Portland Holiday Rentals

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Check prices for these dates

Tonight
26 Nov - 27 Nov
Tomorrow
27 Nov - 28 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Holiday Rentals in Portland

Beach nearby
Beautiful, family friendly Cottage with sea views of Chesil Beach

Beautiful, family friendly Cottage with sea views of Chesil Beach

Fortuneswell
9.4 out of 10, Exceptional, (23)
"This is the second year that we've stayed here and will continue to book in the futue. It is a beautiful accommodation, local to amenities and in walking distance to the beach.I couldn't recommend this property and Alison high enough."
United Kingdom
Rosemarie D.
Beautiful, family friendly Cottage with sea views of Chesil Beach
Outdoor spa tub
The Old Coach House in Dorset's Area of Outstanding Beauty - 1 bedroom

The Old Coach House in Dorset's Area of Outstanding Beauty - 1 bedroom

Maiden Newton
9.6 out of 10, Exceptional, (46)
"A lovely relaxed stay, nice peaceful area, plenty of places to walk, highly recommend gor a bit of r&r."
United Kingdom
Spencer C.
The Old Coach House in Dorset's Area of Outstanding Beauty - 1 bedroom
3 bedrooms, desk, laptop workspace, blackout curtains
The Dorset Resort

The Dorset Resort

4.0 star property
Wareham
9.8 out of 10, Exceptional, (44)
"PRPOERTY VERY SPACIOUS, VERY CLEAN AND JUST A LOVELY PROPERTY TO UNWIND AND RELAX WITH FAMILY, LOVED THE SAUNA"
United Kingdom
tina
The Dorset Resort
Dining
Private detached cottage to rent on Chesil Beach

Private detached cottage to rent on Chesil Beach

Abbotsbury
10.0 out of 10, Exceptional, (68)
"Greenbanks is outstanding and most definitely 5 starLocation is superb , the house was impeccable , we thoroughly enjoyed our stay and will hopefully visit again "
United Kingdom
Anonymous traveller
Private detached cottage to rent on Chesil Beach
Fridge, microwave, oven, stovetop
Apartment near the beach with private parking and pet friendly

Apartment near the beach with private parking and pet friendly

Weymouth
9.2 out of 10, Wonderful, (31)
"Comfortable apartment with just a short walk to the beach and the centre of Weymouth."
United Kingdom
sue p.
Apartment near the beach with private parking and pet friendly
Beach nearby
Luxury mobile home with spectacular sea views.

Luxury mobile home with spectacular sea views.

Weymouth
9.8 out of 10, Exceptional, (124)
"Very clean, great communication, amazing views."
United Kingdom
Neil
Luxury mobile home with spectacular sea views.
Fridge, microwave, oven, stovetop
Buckingham Cottage : Idyllic Getaway Cottage in the rolling hills of Dorset

Buckingham Cottage : Idyllic Getaway Cottage in the rolling hills of Dorset

West Milton
9.8 out of 10, Exceptional, (86)
"Comfortable accommodation in a superb location."
United Kingdom
Amanda S.
Buckingham Cottage : Idyllic Getaway Cottage in the rolling hills of Dorset
Dining
18 Chamberlaine Road

18 Chamberlaine Road

2.5 star property
Weymouth
The price is HK$3,366
HK$4,039 total
includes taxes & fees
3 Dec - 4 Dec
18 Chamberlaine Road
Beach
A beautiful comfortable cottage in the centre of Bridport.

A beautiful comfortable cottage in the centre of Bridport.

Bridport
10.0 out of 10, Exceptional, (2)
"Lovely place to stay! Really great location too - would come back for sure!"
United Kingdom
Ru P.
A beautiful comfortable cottage in the centre of Bridport.
Terrace/patio
Characterful 18th century cottage in Bridport close to the Jurassic Coast.

Characterful 18th century cottage in Bridport close to the Jurassic Coast.

