Portland holiday rentals

We found 165 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Portland to find one that's perfect for your trip. Whether you're staying in a holiday rental with family or friends, you'll find the best amenities for hanging out with the people that matter most, which might include a garden and pool. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Portland

Showing deals for:20 Nov - 27 Nov

Interior
Outdoor patio fireplace, patio heaters.
Pool
Private kitchen
Exceptional
(55 reviews)

Resort style getaway w/pool, spa, game room & more

East Haddam

8% off
AU$10,991
for 7 nights, 1 home
AU$1,570 per night
includes taxes & fees
Resort style getaway w/pool, spa, game room & more
Property grounds
Interior
Room
Living area
Exceptional
(18 reviews)

John Hollister home on the farm

Glastonbury

16% off
AU$3,692
for 7 nights, 1 home
AU$527 per night
includes taxes & fees
John Hollister home on the farm
Dining
Living area
Interior
Front of Historic Mansion B&B
Exceptional
(5 reviews)

Historic Mansion 1841 - The listed price is per Bedroom, Private Entrance

Higganum

8% off
AU$2,526
for 7 nights, 1 room
AU$361 per night
includes taxes & fees
Historic Mansion 1841 - The listed price is per Bedroom, Private Entrance
Room
Property grounds
Private kitchen
One full bedroom w two full sleeper sofas to accommodate 4 guests comfortably.
Exceptional
(63 reviews)

Summer at the Haddam House

Haddam

8% off
AU$2,574
for 7 nights, 1 home
AU$368 per night
includes taxes & fees
Summer at the Haddam House
Interior
Living area
Private kitchen
Private kitchen
Wonderful
(27 reviews)

New!Quaint & Convenient Hideaway: Great Location

East Hartford

7% off
AU$2,099
for 7 nights, 1 home
AU$300 per night
includes taxes & fees
New!Quaint & Convenient Hideaway: Great Location
Living Room
Stairwell
Queen Bedroom 1
Living Room
Wonderful
(7 reviews)

Private Apartment in Berlin

Berlin

7% off
AU$2,337
for 7 nights, 1 apartment
AU$334 per night
includes taxes & fees
Private Apartment in Berlin

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Explore the riverfront setting in Portland

Enjoy the wineries and other features of Portland. Renowned for its rafting, riverfront and theme park, this city welcomes all visitors. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Portland

Do you want to find attractions to see during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Portland a one-of-a-kind holiday spot. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Brownstone Exploration & Discovery Park (0.3 mi / 0.5 km)
  • TPC River Highlands (4.1 mi / 6.6 km)
  • Powder Ridge Mountain Park and Resort (7.1 mi / 11.5 km)
  • Machimoodus State Park (9.9 mi / 16 km)
  • Hawks Landing Country Club (12 mi / 19.4 km)
  • Chatfield Hollow State Park (14.5 mi / 23.3 km)

Exploring the natural features in Portland

Whether you're an active traveller or just want to appreciate the scenery, Portland is a great place to spend some time outside. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • General Mansfield House (1.1 mi / 1.7 km)
  • Dinosaur State Park (5.4 mi / 8.8 km)
  • Lake Beseck Beach (6.2 mi / 10 km)
  • Bashan Lake (13.1 mi / 21.1 km)
  • Mortensen Riverfront Plaza (13.4 mi / 21.5 km)
  • Connecticut River (13.4 mi / 21.6 km)

How to get to and around Portland

The nearest airport is in New Haven, CT (HVN-Tweed - New Haven Regional), located 24.6 mi (39.6 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Hartford, CT (BDL-Bradley Intl.), which is 24.8 mi (39.9 km) away.

