Discover Your Perfect Olde Town Vacation Homes

Why Choose Rent By Owner for your Olde Town Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Olde Town Vacation Rentals

Where are the best neighborhoods to stay in Olde Town?

When choosing where to stay in Olde Town, Issaquah, Washington, you’ll find a neighborhood rich in local charm and convenient access to the area's natural beauty. The quaint streets and welcoming atmosphere make it an ideal spot for those seeking an authentic experience. Staying within this historic district offers a peaceful retreat while still being close to key amenities and scenic surroundings. Whether you're planning a relaxing getaway or an active exploration of the region, finding the perfect vacation rental in Olde Town will enhance your visit to this beloved part of Issaquah.

Park Pointe

Located nearby, Park Pointe offers a peaceful setting with easy access to the charm of Olde Town. Here, you can enjoy a comfortable stay while exploring the scenic surroundings that make this area unique.

View 73+ Rentals in Park Pointe

Squak Mountain

Nestled close to the region’s natural beauty, Squak Mountain provides a tranquil backdrop for your visit, perfect for those seeking outdoor tranquility and convenient proximity to local attractions.

View 80+ Rentals in Squak Mountain

Best Times to Visit Olde Town

When should you plan your Vacation Rentals stay?

Timing your visit to this charming destination can enhance your experience, so consider planning your stay during the region’s most inviting seasons for a memorable and comfortable getaway.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, the area experiences warm weather that attracts visitors looking for outdoor activities and scenic exploration. This is the busiest time for vacation rentals, with higher demand for shorter getaways.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Fall (September to November)

Autumn offers vibrant foliage and mild weather, making it a popular season for those wanting to enjoy outdoor scenery and local events. Expect increased occupancy in cozy rental properties throughout this period.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 45°F to 55°F

Off-Season Highlights

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Winter (December to February)

The quieter winter months feature cooler temperatures and fewer tourists, offering a peaceful escape. It’s an ideal time to find more affordable rates on vacation rentals while enjoying the tranquility of the area.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 30°F to 40°F
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Early Spring (March to May)

As the region transitions into spring, you’ll experience fewer crowds and blooming landscapes. This off-peak season allows for a more relaxed stay with better availability and rates on vacation rentals.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 35°F to 45°F

Weekly Weather Forecast for Olde Town

How to Book Your Olde Town Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Olde Town

More Top-Rated Vacation Rentals in Olde Town Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor seating areas perfect for relaxing and taking in the scenery of the surrounding area.
  • Take advantage of private patios or decks to dine or unwind outdoors amidst nature.
  • Benefit from landscaped yards or gardens that provide a peaceful outdoor retreat.
  • Stay active with access to nearby hiking trails directly accessible from your rental.
  • Make use of outdoor fire pits for cozy evenings under the stars.
  • Utilize outdoor parking spaces designed to accommodate your vehicle conveniently.
  • Explore nearby parks and green spaces that are easily reachable from your accommodation here.

Top Attractions Around Olde Town

What attractions are nearby?

Within this charming area, you can enjoy a variety of outdoor activities and explore local shops and dining options, all just moments from your vacation rental in Olde Town, Issaquah, Washington.

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Family Activities

  • Issaquah Skate Park: Enjoy a family-friendly skateboarding experience at this popular outdoor facility nestled in the area.
  • Issaquah History Museum: Discover local history through engaging exhibits that make for an educational outing with the kids.
  • Lake Sammamish State Park: Spend quality time outdoors with picnicking, swimming, and exploring nature along the scenic shores nearby.
  • Gilman Village: Explore charming shops and dine together in this historic shopping district filled with unique boutiques and inviting cafés.
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Adult Activities

  • Visit the Issaquah Salmon Hatchery: Gain insight into local wildlife conservation efforts by exploring this educational hatchery, a must-see attraction for nature lovers in the area.
  • Explore Lake Sammamish State Park: Enjoy outdoor activities such as kayaking, picnicking, or strolling along scenic trails at this popular park near here.
  • Discover local art galleries and boutiques: Browse unique artworks and handcrafted goods in the charming shops that line the historic streets of Olde Town, offering a taste of regional creativity.
  • Experience culinary delights at local eateries: Indulge in farm-to-table cuisine and fresh seafood at restaurants renowned for their focus on Washington’s regional flavors in the area.

