Holiday Houses in Windham

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111 Holiday homes

Responds fast! avg. 1 hour 50 minutes

from £241 / night

£1,685 / week

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

Windham house

3 bedrooms / 3 bathrooms / sleeps 9

Responds fast! avg. 1 hour 50 minutes

from £258 / night

£1,804 / week

Quiet Lake Serenity Just 10 Miles from Portland

Windham house

3 bedrooms / 2 bathrooms / sleeps 8

from £241 / night

£1,688 / week

Responds fast! avg. 1 hour 50 minutes

from £240 / night

£1,679 / week

Relaxing Maine Likeside Cottage Vacation

Windham cottage

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 7 minutes

from £222 / night

£1,333 / week

K2 Lake Paradise

Windham cottage

2 bedrooms / 1 bathroom / sleeps 6

from £222 / night

£1,555 / week

Waterfront Sebago Lake Cottage w/Dock + Beach

Windham cottage

3 bedrooms / 1 bathroom / sleeps 9

Responds fast! avg. 5 minutes

from £206 / night

£1,443 / week

Lake View Lodge

Windham condo

3 bedrooms / 2 bathrooms / sleeps 8

from £381 / night

£2,668 / week

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

Windham house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 48 minutes

from £132 / night

£924 / week

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

Windham condo

1 bedroom / 1 bathroom / sleeps 2

from £215 / night

£1,502 / week

Great rentals within 20 miles that match your search

Wonderfully Appointed Beach House

Sebago house

3 bedrooms / 2 bathrooms / sleeps 8

from £264 / night

£1,849 / week

Mac Camp

Naples house

2 bedrooms / 1 bathroom / sleeps 8

from £177 / night

£1,237 / week

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

Portland apartment

1 bedroom / 1 bathroom / sleeps 4

from £177 / night

£1,237 / week

Charming 4-bedroom on Beautiful Sebago Lake; Sept, Oct reduced rates

Sebago cottage

4 bedrooms / 2 bathrooms / sleeps 8

11

Responds fast! avg. 16 minutes

from £181 / night

£1,237 - £1,678 / week

Classic Maine Beach Cottage, private beach access

Falmouth cottage

3 bedrooms / 1 bathroom / sleeps 5

from £265 / night

£1,590 / week

Tentrr - The Knoll at Red Tractor Farm

Limington tented camp

1 bedroom / 1 bathroom / sleeps 6

from £107 / night

£747 / week

Direct Waterfront on Sebago Lake Basin

Standish house

2 bedrooms / 2 bathrooms / sleeps 8

from £355 / night

£1,999 / week

Luxurious, Fully Renovated house with Private Beach rights.

Cape Elizabeth house

5 bedrooms / 4 bathrooms / sleeps 10

from £707 / night

£3,531 - £7,431 / week

Luxury Log Home-Raymond,Naples,Windham,Bridgton

Harrison house

5 bedrooms / 2 bathrooms / sleeps 12

7

Responds fast! avg. 3 hours 48 minutes

from £618 / night

£3,105 - £3,416 / week

Waterfront Log Cabin style home on Thompson Lake!

Oxford log cabin

3 bedrooms / 2 bathrooms / sleeps 8

3

from £216 / night

£1,510 / week

Furnished & newly built Modern Cottage, walk to the ocean, 10 min to Portland

Cape Elizabeth house

2 bedrooms / 1 bathroom / sleeps 4

from £254 / night

£1,772 / week

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

Portland apartment

3 bedrooms / 1 bathroom / sleeps 9

from £316 / night

£2,043 - £3,038 / week

Willard Beach Modern Apartment

South Portland apartment

2 bedrooms / 1 bathroom / sleeps 4

from £111 / night

£578 / week

Furnished Two-Bedroom Apartment

Yarmouth house

2 bedrooms / 1 bathroom / sleeps 4

from £116 / night

£647 / week

Willard Beach Get Away - Dog Friendly

South Portland studio

Studio / 1 bathroom / sleeps 3

2

Responds fast! avg. 21 minutes

from £169 / night

£1,066 / week

Also Close to Everything

Portland apartment

5 bedrooms / 1 bathroom / sleeps 10

from £222 / night

£1,555 / week

Fox Crossing - Riverside, walk to restaurants, breweries

Westbrook house

5 bedrooms / 4 bathrooms / sleeps 20

from £844 / night

£5,907 / week

WILLARD BEACH with OCEAN VIEWS ~ 100 yds to beach!

South Portland house

3 bedrooms / 2 bathrooms / sleeps 9

3

from £618 / night

£2,643 - £4,686 / week

Comfort | Location | Charm

Portland house

1 bedroom / 1 bathroom / sleeps 2

1

from £158 / night

£1,101 / week

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

South Portland house

4 bedrooms / 3 bathrooms / sleeps 13

from £973 / night

£4,419 - £8,861 / week

Sun-Drenched, Family-Friendly Oceanfront-Oasis

South Freeport house

4 bedrooms / 3 bathrooms / sleeps 6

from £422 / night

£2,954 / week

Tentrr - Riverside Lavender Farm

Limington tented camp

1 bedroom / 1 bathroom / sleeps 4

from £120 / night

£840 / week

Tentrr - Maine Stay Campsite

Bridgton tented camp

1 bedroom / 1 bathroom / sleeps 4

from £89 / night

£622 / week

Tentrr - Your Own Private Meadow

Pownal tented camp

1 bedroom / 1 bathroom / sleeps 6

from £71 / night

£498 / week

Enjoy a Secluded Location on Mount Desert

Mount Desert house

3 bedrooms / 2 bathrooms / sleeps 8

from £254 / night

£1,777 / week

Tentrr – Hill Top Camp

Danville tented camp

1 bedroom / 1 bathroom / sleeps 10

from £89 / night

£622 - £995 / week

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

Falmouth house

4 bedrooms / 3 bathrooms / sleeps 8

1

from £489 / night

£3,420 / week

True St Freeport

Freeport apartment

2 bedrooms / 2 bathrooms / sleeps 5

from £144 / night

£1,008 / week

Classic Colonial in the Heart of Town!!

Freeport house

3 bedrooms / 2 bathrooms / sleeps 11

Responds fast! avg. 5 minutes

from £96 / night

£672 / week

Breezy Cottage

Sebago cottage

4 bedrooms / 2 bathrooms / sleeps 8

1

from £254 / night

£1,777 / week

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rentals in Windham