Portland Vacation Rentals from $630: Search Short-Term Rentals

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Our top choices for Portland vacation rentals

Mermaid Cottage

Portland

Terry

$548 nightly

Jun 30 - Jul 1

Total with taxes and fees

Sea View Coastal Cottage Sleeps 6 | Jurassic Coast, 6-Min Walk to Beach, Dogs

Fortuneswell

Ruby C.

$487 nightly

Jul 5 - Jul 6

Total with taxes and fees

Beautiful home in Portland by the beach, sleeps 6!

Dorset

$1,088 nightly

Jul 26 - Jul 27

Total with taxes and fees

Lighthouse View

Portland

Anonymous traveler

$314 nightly

Jul 2 - Jul 3

Total with taxes and fees

74 Reap Lane

Portland

$518 nightly

Jun 30 - Jul 1

Total with taxes and fees

Manhattan Beach

Portland

$681 nightly

Jul 10 - Jul 11

Total with taxes and fees

Home From Home

Portland

$525 nightly

Jun 30 - Jul 1

Total with taxes and fees

Old Higher Lighthouse Stopes Cottage

Portland

$800 nightly

Jul 7 - Jul 8

Total with taxes and fees

Anchor Cottage

Portland

$534 nightly

Jul 5 - Jul 6

Total with taxes and fees

Coastguard View

Portland

$641 nightly

Jul 5 - Jul 6

Total with taxes and fees

The Shambles

Portland

$695 nightly

Jun 30 - Jul 1

Total with taxes and fees

Pebbles Reach

Portland

$788 nightly

Jul 6 - Jul 7

Total with taxes and fees

Bear's Apartment

Portland

$629 nightly

Jul 10 - Jul 11

Total with taxes and fees

Jurassic Coast House

Portland

"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...

Michelle

$1,134 nightly

Jul 5 - Jul 6

Total with taxes and fees

Sea Gem

Portland

$1,061 nightly

Jul 19 - Jul 20

Total with taxes and fees

Old Higher Lighthouse Branscombe Lodge

Portland

Trevor

$1,461 nightly

Jul 17 - Jul 18

Total with taxes and fees

The Old Portland Courthouse

Portland

$1,353 nightly

Jul 11 - Jul 12

Total with taxes and fees

The View

Portland

$1,122 nightly

Jul 11 - Jul 12

Total with taxes and fees

39 Greenlands, Littlesea Holiday Park

Weymouth

$375 nightly

Jun 30 - Jul 1

Total with taxes and fees

Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World

Wool

Benjamin

$472 nightly

Jun 30 - Jul 1

Total with taxes and fees

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Top Portland Hotel Reviews

Driftwood B&B

10/10 Excellent

"We chose the hottest days of the year to stay so the room was boiling, fortunately we took a fan with us but the owner also gave us another too. The room was perfectly adequate for our needs good shower but the toilet flush was slow, plenty of tea/coffee. Nothing was too much trouble for the owner. Easy breakfast idea in dining room lots of choice (but no cooked) we knew b4 so never worried us. I thought it was good value for the money more than happy. Big bonus there was parking and 10 min walk to town."

Durdle Door Hotel

8/10 Good

"Stunning location and very friendly, helpful staff. Room decent but a bit small. Could do with a fan as no air conditioning. No lift and don't recommend this area or property if you have mobility issues. You have to pay for breakfast and drinks are also extra. Didn't like that. Breakfast wad ok, bit let down in terms of the very limited offering eg had to pay same for a "veggie option " which was the meat version without sausage/bacon so literally just egg beans and tomatoes which was a rip off. No veg offering at all. No hot options such as porridge or pancakes etc. Continental offering was basic and things not covered so I didn't like that. But it was so so. 5/10 for breakfast. Major issue is that the area becomes log jammed due to the natural beauty which means traffic in and out to this tiny place is horrendous. There is a large carpark opposite the hotel but if you have cases, luggage etc it is not an easy hike up to the hotel from the car as its steep and not near when carrying stuff. There really is not parking for more than a couple of cars on site and the access is difficult unless in a very small car due to the turn into the property and steep hill up."

Find out more about Portland

Everything you need to know about Portland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Portland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Portland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Portland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Portland. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Portland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $630 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Portland rentals

At Expedia, we put the best Portland vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Portland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Portland vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Portland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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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.

How many vacation rentals will I find in Portland?

Choose from 18 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 Weymouth Bay and Dorset and East Devon Coast 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.

Portland Vacation Rentals

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Check prices for these dates

Our top choices for Portland vacation rentals

Mermaid Cottage

Sea View Coastal Cottage Sleeps 6 | Jurassic Coast, 6-Min Walk to Beach, Dogs

Beautiful home in Portland by the beach, sleeps 6!

Lighthouse View

74 Reap Lane

Manhattan Beach

Home From Home

Old Higher Lighthouse Stopes Cottage

Anchor Cottage

Coastguard View

The Shambles

Pebbles Reach

Bear's Apartment

Jurassic Coast House

Sea Gem

Old Higher Lighthouse Branscombe Lodge

The Old Portland Courthouse

The View

39 Greenlands, Littlesea Holiday Park

Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World

Find vacation rentals that suit your style

Top Portland Hotel Reviews

Driftwood B&B

Find out more about Portland

Explore a world of travel with Expedia

Frequently asked questions

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