Portland holiday homes

We found 226 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Portland that are perfect for your trip. Holiday rentals offer the best amenities for your stay with friends, family or just your pet, such as a pool and a washer and dryer. What you'll find is a property to rent that has what everyone needs, including options that are accessible or non-smoking.

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Find the perfect holiday rental for your Portland getaway

Learn about the unique charm of Portland with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in Portland

Are you hoping to discover top things to see and do during your stay? Venture out of your cosy holiday rental and experience everything that Portland has to offer. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Johnson Estate Winery (9.1 mi / 14.6 km)
  • Chautauqua Belle Steamboat (9.8 mi / 15.7 km)
  • 21 Brix Winery (1.7 mi / 2.8 km)
  • Shorewood Country Club (7 mi / 11.2 km)
  • Chautauqua Golf Club (12.1 mi / 19.4 km)
  • Midway State Park (12.7 mi / 20.4 km)

Exploring the natural landscape of Portland

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Portland is a great place to get outside. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Point Gratiot Park (9.1 mi / 14.7 km)
  • Chautauqua Lake (9.3 mi / 14.9 km)
  • Chautauqua Lake (15 mi / 24.1 km)
  • Lakeside Park (10 mi / 16 km)
  • Ripley Community Park (14.9 mi / 23.9 km)
  • Fishermans Beach (18.5 mi / 29.8 km)

How to get to and around Portland

Fly into Jamestown, NY (JHW-Chautauqua County), the closest airport, located 18.7 mi (30.1 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, New York, for a holiday rental, the neighbourhoods of nearby Brocton and Westfield are excellent options. Brocton offers a quaint, small-town atmosphere with a close-knit community feel, making it a charming choice for those looking to unwind. Just a short distance away, Westfield is known for its vibrant arts scene and lovely lakeside views, particularly around Chautauqua Lake, which is a popular spot for boating and fishing.In Brocton, visitors can enjoy the local parks and scenic landscapes, while Westfield boasts attractions such as the historical Westfield Memorial Hospital and the picturesque waterfront. Both areas typically feature a range of properties, from cosy cottages to spacious homes, suiting various group sizes and preferences.
What is the most popular type of holiday rental accomodation in Portland?
In Portland, cottages are the most popular type of holiday rental, with several available throughout the area. These charming properties are often situated in peaceful neighbourhoods, providing a quaint and homely atmosphere. Most cottages come equipped with kitchens for self-catering, comfortable living spaces, and outdoor seating areas to enjoy the pleasant surroundings. Ideal for couples or small families, these rentals offer a superb blend of comfort and convenience, allowing guests to explore the local attractions and natural beauty of the region.
Are there any family house rentals in Portland?
In Portland, New York, there are several family-friendly house rentals available. Visitors can find homes in tranquil neighbourhoods that offer ample space for families to relax and enjoy their time together. Many of these properties feature roomy living areas, fully equipped kitchens for preparing meals, and outdoor spaces where children can play and explore.Families can also take advantage of nearby attractions such as the beautiful shores of Lake Erie, which provide opportunities for swimming, fishing, and picnicking. Local parks and recreational areas are great for outdoor activities, ensuring that there's plenty to keep everyone entertained.
Are there pet-friendly house rentals in Portland?
In Portland, there are several pet-friendly house rentals available, making it a great destination for travellers wishing to bring their furry companions along. Many of these holiday homes are situated in vibrant neighbourhoods like Alberta Arts District and Hawthorne, known for their eclectic atmosphere and local charm.Travellers can expect a variety of amenities, including spacious living areas, fully equipped kitchens, and outdoor spaces, such as private gardens or patios, great for enjoying the fresh air with pets. Some properties even feature conveniences like pet beds and fenced yards, ensuring a comfortable stay for both guests and their pets.The city is also home to numerous parks that are pet-friendly, such as Forest Park, which offers extensive trails for walking and hiking, and the Waterfront Park, where pets can enjoy strolls along the river. Additionally, the local dining scene includes many cafes and restaurants that welcome pets, enhancing the overall experience for pet owners.
Are there any remote work holiday rentals in Portland?
In Portland, New York, there are several remote work holiday rentals available that cater to the needs of professionals seeking a productive environment. Many of these properties come equipped with high-speed Wi-Fi, ensuring reliable connectivity for work tasks. You'll find a range of accommodations, including charming cottages and spacious houses, that often feature dedicated workspaces or desks, allowing for a comfortable and efficient remote working experience.The city itself offers a picturesque setting with access to local parks and scenic views, providing opportunities for relaxation and inspiration during breaks. 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 cater to various guest preferences, ensuring a comfortable stay. Many properties feature a deck or patio, superb for enjoying the outdoors and soaking up the local atmosphere. Additionally, travellers can expect conveniences like coffee and tea makers, allowing them to start their day with a warm beverage at their leisure. For those who appreciate a good read, rentals often include a selection of books to enjoy during downtime. Furthermore, some accommodations welcome dogs exclusively, making them suitable for pet owners looking to explore the city with their furry companions.
When is the best time to visit Portland for a holiday rental?
December is a particularly popular time to visit Portland, as the city transforms into a winter wonderland filled with festive lights and seasonal celebrations. While the peak tourist season generally runs from July to September, December offers a unique charm, where visitors can enjoy outdoor activities like ice skating in Pioneer Courthouse Square or strolling through the beautifully decorated streets.During the winter months, temperatures in Portland typically range from 1 to 10 degrees Celsius. This cooler climate creates a cozy atmosphere great for exploring the city's vibrant culinary scene, with many restaurants and cafés offering warm, inviting spaces to relax after a day of sightseeing.For those looking for a more budget-friendly option, consider planning your visit in October. This month is ideal for enjoying the beauty of autumn foliage in the city's parks and surrounding areas, as well as taking advantage of fewer crowds. The mild weather allows for comfortable outdoor exploration and a chance to experience local events without the hustle and bustle of peak season.Ultimately, the best time to book a holiday rental in Portland depends on your preferences—whether you seek the lively energy of summer or the enchanting tranquillity of winter and fall.
What are the top attractions in Portland?
In Portland, New York, visitors can enjoy a range of attractions that highlight the area's natural beauty and local charm. The town is situated on the shores of Lake Erie, making it great for outdoor enthusiasts. The nearby Barcelona Lighthouse offers picturesque views and a glimpse into the region's maritime history.For those interested in local culture, the Portland Historical Society presents an opportunity to learn about the town's past and its development over the years. Additionally, the scenic trails at the nearby Allegheny State Park are ideal for hiking, biking, and enjoying the natural landscape.If you're looking for a relaxing day, the lakeside parks provide spaces for picnicking and enjoying the serene views of the water.
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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