Portland holiday rentals

We found 725 holiday rentals — enter your dates for availability
Select from 18 homes, 86 cottages and other holiday rentals in Portland to find one that's perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday homes have the best amenities for spending time at your holiday home, which might include a fireplace and a washer and dryer. You'll be able to choose a property to rent that has what everyone needs, including options that are accessible or non-smoking.
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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
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Why visit Portland

  • Coastal Charm: Portland boasts a scenic beach and historic harbour, offering a blend of maritime allure and leisure.
  • Historical Heritage: Explore the notable Portland Castle, a testament to the rich cultural past of this coastal town.
  • Iconic Landmarks: Experience the allure of the Portland Bill Lighthouse, a striking beacon on the rugged coastline.
  • Outdoor Adventures: Enjoy scenic walks along the coast and rugged cliffs, perfect for both relaxation and exploration.
  • Family-friendly Atmosphere: With cosy accommodations and pet-friendly options, Portland is ideal for a memorable holiday with loved ones.

Popular types of accommodation in Portland

Portland, England, is a charming coastal town renowned for its stunning landscapes and rich maritime heritage. Visitors can explore the iconic Portland Bill Lighthouse, the rugged cliffs of the Jurassic Coast, and the historic Portland Castle. For those seeking accommodation, popular options include cosy cottages, private holiday homes, and apartments, many of which are pet-friendly, offering amenities that welcome your furry companions. Enjoy a delightful stay in this picturesque location while making unforgettable memories with your loved ones.

  • Cottages: The most favoured stay in Portland, these cosy cottages offer a charming retreat for an authentic holiday experience.
  • Private Holiday Homes: Enjoy a home-away-from-home vibe with these private holiday homes, ideal for families and couples alike.
  • Apartments: Modern and convenient, apartments in Portland provide a comfortable base for exploring the area.
  • Cabins: Quaint cabins offer a rustic escape, perfect for those seeking a peaceful and unique getaway.
  • Caravan Parks: For a touch of adventure, caravan parks deliver a fun and flexible option for your stay.**

Top attractions in and around Portland

Discover the charm of Portland, England, where outdoor adventures and scenic beauty await. Explore its inviting beach, historic harbour, and the notable Portland Castle, perfect for those seeking culture and coastal experiences. Whether you’re an adventurer or a history enthusiast, Portland offers a delightful blend of natural splendour and cultural heritage for a memorable holiday.

  • Portland Bill Lighthouse: A historic beacon nestled in Portland, offering a glimpse into maritime heritage with unique cultural vibes.
  • Weymouth Beach: A sandy retreat located 8km away, perfect for leisurely strolls and seaside relaxation.
  • Weymouth Harbour: A charming harbour 6km away, celebrated for its scenic views and coastal ambience.

Things to do recommended for couples

Planning a romantic escape in Portland? Explore the quaint coastal paths, savour delicious local seafood, and enjoy a scenic boat trip at dusk. Experience the charm and tranquillity of this beautiful destination together.

Things to do recommended for families

Families visiting Portland can explore the stunning seaside, enjoy a coastal walk, and discover nature trails. There are also local heritage sites and parks offering interactive exhibits and fun-filled activities ideal for a memorable family holiday.

Things to do recommended for groups

Explore the stunning coastlines of Portland with your group, enjoying local seafood, scenic walks along the cliffs, and cultural visits to local museums and galleries, offering an authentic taste of British charm.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Portland

When travelling with a group, family, pets, or planning an extended stay, be sure to refine your search according to your specific priorities. Here are some helpful booking tips from Stayz for you.

  • Traveling to Portland with a group: Think about how many bedrooms you require, as well as additional features like a fully-equipped kitchen or outdoor areas for group gatherings. Thankfully, you can refine your search for all of these options, and many more, on Stayz.
  • Traveling to Portland with young kids: Traveling with young children can be demanding. You must prioritise their comfort and safety, as well as age-appropriate amenities, like a private swimming pool, and it’s wise to consider the proximity to family-friendly attractions.
  • Taking your pets with you to Portland: For many, a family holiday simply isn’t complete without their four-legged companion. If you feel the same, why not explore Stayz’s pet-friendly properties? Most of these accommodations feature feeding bowls and beds, ensuring that everyone feels right at home.
  • Planning for a long term stay visiting Portland: If you’re seeking holiday rentals with special offers for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include amenities such as a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Portland

Portland in England offers a delightful blend of adventure and history. Wander along Portland Beach and explore the scenic Isle of Portland, where friendly locals and family-friendly spots abound. The Portland district provides ample opportunities for outdoor fun and relaxation, while the local attractions promise a mix of luxury and tranquil countryside charm. Embrace a truly memorable holiday in this captivating coastal city.

