Owner Direct Vacation Rentals in Tradewinds Charters

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413 Tradewinds Charters Vacation Homes From $64

Looking for the ideal vacation rental in Tradewinds Charters? Discover an extensive gallery of private rentals offering space, comfort, and authentic local character. Owner Direct simplifies your search by matching you with verified property options.

Depoe Bay Delight
Depoe Bay Delight
House
Depoe Bay, OR, USA
0.2k from Tradewinds Charters center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Hot tubs, Places to stay

2 Bedrooms4 Guests
6.0

Review score

5 reviews

$93
Average price / night
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Depoe Bay Coastal Breeze Cottage * Walk to shops
Depoe Bay Coastal Breeze Cottage * Walk to shops
House
Depoe Bay, OR, 97341, United States
0.2k from Tradewinds Charters center

AC, Dryer, Fireplace, Heater, Internet, Microwave, No Smoking, Toys, TV

2 Bedrooms6 Guests
9.4

Superb

8 reviews

$247
Average price / night
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Coastal Breeze
Coastal Breeze
House
Depoe Bay, OR, USA
0.2k from Tradewinds Charters center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Family

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$64
Average price / night
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Depoe Bay Delight Dog-Friendly Ocean View
Depoe Bay Delight Dog-Friendly Ocean View
House
Depoe Bay, OR, 97341, United States
0.2k from Tradewinds Charters center

Balcony, Fireplace, Hot Tub, Internet, Kitchen, Microwave, No Smoking, Patio, TV

2 Bedrooms4 Guests
9.6

Exceptional

12 reviews

$235
Average price / night
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Gardner Family House #1
Gardner Family House #1
House
Depoe Bay, OR, USA
0.2k from Tradewinds Charters center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

2 Bedrooms6 Guests
8.4

Very Good

5 reviews

$331
Average price / night
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Whales and Outstanding Rocky Surf Views from this Depoe Bay Oceanfront Perch!
Whales and Outstanding Rocky Surf Views from this Depoe Bay Oceanfront Perch!
House
Depoe Bay, OR, 97341, United States
0.2k from Tradewinds Charters center

Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms6 Guests
9.4

Superb

77 reviews

$421
Average price / night
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Gardner Family House #2
Gardner Family House #2
House
Depoe Bay, OR, USA
0.2k from Tradewinds Charters center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

1 Bedroom5 Guests
1.0

Review score

1 reviews

$262
Average price / night
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Walk Out Your Door to a Spectacular, Panoramic Oceanfront View of Depoe Bay!
Walk Out Your Door to a Spectacular, Panoramic Oceanfront View of Depoe Bay!
House
Depoe Bay, OR, 97341, United States
0.2k from Tradewinds Charters center

Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

1 Bedroom5 Guests
9.0

Fabulous

90 reviews

$255
Average price / night
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Bay Echo
Bay Echo
House
Depoe Bay, OR, USA
0.2k from Tradewinds Charters center

Internet, Parking, Security/Safety, Child Friendly

2 Bedrooms8 Guests
8.4

Very Good

17 reviews

$281
Average price / night
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The Captains Lookout  Sleeps 6, Hot Tub, Pet Friendly, Ocean View
The Captains Lookout Sleeps 6, Hot Tub, Pet Friendly, Ocean View
House
Depoe Bay, OR, 97341, United States
0.2k from Tradewinds Charters center

Barbecue, Dryer, Fireplace, Heater, Hot Tub, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

31 reviews

$623
Average price / night
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SeaQuell
SeaQuell
House
Depoe Bay, OR, USA
0.2k from Tradewinds Charters center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

3 Bedrooms8 Guests
9.8

Exceptional

16 reviews

$174
Average price / night
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Bay Suites – Studio A | Modern Coastal Escape in the Heart of Depoe Bay
Bay Suites – Studio A | Modern Coastal Escape in the Heart of Depoe Bay
Apartment
Depoe Bay, OR, 97341, United States
0.3k from Tradewinds Charters center

