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Pirate Cove Cottages - Vacation Rentals in Oakland

Urban Cottage From US $153
         

5.0 (2 Reviews)
Cottage
Urban Cottage
  • Air Conditioner
  • TV
  • Bedding/Linens

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Luxury Places to Stay in Oakland

Over 1123+ Luxury Places to Stay in or Near Oakland
New
Hotel
Luxury 2BR/2BA Suite near McCormick Place, Lakefront with Parking & Gym
  • Air Conditioner
  • Parking
  • TV

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New
Hotel
Chicago 4BR/3BA South Getaway Near McCormick Place
  • Air Conditioner
  • Parking
  • TV

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Sophy Hyde Park From US $2,333
         

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9.1 (220 Reviews)
Hotel
Sophy Hyde Park
  • Air Conditioner
  • Parking
  • Pet Friendly

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McCormick Suites by Slumber Stay From US $2,250
         

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New
Hotel
McCormick Suites by Slumber Stay
  • Air Conditioner
  • Parking
  • Pet Friendly

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Spacious 5BR Luxury Suite Perfect for Group Sleeps 12 Near McCormick Place, Grant Park and Soldier Field From US $2,198
         

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New
Apartment
Spacious 5BR Luxury Suite Perfect for Group Sleeps 12 Near McCormick Place, Grant Park and Soldier Field
  • Air Conditioner
  • Parking
  • Pet Friendly

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Group-Friendly 5BR Suite Sleeps 12 with Billiards, Optional Parking and Gym Access Near McCormick Place and Soldier Field From US $2,158
         

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9.0 (1 Review)
Apartment
Group-Friendly 5BR Suite Sleeps 12 with Billiards, Optional Parking and Gym Access Near McCormick Place and Soldier Field
  • Air Conditioner
  • Parking
  • Pet Friendly

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Spacious 5BR Luxury Suite Perfect for Groups with Gym Access and Optional Parking Near McCormick Place, Grant Park and Soldier Field From US $2,119
         

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New
Apartment
Spacious 5BR Luxury Suite Perfect for Groups with Gym Access and Optional Parking Near McCormick Place, Grant Park and Soldier Field
  • Air Conditioner
  • Parking
  • Pet Friendly

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Hyatt Regency McCormick Place Chicago From US $1,495
         

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8.2 (825 Reviews)
Hotel
Hyatt Regency McCormick Place Chicago
  • Air Conditioner
  • Parking
  • Wheelchair Accessible

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Top-Rated Vacation Rentals with a Pool in Oakland

Over 50+ Top-Rated Vacation Rentals with a Pool in or Near Oakland
Hamaline Luxury - Guest House From US $338
         

9.4 (3 Reviews)
House
Hamaline Luxury - Guest House
  • Air Conditioner
  • Parking
  • Pool

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Home2 Suites by Hilton Chicago McCormick Place From US $374
         

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9.2 (849 Reviews)
Hotel
Home2 Suites by Hilton Chicago McCormick Place
  • Air Conditioner
  • Parking
  • Pool

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Hampton Inn Chicago McCormick Place From US $190
         

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9.0 (1008 Reviews)
Hotel
Hampton Inn Chicago McCormick Place
  • Air Conditioner
  • Parking
  • Pool

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Hilton Garden Inn Chicago McCormick Place From US $189
         

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8.6 (1000 Reviews)
Hotel
Hilton Garden Inn Chicago McCormick Place
  • Air Conditioner
  • Parking
  • Pool

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Home2 Suites By Hilton Chicago McCormick Place From US $291
         

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8.6 (284 Reviews)
Hotel
Home2 Suites By Hilton Chicago McCormick Place
  • Air Conditioner
  • Parking
  • Pet Friendly

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Hampton Inn Chicago McCormick Place From US $185
         

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8.5 (750 Reviews)
Hotel
Hampton Inn Chicago McCormick Place
  • Air Conditioner
  • Parking
  • Pet Friendly

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Hyatt Place Chicago-South/University Medical Center From US $198
         

