Lake Oswego holiday rentals

We found 1,658 holiday rentals — enter your dates for availability
Discover a selection of 30 homes, 11 apartments and other holiday rentals in Lake Oswego that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll find the best amenities for hanging out with the people that matter most, which might include a fireplace and a washer and dryer. No matter what you're looking for, you'll find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Lake Oswego

Showing deals for:25 Dec - 1 Jan

Interior
Exterior
Private kitchen
Interior
Exceptional
(29 reviews)

Huge Luxury Home with huge Deck near Powell Butte Park

Portland

7% off
AU$9,309
for 7 nights, 1 home
AU$1,330 per night
includes taxes & fees
Huge Luxury Home with huge Deck near Powell Butte Park
Terrace/patio
Exterior detail
Dining
Living area
Exceptional
(8 reviews)

Cozy caravan in Mississippi area of Portland with WiFi, AC

Portland

9% off
AU$1,276
for 7 nights, 1 home
AU$182 per night
includes taxes & fees
Cozy caravan in Mississippi area of Portland with WiFi, AC
Property grounds
Terrace/patio
Living area
Property grounds
Wonderful
(65 reviews)

Stafford River House

West Linn

8% off
AU$3,551
for 7 nights, 1 home
AU$507 per night
includes taxes & fees
Stafford River House
Living room to entry access
Exterior detail
Formal living room with floor to ceiling curtains for privacy.
36" Kitchen Aid french door fridge H20 & ice, windows to hot tub.
Excellent
(9 reviews)

Gorgeous private home! Central Air 4 beds, hot tub, patio, designer furnishings

Portland

7% off
AU$6,010
for 7 nights, 1 home
AU$859 per night
includes taxes & fees
Gorgeous private home! Central Air 4 beds, hot tub, patio, designer furnishings
Living area
Living area
Interior
Living area
Exceptional
(22 reviews)

Stunning Ranch Home in Walkable Gorgeous Happy Valley Neighborhood

Happy Valley

8% off
AU$3,672
for 7 nights, 1 home
AU$525 per night
includes taxes & fees
Stunning Ranch Home in Walkable Gorgeous Happy Valley Neighborhood
Private kitchen
Living area
Dining
Room
Exceptional
(6 reviews)

2 King Suites • Mountain Views • Near Rose Garden

Portland

7% off
AU$5,582
for 7 nights, 1 home
AU$797 per night
includes taxes & fees
2 King Suites • Mountain Views • Near Rose Garden
Living area
Property grounds
Property grounds
Private kitchen
Exceptional
(16 reviews)

Charming and minimal with private Backyard ADU 1-bedroom, 1-Bath. Tesla Charger

Portland

7% off
AU$1,749
for 7 nights, 1 home
AU$250 per night
includes taxes & fees
Charming and minimal with private Backyard ADU 1-bedroom, 1-Bath. Tesla Charger
Fully stocked Chef's kitchen.
Picture yourself enjoying a glass of wine surrounded by modern chic.
A lovely cozy room to wake up in.
Oversize custom Italian tiled shower.
Exceptional
(169 reviews)

★ CLEAN ★ NEAR DOWNTOWN + PRIVATE PATIO ★ WALKABLE

Portland

7% off
AU$2,628
for 7 nights, 1 apartment
AU$375 per night
includes taxes & fees
★ CLEAN ★ NEAR DOWNTOWN + PRIVATE PATIO ★ WALKABLE
Stairways to path to enter house/ Six steps, inclined path and another two step
Our home on a snowy day in winter
Living room looking at front door
Living Room from entry way looking to French doors to deck.
Exceptional
(176 reviews)

Sunny 1400 SQFT Dutch Colonial in Portland Heights - 5 min to downtown, NW 23rd

Portland

7% off
AU$2,005
for 7 nights, 1 home
AU$286 per night
includes taxes & fees
Sunny 1400 SQFT Dutch Colonial in Portland Heights - 5 min to downtown, NW 23rd
Living area
Property grounds
Property grounds
Exterior detail
Exceptional
(340 reviews)

A garden view hideaway in the Irvington neighborhood

Portland

7% off
AU$1,637
for 7 nights, 1 apartment
AU$234 per night
includes taxes & fees
A garden view hideaway in the Irvington neighborhood
Interior
Dining
Living area
Property grounds
Exceptional
(17 reviews)

Charming 1-bedroom apt; cleaned with non-toxic, plant based cleaning products

Milwaukie

9% off
AU$1,545
for 7 nights, 1 apartment
AU$221 per night
includes taxes & fees
Charming 1-bedroom apt; cleaned with non-toxic, plant based cleaning products
Private kitchen
Interior
Interior
Outdoor dining
Exceptional
(59 reviews)

Cozy Modern Farmhouse, King bed, great yard, pets!

