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Holiday Lettings
> North America
> United States
> Maine
> Houses and Apartments in Portland

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

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£1 £750 -

Bedrooms

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Filtered properties are rated either by Tripadvisor Vacation Rentals users, or by Vrbo users. Both rating systems are separate, and are depicted differently as shown in the key above. Tripadvisor performs checks on its reviews. Holiday Lettings and companies under Tripadvisor Group do not check Vrbo reviews.
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279 Holiday homes

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Portland holiday apartment rental

Portland apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £493 / night

£2,629 / week

1 / 32

Apartment rental in Portland

Portland apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £187 / night

£1,310 / week

1 / 29

Apartment rental in Portland

Portland apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £187 / night

£1,310 / week

1 / 28

Portland holiday apartment rental

Portland apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £438 / night

£2,362 / week

1 / 33

Portland holiday apartment rental

Portland apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

from £380 / night

£2,656 / week

1 / 39

Portland holiday condo rental

Portland condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £261 / night

£1,824 / week

1 / 45

Holiday cottage in Peaks Island

Peaks Island cottage

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8
2 reviews

from £458 / night

£3,200 / week

1 / 20

Peaks Island holiday cottage rental

Peaks Island cottage

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8
1 review

from £458 / night

£3,200 / week

1 / 11

Holiday apartment in Portland

Portland apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £579 / night

£4,053 / week

1 / 20

Holiday apartment in Portland

Portland apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £499 / night

£3,494 / week

1 / 22

Portland holiday apartment rental

Portland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £200 / night

£1,398 / week

1 / 24

Holiday apartment in Portland

Portland apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

from £302 / night

£2,113 / week

1 / 30

Holiday home in Portland

Portland house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

from £297 / night

£2,080 / week

1 / 16

Holiday apartment in Portland

Portland apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £334 / night

£2,337 / week

1 / 16

Portland holiday apartment rental

Portland apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £86 / night

£598 / week

1 / 18

Holiday apartment in Portland

Portland apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £184 / night

£1,286 / week

1 / 30

Holiday apartment in Portland

Portland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £184 / night

£1,286 / week

1 / 17

Holiday condo in Portland

Portland condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from £715 / night

£5,003 / week

1 / 24

Portland holiday condo rental

Portland condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £81 / night

£565 / week

1 / 18

Holiday home in Portland

Portland house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £262 / night

£1,834 / week

1 / 16

Holiday home in Portland

Portland house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £599 / night

£4,192 / week

1 / 30

Portland holiday condo rental

Portland condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from £340 / night

£2,376 / week

1 / 24

Holiday home rental

Portland house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £89 / night

£621 / week

1 / 16

Ski apartment to rent in Portland

Portland apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £280 / night

£1,957 / week

1 / 20

Holiday apartment in Portland

Portland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £220 / night

£1,537 / week

1 / 26

Portland ski apartment to rent.

Portland apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £158 / night

£1,102 / week

1 / 25

Portland holiday home rental

Portland house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

from £216 / night

£1,510 / week

1 / 17

Home rental in Portland

Portland house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £280 / night

£1,957 / week

1 / 12

Peaks Island holiday cottage rental

Peaks Island cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £254 / night

£1,772 / week

1 / 21

Apartment rental in Portland

Portland apartment

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

from £402 / night

£2,812 / week

1 / 30

Holiday home in Portland

Portland house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £1,597 / night

£11,179 / week

1 / 29

Holiday condo in Portland

Portland condo

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

from £111 / night

£777 / week

1 / 14

Holiday home in Peaks Island

Peaks Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from £470 / night

£3,287 / week

1 / 30

Apartment rental in Portland

Portland apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £343 / night

£2,398 / week

1 / 13

Holiday apartment in Portland

Portland apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £124 / night

£867 / week

1 / 25

Apartment rental in Portland

Portland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £78 / night

£543 / week

1 / 22

Portland holiday apartment rental

Portland apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 10

from £716 / night

£5,008 / week

1 / 30

Holiday home in Portland

Portland house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

from £602 / night

£4,209 / week

1 / 28

Home rental in Portland

Portland house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £219 / night

£1,532 / week

1 / 30

Holiday apartment in Portland

Portland apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

from £180 / night

£1,258 / week

1 / 12

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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