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8.3 (360 Reviews)
Hotel
Hyatt Place Chicago-South/University Medical Center
  • Air Conditioner
  • Pet Friendly
  • Pool

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Beautifully Renovated House 10 mins from Downtown From US $657
         

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8.3 (12 Reviews)
House
Beautifully Renovated House 10 mins from Downtown
  • Air Conditioner
  • Parking
  • Pet Friendly

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Pet-Friendly Vacation Rentals in Oakland

Over 376+ Pet-Friendly Vacation Rentals in or Near Oakland
Spacious 3BR · Bronzeville/South Loop · Sleeps 8 From US $845
         

10.0 (3 Reviews)
House
Spacious 3BR · Bronzeville/South Loop · Sleeps 8
  • Air Conditioner
  • Pet Friendly
  • TV

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Luxurious Stay at Modern Apartment with Self Check-in Mins Frm Downtown From US $299
         

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9.7 (18 Reviews)
Apartment
Luxurious Stay at Modern Apartment with Self Check-in Mins Frm Downtown
  • Air Conditioner
  • Parking
  • Pet Friendly

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Comfortable Condo In The Heart Of Bronzeville 4 Bedroom Condo by RedAwning From US $180
         

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New
Condo
Comfortable Condo In The Heart Of Bronzeville 4 Bedroom Condo by RedAwning
  • Pet Friendly
  • Security/Safety
  • Bedding/Linens

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NEW Eco Stay by UChicago, Lakefront & Hyde Park! From US $271
         

10.0 (2 Reviews)
Apartment
NEW Eco Stay by UChicago, Lakefront & Hyde Park!
  • Air Conditioner
  • Parking
  • Pet Friendly

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South Loop · 3 Kings · Steps from McCormick Place From US $582
         

10.0 (1 Review)
House
South Loop · 3 Kings · Steps from McCormick Place
  • Air Conditioner
  • Pet Friendly
  • TV

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Hyde Park University of Chicago Penthouse 3 bedroom/2 bathroom + gym & office From US $233
         

10.0 (1 Review)
Apartment
Hyde Park University of Chicago Penthouse 3 bedroom/2 bathroom + gym & office
  • Air Conditioner
  • Parking
  • Pet Friendly

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Toca Bella ~ 7mins to Downtownn From US $217
         

9.8 (23 Reviews)
Apartment
Toca Bella ~ 7mins to Downtownn
  • Air Conditioner
  • Parking
  • Pet Friendly

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Bridgeport Place -free parking, McCormick-Sox Park From US $332
         

9.8 (7 Reviews)
Apartment
Bridgeport Place -free parking, McCormick-Sox Park
  • Air Conditioner
  • Parking
  • Pet Friendly

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Large Vacation Homes & Villas in Oakland

Over 144+ Large Vacation Homes & Villas in or Near Oakland
4 #1S - 4 Bedroom/1.5 Bath Condo near McCormick Place, Wintrust Arena From US $447
         

10.0 (22 Reviews)
Apartment
4 #1S - 4 Bedroom/1.5 Bath Condo near McCormick Place, Wintrust Arena
  • Parking
  • TV
  • Security/Safety

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Spacious 6BR Luxury Suite Perfect for Groups Near McCormick Place and Soldier Field From US $1,136
         

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10.0 (3 Reviews)
Apartment
Spacious 6BR Luxury Suite Perfect for Groups Near McCormick Place and Soldier Field
  • Air Conditioner
  • Parking
  • Pet Friendly

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Gorgeous historic mansion on UChicago campus. Renovation with original detail. From US $725
         

10.0 (19 Reviews)
House
Gorgeous historic mansion on UChicago campus. Renovation with original detail.
  • Air Conditioner
  • TV
  • View

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1 #33 - 4 Bedroom/2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown From US $516
         

10.0 (16 Reviews)
Condo
1 #33 - 4 Bedroom/2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
  • Air Conditioner
  • Parking
  • TV

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Modern 4 Bed, 3.5 Bath Home | Near Sox & McCormick From US $800
         