  • Weymouth: This vibrant coastal city, situated 8km from Portland, offers travellers a delightful blend of outdoor activities and stunning seaside scenery. Visitors can enjoy a variety of water sports along the expansive beach, explore a family-friendly beach area, or admire the striking rock formations that dot the shoreline. Theatre enthusiasts can also take in local cultural shows, making it a well-rounded destination for a holiday experience.
  • Dorchester: Located 18km from Portland, Dorchester is a charming city that beckons visitors with its scenic outdoor adventures. The area provides ample opportunities for leisurely pursuits in its recreational areas and outdoor spaces, as well as a round of golf for those seeking a bit of sport. The proximity of natural attractions such as beaches, intriguing rock formations and the bay adds to the allure of this historic locale.
  • South Coast: Merely 10km from Portland, the South Coast is renowned for its rugged outdoor appeal. With accessible hiking trails and expansive recreational areas, it is a haven for adventurers and nature lovers alike. The region is celebrated for its national parks and state parks, along with striking rock formations that enhance its scenic beauty, making it an ideal destination for those seeking both adventure and tranquility.

Best time to go to Portland

If you're planning a trip to Portland, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from July to September, while off-peak times, like January to February and November tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January44.6°F (7.0°C)Light RainMostly CloudyLowAverage
February44.4°F (6.9°C)Light RainMostly CloudyLowSlightly Low
March46.0°F (7.8°C)Light RainMostly CloudyAverageAverage
April49.1°F (9.5°C)Light RainMostly SunnyAverageAverage
May53.8°F (12.1°C)Light RainMostly SunnyAverageAverage
June58.8°F (14.9°C)Light RainMostly SunnyAverageAverage
July62.2°F (16.8°C)Light RainMostly SunnyHighSlightly High
August62.4°F (16.9°C)Light RainMostly SunnyHighSlightly High
September60.3°F (15.7°C)Light RainMostly SunnyHighAverage
October56.5°F (13.6°C)Light RainMostly CloudyAverageSlightly Low
November50.9°F (10.5°C)Light RainMostly CloudyLowSlightly Low
December47.3°F (8.5°C)Light RainMostly CloudyAverageSlightly High

Booking with Stayz is simple

Looking to save on your next journey? Having flexibility with your travel dates may prove beneficial, as prices often fluctuate. You could also secure considerable savings by opting for a longer stay. To discover a Stayz property that suits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Effortless planning

Stayz’s Trip Board provides a convenient platform for you to create new trips, manage your existing plans, or review and organise your bookings. The properties you've saved or booked are now categorised into Potential, Upcoming, or Current Trips. To discover the Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

The friendly city of Portland awaits you

Enjoy the history and other features of Portland. Travellers to this welcoming city praise the sailing, bars and windsurfing. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in and around Portland

Do you want to discover attractions to see while you're in the area? Venture out of your cosy holiday rental and experience everything that makes Portland a fun spot to go on holiday. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • SEA LIFE Centre Weymouth (5.6 mi / 9 km)
  • Abbotsbury Swannery (10.6 mi / 17 km)
  • Monkey World Ape Rescue Center (14.1 mi / 22.7 km)
  • Warmwell Holiday Park Ski Slope (10.7 mi / 17.2 km)
  • The Blue Pool and Tea House (16.6 mi / 26.7 km)
  • Skirmish Dorset (17.5 mi / 28.2 km)

Exploring the natural features in Portland

Whether you're an outdoor enthusiast or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Portland. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Durdle Door (8.7 mi / 14 km)
  • Portland Bill (2.1 mi / 3.3 km)
  • Chesil Beach (2.8 mi / 4.5 km)
  • Weymouth Harbour (4.5 mi / 7.2 km)
  • Weymouth Bay (4.5 mi / 7.2 km)
  • Weymouth Beach (4.6 mi / 7.4 km)

Travelling to and around Portland

The nearest airport is in Bournemouth (BOH-Bournemouth Intl.), located 30.9 mi (49.7 km) from the city centre.

