Portland holiday homes

We found 164 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

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

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

East Haddam

7% off
NZ$13,625
for 7 nights, 1 home
NZ$1,946 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

15% off
NZ$4,500
for 7 nights, 1 home
NZ$643 per night
includes taxes & fees
John Hollister home on the farm
Front of Historic Mansion B&B
Living area
Bedroom with 2 single Beds
Interior
Exceptional
(5 reviews)

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

Higganum

8% off
NZ$3,002
for 7 nights, 1 room
NZ$429 per night
includes taxes & fees
Historic Mansion 1841 - The listed price is per Bedroom, Private Entrance
Private kitchen
Property grounds
Room
One full bedroom w two full sleeper sofas to accommodate 4 guests comfortably.
Exceptional
(63 reviews)

Summer at the Haddam House

Haddam

8% off
NZ$3,060
for 7 nights, 1 home
NZ$437 per night
includes taxes & fees
Summer at the Haddam House
Interior
Living area
Private kitchen
Room
Wonderful
(27 reviews)

New!Quaint & Convenient Hideaway: Great Location

East Hartford

7% off
NZ$2,474
for 7 nights, 1 home
NZ$353 per night
includes taxes & fees
New!Quaint & Convenient Hideaway: Great Location
Living Room
Stairwell
Backyard
Queen Bedroom 1
Wonderful
(7 reviews)

Private Apartment in Berlin

Berlin

8% off
NZ$2,736
for 7 nights, 1 apartment
NZ$391 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

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 Bookabach 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 Bookabach. 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 Bookabach 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 Bookabach holiday properties may also offer discounted weekly or monthly prices, so you can stay longer for less money.