windham Holiday Homes essential information

Accommodation
892 Holiday Homes
Lowest Price
NZ$287
Highest Price
NZ$1,176
Popular accommodation
4-bedroom vacation home steps to Old Orchard Beach Pier, 5 Star Back Cove Apartment with water view!, The Lookout by Bayley Vacation Rentals, Rare West End Home • Walk to Old Port, Harbor View, Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!, Charming Nautical Retreat-3 BR +Fully Equipped+ Short walk to beach!, Sun-Kissed Beach Getaway – Family-Friendly, Close to Beach, Private Yard!, Charming Retreat w/ WiFi, Ping Pong Table & Walking Distance to the Ocean, Luxury Lakefront Estate on 155 Acres - Pickleball, Reunions & Weddings

Top trending hotels in Windham

Dormir

Dormir

3 out of 5
965 Roosevelt Trail Windham ME
Fully refundableReserve now, pay when you stay
The price is NZ$287 per night from 26 May to 27 May
NZ$287
26 May - 27 May
includes taxes & fees
Stay at this business-friendly hotel in Windham. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in ...
Opens in a new windowDormir
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is NZ$417 per night from 25 May to 26 May
NZ$417
25 May - 26 May
includes taxes & fees
Stay at this business-friendly hotel in Portland. Enjoy free Wi-Fi, 3 coffee shops/cafes and breakfast (surcharge). Our guests praise the helpful staff and the ...
Opens in a new windowPortland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
The price is NZ$314 per night from 26 May to 27 May
NZ$314
26 May - 27 May
includes taxes & fees
Stay at this spa hotel in Portland. Enjoy free Wi-Fi, a full-service spa and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in their ...
Opens in a new windowPortland Regency Hotel & Spa
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Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Fully refundable
The price is NZ$335 per night from 25 May to 26 May
NZ$335
25 May - 26 May
includes taxes & fees
Stay at this business-friendly hotel in Portland. Enjoy free Wi-Fi, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the restaurant and ...
Opens in a new windowCambria Hotel Portland Downtown-Old Port
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.