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Apartments in Portland and Houses – Holiday Lettings - Holiday Rentals Portland

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105 Holiday homes

Portland holiday apartment rental

Portland apartment

5 bedrooms / 1 bathroom / sleeps 10

from £236 / night

£1,647 / week

Holiday home in Portland

Portland house

4 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 1 hour 25 minutes

from £518 / night

£5,830 - £7,181 / week

Portland holiday condo rental

Portland condo

1 bedroom / 1 bathroom / sleeps 3

from £269 / night

£1,878 / week

Portland holiday apartment rental

Portland apartment

3 bedrooms / 2 bathrooms / sleeps 8

from £379 / night

£2,244 / week

Portland holiday apartment rental

Portland apartment

2 bedrooms / 2 bathrooms / sleeps 6

from £358 / night

£2,128 / week

Apartment rental in Portland

Portland apartment

2 bedrooms / 2 bathrooms / sleeps 4

from £169 / night

£1,180 / week

Apartment rental in Portland

Portland apartment

2 bedrooms / 2 bathrooms / sleeps 4

from £169 / night

£1,180 / week

Great rentals within 20 miles that match your search

Holiday home rental

Yarmouth house

2 bedrooms / 1 bathroom / sleeps 4

from £123 / night

£684 / week

Holiday apartment in Old Orchard Beach

Old Orchard Beach apartment

2 bedrooms / 1 bathroom / sleeps 5

from £404 / night

£2,824 / week

Old Orchard Beach holiday cottage rental

Old Orchard Beach cottage

2 bedrooms / 1 bathroom / sleeps 6

1

from £255 / night

£1,779 / week

Bailey Island holiday home rental

Bailey Island house

3 bedrooms / 4 bathrooms / sleeps 8

from £805 / night

£5,633 / week

Windham holiday condo let

Windham condo

1 bedroom / 1 bathroom / sleeps 2

from £229 / night

£1,601 / week

Holiday home in Scarborough

Scarborough house

4 bedrooms / 6 bathrooms / sleeps 10

from £942 / night

£6,588 / week

Old Orchard Beach holiday cottage rental

Old Orchard Beach cottage

2 bedrooms / 1 bathroom / sleeps 6

1

from £254 / night

£1,773 / week

Holiday private room in Old Orchard Beach

Old Orchard Beach private room

1 bedroom / 1 bathroom / sleeps 2

from £66 / night

£462 / week

Holiday cottage in Old Orchard Beach

Old Orchard Beach cottage

2 bedrooms / 1 bathroom / sleeps 6

from £195 / night

£1,365 / week

Cottage rental in Harpswell

Harpswell cottage

3 bedrooms / 1 bathroom / sleeps 6

5

from £202 / night

£1,412 - £3,324 / week

Holiday cottage in Old Orchard Beach

Old Orchard Beach cottage

3 bedrooms / 1 bathroom / sleeps 8

2

from £208 / night

£1,451 / week

Windham holiday condo rental

Windham condo

3 bedrooms / 2 bathrooms / sleeps 8

from £390 / night

£2,730 / week

Holiday home in Harpswell

Harpswell house

3 bedrooms / 2 bathrooms / sleeps 5

from £254 / night

£1,776 / week

Home rental in Scarborough

Scarborough house

7 bedrooms / 5 bathrooms / sleeps 28

Responds fast! avg. 2 hours 38 minutes

from £1,677 / night

£9,765 - £14,260 / week

Holiday cottage in Biddeford Pool

Biddeford Pool cottage

2 bedrooms / 1 bathroom / sleeps 6

5

from £255 / night

£1,782 / week

Home letting in South Portland

South Portland house

3 bedrooms / 2 bathrooms / sleeps 9

3

Responds fast! avg. 1 hour 37 minutes

from £582 / night

£2,907 / week

Cape Elizabeth holiday castle rental

Cape Elizabeth castle

6 bedrooms / 7 bathrooms / sleeps 12

from £2,471 / night

£17,297 / week

Falmouth holiday home rental

Falmouth house

3 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 47 minutes

from £407 / night

£2,200 / week

Holiday condo in Old Orchard Beach

Old Orchard Beach condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 44 minutes

