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95 Houses

33

Lakeview home w/ deck, outdoor fireplace & sunset views - steps to sandy beach!

Maine / Windham

Windham house

5 8 min stay varies

  • 5 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$156

Price per night from

$156

15

Quiet Lake Serenity Just 10 Miles from Portland

Maine / Windham

Windham house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly
  • Private garden

Price per night from

$311

Price per night from

$311

5

Relaxing Maine Likeside Cottage Vacation

Maine / Windham

Windham cottage

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$287

Responds fast!
avg. 2 hours 16 minutes

Price per night from

$287

24

Lakefront home w/ screened porch & dock on Sebago Lake Basin - close to Portland

Maine / Windham

Windham house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$223

Price per night from

$223

13

K2 Lake Paradise

Maine / Windham

Windham cottage

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly

Price per night from

$115

Price per night from

$115

Great rentals within 20 miles that match your search

Distance approx 1.08 km from Windham Show on Map

13

Direct Waterfront on Sebago Lake Basin

Maine / Standish

Standish house

2 8 3 nights min

  • 2 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly

Price per night from

$457

Price per night from

$457

Distance approx 9.34 km from Windham

(2) Excellent 

26

Sebago Breezin' Long Beach Sebago Lake Maine

Maine / Sebago

Sebago cottage

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 mi
  • Child Friendly

Price per night from

$189

Price per night from

$189

Distance approx 15.99 km from Windham

(2) Excellent 

13

Blueberry Cove Cottage: Lakefront Getaway with boats near trails, casino &parks!

Maine / Poland

Poland cottage

2 7 min stay varies

  • 2 bedrooms
  • sleeps 7
  • min stay varies
  • Nearest beach 0 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$143

Price per night from

$143

Distance approx 15.53 km from Windham

43

Old Port Style & Luxury

Maine / Portland

Portland apartment

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$138

Responds fast!
avg. 3 hours 44 minutes

Price per night from

$138

Distance approx 9.86 km from Windham

(1) Excellent 

14

Breezy Cottage

Maine / Sebago

Sebago cottage

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$263

Responds fast!
avg. 3 hours 47 minutes

Price per night from

$263

Distance approx 13.63 km from Windham

42

Portland Area Cottage w/OCEAN VIEWS ~ pet friendly

Maine / Falmouth

Falmouth house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Car not necessary

Price per night from

$567

Responds fast!
avg. 1 hour 53 minutes

Price per night from

$567

Distance approx 19.78 km from Windham

(3) Excellent 

Certificate of Excellence

48

Welcoming Spotless Ski Shawnee Peak Bridgton Maine Pet Friendly Bring Fido!

Maine / Denmark

Denmark guest house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 11 mi
  • Child Friendly
  • Air conditioning

Certificate of Excellence

Price per night from

$132

Price per night from

$132

Distance approx 13.54 km from Windham

24

Also Close to Everything

Maine / Portland

Portland apartment

5 10 3 nights min

  • 5 bedrooms
  • sleeps 10
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$287

Price per night from

$287

Distance approx 17.29 km from Windham

(3) Excellent 

72

WILLARD BEACH with OCEAN VIEWS ~ 100 yds to beach!

Maine / South Portland

South Portland house

3 9 min stay varies

  • 3 bedrooms
  • sleeps 9
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$338

Responds fast!
avg. 1 hour 53 minutes

Price per night from

$338

Distance approx 13.13 km from Windham

6

Furnished Two-Bedroom Apartment

Maine / Yarmouth

Yarmouth house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Nearest beach 3 mi
  • Child Friendly
  • Air conditioning

Price per night from

$149

Price per night from

$149

Distance approx 17.25 km from Windham

9

Willard Beach Modern Apartment

Maine / South Portland

South Portland apartment

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly

Price per night from

$143

Price per night from

$143

Distance approx 11.5 km from Windham

31

Dog-friendly lakefront home w/dock, swing & great location - perfect for kids!

Maine / Poland

Poland house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Pet Friendly

Price per night from

$200

Price per night from

$200

Distance approx 18 km from Windham

15

Luxurious, Fully Renovated house with Private Beach rights.

Maine / Cape Elizabeth

Cape Elizabeth house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$568

Responds fast!
avg. 1 hour 53 minutes

Price per night from

$568

Distance approx 17.41 km from Windham

6

Pristine Lake. Pristine Housekeeping Cottage.

Maine / Bridgton

Bridgton cottage

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly

Price per night from

$172

Price per night from

$172

Distance approx 17.17 km from Windham

(1) Excellent 

23

Oceanfront Cottage in Freeport

Maine / Freeport

Freeport house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Private garden

Price per night from

$482

Price per night from

$482

Distance approx 15.08 km from Windham

28

Polished, modern condo w/ balcony - walk to Eastern Promenade & Casco Bay!

