Portland holiday rentals

We found 794 holiday rentals — enter your dates for availability
Select from 17 homes, 91 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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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)
  • Warmwell Holiday Park Ski Slope (10.7 mi / 17.2 km)
  • Monkey World Ape Rescue Center (14.1 mi / 22.7 km)
  • The Blue Pool and Tea House (16.6 mi / 26.7 km)
  • Pirate Adventure Mini Golf (5.7 mi / 9.1 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:

  • 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)
  • Bowleaze Cove Beach (6.3 mi / 10.2 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 rental?
When considering the best area to stay in Portland, England, for a holiday rental, you might want to explore the charming neighbourhoods that showcase the unique character of the island. One of the most appealing areas is the vicinity around the Portland Bill, which is renowned for its iconic lighthouse and stunning coastal views. This area offers an array of holiday rentals, ranging from quaint cottages to modern apartments, allowing visitors to enjoy the beauty of the rugged coastline.Another excellent option is the village of Easton, where you'll find a delightful selection of properties, often featuring picturesque views and easy access to local amenities. Easton is not only a great base for exploring the island but is also close to attractions such as the Portland Museum, which provides fascinating insights into the island's history, and the beautiful Chesil Beach, superb for leisurely walks and enjoying the natural scenery.In total, there are a variety of properties available throughout Portland, suiting different preferences and budgets, making it a wonderful destination for a relaxing getaway.
Where are the best areas for renting a beach house in Portland?
For renting a beach house in Portland, England, the areas around the famous Chesil Beach are highly recommended. This stunning stretch of coastline offers a unique backdrop for holiday rentals, with many properties enjoying breathtaking views of the sea. In the vicinity, you can find charming cottages and contemporary beach houses equipped with amenities such as open-plan living spaces, private gardens, and easy access to the beach for those lazy summer days.Additionally, the nearby village of West Bay, known for its picturesque harbour and dramatic cliffs, presents further options for beach house rentals. Here, visitors can expect properties with features like outdoor seating areas, BBQ facilities, and modern kitchens, great for family gatherings or a relaxing holiday with friends. The area also boasts local shops and eateries, providing convenience for guests.For those looking to explore beyond the beach, the Jurassic Coast World Heritage Site is just a short drive away, offering spectacular walking trails and opportunities for fossil hunting. Many rentals in the Portland area are designed to enhance the coastal experience, with some featuring amenities like surfboards for hire or storage for bicycles, suiting active travellers eager to explore the beautiful surroundings. Find your rental near the beach in Portland.
What is the most popular type of holiday rental accomodation in Portland?
In Portland, cottages are the most popular type of holiday rental, with around 288 available across the area. These charming properties are often located in picturesque settings, superb for a tranquil getaway. Most cottages come equipped with fully functional kitchens, cosy living areas, and outdoor spaces, ideal for enjoying the coastal views and fresh air.Additionally, there are about 56 holiday houses, which cater well to families or larger groups, featuring multiple bedrooms and often private gardens or patios for relaxation. For those seeking a more urban experience, approximately 32 apartments are available, typically located near local amenities and attractions. These units usually offer modern conveniences such as kitchen facilities and comfortable seating areas.
Are there any family house rentals in Portland?
In Portland, there are numerous family-friendly house rentals available, with around 49 options to choose from. This charming town, located along the Jurassic Coast, offers a variety of accommodations suitable for families looking to enjoy their seaside getaway. Many of these properties boast spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play and explore.Visitors will appreciate the close proximity to stunning attractions such as the Portland Bill Lighthouse and the picturesque Chesil Beach, great for beach outings and picnics. Additionally, some homes may feature amenities like game rooms or gardens, providing entertainment for all ages.
Can I rent a holiday home with a pool or hot tub in Portland?
In Portland, England, there are several holiday homes available for rent that feature pools and hot tubs, offering a delightful retreat for travellers. The charming coastal town provides a picturesque backdrop, with many properties located near the scenic Jurassic Coast, a UNESCO World Heritage Site known for its stunning cliffs and fossil-rich beaches.Travellers can expect a variety of amenities in these rentals, including private swimming pools, relaxing hot tubs, and spacious outdoor areas for al fresco dining. Many homes come with fully equipped kitchens, allowing guests to prepare their own meals, and comfortable living spaces for unwinding after a day of exploration.