Dryer, Fireplace, Free Parking, Heater, Internet, Living Area, Microwave, No Smoking, TV

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$382
Average price / night
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Captain's Quarters and Cabins
Captain's Quarters and Cabins
Apartment
Depoe Bay, OR, USA
0.3k from Tradewinds Charters center

Apartments, Accommodations, Pet-friendly, Lodgings, Vacation rentals, Hot tubs, Places to stay

6 Bedrooms14 Guests
5.0

Review score

1 reviews

$702
Average price / night
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Whale Watching Has Never Been Easier At This Studio In Depoe Bay!
Whale Watching Has Never Been Easier At This Studio In Depoe Bay!
Apartment
Depoe Bay, OR, 97341, United States
0.3k from Tradewinds Charters center

AC, Balcony, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom4 Guests
9.8

Exceptional

160 reviews

$256
Average price / night
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Spectacular Ocean Views! Spouting Horn Two
Spectacular Ocean Views! Spouting Horn Two
Apartment
Depoe Bay, OR, USA
0.3k from Tradewinds Charters center

Apartments, Cheap, Accommodations, Pet-friendly, Lodgings, Places to stay, Family

1 Bedroom3 Guests
9.0

Fabulous

3 reviews

$227
Average price / night
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T01 - Anchor@ Trollers Lodge
T01 - Anchor@ Trollers Lodge
Apartment
Depoe Bay, OR, 97341, United States
0.3k from Tradewinds Charters center

Barbecue, Extra Bed, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

2 Bedrooms6 Guests
9.4

Superb

37 reviews

$270
Average price / night
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Ocean View & Whale Watching! Spouting Horn Three
Ocean View & Whale Watching! Spouting Horn Three
Apartment
Depoe Bay, OR, USA
0.3k from Tradewinds Charters center

Apartments, Accommodations, Pet-friendly, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$251
Average price / night
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T05 - Dinghy @ Trollers Lodge
T05 - Dinghy @ Trollers Lodge
Apartment
Depoe Bay, OR, 97341, United States
0.3k from Tradewinds Charters center

Barbecue, Extra Bed, Free Parking, Heater, Internet, Living Area, Microwave, No Smoking, TV

1 Bedroom3 Guests
9.4

Superb

8 reviews

$158
Average price / night
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T11 - Trawler @ Trollers Lodge
T11 - Trawler @ Trollers Lodge
Apartment
Depoe Bay, OR, 97341, United States
0.3k from Tradewinds Charters center

Barbecue, Free Parking, Heater, Internet, Microwave, No Smoking, TV

1 Bedroom2 Guests
9.4

Superb

28 reviews

$129
Average price / night
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T09 - Lighthouse @ Trollers Lodge
T09 - Lighthouse @ Trollers Lodge
Apartment
Depoe Bay, OR, 97341, United States
0.3k from Tradewinds Charters center

Barbecue, Heater, Internet, Microwave, No Smoking, TV

1 Bedroom2 Guests
9.2

Superb

26 reviews

$133
Average price / night
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T04 - Cutter @ Trollers Lodge
T04 - Cutter @ Trollers Lodge
Apartment
Depoe Bay, OR, 97341, United States
0.3k from Tradewinds Charters center

Barbecue, Extra Bed, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, TV

1 Bedroom4 Guests
9.4

Superb

14 reviews

$140
Average price / night
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Pro Tip:
OwnerDirectVacationRental aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Tradewinds Charters.

Tradewinds Charters Vacation Rentals on the Map

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Endless Variety

From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.

Frequently Asked Questions

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

You can explore 413 verified vacation rentals in Tradewinds Charters. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Tradewinds Charters vary depending on the season, property size, and location. Rates typically start from around $64 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Tradewinds Charters include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Tradewinds Charters welcome pets. Currently, 75 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it's recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Tradewinds Charters often include amenities such as Fireplace/Heating, Pet Friendly, and View. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.