Bridport
10.0 out of 10, Exceptional, (71)
"Lovely cottage, perfect location Will definitely try to go again at some point "
United Kingdom
Peter L.
Characterful 18th century cottage in Bridport close to the Jurassic Coast.
Interior
Leo's Place

Leo's Place

3.0 star property
Weymouth
Leo's Place
Fridge, microwave, oven, stovetop
4 Bed-2 Bath-sleeps 8-large Garden-pet Friendly

4 Bed-2 Bath-sleeps 8-large Garden-pet Friendly

2.0 star property
Dorchester
The price is HK$1,923
HK$3,043 total
includes taxes & fees
4 Dec - 5 Dec
4 Bed-2 Bath-sleeps 8-large Garden-pet Friendly
Beach
Purbeck cottage near Swanage & Studland - views of Corfe and I of Wight

Purbeck cottage near Swanage & Studland - views of Corfe and I of Wight

Langton Matravers
9.4 out of 10, Exceptional, (69)
"Lovely cottage we all had a great stay"
United Kingdom
Pat H.
Purbeck cottage near Swanage & Studland - views of Corfe and I of Wight
Interior
The Studio - Arne

The Studio - Arne

3.5 star property
Wareham
The price is HK$11,670
HK$14,004 total
includes taxes & fees
9 Dec - 10 Dec
The Studio - Arne
Fridge, microwave, oven, stovetop
Upwey - Wessex Quarters

Upwey - Wessex Quarters

Weymouth
8.0 out of 10, Very good, (1)
"Excellent location. Well priced convenient parking near property "
United Kingdom
rachel g.
Upwey - Wessex Quarters
Beach nearby
Edwardian House in the Heart of Weymouth 200m from Sandy Beach by the Sea

Edwardian House in the Heart of Weymouth 200m from Sandy Beach by the Sea

Weymouth
8.8 out of 10, Excellent, (45)
"A lovely stay in Weymouth. Minutes to the beach and the train station. Harbour within 15 minutes. Downstairs space amazing . "
United Kingdom
Gemma K.
Edwardian House in the Heart of Weymouth 200m from Sandy Beach by the Sea
Terrace/patio
Tadnoll Escape- Shepards Hut- Sleeps 2- Bbq- Lake

Tadnoll Escape- Shepards Hut- Sleeps 2- Bbq- Lake

2.0 star property
Dorchester
Tadnoll Escape- Shepards Hut- Sleeps 2- Bbq- Lake
Outdoor dining
Delightful thatched cottage in beautiful sleepy Dorset village and countryside

Delightful thatched cottage in beautiful sleepy Dorset village and countryside

West Knighton, nr Dorchester, Dorset
9.8 out of 10, Exceptional, (53)
"Cracking property very well equipped, excellent all round cottage, lovely setting."
United Kingdom
Robert F.
Delightful thatched cottage in beautiful sleepy Dorset village and countryside
Terrace/patio
Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach

Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach

Weymouth
10.0 out of 10, Exceptional, (51)
"Outstanding house in ideal location. I could have sat in the garden all week!"
United Kingdom
Robert G.
Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach
Outdoor dining
Lakeside retreat with hot tub, games room and on-site spa and pool

Lakeside retreat with hot tub, games room and on-site spa and pool

Dorchester
10.0 out of 10, Exceptional, (2)
"This was the perfect house and location for our family stay! Great hot tub, lakeside views, use of paddleboard and kayaks. We were blessed with sunny weather and did not need to leave. Miranda was an available and helpful host and we would definitely love to return another year.! "
United Kingdom
Sally P.
Lakeside retreat with hot tub, games room and on-site spa and pool
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

Best Western Weymouth Hotel Rembrandt

Best Western Weymouth Hotel Rembrandt

10/10 Excellent
"The staff were very friendly and welcoming. The room was very clean & comfortable."
Rebecca 1-night trip
Posted 3 days ago
Best Western Weymouth Hotel Rembrandt

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:

  • View our selection of featured holiday rentals in Portland
  • Use the map to find apartments and other holiday homes in the Portland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Portland while they last

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

Frequently asked questions

Can I find a holiday rental in Portland?

Yes, there are holiday rentals close to the most popular sights in Portland, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Portland has to offer?

Beautiful, family friendly Cottage with sea views of Chesil Beach : This highly rated holiday home rental in Portland is located in a rural location, and has a fireplace, a private garden and a BBQ 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 that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals will I find in Portland?

Choose from 18 Expedia holiday rentals in Portland for a memorable holiday.

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 holiday rentals like in Portland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Portland. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for family gatherings.