10.0 (6 Reviews)
House
Modern 4 Bed, 3.5 Bath Home | Near Sox & McCormick
  • Air Conditioner
  • Parking
  • TV

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Spacious 3BR Corner Family Oasis Near McCormick Place & Soldier Field From US $553
         

10.0 (5 Reviews)
Apartment
Spacious 3BR Corner Family Oasis Near McCormick Place & Soldier Field
  • Air Conditioner
  • Parking
  • TV

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McCormick 6B/4Ba Luxury Suite for groups/12 guests From US $1,023
         

10.0 (4 Reviews)
Apartment
McCormick 6B/4Ba Luxury Suite for groups/12 guests
  • Air Conditioner
  • Parking
  • TV

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McCormick Apt 3BR Corner Oasis Near Soldier Field & Museum Campus From US $642
         

10.0 (4 Reviews)
House
McCormick Apt 3BR Corner Oasis Near Soldier Field & Museum Campus
  • Air Conditioner
  • Parking
  • TV

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Wheelchair Accessible Vacation Homes in Oakland

Over 384+ Wheelchair Accessible Vacation Homes in or Near Oakland
McCormick 3B/2Ba Family Oasis up to 8 guests with Parking-Optional/Gym/Patio From US $526
         

10.0 (3 Reviews)
Apartment
McCormick 3B/2Ba Family Oasis up to 8 guests with Parking-Optional/Gym/Patio
  • Air Conditioner
  • Parking
  • TV

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Stylish 3BR Gem in Prime Location From US $441
         

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10.0 (1 Review)
House
Stylish 3BR Gem in Prime Location
  • Air Conditioner
  • Pet Friendly
  • View

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Sophy Hyde Park From US $415
         

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9.6 (1007 Reviews)
Hotel
Sophy Hyde Park
  • Air Conditioner
  • TV
  • Wheelchair Accessible

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McCormick Place 2b/2b family unit with optional parking for up to 8 guests From US $408
         

10.0 (3 Reviews)
Apartment
McCormick Place 2b/2b family unit with optional parking for up to 8 guests
  • Air Conditioner
  • Parking
  • TV

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McCormick Place city view 2br/2ba with optional parking for up to 8 guests From US $405
         

10.0 (3 Reviews)
Apartment
McCormick Place city view 2br/2ba with optional parking for up to 8 guests
  • Air Conditioner
  • Parking
  • TV

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McCormick Place Patio skyline 2b/2b with optional Parking for up to 6 people From US $399
         

10.0 (3 Reviews)
Apartment
McCormick Place Patio skyline 2b/2b with optional Parking for up to 6 people
  • Air Conditioner
  • Parking
  • TV

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McCormick Patio skyline view 2b/2b with optional Parking/sleep 6 From US $371
         

10.0 (3 Reviews)
Apartment
McCormick Patio skyline view 2b/2b with optional Parking/sleep 6
  • Air Conditioner
  • Parking
  • TV

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South Loop Chicago 3BR Corner Suite Near Museum Campus & Millennium Park From US $495
         

10.0 (2 Reviews)
Apartment
South Loop Chicago 3BR Corner Suite Near Museum Campus & Millennium Park
  • Air Conditioner
  • Parking
  • TV

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Oakland Vacation Rentals and Airbnb Places to Stay Under $200

Over 335+ Oakland Vacation Rentals and Airbnb Places to Stay Under $200
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum From US $174
         

9.6 (76 Reviews)
Apartment
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
  • Air Conditioner
  • Parking
  • TV

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A Stylish & Cozy Apartment near Downtown Chicago From US $150
         

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9.0 (1 Review)
Apartment
A Stylish & Cozy Apartment near Downtown Chicago
  • Air Conditioner
  • Parking
  • Child Friendly

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Villa Dubois Guest House From US $190
         

8.6 (89 Reviews)
House
Villa Dubois Guest House
  • Air Conditioner
  • Parking
  • Balcony/Terrace