Frequently asked questions

What is the best area to stay in Portland when booking a holiday home?
If you're thinking about a stop in Portland, Southwell is one of the more sought-after locations to spend a getaway. While you're here, pay a visit to fantastic attractions like Portland Bill Lighthouse and Church Ope Cove.
What is the most popular type of holiday home accommodation in Portland?
Based on our data, cottages are the most desirable type of property in Portland. But of course, everyone's idea of an epic trip can differ. Stayz has holiday homes of all shapes and sizes, and we'll help you find the perfect fit.
How much does it cost to rent a holiday home in Portland?
Length of stay, property type and time of year are some of the things that can affect the price of a holiday home. Simply enter your dates of travel to find your perfect match. From comfy cabins to sprawling luxury villas, all Stayz holiday homes offer amazing value.
How much does it cost to rent a beach house in Portland?
When you travel and the size and style of the property will influence how much you'll pay for your beachside stay. Put in your Portland travel dates to see all your options on Stayz. Did someone just say "private pool"? Use our filters to choose the amenities and features you need.
Are there pet-friendly holiday homes in Portland?
With 68 holiday homes that welcome four-legged guests, your furry companion can join in the fun on your Portland holiday. Use the filter tool to search our pet-friendly holiday homes and find your pawfect digs on Stayz.
Can I rent a house with a pool in Portland?
Add an extra layer of fun to your trip by booking your crew into one of the four houses with a private pool in Portland. Use our handy search filter to find the kind of property you want on Stayz, and then spend leisurely days frolicking in a swimming pool that's for your use only.
What are popular home amenities in Portland?
A firepit, a fireplace and a swimming pool are the most popular home amenities in Portland. Whether you're planning to travel on your own, with your significant other or a group of family members, Stayz can help you find a holiday home that matches your tastes with a load of extras you'll love.
Are there large group holiday homes in Portland?
With 29 Portland holiday homes that can sleep five or more people, you can bring a few extra friends or family members along. Whether you're planning an informal get-together or a birthday party, we'll help you find a comfortable space to match the occasion.
Are there holiday homes in Portland that welcome kids?
Bring the entire family together for an adventure in Portland at one of our 68 family-friendly holiday homes. A lot of these stays offer conveniences that are ideal for trips with children, including full kitchens, extra bedrooms and patios. Just click on the "Properties good for families" filter and choose your favourite.
What are the top attractions for families in Portland?
Keeping the kids occupied during your Portland holiday is easy with these fabulous family-friendly attractions:

  • Weymouth Beach
  • Chesil Beach
  • SEA LIFE Centre Weymouth

Are there one-bedroom holiday homes in Portland?
Yes, Portland has seven one-bedroom homes on offer. Usually located in prime areas thanks to their compact size, a one-bedroom property is perfect if you're travelling with your partner or a buddy. And with home comforts such as air conditioning and more privacy than a standard hotel, you'll be able to chill out while exploring this amazing destination.
Can I find two-bedroom holiday homes in Portland?
Gather your nearest and dearest and relax in total privacy and comfort in one of the 25 two-bedroom holiday properties Portland has to offer.
Are there holiday homes with WiFi in Portland?
Take your pick of seven holiday homes with WiFi in Portland. If you'd like to disconnect from the world on your holiday, but still want to be connected to the internet, these properties have what you need. Narrow your search by applying the WiFi filter on Stayz.
How old do you have to be to rent a holiday home in Portland?
The minimum required age is generally 16, 18 or 21. It can vary between properties on Stayz, so look at the rules of your preferred Portland stay before booking your escape.
How long can I rent a holiday home in Portland for?
The amount of time you can stay in a Portland holiday home for differs depending on the property. Just tap in your preferred travel dates to see available options that offer long-term stays. They come with all you require to make your extended break more comfortable like kitchens and laundries. Some properties might also offer discounted weekly or monthly prices, so you can stay even longer for less.