Milwaukie

17% off
AU$3,806
for 7 nights, 1 home
AU$544 per night
includes taxes & fees
Cozy Modern Farmhouse, King bed, great yard, pets!
Exterior
Dining
Living area
Property grounds
Exceptional
(126 reviews)

Portland Sanctuary

Portland

7% off
AU$2,440
for 7 nights, 1 apartment
AU$349 per night
includes taxes & fees
Portland Sanctuary
Exterior
Exterior
Interior
Property grounds
Exceptional
(91 reviews)

Charming, Private, Detached Studio!

Portland

7% off
AU$914
for 7 nights, 1 apartment
AU$131 per night
includes taxes & fees
Charming, Private, Detached Studio!
nice details, fun lighting.
Living area
clean and fully stocked professional kitchen
Approach to guesthouse
Exceptional
(47 reviews)

Cottage in Historic Irvington neighborhood near Convention Center and shops!

Portland

7% off
AU$1,655
for 7 nights, 1 room
AU$236 per night
includes taxes & fees
Cottage in Historic Irvington neighborhood near Convention Center and shops!
Exterior detail
Exterior detail
Outdoor dining
Garden gnomes abound!
Exceptional
(272 reviews)

Peaceful Garden Cottage, Close to Mt. Tabor Park & Downtown Bus

Portland

6% off
AU$1,637
for 7 nights, 1 cottage
AU$234 per night
includes taxes & fees
Peaceful Garden Cottage, Close to Mt. Tabor Park & Downtown Bus
Bathroom
Living area
Exterior detail
Living area
Exceptional
(5 reviews)

Cozy ADU with AC in charming Oregon City

Oregon City

9% off
AU$1,942
for 7 nights, 1 apartment
AU$277 per night
includes taxes & fees
Cozy ADU with AC in charming Oregon City
Room
Living area
Interior
Private kitchen
Exceptional
(17 reviews)

Private, comfy and cozy apartment in family neighborhood

Oregon City

8% off
AU$1,134
for 7 nights, 1 apartment
AU$162 per night
includes taxes & fees
Private, comfy and cozy apartment in family neighborhood
Room
Living area
Interior
Living area
Exceptional
(15 reviews)

Cozy Newly Remodeled Duplex

Milwaukie

8% off
AU$1,038
for 7 nights, 1 home
AU$148 per night
includes taxes & fees
Cozy Newly Remodeled Duplex
Cozy living room, with live plants where you can watch deer, birds, squirrels….
Covered patio with gas fire, swinging bench & expansive view of private lawn.
Path to lower covered patio with gas fireplace and 2nd entry door/slider.
Path from parking thru gardens to the private front porch.
Exceptional
(141 reviews)

Comfort Close To Portland, Wine Country, Beaches, Rivers, And Mt. Hood

Beaverton

8% off
AU$2,344
for 7 nights, 1 apartment
AU$335 per night
includes taxes & fees
Comfort Close To Portland, Wine Country, Beaches, Rivers, And Mt. Hood
Dining
Outdoor dining
Exterior
Living area
Exceptional
(5 reviews)

1BR Apartment w/ Hot tub, walk to shops & food!

West Linn

7% off
AU$2,615
for 7 nights, 1 apartment
AU$374 per night
includes taxes & fees
1BR Apartment w/ Hot tub, walk to shops & food!
Private kitchen
Property grounds
Living area
Room
Exceptional
(75 reviews)

Creekside Haven

Wilsonville

9% off
AU$1,457
for 7 nights, 1 home
AU$208 per night
includes taxes & fees
Creekside Haven
Outdoor dining
Front of main house
Room
Private kitchen
Exceptional
(102 reviews)

Welcome to our Luxury Memory Lane Hideaway

Portland

7% off
AU$1,543
for 7 nights, 1 apartment
AU$220 per night
includes taxes & fees
Welcome to our Luxury Memory Lane Hideaway
Private kitchen
Exterior
Outdoor dining
Room
Exceptional
(9 reviews)

Charming, close-in 2-bedroom modern apartment in Hip Portland Neighborhood.

Portland

7% off
AU$2,384
for 7 nights, 1 apartment
AU$341 per night
includes taxes & fees
Charming, close-in 2-bedroom modern apartment in Hip Portland Neighborhood.

