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
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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 ￥49,623
￥59,548 total
includes taxes & fees
Nov 5 - Nov 6
Lighthouse View
A wide, pebbled beach with a clear sky and calm sea.

2. Lily's Pad

Lily's Pad
3.0 star property
Portland
The price is ￥72,071
￥86,485 total
includes taxes & fees
Nov 7 - Nov 8
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 ￥86,662
￥103,994 total
includes taxes & fees
Nov 6 - Nov 7
Mermaid Cottage
A wide, pebbled beach with a clear sky and calm sea.

4. Chandlers Nook

Chandlers Nook
3.0 star property
Portland
The price is ￥67,699
￥81,240 total
includes taxes & fees
Nov 5 - Nov 6
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 ￥84,358
￥101,230 total
includes taxes & fees
Nov 8 - Nov 9
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 ￥81,877
￥98,253 total
includes taxes & fees
Nov 16 - Nov 17
74 Reap Lane
A room with a large window, two grey chairs with red cushions, a floor lamp, and a view of the sea and greenery.

7. Portland View

Portland View
3.0 star property
Portland
The price is ￥80,105
￥96,127 total
includes taxes & fees
Nov 5 - Nov 6
Portland View
A dining area with a wooden table and chairs, a kitchen in the background, and a sliding glass door leading to a backyard.

8. 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 ￥179,173
￥215,008 total
includes taxes & fees
Nov 6 - Nov 7
Jurassic Coast House
A coastal residential area with houses, a grassy field, and a beach with colorful kayaks.

9. Home From Home

Home From Home
3.0 star property
Portland
The price is ￥79,042
￥94,851 total
includes taxes & fees
Nov 5 - Nov 6
Home From Home
A spacious loft with high ceilings, exposed wooden beams, and large windows.

10. The Old Portland Courthouse

The Old Portland Courthouse
3.5 star property
Portland
The price is ￥214,263
￥257,115 total
includes taxes & fees
Nov 5 - Nov 6
The Old Portland Courthouse
A room with a large window overlooking a coastal landscape, featuring a wooden interior and a cushioned seating area.

11. 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 ￥92,156
￥110,587 total
includes taxes & fees
Nov 16 - Nov 17
Old Higher Lighthouse Branscombe Lodge
A coastal view from a high vantage point with a grassy area and a railing.

12. Old Higher Lighthouse Stopes Cottage

Old Higher Lighthouse Stopes Cottage
3.0 star property
Portland
The price is ￥92,156
￥110,587 total
includes taxes & fees
Nov 6 - Nov 7
Old Higher Lighthouse Stopes Cottage
A wide, pebbled beach with a clear sky and calm sea.

13. The View

The View
3.0 star property
Portland
The price is ￥139,475
￥167,371 total
includes taxes & fees
Nov 5 - Nov 6
The View
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.

14. 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 ￥82,232
￥98,678 total
includes taxes & fees
Nov 15 - Nov 16
Groves House
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 ￥124,588
￥149,505 total
includes taxes & fees
Nov 6 - Nov 7
Pebbles Reach
A wide, pebbled beach with a clear sky and calm sea.

16. Sea Gem

Sea Gem
3.5 star property
Portland
The price is ￥168,008
￥201,609 total
includes taxes & fees
Dec 1 - Dec 2
Sea Gem
A balcony with a view of a marina and cityscape.

17. Manhattan Beach

Manhattan Beach
3.0 star property
Portland
The price is ￥107,575
￥129,091 total
includes taxes & fees
Nov 5 - Nov 6
Manhattan Beach
A pebble beach with a clear sky and calm sea.

18. The Shambles

The Shambles
3.5 star property
Portland
The price is ￥109,878
￥131,854 total
includes taxes & fees
Nov 5 - Nov 6
The Shambles
A boat on a pebbled beach with a clear view of the sea.

19. St Johns View

St Johns View
3.5 star property
Portland
The price is ￥111,296
￥133,554 total
includes taxes & fees
Nov 14 - Nov 15
St Johns View
A balcony with wicker furniture, a glass table, and a view of the sea and buildings.

20. Bear's Apartment

Bear's Apartment
3.0 star property
Portland
The price is ￥99,422
￥119,307 total
includes taxes & fees
Nov 6 - Nov 7
Bear's Apartment
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

Fairhaven Hotel

Fairhaven Hotel

10/10 Excellent
"Very good value - thank you"
Steve 3-night trip
Posted 14 hours ago
Fairhaven Hotel

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.

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.