Book Holiday Homes in Windham

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Featured Holiday Homes in Windham

Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

2 out of 5
Scarborough
Stay at this vacation home in Scarborough. Enjoy in-room jetted tubs and air conditioning. Popular attractions Engine and Grand Beach are located nearby.
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
Stille Wasser, Quiet, secluded spot on Saco River with Dock (Boat lift option)

Stille Wasser, Quiet, secluded spot on Saco River with Dock (Boat lift option)

Buxton
Stay at this vacation home in Buxton. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attraction Swan Pond is located nearby.
Stille Wasser, Quiet, secluded spot on Saco River with Dock (Boat lift option)
The Moonglow! A beautiful ocean view house in Biddeford!

The Moonglow! A beautiful ocean view house in Biddeford!

Biddeford
Stay at this vacation home in Biddeford. Enjoy patios, cable/satellite TV service, and air conditioning. Popular attractions Engine and The Pool are located ...
The Moonglow! A beautiful ocean view house in Biddeford!
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Beach House ∆ Prime Location ∆ Steps to the Ocean

Beach House ∆ Prime Location ∆ Steps to the Ocean

Old Orchard Beach
The price is NZ$861 per night from 5 Jan to 6 Jan
NZ$861
includes taxes & fees
5 Jan - 6 Jan 2025
Book a stay at this beach vacation home in Old Orchard Beach. Enjoy free WiFi, a beach locale, and balconies. Popular attractions Engine and Old Orchard Beach ...
Beach House ∆ Prime Location ∆ Steps to the Ocean
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

Portland
Book a stay at this family-friendly vacation home in Portland. Enjoy free WiFi, a water park, and a garden. Popular attractions Maine Mall and Deering Oaks Park ...
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Lakefront House

Lakefront House

Windham
The price is NZ$1,367 per night from 20 Jan to 21 Jan
NZ$1,367
includes taxes & fees
20 Jan - 21 Jan 2025
Stay at this vacation home in Windham. Enjoy free WiFi, a garden, and patios. Popular attractions Maine Wildlife Park and MAGAN Trailhead are located ...
Lakefront House
Beautiful Combo Home Located in Downtown Portland - Close to the Beach

Beautiful Combo Home Located in Downtown Portland - Close to the Beach

Portland
Stay at this vacation home in Portland. Enjoy a water park, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Maine Mall and Maine ...
Beautiful Combo Home Located in Downtown Portland - Close to the Beach
Modern, Luxury Lakefront Home on Crescent Lake, Maine

Modern, Luxury Lakefront Home on Crescent Lake, Maine

Raymond
Book a stay at this family-friendly vacation home in Raymond. Enjoy free WiFi, a water park, and a sauna. Popular attractions Crescent Lake and Raymond Pond ...
Modern, Luxury Lakefront Home on Crescent Lake, Maine
Charming 110-year former Inn 10' from the Ocean!

Charming 110-year former Inn 10' from the Ocean!

South Portland
Book a stay at this beach vacation home in South Portland. Enjoy free WiFi, a beach locale, and a water park. Popular attractions Maine Mall and Willard Beach ...
Charming 110-year former Inn 10' from the Ocean!
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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
711 Holiday Homes
Lowest Price
NZ$183
Highest Price
NZ$1,367
Popular accommodation
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough, Stille Wasser, Quiet, secluded spot on Saco River with Dock (Boat lift option), The Moonglow! A beautiful ocean view house in Biddeford!, Beach House ∆ Prime Location ∆ Steps to the Ocean, Spacious & Sunny 4 Bedroom Close to Downtown, hot tub, Lakefront House, Beautiful Combo Home Located in Downtown Portland - Close to the Beach, Modern, Luxury Lakefront Home on Crescent Lake, Maine, Charming 110-year former Inn 10' from the Ocean!

Top trending hotels in Windham

Microtel Inn & Suites By Wyndham Windham

Microtel Inn & Suites By Wyndham Windham

3 out of 5
965 Roosevelt Trail, Windham, ME
Fully refundableReserve now, pay when you stay
The price is NZ$195 per night from 25 Dec to 26 Dec
NZ$195
includes taxes & fees
25 Dec - 26 Dec
Stay at this 3-star business-friendly hotel in Windham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Microtel Inn & Suites By Wyndham Windham
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is NZ$194 per night from 7 Jan to 8 Jan
NZ$194
includes taxes & fees
7 Jan - 8 Jan 2025
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the bar and the helpful staff in ...
The Westin Portland Harborview
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is NZ$183 per night from 25 Dec to 26 Dec
NZ$183
includes taxes & fees
25 Dec - 26 Dec
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, free parking, and 2 spa tubs. Our guests praise the restaurant and the helpful staff ...
Ramada Plaza by Wyndham Portland
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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$285 per night from 25 Dec to 26 Dec
NZ$285
includes taxes & fees
25 Dec - 26 Dec
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the bar and the ...
Portland Harbor Hotel
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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.

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^Subject to availability and chosen travel dates.