Maine / Portland

Portland house

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Car not necessary

Price per night from

$122

Price per night from

$122

Distance approx 17.26 km from Windham

22

Willard Beach - Simone By The Sea - New Home

Maine / South Portland

South Portland house

3 4 3 nights min

  • 3 bedrooms
  • sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation

Price per night from

$458

Responds fast!
avg. 3 hours 5 minutes

Price per night from

$458

Distance approx 11.69 km from Windham

7

Mac Camp

Maine / Naples

Naples house

2 8 7 nights min

  • 2 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly

Price per night from

$229

Responds fast!
avg. 1 hour 23 minutes

Price per night from

$229

Distance approx 9.97 km from Windham

24

NEW! Cozy Westbrook Apt w/Fire Pit- Near Portland!

Maine / Westbrook

Westbrook apartment

1 6 min stay varies

  • 1 bedroom
  • sleeps 6
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$68

Responds fast!
avg. 39 minutes

Price per night from

$68

Distance approx 17.27 km from Windham

63

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

Maine / South Portland

South Portland house

4 13 min stay varies

  • 4 bedrooms
  • sleeps 13
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$681

Responds fast!
avg. 1 hour 53 minutes

Price per night from

$681

Distance approx 7.68 km from Windham

21

Enjoy a Secluded Location on Mount Desert

Mount Desert Island / Mount Desert

Mount Desert house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$328

Price per night from

$328

Distance approx 5.14 km from Windham

44

Raymond Retreat Brand New Luxury Lake House on Panther Pond

Maine / Raymond

Raymond house

4 16 min stay varies

  • 4 bedrooms
  • sleeps 16
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$793

Price per night from

$793

Distance approx 16.8 km from Windham

71

WILLARD BEACH: Stunning newly RENOVATED HOUSE! 4 Mins to DT Portland.

Maine / Portland

Portland house

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Nearest beach 0 mi
  • Child Friendly

Price per night from

$567

Responds fast!
avg. 1 hour 53 minutes

Price per night from

$567

Distance approx 16.79 km from Windham

28

NEW! Waterfront Apt w/Deck - 22 Min. to Portland!

Maine / Freeport

Freeport apartment

1 3 3 nights min

  • 1 bedroom
  • sleeps 3
  • 3 nights min
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$121

Responds fast!
avg. 28 minutes

Price per night from

$121

Distance approx 15.43 km from Windham

(1) Excellent 

6

Comfort | Location | Charm

Maine / Portland

Portland house

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Air conditioning

Price per night from

$203

Price per night from

$203

Distance approx 15.21 km from Windham

28

East End, Portland, - top neighborhood, near ocean and town

Maine / Portland

Portland apartment

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Nearest beach 0.4 mi
  • Child Friendly
  • Air conditioning

Price per night from

$372

Responds fast!
avg. 1 hour 59 minutes

Price per night from

$372

Distance approx 16.71 km from Windham

14

True St Freeport

Maine / Freeport

Freeport apartment

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Child Friendly

Price per night from

$143

Price per night from

$143

Distance approx 17.57 km from Windham

24

Grace Cottage

Maine / Long Island

Long Island house

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly

Price per night from

$412

Price per night from

$412

Distance approx 15.09 km from Windham

24

Sleek condo w/unbelievable water views - newly renovated, walk to the bay!

Maine / Portland

Portland house

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$196

Price per night from

$196

Distance approx 19.09 km from Windham

(10) Very Good 

24

Quiet Waterfront Summer Rental

Maine / Waterboro

Waterboro house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Pet Friendly

Price per night from

$100

Price per night from

$100

Distance approx 19.03 km from Windham

(9) Excellent 

54

LONG LAKE CAMP Maine Naples -Waterfront,Cable,W/D

Maine / Harrison

Harrison chalet

5 8 7 nights min

  • 5 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$229

Responds fast!
avg. 2 hours 40 minutes

Price per night from

$229

Distance approx 7.61 km from Windham

(12) Excellent 

23

Beautiful Cottage on Crystal Lake

Maine / Gray

Gray house

3 7 7 nights min

  • 3 bedrooms
  • sleeps 7
  • 7 nights min
  • Beach / lakeside relaxation
  • Ask about children
  • Air conditioning

Price per night from

$171

Price per night from

$171

Distance approx 17.33 km from Windham

(2) Excellent 

20

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

Maine / Peaks Island

Peaks Island cottage

5 8 min stay varies

  • 5 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly

Price per night from

$401

Responds fast!
avg. 2 hours 52 minutes

Price per night from

$401