
Portland Vacation Rentals
- Bundle & SaveGet more, spend less whenever you see Bundle & Save deals
- OneKeyCashEarn OneKeyCash on all your eligible bookings
- Upfront pricingWe are not like the others - we include taxes and fees
Check prices for these dates
Our top choices for Portland vacation rentals

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
#24 *Serenity* A Lakefront Cottage Retreat
#24 *Serenity* A Lakefront Cottage Retreat
Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Entire guest suite in South Windsor, Connecticut
Entire guest suite in South Windsor, ConnecticutFind vacation rentals that suit your style
Top Portland Hotel Reviews

Holiday Inn Express Southington by IHG
Find out more about Portland
Everything you need to know about Portland vacation rentals
Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Portland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.
There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Portland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.
Portland vacation rentals: An excellent choice for every season
Whenever you want to travel, a warm welcome awaits you in Portland. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Portland in high season.
Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $211 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!
How to find incredible deals on Portland rentals
At Expedia, we put the best Portland vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.
To find some top Portland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Portland vacation.
If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Portland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.
Explore a world of travel with Expedia
- Hotels near Brownstone Exploration & Discovery Park
- Middletown Hotels
- Cheap Hotels in Middletown
- B&B in Middletown
- Motels in Middletown
- Hotels with Hot Tubs in Middletown
- Pet-Friendly Hotels in Middletown
- Hotel Wedding Venues Hotels in Middletown
- Resorts & Hotels with Spas in Middletown
- Hilton Hotels in Middletown
- 5 Star Hotels in Middletown
- Hotels with an Indoor Pool in Middletown
- 4 Star Hotels in Middletown
- Rv Parks in Middletown
- Hotels with Bars in Middletown
- Romantic Hotels in Middletown
- Main Street Historic District Hotels
- Cabin Rentals in Main Street Historic District
- 5 Star Hotels in Main Street Historic District
- Extended Stay America Hotels in Middletown
- La Quinta Inn & Suites Hotels in Middletown
- Hotels with an Outdoor Pool in Middletown
- Hotels with a Gym in Middletown
- Resorts in Middletown
- Condo Rentals in Middletown
- Cabin Rentals in Middletown
- Cottages in Middletown
- Winery Hotels in Middletown
- Family Hotels in Middletown
- Red Lion Hotels in Middletown
- Ski Hotels in Middletown
- Luxury Hotels in Middletown
- Hotels with Room Service in Middletown
- Hotels with Restaurants in Middletown
- Marriott Hotels & Resorts in Middletown
- Omni Hotels in Middletown
- Apartments in Middletown
- Hotels with a Pool in Middletown
- Red Roof Inn Hotels in Middletown
- Vacation Homes in Middletown
- 3 Star Hotels in Middletown
- Non-Smoking Hotels in Middletown
- Aparthotels in Middletown
- Historic Hotels in Middletown
- Hotels near Connecticut River State Wildlife Area
- Hotels near Harbor Park
- Hotels near Kidcity Children's Museum
- Washington Street Historic District Hotels
- Apartments in Washington Street Historic District
- Hotels near Wesleyan University
- Cromwell Hotels
- Hotels near Van Vleck Observatory
- Cheap Hotels in Cromwell
- Hotels with an Indoor Pool in Cromwell
- Pet-Friendly Hotels in Cromwell
- Hotels with Hot Tubs in Cromwell
- Hilton Hotels in Cromwell
- B&B in Cromwell
- Resorts & Hotels with Spas in Cromwell
- Hotels with a Pool in Cromwell
- Hotels with Restaurants in Cromwell
- Motels in Cromwell
- Beach Hotels in Cromwell
- Luxury Hotels in Cromwell
- Extended Stay America Hotels in Cromwell
- Hotels with Bars in Cromwell
- Apartments in Cromwell
- Golf Hotels in Cromwell
- 4 Star Hotels in Cromwell
- Hotel Wedding Venues Hotels in Cromwell
- Winery Hotels in Cromwell
- Brownstone Exploration & Discovery Park
- Visit Middletown
- Visit Main Street Historic District
- Main Street Historic District Vacations
- Middletown Vacations
- Connecticut River State Wildlife Area
- Harbor Park
- Kidcity Children's Museum
- General Mansfield House
- Van Vleck Observatory
- Visit Cromwell
- Cromwell Vacations
- Car rentals near Middletown
- Enterprise Rental Cars in Middletown
- Hertz Rental Cars in Middletown
- Car rentals near Main Street Historic District
- Thrifty Car Rental Rental Cars in Middletown
- National Car Rental Rental Cars in Middletown
- Europcar Rental Cars in Middletown
- Midway Car Rental Rental Cars in Middletown
- Rent A Wreck Rental Cars in Middletown
- Car rentals near Washington Street Historic District
- Car rentals near Wesleyan University
- Car rentals near Cromwell


















































































