Portland, Connecticut holiday accommodation: short-term house rentals & properties

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.

Find the best place to stay - Portland

lakefront estate

Sleeps 10 · 5 bedrooms · 2+ bathrooms

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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)
Cabela's (12.7 mi / 20.4 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:

Wadsworth Falls State Park (3.7 mi / 6 km)
Dinosaur State Park (5.4 mi / 8.8 km)
Lake Beseck Beach (6.2 mi / 10 km)
Machimoodus State Park (9.9 mi / 16 km)
Hubbard Park (10.1 mi / 16.3 km)
Mortensen Riverfront Plaza (13.4 mi / 21.5 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

How much does it cost to rent a holiday home in Portland?

Property type, length of stay and season are among the factors that can influence the price of a holiday home. Simply click on your dates of travel to find the ultimate escape. From comfy cabins to sprawling luxury villas, all Stayz holiday homes provide 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 the cost of your beachside escape. Enter your Portland travel dates to view your available options on Stayz. Can't live without a hot tub, or maybe a private pool? Use the filters to select the features and amenities you want.

What are the top attractions for families in Portland?

Keeping the kids happy during your Portland holiday is easy with these cool family-friendly attractions:

Brownstone Exploration & Discovery Park
Lake Beseck Beach
Checkered Flag Raceway

How old do you have to be to rent a holiday home in Portland?

We recommend checking with the Portland holiday property you're considering on Stayz as the minimum age differs. However, generally it's 16, 18 or 21.

How long can I rent a holiday home in Portland for?

The amount of time you can rent a Portland holiday home for is down to the property. Just put in your travel dates to browse options that offer extended stays. They have everything you need to make your extended break more enjoyable such as kitchens and laundries. Some Stayz holiday properties may also offer discounted weekly or monthly prices, so you can stay longer for less money.