1+ Vacation Rentals Near Oshawa |
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Cruise Vacations - Vacation Rentals in Oshawa

Sleep on a boat :) Enjoy your summer adventure on this classic YACHT 43 foot From US $122
         

New
Boat Rental
Sleep on a boat :) Enjoy your summer adventure on this classic YACHT 43 foot
  • Parking
  • Pet Friendly
  • Balcony/Terrace

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Luxury Places to Stay in Oshawa

Over 1016+ Luxury Places to Stay in or Near Oshawa
4 Bedroom Family Home Close To Pickering Casino From US $3,701
         

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New
Villa
4 Bedroom Family Home Close To Pickering Casino
  • Air Conditioner
  • Parking
  • View

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Nice Room In Renovated Basement From US $3,684
         

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New
Villa
Nice Room In Renovated Basement
  • Air Conditioner
  • Security/Safety
  • Internet

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Spacious & Stylish 4BR Villa-Sleep 9-Free Parking From US $3,523
         

New
Villa
Spacious & Stylish 4BR Villa-Sleep 9-Free Parking
  • Parking
  • Pet Friendly
  • Security/Safety

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Nestled in the heart of Clarington with its own fresh-water swimming pond! From US $3,481
         

New
House
Nestled in the heart of Clarington with its own fresh-water swimming pond!
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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Exquisite private Villa just outside of the city. From US $3,154
         

10.0 (1 Review)
Villa
Exquisite private Villa just outside of the city.
  • Air Conditioner
  • Parking
  • Pool

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Luxury 4BR Villa From US $1,549
         

New
House
Luxury 4BR Villa
  • Parking
  • Pet Friendly
  • Child Friendly

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The Perfect Getaway from The Everyday !nFraser Beach Resort From US $1,183
         

10.0 (4 Reviews)
Cottage
The Perfect Getaway from The Everyday !nFraser Beach Resort
  • Air Conditioner
  • Parking
  • Pet Friendly

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Privacy Magical Forest Cottage 30+ Party Room, Disco KTV From US $1,174
         

8.0 (2 Reviews)
Cottage
Privacy Magical Forest Cottage 30+ Party Room, Disco KTV
  • Air Conditioner
  • Parking
  • TV

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Top-Rated Vacation Rentals with a Pool in Oshawa

Over 59+ Top-Rated Vacation Rentals with a Pool in or Near Oshawa
多伦多湖畔别墅双人间3 From US $41
         

10.0 (2 Reviews)
House
多伦多湖畔别墅双人间3
  • Air Conditioner
  • Parking
  • Pool

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Enniskillen Vacation Home Retreat! From US $524
         

10.0 (1 Review)
House
Enniskillen Vacation Home Retreat!
  • Air Conditioner
  • Parking
  • Pool

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VRBO - Huge King Bed, Beautiful City&lake Views, Private Balcony & Parking From US $122
         

10.0 (1 Review)
Apartment
VRBO - Huge King Bed, Beautiful City&lake Views, Private Balcony & Parking
  • Air Conditioner
  • Parking
  • Pet Friendly

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Home away from home family get away From US $107
         

10.0 (1 Review)
Apartment
Home away from home family get away
  • Air Conditioner
  • Parking
  • Pool

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Our Valley View Bed & Breakfast From US $146
         

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9.8 (38 Reviews)
Bed & Breakfast
Our Valley View Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool

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GORGEOUS 1 BDR PRIME KITCHEN No sharing spaces/WIFI+ Parking From US $117
         

9.4 (21 Reviews)
House
GORGEOUS 1 BDR PRIME KITCHEN No sharing spaces/WIFI+ Parking
  • Air Conditioner
  • Parking
  • Pool

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Holiday Inn Express Whitby by IHG From US $119
         

9.2 (1121 Reviews)
Hotel
Holiday Inn Express Whitby by IHG
  • Air Conditioner
  • Parking
  • Pool

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TownePlace Suites by Marriott Oshawa From US $144
         

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9.2 (505 Reviews)
Hotel
TownePlace Suites by Marriott Oshawa
  • Air Conditioner
  • Parking
  • Pool

