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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Portland vacation rentals

A kitchen with a dining table, chairs, a window with curtains, a potted plant, and a pot on the counter.

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 traveler
The price is P19,712
P23,655 total
includes taxes & fees
Oct 11 - Oct 12
Lighthouse View
A neatly made bed with a tufted headboard, a decorative wall fan, and a carpeted floor.

2. Lily's Pad

Lily's Pad
3.0 star property
Portland
The price is P25,919
P31,102 total
includes taxes & fees
Oct 17 - Oct 18
Lily's Pad
A spacious kitchen with a dining area, a grey sofa, and a vintage trunk.

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 P34,629
P41,555 total
includes taxes & fees
Oct 11 - Oct 12
Mermaid Cottage
A living room with a television, dark-colored furniture, a white door, and a window with blinds.

4. Chandlers Nook

Chandlers Nook
2.0 star property
Portland
The price is P26,893
P32,272 total
includes taxes & fees
Oct 20 - Oct 21
Chandlers Nook
A coastal hotel with a paved walkway and seating area, overlooking a pebble beach and cliffs.

5. Anchor Cottage

Anchor Cottage
3.0 star property
Portland
The price is P33,511
P40,213 total
includes taxes & fees
Oct 10 - Oct 11
Anchor Cottage
A wide, pebbled beach with a clear sky and calm sea.

6. 74 Reap Lane

74 Reap Lane
3.0 star property
Portland
The price is P32,525
P39,030 total
includes taxes & fees
Oct 11 - Oct 12
74 Reap Lane
A modern kitchen with white cabinets, a microwave, toaster, kettle, and a refrigerator.

7. Portland View

Portland View
2.0 star property
Portland
The price is P32,009
P38,410 total
includes taxes & fees
Oct 11 - Oct 12
Portland View
A coastal residential area with houses, a grassy field, and a beach with colorful kayaks.

8. Home From Home

Home From Home
3.0 star property
Portland
The price is P31,399
P37,678 total
includes taxes & fees
Oct 16 - Oct 17
Home From Home
A coastal view from a high vantage point with a grassy area and a railing.

9. Old Higher Lighthouse Stopes Cottage

Old Higher Lighthouse Stopes Cottage
3.0 star property
Portland
The price is P36,895
P44,274 total
includes taxes & fees
Oct 22 - Oct 23
Old Higher Lighthouse Stopes Cottage
A room with a large window overlooking a coastal landscape, featuring a wooden interior and a cushioned seating area.

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 P36,608
P43,930 total
includes taxes & fees
Nov 4 - Nov 5
Old Higher Lighthouse Branscombe Lodge
A spacious loft with high ceilings, exposed beams, and large windows. It features a yellow sofa, a blue sofa, and a dining area with a kitchen in the background.

11. Groves House

Groves House
3.0 star property
Portland
8.0 out of 10, Very good, (1 review)
"A nice clean house in a decent location. Not far to walk for some decent pubs. Comfortable beds etc. A few small niggles. The hob was not fully functional and the kitchen tap was falling apart. Still usable though. Overall pretty decent."
United Kingdom
David
The price is P32,666
P39,199 total
includes taxes & fees
Oct 31 - Nov 1
Groves House
A boat on a pebbled beach with a clear view of the sea.

12. St Johns View

St Johns View
3.5 star property
Portland
The price is P44,212
P53,054 total
includes taxes & fees
Oct 13 - Oct 14
St Johns View
A wide, pebbled beach with a clear sky and calm sea.

13. Sea Gem

Sea Gem
3.5 star property
Portland
The price is P67,133
P80,560 total
includes taxes & fees
Oct 16 - Oct 17
Sea Gem
A spacious loft with high ceilings, exposed wooden beams, and large windows.

14. The Old Portland Courthouse

The Old Portland Courthouse
3.5 star property
Portland
The price is P85,616
P102,739 total
includes taxes & fees
Oct 11 - Oct 12
The Old Portland Courthouse
A wooden sign with maritime-themed decorations and text, mounted on a green building.

15. Pebbles Reach

Pebbles Reach
3.5 star property
Portland
The price is P49,783
P59,740 total
includes taxes & fees
Oct 11 - Oct 12
Pebbles Reach
A balcony with a view of a marina and cityscape.

16. Manhattan Beach

Manhattan Beach
3.0 star property
Portland
The price is P42,985
P51,582 total
includes taxes & fees
Oct 11 - Oct 12
Manhattan Beach
A pebble beach with a clear sky and calm sea.

17. The Shambles

The Shambles
3.5 star property
Portland
The price is P43,906
P52,687 total
includes taxes & fees
Oct 11 - Oct 12
The Shambles
A wide, pebbled beach with a clear sky and calm sea.

18. The View

The View
2.0 star property
Portland
The price is P55,732
P66,878 total
includes taxes & fees
Oct 31 - Nov 1
The View
A balcony with wicker furniture, a glass table, and a view of the sea and buildings.

19. Bear's Apartment

Bear's Apartment
2.0 star property
Portland
The price is P39,495
P47,394 total
includes taxes & fees
Nov 6 - Nov 7
Bear's Apartment
A dining area with a wooden table and chairs, a kitchen in the background, and a sliding glass door leading to a backyard.

20. 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 P71,175
P85,410 total
includes taxes & fees
Oct 10 - Oct 11
Jurassic Coast House
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

The Jubilee Hotel West- with Spa Facilities

The Jubilee Hotel West- with Spa Facilities

10/10 Excellent
"The room was a good size, we had a family room for 5. The room was clean and tidy and good amenities in the room itself. The best aspect was the seaview which was fantastic helped by some good October weather. We didn't use the bar much as we were visiting relatives who live in Weymouth - but it looked good with plenty to do. The best thing about staying in the older hotels on the front is access to the beach/Weymouth centre, room size and view. Overall very happy with the hotel and the price. Would definitely stay again - thanks."
Ben 2-night trip
Posted 2 days ago
The Jubilee Hotel West- with Spa Facilities

Find out more about Portland

Search for holiday rentals in Portland on Expedia! You can easily find your home rentals, villas, holiday apartments in Portland using one of the methods below:

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Look no further and take a look at our great range of rental properties in Portland!

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.

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.