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The 10 Best Holiday Rentals in Portland, USA

Check out our pick of great holiday rentals in Portland

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Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
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West End Inn is located in Portland, 1 km from Victoria Mansion.

Each room at this bed and breakfast is air conditioned and comes with a flat-screen TV with cable channels. Rooms come with a private bathroom fitted with a shower. Extras include free toiletries and a hairdryer. West End Inn features free WiFi .

Good location in a quiet area, walking distance to downtown attractions. Large comfortable room. Great breakfast cooked to order. Helpful and friendly host

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9.3
Superb
111 reviews
Price from
£208
per night

Located in Portland in the Maine region, with East End Beach and Portland Observatory nearby, Island View House BnB Self Check-In provides accommodation with free WiFi and free private parking. The property is set 26 km from Funtown Splashtown USA, 23 km from Aquaboggan Water Park and 28 km from Palace Playland. Every room has a flat-screen TV with streaming services.

Comfortable, well-appointed, spotlessly clean and good location.

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9
Superb
27 reviews
Price from
£199
per night

Featuring air-conditioned accommodation with a patio, The Brew House - 2nd Floor Private Apartment is located in Portland. The property is around 25 km from Funtown Splashtown USA, 23 km from Aquaboggan Water Park and 27 km from Palace Playland. There is a sun terrace and guests can make use of free WiFi and free private parking.

Nice place to stay and visit the city.

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9.4
Superb
21 reviews
Price from
£267
per night

Located in Portland, 1.5 km from East End Beach and 25 km from Funtown Splashtown USA, Bright Spacious Apartment - 2 BR 2 BA provides spacious air-conditioned accommodation with a balcony and free WiFi. The property is set 23 km from Aquaboggan Water Park, 27 km from Palace Playland and 27 km from Old Orchard Beach Pier. There is private parking and the property offers an electric vehicle charging station.

The property owners, Jen & David, were a joy to rent from for our long weekend. They reached out a few days ahead of time, on top of answering a few questions I had 1-2 weeks in advance. David called on our way to the property to double check any last minute items. We were able to visit David's ice cream shop in South Portland, and it was fantastic! Great visit, and the town of Portland was great!

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9.6
Exceptional
7 reviews
Price from
£319
per night

Set in Portland, 1.3 km from East End Beach and 25 km from Funtown Splashtown USA, East end. Walk to food, beer and downtown fun. Offers accommodation with free WiFi in a historic building. The air-conditioned accommodation is 300 metres from Portland Observatory. The property is non-smoking and is located less than 1 km from Merrill Auditorium.

The apartment was very cozy. Separate bedrooms. In a neighborhood setting. Close to the old port and town. Close to the recreational trails. Clean. Fairly priced. Well equipped kitchen was great although I was not able to take advantage of it. Good to know for future return ... which I hope to do!

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9.1
Superb
21 reviews
Price from
£245
per night

Set 1.1 km from East End Beach, 25 km from Funtown Splashtown USA and a few steps from Portland Observatory, Best Bower offers accommodation located in Portland. Featuring garden and inner courtyard views, this guest house also has free WiFi. The guest house features family rooms as well as facilities for disabled guests.

Elegant rooms, a great deal of time and effory was spent creating style atmistphere and it was eloquently done. We loved it.

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9.5
Exceptional
98 reviews
Price from
£151
per night

Set in Portland, 2.1 km from East End Beach and 24 km from Funtown Splashtown USA, The Docent's Collection offers accommodation with free WiFi in a historic building. The air-conditioned accommodation is 500 metres from Merrill Auditorium. The accommodation features a 24-hour front desk and a lift for guests.

The apartment was fantastic. It's so big I couldn't find the third bedroom! Nicely appointed.

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9.3
Superb
85 reviews
Price from
£903
per night

Located within 23 km of Funtown Splashtown USA and 2.1 km of Merrill Auditorium, The Chadwick Bed and Breakfast offers rooms with air conditioning and a private bathroom in Portland. This bed and breakfast provides free private parking and luggage storage space. On clear days, guests can head outside to enjoy the bed and breakfast's outdoor fireplace or simply kick back and relax.

Erin, lily and the pups were so welcoming! The bed was amazing, the shower was glorious, the breakfast was 10/10... check in/out was super easy! I couldn't recommend this accommodation more!

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9.3
Superb
46 reviews
Price from
£182
per night

The holiday home has 1 bedroom, a TV with cable channels, a fully equipped kitchen with an oven and a microwave, and 1 bathroom with an a bath or shower. Towels and bed linen are available in the holiday home. The accommodation offers a fireplace.

Beautiful views, ample living space, clean and comfortable, cozy bedroom with a wood stove, and a kitchen with plenty of dishes, pots, pans, and utensils.

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8
Very good
10 reviews
Price from
£162
per night

Portland International Jetport is just an 8-minute drive from this bed and breakfast. It serves a free full breakfast and offers free Wi-Fi in every room. Guests are greeted by the resident cats.

The individually decorated rooms at Fleetwood House Bed and Breakfast provide cable TV and a seating area. They also have wooden floors and a bathrobe. The private or shared bathroom includes a hairdryer.

I just enjoyed staying at Fleetwood House! Linda and Jim are really sweet hosts, breakfast was plenty and good, the place itself is cosy and I wood always come back, when in the area. And I love the cats :-)

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8.4
Very good
77 reviews
Price from
£199
per night

Most booked holiday rentals in Portland this month

Enjoy breakfast in Portland!

  • West End Inn
    Breakfast options
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 113 reviews

    West End Inn is located in Portland, 1 km from Victoria Mansion. Each room at this bed and breakfast is air conditioned and comes with a flat-screen TV with cable channels.

