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Windham Rentals

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117 Results

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117 Houses

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

Falmouth Foreside Maine Contemporary Cottage Home - indoor lap pool, roof deck

Falmouth house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$639

Waterfront Log Cabin style home on Thompson Lake!

Oxford log cabin

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$282

WILLARD BEACH with OCEAN VIEWS ~ 100 yds to beach!

South Portland house

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 2 hours 57 minutes

Price per night from

$626

Fox Crossing - Riverside, walk to restaurants, breweries

Westbrook house

5 bedrooms / 4 bathrooms / sleeps 20

Price per night from

$1,103

Breezy Cottage

Sebago cottage

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$332

Charming Downtown 1BR w/ Parking, Short Walk to Old Port

Portland apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$233

Classic, cozy family cottage with modern amenities and ocean view from porch

Peaks Island cottage

5 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 28 minutes

Price per night from

$465

Mac Camp

Naples house

2 bedrooms / 1 bathroom / sleeps 8

Price per night from

$233

Quiet Waterfront Summer Rental

Waterboro house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$290

Comfort | Location | Charm

Portland house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$206

Also Close to Everything

Portland apartment

5 bedrooms / 1 bathroom / sleeps 10

Price per night from

$291

Enjoy Sweeping Waterfront View, Watch Lobster Boats from Porch

Peaks Island cottage

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 28 minutes

Price per night from

$465

Multi-Family Vacations-Anniversaries-Reunions. 8 Spacious Bedrooms

Raymond lodge

8 bedrooms / 5 bathrooms / sleeps 21

Price per night from

$870

Enjoy a Secluded Location on Mount Desert

Mount Desert house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$332

Bay Sunrise Vista Helmet

Portland condo

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$331

Waterfront Fun Pet Friendly Vacation Rental Camp

Gorham log cabin

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 3 hours 59 minutes

Price per night from

$175

Waterfront villa, Coastal Southern Maine

Scarborough house

4 bedrooms / 6 bathrooms / sleeps 10

Price per night from

$1,161

Private Lakefront Cottage on a Unique Setting - Maine At It's Best!

Limerick house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$183

WELCOME Summer*Bridgton Bungalow Cottage*Bring Fido! Denmark Stage Stop House

Denmark cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 41 minutes

Price per night from

$115

True St Freeport

Freeport apartment

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$188

Viewing 38 of 117
rentals in Windham

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