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Chic 1-bedroom apartment,15mims from downtown From US $171
         

9.6 (4 Reviews)
Apartment
Chic 1-bedroom apartment,15mims from downtown
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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Animal House Near Sox Stadium From US $176
         

8.6 (16 Reviews)
Apartment
Animal House Near Sox Stadium
  • Air Conditioner
  • Parking
  • Pet Friendly

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Scott House in Woodlawn - Entire Building - includes basement space From US $184
         

7.0 (7 Reviews)
House
Scott House in Woodlawn - Entire Building - includes basement space
  • Air Conditioner
  • Parking
  • TV

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Stylish 1BR in Bronzeville Near Downtown Cozy Stay w/Free Wifi From US $197
         

New
Condo
Stylish 1BR in Bronzeville Near Downtown Cozy Stay w/Free Wifi
  • Air Conditioner
  • TV
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Trendy Unit-15mins to downtown! From US $191
         

New
Apartment
Trendy Unit-15mins to downtown!
  • Air Conditioner
  • TV
  • Balcony/Terrace

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Instantly Bookable Vacation Homes in Oakland

Over 527+ Instantly Bookable Vacation Homes in or Near Oakland
Penthouse, Lux stay near Downtown, McComick & Lake From US $310
         

10.0 (18 Reviews)
Apartment
Penthouse, Lux stay near Downtown, McComick & Lake
  • Air Conditioner
  • Parking
  • TV

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Spacious 5BR Chicago Suite Near McCormick Place & Soldier Field From US $548
         

8.0 (1 Review)
Apartment
Spacious 5BR Chicago Suite Near McCormick Place & Soldier Field
  • Air Conditioner
  • Parking
  • Designated Smoking Area

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The Landmark; a comfy suite near McCormick Place From US $321
         

10.0 (10 Reviews)
Apartment
The Landmark; a comfy suite near McCormick Place
  • Air Conditioner
  • TV
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Spacious 3BR on UChicago Campus & Hospitals Free Street Parking From US $855
         

10.0 (7 Reviews)
Condo
Spacious 3BR on UChicago Campus & Hospitals Free Street Parking
  • Air Conditioner
  • Parking
  • TV

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Comfy 3BR Chicago Retreat 420 Friendly Unit Near McCormick Place & Soldier Field From US $507
         

10.0 (6 Reviews)
Apartment
Comfy 3BR Chicago Retreat 420 Friendly Unit Near McCormick Place & Soldier Field
  • Air Conditioner
  • Parking
  • Designated Smoking Area

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High-end 2Bdrm Garden Apt. Where Comfort Meets Style From US $230
         

10.0 (5 Reviews)
Apartment
High-end 2Bdrm Garden Apt. Where Comfort Meets Style
  • Air Conditioner
  • Parking
  • TV

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Bronzeville Jazz Room. Beautiful, cozy, centered, relaxing, rustic. From US $679
         

10.0 (3 Reviews)
House
Bronzeville Jazz Room. Beautiful, cozy, centered, relaxing, rustic.
  • Air Conditioner
  • Parking
  • TV

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Discover the Heart of Chicago from Our Modern 3 Bed/2.5 Bath Home From US $380
         

10.0 (3 Reviews)
House
Discover the Heart of Chicago from Our Modern 3 Bed/2.5 Bath Home
  • Air Conditioner
  • TV
  • Balcony/Terrace

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About Oakland Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Piratecovecottages Oakland, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Oakland. Places to stay near Oakland with prices averaging US $153 a night.

Piratecovecottages makes it easy and safe to find and compare vacation rentals in Oakland with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Oakland

Type Count
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Oakland

★ Pro Tip: Piratecovecottages makes it easy to compare the best listings on Piratecovecottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Piratecovecottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Oakland.

Weather in Oakland

View the weather forecast for Oakland before booking your Oakland Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Other Places to Stay Near Oakland, IL


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Oakland Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Oakland?

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

How many vacation rentals are available in Oakland?

Currently, the total number of properties listed in 2026 is over 1 in the Oakland area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Oakland.