    We really enjoyed the cleanliness and the location.

  • Fleetwood House Bed and Breakfast
    8.4
    Scored 8.4
    Very good
    Rated very good
     · 77 reviews

    Portland International Jetport is just an 8-minute drive from this bed and breakfast. It serves a free full breakfast and offers free Wi-Fi in every room. Guests are greeted by the resident cats.

    Excellent breakfast. charming host. Nice old house

  • East end. Walk to food, beer and downtown fun.
    9.1
    Scored 9.1
    Superb
    Rated superb
     · 21 reviews

    Set in Portland, 1.3 km from East End Beach and 25 km from Funtown Splashtown USA, East end. Walk to food, beer and downtown fun. Offers accommodation with free WiFi in a historic building.

    location was convenient to town enjoyed the jigsaw puzzle.

  • Best Bower
    Breakfast options
    9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 98 reviews

    Set 1.1 km from East End Beach, 25 km from Funtown Splashtown USA and a few steps from Portland Observatory, Best Bower offers accommodation located in Portland.

    There is a really nice patio where we sat and had our morning coffee.

  • The Docent's Collection
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 85 reviews

    Set in Portland, 2.1 km from East End Beach and 24 km from Funtown Splashtown USA, The Docent's Collection offers accommodation with free WiFi in a historic building.

    Very nice layout. Very comfortable and good location.

  • The Chadwick Bed and Breakfast
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 46 reviews

    Located within 23 km of Funtown Splashtown USA and 2.1 km of Merrill Auditorium, The Chadwick Bed and Breakfast offers rooms with air conditioning and a private bathroom in Portland.

    Einzigartiges Frühstück, familiär und liebevoll geführtes b&b

  • East End Annex
    Breakfast options
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 10 reviews

    Situated in Portland, 1.1 km from East End Beach and 25 km from Funtown Splashtown USA, East End Annex features air-conditioned accommodation with a balcony and free WiFi.

  • Historic East End - Top of Munjoy Hill!
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 1 review

    Situated in Portland in the Maine region, with East End Beach and Portland Observatory nearby, Historic East End - Top of Munjoy Hill! features accommodation with free WiFi and free private parking.

These holiday rentals in Portland have options with FREE cancellation

  • Island View House BnB Self Check-In
    Free cancellation options available
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 27 reviews

    Located in Portland in the Maine region, with East End Beach and Portland Observatory nearby, Island View House BnB Self Check-In provides accommodation with free WiFi and free private parking.

    stellar location, clean and roomy for our family of 4

  • Back Cove Views
    Free cancellation options available
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Back Cove Views in Portland features accommodation with free WiFi, 1.5 km from East End Beach, 25 km from Funtown Splashtown USA and 400 metres from Portland Observatory.

  • Pearl of Portland
    Free cancellation options available

    Pearl of Portland is set in Portland, 25 km from Funtown Splashtown USA, 400 metres from Portland Observatory, as well as 700 metres from Merrill Auditorium.

  • Cumberland Casa - B
    Free cancellation options available
    6.2
    Scored 6.2
    Pleasant
    Rated pleasant
     · 5 reviews

    Situated in Portland, 1.2 km from Merrill Auditorium and 1.9 km from Portland Observatory, Cumberland Casa - B offers air conditioning.

  • City Charm, Old Port Oasis
    Free cancellation options available
    9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 2 reviews

    Offering city views, City Charm, Old Port Oasis is an accommodation set in Portland, 24 km from Funtown Splashtown USA and 400 metres from Merrill Auditorium.

  • Cumberland Casa - A
    Free cancellation options available
    5.5
    Scored 5.5
    Average
    Rated passable
     · 2 reviews

    Cumberland Casa - A, a property with a garden, is located in Portland, 1.2 km from Merrill Auditorium, 1.9 km from Portland Observatory, as well as 21 km from Aquaboggan Water Park.

  • Historic Casco Bay Home on Great Diamond Island

    Boasting a spa bath, Historic Casco Bay Home on Great Diamond Island is set in Portland. Free WiFi is available throughout the property and West Shore Sandy Beach is 2.7 km away.

  • Spacious Portland Home Walk Downtown!
    Free cancellation options available

    Located in Portland, 25 km from Funtown Splashtown USA and 500 metres from Merrill Auditorium, Spacious Portland Home Walk Downtown! offers a bar and air conditioning.

Highly rated holiday rentals in Portland

  • The Brew House - 2nd Floor Private Apartment
    9.4
    Scored 9.4
    Superb
    Rated superb
     · 21 reviews

    Featuring air-conditioned accommodation with a patio, The Brew House - 2nd Floor Private Apartment is located in Portland.

    Host was accommodating, friendly, helpful, communicative.

  • Bright Spacious Apartment - 2 BR 2 BA
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 7 reviews

    Located in Portland, 1.5 km from East End Beach and 25 km from Funtown Splashtown USA, Bright Spacious Apartment - 2 BR 2 BA provides spacious air-conditioned accommodation with a balcony and free...

  • East Bayside/ Munjoy - Charming Downtown Escape
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 2 reviews

    East Bayside/ Munjoy - Charming Downtown Escape is set in Portland, 400 metres from Portland Observatory, 700 metres from Merrill Auditorium, as well as 23 km from Aquaboggan Water Park.

  • Crow's Nest
    8.0+ review score
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 1 review

    Situated in Portland in the Maine region, with East End Beach and Portland Observatory nearby, Crow's Nest features accommodation with free private parking.

  • Monument Garden SWEET
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 2 reviews

    Featuring a garden and free WiFi, Monument Garden SWEET features accommodation attractively situated in Portland, within a short distance of East End Beach, Portland Observatory and Merrill Auditorium...

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