Portland Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Portland vacation rentals

A wide, pebbled beach with a clear sky and calm sea.

1. Lily's Pad

Lily's Pad
3.0 star property
Portland
$456 nightly
The price is $547
Nov 13 - Nov 14
Total with taxes and fees
Lily's Pad
A spacious kitchen with a dining area, a grey sofa, and a vintage trunk.

2. 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
$609 nightly
The price is $731
Nov 13 - Nov 14
Total with taxes and fees
Mermaid Cottage
A kitchen with a dining table, chairs, a window with curtains, a potted plant, and a pot on the counter.

3. 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
$349 nightly
The price is $419
Nov 15 - Nov 16
Total with taxes and fees
Lighthouse View
A wide, pebbled beach with a clear sky and calm sea.

4. Chandlers Nook

Chandlers Nook
3.0 star property
Portland
$466 nightly
The price is $559
Nov 16 - Nov 17
Total with taxes and fees
Chandlers Nook
A room with a large window overlooking a coastal landscape, featuring a wooden interior and a cushioned seating area.

5. 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
$648 nightly
The price is $778
Nov 16 - Nov 17
Total with taxes and fees
Old Higher Lighthouse Branscombe Lodge
A room with a large window, two grey chairs with red cushions, a floor lamp, and a view of the sea and greenery.

6. Portland View

Portland View
3.0 star property
Portland
$551 nightly
The price is $661
Nov 16 - Nov 17
Total with taxes and fees
Portland View
A coastal hotel with a paved walkway and seating area, overlooking a pebble beach and cliffs.

7. Anchor Cottage

Anchor Cottage
3.0 star property
Portland
$593 nightly
The price is $712
Nov 13 - Nov 14
Total with taxes and fees
Anchor Cottage
A wide, pebbled beach with a clear sky and calm sea.

8. 74 Reap Lane

74 Reap Lane
3.0 star property
Portland
$550 nightly
The price is $660
Nov 16 - Nov 17
Total with taxes and fees
74 Reap Lane
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
$531 nightly
The price is $637
Nov 16 - Nov 17
Total with taxes and fees
Home From Home
A coastal view from a high vantage point with a grassy area and a railing.

10. Old Higher Lighthouse Stopes Cottage

Old Higher Lighthouse Stopes Cottage
3.0 star property
Portland
$648 nightly
The price is $778
Nov 14 - Nov 15
Total with taxes and fees
Old Higher Lighthouse Stopes Cottage
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
$578 nightly
The price is $694
Nov 15 - Nov 16
Total with taxes and fees
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
$783 nightly
The price is $939
Nov 14 - Nov 15
Total with taxes and fees
St Johns View
A balcony with a view of a marina and cityscape.

13. Manhattan Beach

Manhattan Beach
3.0 star property
Portland
$756 nightly
The price is $908
Nov 20 - Nov 21
Total with taxes and fees
Manhattan Beach
A balcony with wicker furniture, a glass table, and a view of the sea and buildings.

14. Bear's Apartment

Bear's Apartment
3.0 star property
Portland
$699 nightly
The price is $839
Nov 13 - Nov 14
Total with taxes and fees
Bear's Apartment
A pebble beach with a clear sky and calm sea.

15. The Shambles

The Shambles
3.5 star property
Portland
$773 nightly
The price is $927
Nov 13 - Nov 14
Total with taxes and fees
The Shambles
A wide, pebbled beach with a clear sky and calm sea.

16. The View

The View
3.0 star property
Portland
$981 nightly
The price is $1,177
Nov 13 - Nov 14
Total with taxes and fees
The View
A spacious loft with high ceilings, exposed wooden beams, and large windows.

17. The Old Portland Courthouse

The Old Portland Courthouse
3.5 star property
Portland
$1,507 nightly
The price is $1,808
Nov 18 - Nov 19
Total with taxes and fees
The Old Portland Courthouse
A wooden sign with maritime-themed decorations and text, mounted on a green building.

18. Pebbles Reach

Pebbles Reach
3.5 star property
Portland
$876 nightly
The price is $1,051
Nov 13 - Nov 14
Total with taxes and fees
Pebbles Reach
A dining area with a wooden table and chairs, a kitchen in the background, and a sliding glass door leading to a backyard.

19. 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
$1,260 nightly
The price is $1,512
Nov 13 - Nov 14
Total with taxes and fees
Jurassic Coast House
A wide, pebbled beach with a clear sky and calm sea.

20. Sea Gem

Sea Gem
3.5 star property
Portland
$1,181 nightly
The price is $1,418
Nov 29 - Nov 30
Total with taxes and fees
Sea Gem
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

A table with a view of a beach and the Olympic rings sculpture.
Heights Hotel

Heights Hotel

Heights Hotel
Portland

10/10 Excellent

Enjoyable stay and great service from the staff - they even gave us a celebration balloon for our anniversary - a great place as a base to explore the local area, with lovely scenery nearby.
United States
Anonymous traveler
Reviewed August 24, 2017
Heights Hotel

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 $418 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.

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.

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