  • Peace of mind

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  • More quality time

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    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Friendly Lake Oswego will entice you

Enjoy the temples and other features of Lake Oswego. Revered for its lake, shopping and restaurants, this city is both welcoming and walkable. Oregon Convention Center and Moda Center are just a couple of the must-see attractions in the area. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in and around Lake Oswego

Are you searching for attractions to visit while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Lake Oswego a fun place to get away to. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Oswego Hills Vineyard and Winery (2.3 mi / 3.7 km)
  • Oaks Amusement Park (3.6 mi / 5.8 km)
  • Eastmoreland Golf Course (4 mi / 6.5 km)
  • Oregon Golf Club (6.2 mi / 10.1 km)
  • Oregon Zoo (6.5 mi / 10.4 km)
  • Rose City Golf Course (9 mi / 14.4 km)

Exploring the natural landscape of Lake Oswego

Whether you're an outdoor enthusiast or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Lake Oswego. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Sellwood Riverfront Park (3.3 mi / 5.3 km)
  • Westmoreland Park (3.5 mi / 5.7 km)
  • Gabriel Park (4.4 mi / 7 km)
  • Crystal Springs Rhododendron Garden (4.4 mi / 7 km)
  • Pendleton Park (5.1 mi / 8.2 km)
  • Willamette Falls (5.4 mi / 8.7 km)

Travelling to and around Lake Oswego

The nearest airport is in Portland International Airport (PDX), located 12.2 mi (19.7 km) from the city centre.