Are there pet-friendly house rentals in Portland?
In Portland, there are several pet-friendly house rentals available, with a total of around 42 options for travellers to choose from. Many of these holiday homes are situated in charming locations that provide easy access to the beautiful countryside and coastal areas. Guests can expect amenities such as fully equipped kitchens, spacious living areas, and private gardens, making them ideal for families or groups travelling with pets.The town itself is well-positioned for exploring the stunning landscapes of the Jurassic Coast, where pets are often welcome on various trails and beaches. Additionally, the surrounding areas offer picturesque walks and scenic spots that are great for pet owners looking to enjoy the outdoors.
Are there any remote work holiday rentals in Portland?
In Portland, England, there is a substantial selection of remote work holiday rentals available, with around 376 options to choose from. Many of these properties are equipped with essential amenities tailored for remote workers, including reliable Wi-Fi in both public areas and within individual rooms. This ensures that guests can stay connected and productive during their stay.The town is known for its picturesque coastal scenery and historic landmarks, making it an appealing destination for those looking to blend work with leisure. Accommodations often feature comfortable workspaces, allowing for a conducive environment to focus on tasks while enjoying the tranquil surroundings.Additionally, Portland offers easy access to local attractions, such as the iconic Portland Bill Lighthouse and the stunning Chesil Beach, providing a great backdrop for unwinding after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Portland?
In Portland, popular holiday rental amenities include fully equipped kitchens, allowing guests to prepare their own meals. Many properties are located near the beach, making it easy for visitors to enjoy coastal activities. Additionally, a number of rentals permit pets, ensuring that travellers can bring their furry companions along. For those with service animals, these accommodations are also accommodating. Free WiFi is commonly available, enabling guests to stay connected during their stay.
When is the best time to visit Portland for a holiday rental?
August is the most popular time to visit Portland, offering a vibrant setting that attracts holidaymakers eager to explore the charming streets and coastal beauty of this historic town. During the peak season, which spans from June to August, visitors can enjoy warm temperatures averaging around 18 to 22 degrees Celsius, superb for outdoor activities and leisurely sightseeing.The summer months are particularly lively, with plenty of events, festivals, and activities taking place. Whether you're strolling along the picturesque shoreline or indulging in the local culinary scene, there are endless opportunities to immerse yourself in Portland's unique character and scenic surroundings.If you're looking for a more budget-friendly time to visit, consider coming in December. Although it's part of the low season, the festive atmosphere during this month can be quite enchanting, with holiday decorations and local markets adding to the charm. You may find great value in holiday rentals, allowing you to experience Portland's winter wonderland without the summer crowds.Ultimately, the best time to book a holiday rental in Portland hinges on your preferences—whether you seek the bustling energy of summer or the quieter, cosy charm of winter.
What are the top attractions in Portland?
In Portland, England, visitors can explore a variety of attractions that highlight the area's natural beauty and maritime heritage. The iconic Portland Bill Lighthouse, located at the southern tip of the island, offers stunning coastal views and is a popular spot for photography. Nearby, the unique rock formations of the Jurassic Coast, a UNESCO World Heritage Site, provide opportunities for fossil hunting and scenic walks along the cliffs.The Nothe Fort, a Victorian coastal artillery fort, offers fascinating insights into the region's military history and stunning views over Weymouth and the coastline. For those interested in marine life, the Portland Marina provides access to sailing, boating, and other water activities.In the heart of the island, the village of Fortuneswell features quaint shops and local eateries, while the surrounding countryside offers beautiful walking trails, such as those on the South West Coast Path, allowing visitors to immerse themselves in the area's natural landscapes.
Are all fees included in the Portland holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Portland holiday homes with parking?
Stayz offers a wide selection of holiday homes in Portland with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Portland holiday homes?
You can find great discounts on holiday homes in Portland on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Portland holiday home booking on Stayz?
To find Portland holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Portland?
A long-stay holiday home in Portland is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Portland holiday home?
Book your Portland holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Portland?
Prices for holiday homes in Portland vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Portland to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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