from £164 / night

£1,146 / week

Old Orchard Beach holiday condo rental

Old Orchard Beach condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 44 minutes

from £156 / night

£1,089 / week

Holiday condo in Old Orchard Beach

Old Orchard Beach condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 44 minutes

from £164 / night

£1,146 / week

Holiday condo in Old Orchard Beach

Old Orchard Beach condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 44 minutes

from £148 / night

£1,031 / week

Holiday condo with shared pool in Old Orchard Beach

Old Orchard Beach condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 44 minutes

from £164 / night

£1,146 / week

Holiday condo in Old Orchard Beach

Old Orchard Beach condo

2 bedrooms / 1 bathroom / sleeps 6

10

from £188 / night

£1,316 / week

Holiday home with golf nearby in South Portland

South Portland house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 2 hours 11 minutes

from £902 / night

£4,095 / week

Holiday home rental

Old Orchard Beach house

3 bedrooms / 2 bathrooms / sleeps 7

1

Responds fast! avg. 1 hour 55 minutes

from £243 / night

£1,702 / week

Cape Elizabeth holiday home rental

Cape Elizabeth house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 52 minutes

from £804 / night

£4,924 / week

Holiday condo rental

Old Orchard Beach condo

2 bedrooms / 2 bathrooms / sleeps 4

from £67 / night

£468 / week

Holiday home in Old Orchard Beach

Old Orchard Beach house

3 bedrooms / 3 bathrooms / sleeps 7

3

from £209 / night

£1,838 - £2,715 / week

Holiday home in Old Orchard Beach

Old Orchard Beach house

2 bedrooms / 1 bathroom / sleeps 6

13

from £126 / night

£835 / week

Holiday guest house in Biddeford

Biddeford guest house

1 bedroom / 1 bathroom / sleeps 4

from £543 / night

£3,800 / week

Biddeford holiday cottage rental

Biddeford cottage

2 bedrooms / 1 bathroom / sleeps 4

5

from £129 / night

£872 - £1,246 / week

Holiday home rental

Old Orchard Beach house

3 bedrooms / 2 bathrooms / sleeps 8

from £221 / night

£1,539 / week

Viewing 40 of 105
rentals in Portland

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Portland holidays

Portland is a quaint New England city located on the southern edge of the Casco Bay inlet, which runs from Cape Small to Cape Elizabeth. The Portland area is steeped in American history, as Casco Bay has been home to European settlers since 1623.

Today, Portland is the largest city in Maine, with a pronounced maritime feel befitting of its long and colourful past. Visit the city's central core as well as the busy waterfront and the quaint Old Port district, lined with narrow cobblestone streets and charming pubs and restaurants.

Other popular attractions and activities include:

  • Eastern and Western Promenades: Enjoy spectacular views of Casco Bay and take in the splendour of the city's oldest and finest neighbourhoods.
  • Victoria Mansion: Considered one of the most sublime surviving examples of pre-Civil War-era residential architecture in America, this stately manor is a must-see.
  • Go fishing: Portland offers many angling opportunities, for both deep-sea and freshwater fishing enthusiasts.
  • Take a hike: Some of New England's most spectacular scenery lies just outside Portland, making for excellent hiking and camping.
  • Portland Head Light and Museum: Open year-round, with free access to the grounds, the Portland Head Light and Museum is considered one of the most scenic lighthouses in the United States.

While the city is home to a complete range of major hotel chains as well as independently owned establishments and bed-and-breakfasts, the advantages of staying in condo or apartment style holiday rental should not be overlooked. These accommodations offer more privacy and more room, and include amenities like fully equipped kitchens and comfortable living rooms that make them feel like home.

The city is alive with activity during the warm-weather months, particularly in late spring and summer. If you visit Portland during the autumn, you'll be treated to some of the most brilliant displays of fall foliage anywhere in the world.

Nearby Cape Elizabeth makes a perfect day trip if you want to enjoy some beaches or see some of the region's other lighthouses. Old Orchard Beach is a resort town worth a visit if you're in the area during the summer, and to the north of the city, you'll find scenic macworth Island if you're in the mood for the outdoors.

Also consider