A coastal town with colorful houses, a prominent hill in the background, and a clear blue sky.

Portland Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Portland vacation rentals

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 traveler
$318 nightly
The price is $381
Jul 19 - Jul 20
Total with taxes and fees
Lighthouse View
Beach

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

Sea View Coastal Cottage Sleeps 6 | Jurassic Coast, 6-Min Walk to Beach, Dogs
Fortuneswell
10.0 out of 10, Exceptional, (3 reviews)
"We had a great stay in Portland. The house had everything we needed, as a base to explore the local area. "
United Kingdom
Ruby C.
$545 nightly
The price is $545
Aug 14 - Aug 15
Total with taxes and fees
Sea View Coastal Cottage Sleeps 6 | Jurassic Coast, 6-Min Walk to Beach, Dogs
Beach nearby

Anchor Cottage

Anchor Cottage
3.0 star property
Portland
$540 nightly
The price is $648
Jul 25 - Jul 26
Total with taxes and fees
Anchor Cottage
Interior

Mermaid Cottage

Mermaid Cottage
3.0 star property
Portland
10.0 out of 10, Exceptional, (1 review)
"Very nice cottage in quiet location with room opening onto garden with lots of bird song. Snug with TV is very comfortable. Parking spot just outside cottage. Well appointed kitchen. Location is good for access to portland, but going elsewhere requires travelling through Weymouth which can be slow."
United Kingdom
Terry
$555 nightly
The price is $666
Jul 31 - Aug 1
Total with taxes and fees
Mermaid Cottage
Beach nearby

Home From Home

Home From Home
3.0 star property
Portland
$531 nightly
The price is $637
Jul 20 - Jul 21
Total with taxes and fees
Home From Home
Beach

74 Reap Lane

74 Reap Lane
3.0 star property
Portland
$524 nightly
The price is $629
Jul 19 - Jul 20
Total with taxes and fees
74 Reap Lane
Dining

Coastguard View

Coastguard View
3.0 star property
Portland
$649 nightly
The price is $779
Jul 25 - Jul 26
Total with taxes and fees
Coastguard View
Property grounds

Manhattan Beach

Manhattan Beach
3.0 star property
Portland
$689 nightly
The price is $826
Jul 20 - Jul 21
Total with taxes and fees
Manhattan Beach
Living area

Groves House

Groves House
3.0 star property
Portland
$526 nightly
The price is $632
Aug 10 - Aug 11
Total with taxes and fees
Groves House
Property grounds

Bear's Apartment

Bear's Apartment
2.0 star property
Portland
$636 nightly
The price is $764
Jul 18 - Jul 19
Total with taxes and fees
Bear's Apartment
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
$870 nightly
The price is $1,044
Jul 18 - Jul 19
Total with taxes and fees
Old Higher Lighthouse Branscombe Lodge
Cottage | Interior

Pebbles Reach

Pebbles Reach
3.5 star property
Portland
$798 nightly
The price is $957
Jul 26 - Jul 27
Total with taxes and fees
Pebbles Reach
Cottage | Interior

Sea Gem

Sea Gem
3.5 star property
Portland
$1,076 nightly
The price is $1,291
Jul 18 - Jul 19
Total with taxes and fees
Sea Gem
Cottage | Property grounds

Old Higher Lighthouse Stopes Cottage

Old Higher Lighthouse Stopes Cottage
3.0 star property
Portland
$1,822 nightly
The price is $2,187
Aug 7 - Aug 8
Total with taxes and fees
Old Higher Lighthouse Stopes Cottage
Cottage | Beach | Beach nearby

The View

The View
2.0 star property
Portland
$1,165 nightly
The price is $1,398
Jul 18 - Jul 19
Total with taxes and fees
The View
Cottage | Living room | TV

The Old Portland Courthouse

The Old Portland Courthouse
3.5 star property
Portland
$1,372 nightly
The price is $1,646
Jul 19 - Jul 20
Total with taxes and fees
The Old Portland Courthouse
Cottage | Interior

St Johns View

St Johns View
3.5 star property
Portland
$1,495 nightly
The price is $1,794
Aug 1 - Aug 2
Total with taxes and fees
St Johns View
Cottage | Interior

Kimberlin

Kimberlin
3.5 star property
Portland
$2,383 nightly
The price is $2,859
Aug 7 - Aug 8
Total with taxes and fees
Kimberlin
Property grounds

Beautiful Pad Near World Heritage Jurassic Coast

Beautiful Pad Near World Heritage Jurassic Coast
3.0 star property
Bridport
$223 nightly
The price is $267
Jul 18 - Jul 19
Total with taxes and fees
Beautiful Pad Near World Heritage Jurassic Coast
Beach

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

Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World
Wool
10.0 out of 10, Exceptional, (4 reviews)
"Responsive owner and lovely property"
United Kingdom
Benjamin
$481 nightly
The price is $481
Jul 19 - Jul 20
Total with taxes and fees
Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World
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

Aaran Guesthouse

Aaran Guesthouse

10/10 Excellent
"We loved this place. Our room looked out on the English Channel, giving us a delightful view of the beach. Our hosts were wonderful and a pleasure to spend time with. We will return!!😎"
Jonathan 2-night trip
Posted 11 hours ago
Aaran Guesthouse

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 $637 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.

Explore a world of travel with Expedia

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 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.