Portland Vacation Rentals

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Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for Portland vacation rentals

Beach nearby

74 Reap Lane

74 Reap Lane
3.0 star property
Portland
The price is CA $732
CA $878 total
includes taxes & fees
Apr 23 - Apr 24
74 Reap Lane
Room

Kimberlin, Chiswell On Portland

Kimberlin, Chiswell On Portland
Portland
The price is CA $1,168
CA $1,168 total
includes taxes & fees
Apr 18 - Apr 19
Kimberlin, Chiswell On Portland
Beach nearby

Home From Home

Home From Home
3.0 star property
Portland
The price is CA $741
CA $889 total
includes taxes & fees
Apr 15 - Apr 16
Home From Home
Cottage | Property grounds

Old Higher Lighthouse Stopes Cottage

Old Higher Lighthouse Stopes Cottage
3.0 star property
Portland
The price is CA $855
CA $1,026 total
includes taxes & fees
Apr 24 - Apr 25
Old Higher Lighthouse Stopes Cottage
Cottage | Interior

Old Higher Lighthouse Branscombe Lodge

Old Higher Lighthouse Branscombe Lodge
3.0 star property
Portland
10.0 out of 10, Exceptional, (1 review)
"This property was absolutely amazed and having Access to one of the first lighthouses there "
United Kingdom
Trevor
The price is CA $830
CA $996 total
includes taxes & fees
May 3 - May 4
Old Higher Lighthouse Branscombe Lodge
Cottage | Interior

Pebbles Reach

Pebbles Reach
3.5 star property
Portland
The price is CA $1,113
CA $1,336 total
includes taxes & fees
Apr 15 - Apr 16
Pebbles Reach
Dining

Coastguard View

Coastguard View
3.0 star property
Portland
The price is CA $906
CA $1,087 total
includes taxes & fees
Apr 15 - Apr 16
Coastguard View
Cottage | Interior

The Shambles

The Shambles
3.5 star property
Portland
The price is CA $982
CA $1,178 total
includes taxes & fees
Apr 24 - Apr 25
The Shambles
Interior

Mermaid Cottage

Mermaid Cottage
3.0 star property
Portland
The price is CA $775
CA $929 total
includes taxes & fees
Apr 17 - Apr 18
Mermaid Cottage
Beach nearby

Anchor Cottage

Anchor Cottage
3.0 star property
Portland
The price is CA $754
CA $905 total
includes taxes & fees
May 9 - May 10
Anchor Cottage
Property grounds

Manhattan Beach

Manhattan Beach
3.0 star property
Portland
The price is CA $961
CA $1,154 total
includes taxes & fees
Apr 16 - Apr 17
Manhattan Beach
Property grounds

Bear's Apartment

Bear's Apartment
2.0 star property
Portland
The price is CA $889
CA $1,066 total
includes taxes & fees
Apr 18 - Apr 19
Bear's Apartment
Cottage | Dining

Lighthouse View

Lighthouse View
3.5 star property
Portland
6.0 out of 10, (1 review)
"Bed was not comfy as we had backache after second night , we turned mattress round was ok that night but the after that . The step into the shower was too high and we had to buy a step to get in it and also the floor surface was very slippy . Was ck an and tidy and overall not a bad place to stay and would recommend and return at some point "
United Kingdom
Anonymous traveller
The price is CA $443
CA $532 total
includes taxes & fees
Apr 15 - Apr 16
Lighthouse View
Cottage | Interior

St Johns View

St Johns View
3.5 star property
Portland
The price is CA $1,026
CA $1,232 total
includes taxes & fees
Apr 18 - Apr 19
St Johns View
Cottage | Beach

The View

The View
2.5 star property
Portland
The price is CA $1,246
CA $1,496 total
includes taxes & fees
Apr 18 - Apr 19
The View
Cottage | Interior

Kimberlin

Kimberlin
3.5 star property
Portland
The price is CA $928
CA $1,114 total
includes taxes & fees
Apr 18 - Apr 19
Kimberlin
Cottage | Interior

Sea Gem

Sea Gem
3.5 star property
Portland
The price is CA $1,501
CA $1,802 total
includes taxes & fees
Apr 15 - Apr 16
Sea Gem
Cottage | Dining

Jurassic Coast House

Jurassic Coast House
3.5 star property
Portland
8.0 out of 10, Very good, (1 review)
"Nice size property. Missing the more luxury/comfort items. Garden furniture ok not as images. Has a comfy dining table. Balcony furniture present but not suitable for the area. High stools and table not appropriate needs more relaxing items to make area useful otherwise it was good for drying clothes. Area is central and easy for amenities, cafes, beach, shops etc all easy to walk to. Noisy as near heliport and some days this is busy from early morning till after 10 at night. Not overly...
United Kingdom
Michelle
The price is CA $1,601
CA $1,922 total
includes taxes & fees
May 3 - May 4
Jurassic Coast House
Cottage | Living room

The Old Portland Courthouse

The Old Portland Courthouse
3.5 star property
Portland
The price is CA $1,915
CA $2,298 total
includes taxes & fees
Apr 15 - Apr 16
The Old Portland Courthouse
Cottage | Interior

Jay Cottage

Jay Cottage
3.5 star property
Weymouth
The price is CA $584
CA $701 total
includes taxes & fees
May 1 - May 2
Jay Cottage
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Portland Hotel Reviews

Best Western Weymouth Hotel Rembrandt

Best Western Weymouth Hotel Rembrandt

8/10 Good
"Very good Breakfast "
Barry 2-night trip
Posted 7 hours ago
Best Western Weymouth Hotel Rembrandt

Find out more about Portland

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Portland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Portland?

Yes, you can find vacation rentals in Portland close to Osprey Leisure Centre, or you can select a more secluded option if you'd like a relaxing place to stay. Tourists appreciate the top-notch restaurants and bars in Portland. Make sure you have time to check out the university setting while you're in the area.

What are some of the best vacation rentals in Portland?

Beautiful, family friendly Cottage with sea views of Chesil Beach : Visitors give good reviews to this Portland vacation home rental, which is located in a rural location and has a fireplace, a private yard, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind. Our travelers also rate Bright & beautiful 4 bedroom house with sea views as a favorite home for rent in Portland.

How many vacation rentals will I find in Portland?

Choose from 17 Expedia vacation rentals in Portland for a memorable vacation.

What can I see and do in Portland?

Cultural attractions include Portland Museum and Tout Quarry Sculpture Park, whereas Portland Bill and Weymouth Bay are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Portland Harbour and Portland Bill Lighthouse.

What are vacation rentals like in Portland?

Vacation rentals are private properties you can stay in for a couple days or more in Portland. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and busy front desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for family trips.