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

Portland Vacation Rentals

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Our top choices for Portland vacation rentals

1. 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 $447
CA $536 total
includes taxes & fees
Oct 11 - Oct 12
Lighthouse View

2. Lily's Pad

Lily's Pad
3.0 star property
Portland
The price is CA $584
CA $701 total
includes taxes & fees
Oct 17 - Oct 18
Lily's Pad

3. 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
The price is CA $780
CA $936 total
includes taxes & fees
Oct 5 - Oct 6
Mermaid Cottage

4. Chandlers Nook

Chandlers Nook
2.0 star property
Portland
The price is CA $609
CA $731 total
includes taxes & fees
Oct 5 - Oct 6
Chandlers Nook

5. Anchor Cottage

Anchor Cottage
3.0 star property
Portland
The price is CA $759
CA $911 total
includes taxes & fees
Oct 11 - Oct 12
Anchor Cottage

6. 74 Reap Lane

74 Reap Lane
3.0 star property
Portland
The price is CA $737
CA $885 total
includes taxes & fees
Oct 11 - Oct 12
74 Reap Lane

7. Home From Home

Home From Home
3.0 star property
Portland
The price is CA $712
CA $854 total
includes taxes & fees
Oct 11 - Oct 12
Home From Home

8. Portland View

Portland View
2.0 star property
Portland
The price is CA $721
CA $865 total
includes taxes & fees
Oct 11 - Oct 12
Portland View

9. The Old Portland Courthouse

The Old Portland Courthouse
3.5 star property
Portland
The price is CA $1,929
CA $2,315 total
includes taxes & fees
Oct 4 - Oct 5
The Old Portland Courthouse

10. 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 $831
CA $997 total
includes taxes & fees
Oct 16 - Oct 17
Old Higher Lighthouse Branscombe Lodge

11. Old Higher Lighthouse Stopes Cottage

Old Higher Lighthouse Stopes Cottage
3.0 star property
Portland
The price is CA $831
CA $997 total
includes taxes & fees
Oct 22 - Oct 23
Old Higher Lighthouse Stopes Cottage

12. Sea Gem

Sea Gem
3.5 star property
Portland
The price is CA $1,512
CA $1,815 total
includes taxes & fees
Oct 16 - Oct 17
Sea Gem

13. Pebbles Reach

Pebbles Reach
3.5 star property
Portland
The price is CA $1,122
CA $1,346 total
includes taxes & fees
Oct 4 - Oct 5
Pebbles Reach

14. St Johns View

St Johns View
3.5 star property
Portland
The price is CA $1,002
CA $1,202 total
includes taxes & fees
Oct 4 - Oct 5
St Johns View

15. Manhattan Beach

Manhattan Beach
3.0 star property
Portland
The price is CA $968
CA $1,162 total
includes taxes & fees
Oct 4 - Oct 5
Manhattan Beach

16. The Shambles

The Shambles
3.5 star property
Portland
The price is CA $989
CA $1,187 total
includes taxes & fees
Oct 5 - Oct 6
The Shambles

17. 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 $1,613
CA $1,936 total
includes taxes & fees
Oct 13 - Oct 14
Jurassic Coast House

18. The View

The View
2.0 star property
Portland
The price is CA $1,263
CA $1,516 total
includes taxes & fees
Oct 31 - Nov 1
The View

19. Bear's Apartment

Bear's Apartment
2.0 star property
Portland
The price is CA $895
CA $1,074 total
includes taxes & fees
Oct 11 - Oct 12
Bear's Apartment

20. The Sailors Studio|Sleeps2|Weymouth Beach|

The Sailors Studio|Sleeps2|Weymouth Beach|
Weymouth Town Center
The price is CA $113
CA $253 total
includes taxes & fees
Oct 6 - Oct 7
The Sailors Studio|Sleeps2|Weymouth Beach|
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

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. Some other top choices in Portland are Coastal bungalow retreat on the Jurassic Coast at Portland, Dorset. and 4 bedroom accommodation in Portland.

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.