Portland Holidays
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Portland Holiday
Portland Beach Holiday
Get set to live out those beachy daydreams on your Portland holiday. Embark on a romantic stroll, soak up the spectacular coastal views and pick up pretty seashells on your trip to Portland. Only 0.97 kilometres from the centre of town, Church Ope Cove is the place to be for many travellers. Browse our Portland holiday packages and watch your travel budget stretch further!
Things You Should Know About Portland
- Check into one of our Portland beach hotels and experience this destination at its very best. Wander along the shoreline and marvel in the gorgeous sunsets right on your front door.
- Our cottages, like Heights Hotel and The Aqua, are popular with visitors of all types. Check out the amenities and get ready for your holiday in Portland!
- Some 12 700 people live in Portland. If you want recommendations about what to see and do around these parts, why not ask a couple of the friendly locals? Our Portland things to do page is also a handy source of information.
- Don't leave town without checking out Portland Harbour, Portland Bill and Weymouth and Portland National Sailing Academy. With the money you save through our Portland holiday deals, you can see more top sights like these.
Our pick of the best Portland Hotel Deals
Heights Hotel
Yeates Road Portland England
8.4/10 Very Good! (687 reviews)
Yes, the room was spotless but it is the friendliness of the staff that makes our stay most enjoyable. The wide choice of breakfast suits everyone. Unfortunately we found the evening dinners a little too rich for our taste on this visit. Previous visits have had more choice for the evening meal, ...
Reviewed on 30 Jan 2026
Beautiful, family friendly Cottage with sea views of Chesil Beach
Fortuneswell ENG
9.2/10 Wonderful! (25 reviews)
Lovely cottage - clean and nicely furnished. Good location to explore
Reviewed on 19 Jan 2026
One bed apartment next to Chesil Beach Dorset
Portland England
9.4/10 Exceptional! (8 reviews)
Excellent location with quick access to Chesil Beach. The bus stops directly outside to take you into Weymouth if you don't want to drive in. A beautiful flat with a great range of amenities and super communicatoon from Helen the host.
Reviewed on 28 Dec 2025
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.
Discover the most popular places to visit in Portland
Weymouth and Portland National Sailing Academy
Enjoy the student vibe when you visit Weymouth and Portland National Sailing Academy during your travels in Portland. Wander the area's beautiful beaches or simply enjoy one of its lively bars.
What to do in Portland
Pauls Walking Tour - Sundays at 10:00am - or Group
NZ$23
per adult
Half-Day Guided E-Bike Tour Portland with Brunch
NZ$296
per adult
Explore a world of travel with Expedia
- Cottages in Upwey
- B&B in Upwey
- Caravan Parks in Radipole
- Holiday Homes in Weymouth
- Guest Houses in Weymouth
- Holiday Parks in Weymouth
- B&B in Weymouth
- Apartments in Weymouth
- Caravan Parks in Weymouth
- Cottages in Osmington
- Hostels in Portland
- Residences in Weymouth and Portland District
- Inns in Weymouth and Portland District
- Caravan Parks in Weymouth and Portland District
- Cottages in Weymouth and Portland District
- Holiday Homes in Weymouth and Portland District
- Lodges in Weymouth and Portland District
- Castles in South Coast
- Inns in South Coast
- Cabin Rentals in South Coast
- Holiday Homes in South Coast
- Hotels near Portland Bill Lighthouse
- Hotels near Weymouth Beach
- Hotels near Chesil Beach Visitors Centre
- Upwey Hotels
- Osmington Hotels
- Hotels near Portland Harbour
- Wyke Regis Hotels
- Chickerell Hotels
- Radipole Hotels
- Weymouth Hotels
- Osmington Mills Hotels
- Hotels near Chesil Beach
- Portland Hotels
- Bincombe Hotels
- Broadwey Hotels
- Hotels near Durdle Door Beach
- Cheap Hotels in Weymouth and Portland District
- Beach Hotels in Weymouth and Portland District
- Luxury Hotels in Weymouth and Portland District
- Golf Hotels in South Coast
- Luxury Hotels in South Coast
- Pet Friendly Hotels in South Coast
- All Inclusive Hotels in South Coast
- Hotels with Parking in South Coast
- Boutique Hotels in South Coast
- Scuba Diving Hotels in South Coast
- Beach Hotels in South Coast
- Hotels with Parking in Weymouth
- Spa Hotels in Weymouth
- Beach Hotels in Weymouth
- Cheap Hotels in Weymouth
- Pet Friendly Hotels in Weymouth
- Family Hotels in Weymouth
- Hotels with Pool in Weymouth
- Romantic Hotels in Weymouth
- Historic Hotels in Weymouth
- Luxury Hotels in Weymouth
- Fjb Hotels in South Coast
- Britannia Hotels in South Coast
- Bowleaze Cove Beach
- Dorset Teddy Bear Museum
- Lulworth Cove
- Weymouth Holidays
- Weymouth Beach
- Dorset Holidays
- Abbotsbury Swannery
- St. Catherine's Chapel
- Durdle Door
- Sea LIFE Centre Weymouth
- Durdle Door Beach
- Castle Cove Beach
- Weymouth and Portland National Sailing Academy
- Lulworth Cove Beach
- Pirate Adventure Mini Golf
- Dorchester Holidays
- Maiden Castle
- Abbotsbury Sub-Tropical Gardens
- Ringstead Beach
- Visit Weymouth
- Scuba Diving Holiday Packages South Coast
- Yoga Holiday Packages Weymouth and Portland District
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
