Portland holiday homes

We found 793 holiday rentals — enter your dates for availability
Select from 19 homes, 92 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 Adventures: Enjoy rugged cliffs, pristine beaches, and scenic coastal walks, perfect for outdoor enthusiasts.
  • Historic Heritage: Discover the ancient castle and immerse yourself in Portland’s rich history.
  • Picturesque Harbour: Wander the charming harbour area and relish the coastal ambience.
  • Family Fun: Experience safe, family-friendly activities along the beautiful coastline.
  • Outdoor Escapes: Embrace the natural beauty and adventure opportunities scattered throughout the city.

Top attractions near Portland

Portland, England, is a stunning destination perfect for outdoor enthusiasts and adventure seekers. Explore its beautiful beaches, historic castle, and picturesque harbour, offering a blend of culture and scenic experiences. Whether you're soaking up the sun or enjoying a coastal walk, Portland's attractions promise a memorable holiday for families, groups, or couples alike. Embrace the natural beauty and rich heritage that this charming city has to offer.

  • Weymouth Beach: Experience a vibrant seaside vibe with golden sands and the refreshing sea breeze, perfect for a relaxed day out.
  • Weymouth Harbour: Enjoy scenic views and gentle coastal ambience at this charming harbour, ideal for a leisurely stroll.
  • Weymouth Bay: Revel in the great outdoors with panoramic coastal scenery and a mix of beach and outdoor attractions, offering a unique blend of nature and leisure.

Things to do recommended for couples

For a romantic getaway in Portland, explore the stunning coastal paths with breathtaking views. Enjoy a leisurely picnic at the scenic Portland Bill, or take a sunset stroll along Chesil Beach. Don’t miss the local seafood dining for a perfect evening together.

Things to do recommended for families

Families visiting Portland can explore the fascinating Portland Bill Lighthouse and enjoy a day at the sandy Chesil Beach. The Portland Museum offers engaging exhibits, while the nearby Jurassic Coast provides a chance to discover fossils and stunning coastal scenery, making it a perfect family adventure.

Things to do recommended for groups

Explore Portland's rich maritime history and enjoy local seafood feasts with your mates, or take part in traditional boat-building workshops, creating unforgettable memories with your group.

*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

Whether you're travelling with a group, as a family, with your pets, or seeking extended stays, be sure to refine your search with the appropriate priorities. Here are some Vrbo booking tips for you.

  • Traveling to Portland with a group: Consider the number of bedrooms required, along with amenities like a fully equipped kitchen or an outdoor area suitable for group gatherings. Luckily, you can easily filter for these and many additional features on Vrbo.
  • Traveling to Portland with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, while also looking for amenities that suit their age, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Portland: For many families, a trip wouldn’t feel complete without their furry companion. If that resonates with you, consider exploring Vrbo properties that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Portland: If you're in search of holiday rentals offering deals for stays of a month or more, you've come to the right spot. With the appropriate filter, you can effortlessly locate and save on monthly rentals. Don't forget to consider including extras like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Portland

Portland, England, is a captivating destination that offers stunning coastal scenery and rich history. Explore the rugged cliffs of the Isle of Portland, where adventure awaits with breathtaking views and outdoor activities. Enjoy the pristine beaches, perfect for relaxation or family-friendly fun. Discover the historic landmarks and enjoy the warm, friendly atmosphere that makes Portland a unique getaway in Dorset, ideal for those seeking both adventure and tranquility.

  • Weymouth: Nestled a short 8km from Portland, Weymouth is a vibrant seaside city celebrated for its expansive outdoor options and scenic charm. Visitors are drawn to its inviting beach and dramatic rock formations, perfect for family outings or a leisurely day by the sea. Local highlights include engaging water sports and the charm of a traditional recreational area, while nearby theatres offer a cultural twist to an otherwise nature-focused escape.
  • Dorchester: Situated 18km from Portland, Dorchester is a bustling city that appeals to those seeking outdoor adventures and breathtaking scenery. Its unique blend of natural beauty and recreational spaces makes it a prime destination for golf enthusiasts and explorers alike. The city’s environment is enriched by its proximity to a diverse bay and intriguing rock formations, offering a dynamic backdrop for a memorable holiday journey.
  • South Coast: Located 10km from Portland, the South Coast beckons with its promise of outdoor activities and rugged adventure. Ideal for hiking enthusiasts, its network of trail access and scenic hiking paths leads to a vast recreational area. The natural allure of national parks and striking rock formations provides a perfect setting for exploration and discovery, making it a must-visit for those who cherish unspoilt landscapes.

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.

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

Booking with Vrbo is simple

Looking to save on your next holiday? Try keeping your travel dates flexible since prices can fluctuate. Plus, booking a longer stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, simply use our filters to search by price, location, and type of holiday accommodation.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides you with a dedicated space to start new journeys, pick up where you left off, or manage your existing bookings. Your saved or booked properties are neatly organised into Potential, Upcoming, or Current Trips. To explore Trip Boards, visit: https://www.bookabach.co.nz/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:

  • 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)
  • SEA LIFE Centre Weymouth (5.6 mi / 9 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:

  • 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)
  • Lodmoor Country Park (5.9 mi / 9.6 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 Bookabach.
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 Bookabach?
Bookabach 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?
Bookabach 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 Bookabach, 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 Bookabach?
To find Portland holiday rentals with free cancellation, just use Bookabach'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, Bookabach 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 Bookabach?
Bookabach'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 Bookabach 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. Bookabach offers something for every taste and budget, from affordable homes in Portland to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach 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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