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117 Houses

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Cozy cottage w/deck, grill, & outdoor firepit - near town & slopes

Windham house

3 bedrooms / 3 bathrooms / sleeps 9

Price per night from

$324

Quiet Lake Serenity Just 10 Miles from Portland

Windham house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$315

Relaxing Maine Likeside Cottage Vacation

Windham cottage

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 7 minutes

Price per night from

$289

K2 Lake Paradise

Windham cottage

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$291

Waterfront Sebago Lake Cottage w/Dock + Beach

Windham cottage

3 bedrooms / 1 bathroom / sleeps 9

Responds fast! avg. 4 minutes

Price per night from

$242

Lake View Lodge

Windham condo

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$498

Lake View Lodge Unit #2 Can be rented w/ Unit # 1

Windham condo

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$282

Lakefront home w/ private dock, kayaks, canoe & incredible views!

Windham house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$181

Great rentals within 20 miles that match your search

Secluded & Serene location. Just perfect for your Family to reconnect.

Raymond cottage

3 bedrooms / 1 bathroom / sleeps 8

Price per night from

$304

Oceanfront Cottage in Freeport

Freeport house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$488

Luxury Log Home-Raymond,Naples,Windham,Bridgton

Harrison house

5 bedrooms / 2 bathrooms / sleeps 12

“Just what we were looking for.” Had a wonderful girls weekend here. We are looking forward to going again this year. Hands down, the best place I have ever rented.

Price per night from

$806

East End 3BR, Portland, - Great neighborhood - 2 blocks from ocean yet near town

Portland apartment

3 bedrooms / 1 bathroom / sleeps 9

Price per night from

$412

Furnished Two-Bedroom Apartment

Yarmouth house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$151

Portland Area Cottage w/OCEAN VIEWS ~ pet friendly

Falmouth house

3 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 57 minutes

Price per night from

$574

NEW LISTING: Stunningly Renovated Beach House with OCEAN VIEWS-150 yds to beach

South Portland house

4 bedrooms / 3 bathrooms / sleeps 13

Responds fast! avg. 3 hours 57 minutes

Price per night from

$1,269

Beautiful Cottage on Crystal Lake

Gray house

3 bedrooms / 1 bathroom / sleeps 7

Price per night from

$173

Andy's Retreat - Heated outdoor pool, Hot Spring jacuzzi, central AC, BBQ

Falmouth house

4 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$561

Portland, Maine - East End Rental

Portland apartment

3 bedrooms / 2 bathrooms / sleeps 6

“Enjoyed East End!” We and our friends celebrated both our 29th anniversaries the first weekend in Nov. the East End-er was a great choice... We sincerely recommend this option over any hotel...its more like staying at a good friend's home, with everything there you need, that makes it a home. You'll enjoy the great open kitchen and the "home" attached... we enjoyed making meals, drinks, conversation and laughs here, something you'd never do comfortably in a hotel...and even with so many great eateries nearby, we could have tried... Its on the hill, with views west to the Back Cove and east to the Port. and complete view south to downtown and the sun that keeps things cheery and bright. Easy .7 mile walk down Congress to India to Middle to the Old Port shopping/restaurant area. Close access to Franklin St. to pop down to Trader Joe's for great groceries and deals on wine :-) and easy on/off I-295 for day trips to Freeport. Portland area has so much to do, anytime of year, and this is the perfect home to really make your visit in! R&L;

Price per night from

$418