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

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95 Holiday homes

Portland holiday apartment rental

Portland apartment

3 bedrooms • 2 bathrooms • sleeps 8

from £383 / night

£2,273 / week

1 / 32

Apartment rental in Portland

Portland apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £171 / night

£1,195 / week

1 / 28

Portland holiday apartment rental

Portland apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £363 / night

£2,155 / week

1 / 33

Apartment rental in Portland

Portland apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £171 / night

£1,195 / week

1 / 29

Portland holiday condo rental

Portland condo

1 bedroom • 1 bathroom • sleeps 3

from £238 / night

£1,661 / week

1 / 45

Great rentals within 20 miles that match your search

Holiday home in Old Orchard Beach

Old Orchard Beach house

2 bedrooms • 1 bathroom • sleeps 6

from £125 / night

£831 / week

1 / 12

Holiday cottage in Biddeford Pool

Biddeford Pool cottage

2 bedrooms • 1 bathroom • sleeps 6

from £250 / night

£1,745 / week

1 / 15

Holiday home in Scarborough

Scarborough house

4 bedrooms • 6 bathrooms • sleeps 10

from £831 / night

£5,817 / week

1 / 15

Holiday home rental

Old Orchard Beach house

3 bedrooms • 2 bathrooms • sleeps 8

from £221 / night

£1,538 / week

1 / 8

Holiday cottage in Old Orchard Beach

Old Orchard Beach cottage

3 bedrooms • 1 bathroom • sleeps 8

from £190 / night

£1,330 / week

1 / 14

Holiday apartment in Old Orchard Beach

Old Orchard Beach apartment

3 bedrooms • 1 bathroom • sleeps 10

from £297 / night

£2,078 / week

1 / 21

Holiday condo in Scarborough

Scarborough condo

1 bedroom • 1 bathroom • sleeps 2

from £92 / night

£748 / week

1 / 27

Holiday condo in Old Orchard Beach

Old Orchard Beach condo

2 bedrooms • 1 bathroom • sleeps 6

from £191 / night

£1,332 / week

1 / 11

Holiday guest house in Biddeford

Biddeford guest house

1 bedroom • 1 bathroom • sleeps 4

from £542 / night

£3,788 / week

1 / 16

Old Orchard Beach holiday cottage rental

Old Orchard Beach cottage

2 bedrooms • 1 bathroom • sleeps 6

from £225 / night

£1,574 / week

1 / 29

Old Orchard Beach holiday cottage rental

Old Orchard Beach cottage

2 bedrooms • 1 bathroom • sleeps 6

from £224 / night

£1,568 / week

1 / 27

Holiday home in Old Orchard Beach

Old Orchard Beach house

3 bedrooms • 2 bathrooms • sleeps 6

from £214 / night

£1,499 / week

1 / 12

Holiday home in Ocean Park

Ocean Park house

3 bedrooms • 1 bathroom • sleeps 8

from £204 / night

£1,428 / week

1 / 10

West Scarborough holiday home rental

West Scarborough house

2 bedrooms • 1 bathroom • sleeps 8

from £229 / night

£1,603 / week

1 / 17

Holiday home rental

Old Orchard Beach house

3 bedrooms • 2 bathrooms • sleeps 7

from £246 / night

£1,720 / week

1 / 13

Holiday apartment in Old Orchard Beach

Old Orchard Beach apartment

3 bedrooms • 1 bathroom • sleeps 10

from £298 / night

£2,082 / week

1 / 11

Scarborough holiday home rental

Scarborough house

6 bedrooms • 3 bathrooms • sleeps 19

from £1,547 / night

£10,823 / week

1 / 34

Holiday cottage in Old Orchard Beach

Old Orchard Beach cottage

2 bedrooms • 1 bathroom • sleeps 6

from £173 / night

£1,208 / week

1 / 10

Holiday apartment in Old Orchard Beach

Old Orchard Beach apartment

2 bedrooms • 1 bathroom • sleeps 5

from £357 / night

£2,498 / week

1 / 28

Holiday condo with shared pool in Old Orchard Beach

Old Orchard Beach condo

2 bedrooms • 1 bathroom • sleeps 6

from £341 / night

£2,384 / week

1 / 12

Holiday condo with shared pool in Old Orchard Beach

Old Orchard Beach condo

2 bedrooms • 1 bathroom • sleeps 6

from £349 / night

£2,442 / week

1 / 12

Holiday condo with shared pool in Old Orchard Beach

Old Orchard Beach condo

2 bedrooms • 1 bathroom • sleeps 6

from £333 / night

£2,326 / week

1 / 12

Holiday condo with shared pool in Old Orchard Beach

Old Orchard Beach condo

1 bedroom • 1 bathroom • sleeps 4

from £324 / night

£2,267 / week

1 / 20

Holiday condo letting

Old Orchard Beach condo

1 bedroom • 1 bathroom • sleeps 4

from £333 / night

£2,326 / week

1 / 20

Holiday condo in Old Orchard Beach

Old Orchard Beach condo

1 bedroom • 1 bathroom • sleeps 4

from £333 / night

£2,326 / week

1 / 10

Holiday condo in Old Orchard Beach

Old Orchard Beach condo

2 bedrooms • 1 bathroom • sleeps 6

from £358 / night

£2,500 / week

1 / 13

Holiday condo in Old Orchard Beach

Old Orchard Beach condo

1 bedroom • 1 bathroom • sleeps 4

from £324 / night

£2,267 / week

1 / 16

Old Orchard Beach holiday condo rental

Old Orchard Beach condo

2 bedrooms • 1 bathroom • sleeps 6

from £324 / night

£2,267 / week

1 / 12

Holiday condo accommodation

Old Orchard Beach condo

2 bedrooms • 1 bathroom • sleeps 6

from £324 / night

£2,267 / week

1 / 13

Holiday condo in Old Orchard Beach

Old Orchard Beach condo

2 bedrooms • 1 bathroom • sleeps 6

from £349 / night

£2,442 / week

1 / 13

Holiday condo in Old Orchard Beach

Old Orchard Beach condo

1 bedroom • 1 bathroom • sleeps 4

from £316 / night

£2,209 / week

1 / 12

Holiday condo in Old Orchard Beach

Old Orchard Beach condo

2 bedrooms • 1 bathroom • sleeps 6

from £333 / night

£2,326 / week

1 / 13

Windham holiday condo rental

Windham condo

3 bedrooms • 2 bathrooms • sleeps 8

from £358 / night

£2,500 / week

1 / 8

Windham holiday condo let

Windham condo

1 bedroom • 1 bathroom • sleeps 2

from £203 / night

£1,417 / week

1 / 5

Holiday condo rental

Old Orchard Beach condo

2 bedrooms • 2 bathrooms • sleeps 4

from £142 / night

£991 / week

1 / 50

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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