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. 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 $781
CA $937 total
includes taxes & fees
Sep 3 - Sep 4
Mermaid Cottage

2. 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 $537 total
includes taxes & fees
Aug 21 - Aug 22
Lighthouse View

3. Groves House

Groves House
3.0 star property
Portland
The price is CA $741
CA $889 total
includes taxes & fees
Sep 1 - Sep 2
Groves House

4. Home From Home

Home From Home
3.0 star property
Portland
The price is CA $747
CA $897 total
includes taxes & fees
Aug 24 - Aug 25
Home From Home

5. 74 Reap Lane

74 Reap Lane
3.0 star property
Portland
The price is CA $738
CA $885 total
includes taxes & fees
Aug 19 - Aug 20
74 Reap Lane

6. Pebbles Reach

Pebbles Reach
3.5 star property
Portland
The price is CA $1,123
CA $1,347 total
includes taxes & fees
Sep 2 - Sep 3
Pebbles Reach

7. Coastguard View

Coastguard View
3.0 star property
Portland
The price is CA $913
CA $1,096 total
includes taxes & fees
Sep 3 - Sep 4
Coastguard View

8. Bear's Apartment

Bear's Apartment
2.0 star property
Portland
The price is CA $896
CA $1,075 total
includes taxes & fees
Aug 21 - Aug 22
Bear's Apartment

9. Manhattan Beach

Manhattan Beach
3.0 star property
Portland
The price is CA $969
CA $1,163 total
includes taxes & fees
Sep 12 - Sep 13
Manhattan Beach

10. Sea Gem

Sea Gem
3.5 star property
Portland
The price is CA $1,514
CA $1,816 total
includes taxes & fees
Aug 29 - Aug 30
Sea Gem

11. St Johns View

St Johns View
3.5 star property
Portland
The price is CA $1,595
CA $1,914 total
includes taxes & fees
Aug 29 - Aug 30
St Johns View

12. Kimberlin

Kimberlin
3.5 star property
Portland
The price is CA $3,056
CA $3,667 total
includes taxes & fees
Sep 4 - Sep 5
Kimberlin

13. The Old Portland Courthouse

The Old Portland Courthouse
3.5 star property
Portland
The price is CA $1,931
CA $2,317 total
includes taxes & fees
Aug 21 - Aug 22
The Old Portland Courthouse

14. 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 $1,985
CA $2,382 total
includes taxes & fees
Aug 29 - Aug 30
Jurassic Coast House

15. Coastguard Lookout

Coastguard Lookout
2.0 star property
Weymouth
The price is CA $715
CA $858 total
includes taxes & fees
Sep 7 - Sep 8
Coastguard Lookout

16. Seaside Escape - Free parking! 4 minutes to the beach! Pet friendly!

Seaside Escape - Free parking! 4 minutes to the beach! Pet friendly!
Weymouth
8.4 out of 10, Very good, (5 reviews)
"Lovely property, well equipped and comfy beds"
United Kingdom
Kim E.
The price is CA $172
CA $250 total
includes taxes & fees
Sep 13 - Sep 14
Seaside Escape - Free parking! 4 minutes to the beach! Pet friendly!

17. 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
The price is CA $282
CA $642 total
includes taxes & fees
Sep 7 - Sep 8
Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World

18. Bluebell Wood cosy Woodland Shepherds Hut in Harmans Cross near Swanage

Bluebell Wood cosy Woodland Shepherds Hut in Harmans Cross near Swanage
Harman's Cross
The price is CA $319
CA $363 total
includes taxes & fees
Aug 20 - Aug 21
Bluebell Wood cosy Woodland Shepherds Hut in Harmans Cross near Swanage

19. Hardy View Farm House

Hardy View Farm House
Dorchester
10.0 out of 10, Exceptional, (3 reviews)
"Absolutely Fabulous Stay at this Farmhouse. Wonderful hosts in Luba and Chris who were so informative and helpful.Lovely property inside and out. So relaxing and peaceful. Missing the wonderful breakfasts already. 10 out of 10 !!"
Australia
Carol S.
The price is CA $282
CA $317 total
includes taxes & fees
Sep 2 - Sep 3
Hardy View Farm House

20. Willow’s Nest Countryside Shepherd’s Hut Retreat Near Swanage

Willow’s Nest Countryside Shepherd’s Hut Retreat Near Swanage
Harman's Cross
The price is CA $369
CA $420 total
includes taxes & fees
Aug 17 - Aug 18
Willow’s Nest Countryside Shepherd’s Hut Retreat Near Swanage
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

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Portland vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Portland vacation rentals we have selected for you start as low as CA $897 per night. Entering your travel dates in the search wizard 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. 

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 20 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.