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Pet-Friendly Vacation Rentals in Oshawa

Over 243+ Pet-Friendly Vacation Rentals in or Near Oshawa
Entire Lakefront Cottage + BoathousenCozy & Peaceful with Stunning Views From US $396
         

10.0 (41 Reviews)
Cottage
Entire Lakefront Cottage + BoathousenCozy & Peaceful with Stunning Views
  • Air Conditioner
  • Parking
  • Pet Friendly

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THE TARTAN HOUSE BED & BREAKFAST From US $163
         

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9.8 (46 Reviews)
Bed & Breakfast
THE TARTAN HOUSE BED & BREAKFAST
  • Air Conditioner
  • Parking
  • Pet Friendly

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Tru By Hilton Oshawa From US $93
         

9.4 (43 Reviews)
Hotel
Tru By Hilton Oshawa
  • Air Conditioner
  • Parking
  • Pet Friendly

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nExperience Blissful Lakeside Living: Retreat with Stunning Views, Beach Access From US $280
         

10.0 (6 Reviews)
Cottage
nExperience Blissful Lakeside Living: Retreat with Stunning Views, Beach Access
  • Air Conditioner
  • Parking
  • Pet Friendly

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Luxury Remodel w HOT TUB, 6 Bdrm w 3 King beds. From US $437
         

10.0 (5 Reviews)
House
Luxury Remodel w HOT TUB, 6 Bdrm w 3 King beds.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Modern Nest - 4 BR House, 5 Beds, 2.5 Baths, 3 Park From US $311
         

10.0 (5 Reviews)
House
Modern Nest - 4 BR House, 5 Beds, 2.5 Baths, 3 Park
  • Air Conditioner
  • Parking
  • Pet Friendly

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Cozy Clean & Bright - Host your family Christmas in our magnificent home From US $583
         

10.0 (2 Reviews)
House
Cozy Clean & Bright - Host your family Christmas in our magnificent home
  • Air Conditioner
  • Parking
  • Pet Friendly

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DT Retreat : Firepit, Backyard, Arcade From US $280
         

10.0 (2 Reviews)
House
DT Retreat : Firepit, Backyard, Arcade
  • Air Conditioner
  • Parking
  • Pet Friendly

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Large Vacation Homes & Villas in Oshawa

Over 139+ Large Vacation Homes & Villas in or Near Oshawa
Castle in Bowman*Close to Port Darlington*Whole House*Arcade*King Bed*Backyard* From US $352
         

10.0 (4 Reviews)
House
Castle in Bowman*Close to Port Darlington*Whole House*Arcade*King Bed*Backyard*
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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Cosy 3-Bedroom Home in Quiet Cul-de-Sac. From US $168
         

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9.9 (29 Reviews)
Villa
Cosy 3-Bedroom Home in Quiet Cul-de-Sac.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Cozy 10acre Farm Cottage in Goodwood: @HermosoStay From US $890
         

New
Cottage
Cozy 10acre Farm Cottage in Goodwood: @HermosoStay
  • Air Conditioner
  • Bedding/Linens
  • Fireplace/Heating

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Entire Home | Toronto Hub | Therma SPA | 12 Guests | Dagmar | Sports Arenas From US $461
         

10.0 (2 Reviews)
House
Entire Home | Toronto Hub | Therma SPA | 12 Guests | Dagmar | Sports Arenas
  • Air Conditioner
  • Parking
  • TV

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Otters Cove 5 Bedroom Luxury Cottage From US $811
         

10.0 (1 Review)
Cottage
Otters Cove 5 Bedroom Luxury Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly

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Willow Nest - 5 Beds, 2.5 Baths, 3 Park, Thermea Spa From US $313
         

10.0 (1 Review)
House
Willow Nest - 5 Beds, 2.5 Baths, 3 Park, Thermea Spa
  • Air Conditioner
  • Parking
  • Pet Friendly

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Serene Stays - Pickering (5 Beds, 2.5 Baths, 4 Parking) From US $309
         

10.0 (1 Review)
House
Serene Stays - Pickering (5 Beds, 2.5 Baths, 4 Parking)
  • Air Conditioner
  • Parking
  • Pet Friendly