Frequently asked questions

What is the best area to stay in Lake Oswego when booking a holiday rental?
When considering a holiday rental in Lake Oswego, Oregon, the area around the downtown region is particularly appealing. This charming neighbourhood boasts a delightful mix of boutique shops, cafes, and restaurants, making it a vibrant hub for visitors. One of the top attractions nearby is the serene Lake Oswego itself, superb for leisurely strolls, kayaking, or simply enjoying the picturesque views. Additionally, the nearby Oswego Heritage House offers fascinating insights into the local history and culture.Another great option is the area surrounding George Rogers Park, which is known for its beautiful green spaces and scenic walking trails alongside the Willamette River. This park not only provides ample opportunities for outdoor activities but also hosts various community events throughout the year, enhancing the local experience.In terms of properties, the downtown area features a good selection of rentals, ranging from cosy apartments to larger family homes, suiting a variety of preferences and budgets.
Where are the best areas for renting a beach house in Lake Oswego?
For renting a beach house in Lake Oswego, consider the picturesque areas along the shores of the Willamette River and the nearby Oswego Lake. The waterfront properties on the eastern side of Oswego Lake provide stunning views and a tranquil atmosphere, great for families or groups looking to enjoy a lakeside retreat. Many of these properties come with amenities such as private docks, outdoor decks, and spacious living areas, ideal for entertaining or relaxing after a day of water activities.The area around George Rogers Park is particularly appealing, as it offers easy access to sandy beaches and picnic spots. Rentals in this vicinity often feature well-equipped kitchens, fire pits, and large outdoor spaces for barbecues and gatherings, making them excellent choices for summer getaways.Additionally, the nearby Lake Oswego Village offers a charming atmosphere with boutique shops and dining options, adding convenience for travellers. Properties here may also include access to community amenities like swimming pools and walking trails, ensuring a comfortable and enjoyable stay.
What is the most popular type of holiday rental accomodation in Lake Oswego?
In Lake Oswego, holiday houses are the predominant type of holiday rental, with approximately 124 available throughout the area. These spacious homes typically feature multiple bedrooms, fully equipped kitchens, and private outdoor spaces such as gardens or patios, making them ideal for families or groups seeking comfort and convenience. Additionally, there are around 48 apartments and 28 condos, which offer a more compact living arrangement. These properties often include amenities like modern kitchens, communal facilities, and proximity to local attractions such as the scenic Lake Oswego waterfront and the charming downtown area.
Are there any family house rentals in Lake Oswego?
In Lake Oswego, Oregon, there are numerous family-friendly house rentals available, with around 25 options to choose from. This picturesque area is known for its beautiful parks, scenic waterfronts, and a welcoming community atmosphere, making it an excellent choice for families. Many of these homes provide spacious living areas, fully equipped kitchens for family meals, and outdoor spaces where children can play and enjoy the fresh air. Essential amenities such as Wi-Fi and air conditioning are typically included, ensuring a comfortable stay.Families can explore the nearby parks, such as George Rogers Park, which offers playgrounds, walking trails, and stunning views of the lake. The local community also hosts various events and activities throughout the year, providing a vibrant setting for family outings.
Can I rent a holiday home with a pool or hot tub in Lake Oswego?
In Lake Oswego, there are several holiday homes available for rent that come with pools or hot tubs. This picturesque city, located just south of Portland, offers a variety of charming neighbourhoods with access to serene lakes and wooded areas. Many of the rentals feature private pools, hot tubs, and spacious outdoor patios, ideal for relaxation and entertaining.Travellers can expect amenities such as fully equipped kitchens, comfortable living spaces, and often access to beautiful gardens or lake views, enhancing the overall experience. The community also boasts nearby parks and recreational areas, providing opportunities for outdoor activities like hiking and boating.
Are there pet-friendly house rentals in Lake Oswego?
In Lake Oswego, there are numerous pet-friendly house rentals available, with a total of 27 options for travellers seeking to bring their furry companions along. The area is known for its beautiful surroundings, including picturesque parks and scenic waterfronts, making it an inviting destination for both pets and their owners.Many of the holiday rentals in Lake Oswego feature amenities such as spacious backyards, fully equipped kitchens, and comfortable living spaces, great for families or groups. Some properties may even offer additional features like outdoor patios or decks, providing a lovely space to relax while enjoying the views of the lake or gardens.Within Lake Oswego, visitors can explore several parks that are ideal for pets, including George Rogers Park, which offers walking paths, picnic areas, and access to the Willamette River. The local community is generally pet-friendly, with various shops and cafes welcoming pets, enhancing the overall experience for those travelling with animals.
Are there any remote work holiday rentals in Lake Oswego?
In Lake Oswego, there are numerous remote work-friendly holiday rentals available, with around 184 options to choose from. This picturesque city, located just south of Portland, offers a serene environment ideal for productivity while enjoying a pleasant stay. Many of the rentals come equipped with essential amenities for remote work, including high-speed Wi-Fi, dedicated workspaces, and printers.Travellers can expect various property types, from modern apartments to spacious homes, often featuring comfortable living areas and well-equipped kitchens for easy meal preparation. The scenic surroundings include beautiful parks, such as George Rogers Park and Lake Oswego itself, providing opportunities for outdoor breaks and relaxation. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Lake Oswego?
In Lake Oswego, popular rental amenities include fully equipped kitchens, making it convenient for guests to prepare their own meals. Many properties also offer onsite parking, which is a bonus for travellers with vehicles. Additionally, rentals typically feature coffee and tea makers for a quick caffeine fix, and most come with decks or patios where guests can relax and enjoy the pleasant surroundings. Furthermore, a number of these holiday rentals permit pets, allowing guests to bring their furry companions along for the stay.
When is the best time to visit Lake Oswego for a holiday rental?
The best time to visit Lake Oswego for a holiday rental is during the peak season from June to August, with July being the most popular month. This vibrant period attracts families and outdoor enthusiasts eager to enjoy the picturesque parks, lakes, and local events. The warm weather, often reaching the high 20s Celsius, creates the superb environment for activities such as hiking, kayaking, and picnicking along the scenic waterfront.July in Lake Oswego is particularly enchanting, as the community comes alive with summer festivals and outdoor concerts. Visitors can engage in the lively option while exploring the quaint downtown area, filled with charming shops and delightful dining options.For those looking to experience Lake Oswego at a more relaxed pace, consider visiting in November. This month offers a quieter experience, allowing you to appreciate the beauty of the autumn leaves and the tranquil surroundings. While the weather can be cooler, generally ranging from 0 to 10 degrees Celsius, it provides an excellent opportunity for peaceful walks and enjoying the local art scene without the crowds.
What are the top attractions in Lake Oswego?
In Lake Oswego, visitors can enjoy a variety of attractions that showcase the area's natural beauty and community spirit. The picturesque Lake Oswego itself is a focal point, offering opportunities for boating, kayaking, and scenic walks along the waterfront. The nearby Oswego Heritage House provides insights into the local history and culture, while the charming downtown area features boutique shops and delightful eateries.For outdoor enthusiasts, the stunning parks like George Rogers Park and the expansive Tryon Creek State Natural Area offer lush trails for hiking and nature walks. The city's vibrant arts scene is highlighted by the Lakewood Centre for the Arts, where guests can catch performances or view local art exhibitions.
Are all fees included in the Lake Oswego 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 Lake Oswego holiday homes with parking?
Stayz offers a wide selection of holiday homes in Lake Oswego 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 Lake Oswego holiday homes?
You can find great discounts on holiday homes in Lake Oswego 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 Lake Oswego holiday home booking on Stayz?
To find Lake Oswego 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 Lake Oswego?
A long-stay holiday home in Lake Oswego 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 Lake Oswego holiday home?
Book your Lake Oswego 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 Lake Oswego?
Prices for holiday homes in Lake Oswego 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 Lake Oswego 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.

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