Frequently asked questions

What is the best area to stay in Portland when booking a holiday rental?
When considering a holiday rental in Portland, Connecticut, one of the most appealing areas to stay is along the Connecticut River. This picturesque location not only offers stunning views but also provides easy access to outdoor activities such as hiking and kayaking. The nearby Wadsworth Falls State Park is a fantastic attraction, showcasing beautiful waterfalls and scenic trails, great for nature enthusiasts.Another charming neighbourhood to consider is the historic district, where you can immerse yourself in the local culture and architecture. This area boasts several quaint shops and eateries, making it a delightful spot to explore. Additionally, the Portland Museum of Art is a great point of interest, featuring a diverse collection of works that reflect the area's rich artistic heritage.While the exact number of properties can vary, there are a range of cosy holiday rentals available, suiting different preferences and budgets.
What is the most popular type of holiday rental accomodation in Portland?
In Portland, Connecticut, several apartments and holiday houses are available for visitors. The apartments, often found in charming residential areas, typically include amenities such as fully equipped kitchens, comfortable living spaces, and convenient access to local attractions. Meanwhile, the holiday houses provide a more spacious option, featuring multiple bedrooms, private gardens, and outdoor seating areas, making them ideal for families or groups seeking a more home-like experience.
Are there pet-friendly house rentals in Portland?
In Portland, Connecticut, there are several pet-friendly house rentals available, offering a welcoming environment for travellers with pets. Many of these homes come equipped with modern amenities such as spacious kitchens, comfortable living areas, and outdoor spaces where pets can roam freely.The neighbourhoods around the Connecticut River provide a scenic backdrop for your stay, with easy access to parks and green spaces. For instance, the nearby Wadsworth Falls State Park is a fantastic spot for pet owners, featuring walking trails and beautiful nature views, making it great for daily walks with your furry companions.Additionally, some rentals may include features such as fenced yards, allowing pets to enjoy the outdoors safely while you relax.
Are there any remote work holiday rentals in Portland?
In Portland, Connecticut, there are several remote work holiday rentals available, making it a great choice for those looking to blend work and leisure. Many of these properties come equipped with reliable internet connections, essential for those who need to stay productive during their stay.You can expect a variety of accommodations, including charming homes and modern apartments that often feature dedicated workspaces, comfortable living areas, and fully equipped kitchens for convenient meal preparation. The scenic beauty of Portland, with its proximity to the Connecticut River and local parks, provides a lovely backdrop for both work and relaxation.Additionally, the town offers a peaceful environment with nearby attractions such as the historic Goodspeed Opera House and various nature trails, making it easy to unwind after a day of remote 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, Connecticut, holiday rentals typically include a variety of popular amenities that enhance the stay for visitors. Most properties come equipped with a kitchen, allowing guests to prepare their own meals and enjoy a home-cooked dining experience. Onsite parking is commonly available, which is particularly convenient for those travelling with their own vehicles. Accessible parking options are also offered, suiting the needs of all guests. Additionally, many rentals feature a coffee and tea maker, superb for enjoying a warm beverage at any time of the day. Outdoor space is another appealing aspect, with decks or patios providing a lovely spot to relax and take in the surroundings.
When is the best time to visit Portland for a holiday rental?
The peak travel season in Portland, Connecticut, occurs from June to August, with July being the highlight for many visitors. During this vibrant period, the town comes alive with summer activities, including outdoor festivals, boating on the Connecticut River, and beach outings along the picturesque shoreline. The warm weather, typically ranging from 20 to 30 degrees Celsius, makes it an ideal time for both relaxation and exploration.While July boasts the highest tourist activity, those seeking a more tranquil experience might find November an appealing alternative. This quieter month offers a unique charm, with the opportunity to enjoy the stunning autumn scenery as the leaves change colour, creating a beautiful backdrop for leisurely walks and scenic drives. Additionally, accommodation prices tend to be lower, providing excellent value without compromising comfort.Whether you prefer the bustling summer atmosphere or the peacefulness of the fall, Portland presents a variety of experiences tailored to different preferences.
What are the top attractions in Portland?
In Portland, Connecticut, visitors can enjoy a variety of attractions that showcase the town's charm and natural beauty. The historic Main Street is lined with quaint shops and cafes, making it a pleasant area to explore. A highlight is the Portland Historical Society, where guests can learn about the town's rich heritage.For outdoor enthusiasts, the nearby Wadsworth Falls State Park offers picturesque trails and scenic waterfalls, great for hiking and picnicking. Additionally, the Connecticut River provides opportunities for boating and fishing, with lovely views along its banks.Families may also appreciate the proximity to the nearby Dinosaur State Park in Rocky Hill, where interactive exhibits and dinosaur tracks offer an educational experience.
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.