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Grand Waterfront Retreat – Under 1hr from Toronto From US $294
         

9.8 (21 Reviews)
Villa
Grand Waterfront Retreat – Under 1hr from Toronto
  • Air Conditioner
  • Parking
  • Pet Friendly

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Wheelchair Accessible Vacation Homes in Oshawa

Over 42+ Wheelchair Accessible Vacation Homes in or Near Oshawa
Private Cozy 1 Bedroom Apartment! Dedicated Wok Desk and Free Parking. From US $86
         

9.8 (16 Reviews)
House
Private Cozy 1 Bedroom Apartment! Dedicated Wok Desk and Free Parking.
  • Air Conditioner
  • Parking
  • TV

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Pickering Casino Resort From US $166
         

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8.6 (1261 Reviews)
Resort
Pickering Casino Resort
  • Air Conditioner
  • Parking
  • Pet Friendly

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Pickering Casino Resort Hotel From US $98
         

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9.0 (4015 Reviews)
Hotel
Pickering Casino Resort Hotel
  • Air Conditioner
  • Parking
  • Pool

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Skyline Serenity 4000+ SqFt of Luxury with Rooftop Terrace | Elevator &Lake View From US $412
         

New
House
Skyline Serenity 4000+ SqFt of Luxury with Rooftop Terrace | Elevator &Lake View
  • Air Conditioner
  • Parking
  • TV

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UltimateKING&QUEEN,PrivateBalcony, FreeParking complimentary VintageItalianWine From US $146
         

New
Condo
UltimateKING&QUEEN,PrivateBalcony, FreeParking complimentary VintageItalianWine
  • Air Conditioner
  • Parking
  • Pool

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New Luxury Condo w/rooftop terrace pool by casino From US $109
         

10.0 (2 Reviews)
Condo
New Luxury Condo w/rooftop terrace pool by casino
  • Air Conditioner
  • Parking
  • Pet Friendly

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Home Away From Home From US $71
         

New
Condo
Home Away From Home
  • Air Conditioner
  • Pool
  • TV

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Pet friendly Cozy private backyard garden suite From US $68
         

New
House
Pet friendly Cozy private backyard garden suite
  • Air Conditioner
  • Pet Friendly
  • TV

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Oshawa Varoom and Airbnb Places to Stay Under $200

Over 649+ Oshawa Varoom and Airbnb Places to Stay Under $200
💫 DreamCatcher Modern Romantic Suite w/Fireplace Pool Table near Thermea Spa From US $133
         

10.0 (28 Reviews)
Apartment
💫 DreamCatcher Modern Romantic Suite w/Fireplace Pool Table near Thermea Spa
  • Air Conditioner
  • Parking
  • TV

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Family Getaway From US $114
         

New
Apartment
Family Getaway
  • Air Conditioner
  • Parking
  • Pool

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Rising Spirit Bed & Breakfast From US $121
         

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9.8 (65 Reviews)
Bed & Breakfast
Rising Spirit Bed & Breakfast
  • Parking
  • Balcony/Terrace
  • Business Services

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RedDore - 2 Bedroom Cozy Basement Suite From US $126
         

10.0 (27 Reviews)
House
RedDore - 2 Bedroom Cozy Basement Suite
  • Air Conditioner
  • Parking
  • TV

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One bedroom apartment/suite From US $117
         

10.0 (21 Reviews)
Apartment
One bedroom apartment/suite
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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Brand New Luxury Entire Private Suite, Open Concept Retreat, close to everything From US $140
         

10.0 (11 Reviews)
House
Brand New Luxury Entire Private Suite, Open Concept Retreat, close to everything
  • Air Conditioner
  • Parking
  • TV

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Vacation Home in Pickering From US $187
         

10.0 (6 Reviews)
Apartment
Vacation Home in Pickering
  • Air Conditioner
  • Parking
  • TV

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Pinnacle of Luxury & Leisure -2 Bedroom |2 full Bathroom | Full Kitchenn From US $148
         

10.0 (6 Reviews)
Apartment
Pinnacle of Luxury & Leisure -2 Bedroom |2 full Bathroom | Full Kitchenn
  • Air Conditioner
  • Parking
  • TV

