Portland Vacation Rentals from $236: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Portland vacation rentals

1. Lighthouse View

Portland

Anonymous traveler

$322 nightly

Sep 3 - Sep 4

Total with taxes and fees

2. Mermaid Cottage

Portland

Terry

$563 nightly

Sep 3 - Sep 4

Total with taxes and fees

3. Chandlers Nook

Portland

$440 nightly

Sep 5 - Sep 6

Total with taxes and fees

4. Anchor Cottage

Portland

$548 nightly

Sep 13 - Sep 14

Total with taxes and fees

5. Portland View

Portland

$520 nightly

Sep 13 - Sep 14

Total with taxes and fees

6. Old Higher Lighthouse Branscombe Lodge

Portland

Trevor

7. 74 Reap Lane

Portland

$532 nightly

Sep 18 - Sep 19

Total with taxes and fees

8. Home From Home

Portland

$539 nightly

Sep 13 - Sep 14

Total with taxes and fees

9. Groves House

Portland

$534 nightly

Sep 6 - Sep 7

Total with taxes and fees

10. St Johns View

Portland

$1,150 nightly

Sep 3 - Sep 4

Total with taxes and fees

11. Pebbles Reach

Portland

$809 nightly

Sep 3 - Sep 4

Total with taxes and fees

12. Coastguard View

Portland

$658 nightly

Sep 3 - Sep 4

Total with taxes and fees

13. Manhattan Beach

Portland

$698 nightly

Sep 12 - Sep 13

Total with taxes and fees

14. Sea Gem

Portland

$1,091 nightly

Sep 2 - Sep 3

Total with taxes and fees

15. The Shambles

Portland

$713 nightly

Sep 13 - Sep 14

Total with taxes and fees

16. Bear's Apartment

Portland

$646 nightly

Sep 18 - Sep 19

Total with taxes and fees

17. The View

Portland

$906 nightly

Sep 12 - Sep 13

Total with taxes and fees

18. The Old Portland Courthouse

Portland

$1,391 nightly

Sep 13 - Sep 14

Total with taxes and fees

19. Kimberlin

Portland

$2,202 nightly

Sep 4 - Sep 5

Total with taxes and fees

20. 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

$1,163 nightly

Sep 18 - Sep 19

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Cottages

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Portland Hotel Reviews

Fairhaven Hotel

10/10 Excellent

"The Hotel was very relaxed - I felt really comfortable and safe staying as a single lady - the staff were always to hand if I needed anything. I will be staying again next year or sooner. Thank you Fairhaven Hotel."

George Albert Hotel & Spa

10/10 Excellent

"The front of the hotel looks old could do with brightening up. But soon as you entre it's a different feeling it's lovely and clean. Very well presented the rooms are large and more than enough space for all your belongings. Well presented room. Room service each day and all things replaced including bottles of water and biscuits. Its the little things that count.parkjng right outside the main door. Good quiet location but easy to get to other towns by car."

Sleeping Bear Hotel Dorchester

10/10 Excellent

"We arrived late at the Sleeping Bear Hotel and the self check-in was incredibly easy and smooth. We simply pressed the green button by the door and followed the instructions. Walking through the hallway, staircase and lovely sitting/living room area with my daughter, we were pleasantly surprised by how beautiful and cosy everything looked. There were lots of comfortable sofas with cushions, making it feel just like home, and we loved that we could make coffee from the machine whenever we wanted. Our room was very clean and cosy, and the mattress was unbelievably comfortable and soft. At check-out, the two lovely ladies at reception even found me a takeaway cup so I could take my coffee with me. A truly wonderful stay — I will definitely be coming back!"

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 $236 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 19 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.

Portland Vacation Rentals

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Portland vacation rentals

1. Lighthouse View

2. Mermaid Cottage

3. Chandlers Nook

4. Anchor Cottage

5. Portland View

6. Old Higher Lighthouse Branscombe Lodge

7. 74 Reap Lane

8. Home From Home

9. Groves House

10. St Johns View

11. Pebbles Reach

12. Coastguard View

13. Manhattan Beach

14. Sea Gem

15. The Shambles

16. Bear's Apartment

17. The View

18. The Old Portland Courthouse

19. Kimberlin

20. Jurassic Coast House

Find vacation rentals that suit your style

Top Portland Hotel Reviews

Fairhaven Hotel

Find out more about Portland

Explore a world of travel with Expedia

Frequently asked questions

Expedia's Latest Trends

Go further with the Expedia app