Other Places to Stay in Olde Town, WA

Village Theater First Stage Theatre
Village Theater First Stage Theatre Vacation Rentals
Village Theater Francis J. Gaudette Theatre
Village Theater Francis J. Gaudette Theatre Vacation Rentals
Downtown Issaquah
Downtown Issaquah Vacation Rentals
Issaquah Salmon Hatchery
Issaquah Salmon Hatchery Vacation Rentals
More Places to Stay Near Olde Town

Olde Town Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining and Shops: Take advantage of the nearby restaurants and boutiques to experience the authentic charm of this destination's vibrant community.
  • Plan Outdoor Activities: Use the region’s parks and trails to enjoy the scenic beauty and make the most of your outdoor adventures during your stay.
  • Visit Key Attractions Early: Arrive early at popular sites to avoid crowds and secure a more relaxed visit to this area's renowned spots.
  • Book Accommodation Close to Main Streets: Select vacation rentals near the heart of Olde Town for easy access to local amenities and a truly immersive experience.

Transportation Options

  • Personal Vehicle: Having your own car offers the ultimate flexibility to explore the scenic region around Olde Town and enjoy convenient access to local attractions.
  • Public Transit: The area is well-connected by bus services, making it easy for you to reach downtown Issaquah and neighboring communities without hassle.
  • Rideshare Services: Rideshare options like Uber and Lyft provide a reliable and quick way to get around here, especially if you're avoiding parking concerns during your stay.
  • Bicycle Rentals: Cycling is a popular choice to explore the charming streets of this destination while enjoying the fresh air and scenic views.

Local Customs Options

  • Local Artisans and Crafts: In this area, supporting local artisans is a cherished tradition, reflected in the handcrafted goods and art you’ll find throughout Olde Town.
  • Seasonal Festivals: The region celebrates its history and community through seasonal festivals that showcase local culture and bring residents and visitors together.
  • Historic Preservation: Respect for the area's history is evident in the preservation of old buildings and landmarks that tell the story of this destination's past.
  • Outdoor Community Activities: Engaging in outdoor events and activities is a common custom here, emphasizing the region’s appreciation for nature and active lifestyles.

Frequently Asked Questions About Olde Town?

1. What are the top vacation rentals in Olde Town?

There are a lot of options in Olde Town. If you plan on staying in the Olde Town area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Olde Town:

2. Which vacation homes in Olde Town are best for families?

If you are looking for a family-friendly vacation home in Olde Town, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Olde Town:

3. How many Rentbyowner vacation rentals are available in Olde Town?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 72 in the Olde Town area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Olde Town. 

4. What is the cancellation policy for vacation rentals in Olde Town, Issaquah?

The cancellation policies vary depending on the listing. You should review the specific terms outlined in the property description or contact the host directly to understand the cancellation window and any applicable fees.

5. Are there any additional fees I should be aware of when booking a vacation rental here?

Additional fees such as cleaning fees, service charges, or security deposits are often specified in the listing details. It’s recommended to read the full description or reach out to the host for clarification before completing your booking.

6. How do I confirm the availability of a vacation rental in this area?

Availability can be checked by entering your desired dates on the listing page. For real-time confirmation, contacting the host directly is helpful, especially during peak seasons or for last-minute reservations.

7. Can I make special requests or modifications to my reservation?

Yes, many hosts offer the option to communicate special requests or modifications. It’s best to contact the host directly through the platform to discuss your needs before finalizing your booking.

8. What amenities are typically included with a vacation rental here?

Most listings detail the amenities provided, which may include essentials like Wi-Fi, kitchen access, parking, and laundry facilities. To ensure the property meets your needs, review the listed amenities carefully or contact the host for further information.