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Instantly Bookable Vacation Homes in Oshawa

Over 477+ Instantly Bookable Vacation Homes in or Near Oshawa
King Bed I Chefs Kitchen I Toronto Hub I 5 Beds 3.5 Bath I 8km from Tesla Chrg From US $364
         

10.0 (25 Reviews)
House
King Bed I Chefs Kitchen I Toronto Hub I 5 Beds 3.5 Bath I 8km from Tesla Chrg
  • Air Conditioner
  • Parking
  • TV

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Cozy ensuite w/seperate entrance & balcony, 1 minute to grocery and Rotary Park From US $71
         

9.4 (3 Reviews)
House
Cozy ensuite w/seperate entrance & balcony, 1 minute to grocery and Rotary Park
  • Air Conditioner
  • Parking
  • Pet Friendly

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Deluxe Tree House 1 Hour from Toronto From US $208
         

10.0 (5 Reviews)
Cabin
Deluxe Tree House 1 Hour from Toronto
  • Parking
  • Security/Safety
  • Fireplace/Heating

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Lakeside Luxe From US $487
         

10.0 (4 Reviews)
House
Lakeside Luxe
  • Air Conditioner
  • Parking
  • Security/Safety

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Elegant Safe Haven W/Home Theatre,Arcades, MSG Chair, Bckyrd ,Skylight near 401 From US $311
         

10.0 (4 Reviews)
House
Elegant Safe Haven W/Home Theatre,Arcades, MSG Chair, Bckyrd ,Skylight near 401
  • Air Conditioner
  • Parking
  • TV

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Unique Private Lodge one hour from Toronto. From US $184
         

10.0 (3 Reviews)
Cabin
Unique Private Lodge one hour from Toronto.
  • Security/Safety
  • Child Friendly

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Elegant 2-bedroom townhome in Pickering with AC Free Wifi and Parking included From US $145
         

10.0 (3 Reviews)
House
Elegant 2-bedroom townhome in Pickering with AC Free Wifi and Parking included
  • Air Conditioner
  • Parking
  • TV

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Lake Breeze Apartment, EV Charging & Free Parking From US $136
         

10.0 (3 Reviews)
Apartment
Lake Breeze Apartment, EV Charging & Free Parking
  • Air Conditioner
  • Parking
  • TV

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About Oshawa Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Cruisevacations Oshawa, 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 Oshawa. Places to stay near Oshawa with prices averaging $122 a night.

Cruisevacations makes it easy and safe to find and compare vacation rentals in Oshawa 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 Oshawa

Type Count

Use these Quick Filters to Find a Vacation Rental in Oshawa

★ Pro Tip: Cruisevacations makes it easy to compare the best listings on Cruisevacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Cruisevacations 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 Oshawa.

Weather in Oshawa

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

December - February
High 23°F       Low 2°F
March - May
High 65°F       Low 12°F
June - August
High 76°F       Low 49°F
September - November
High 65°F       Low 8°F

Top Attractions Around Oshawa, ON

Cruisevacations offers a large selection of top attractions around Oshawa. Research things to do on your vacation before you visit Oshawa.


Oshawa Centre Tribute Communities Centre Ajax Convention Centre Skyloft Ski Resort Rotary Park Royal Ashburn Golf Club Goodwood Kartways Canadian Tire Motorsport Park Newcastle Memorial Arena Jungle Cat World Wildlife Park Airzone Jungle Cat World Zoo Lakeridge Health Bowmanville Creative Play Indoor Playground & Party Centre Oshawa Valley Botanical Gardens Whitby History Museum & Children's Centre Canadian Automotive Museum Wooden Sticks Golf Course Uxbridge Historical Centre Herongate Barn Theatre

Other Places to Stay Near Oshawa, ON


Lakeview 120 Properties Pickering 115 Properties Whitby 112 Properties Ajax 103 Properties Clarington 100 Properties Uxbridge 99 Properties Enniskillen 84 Properties Courtice 74 Properties Bowmanville 48 Properties Port Perry 35 Properties Tyrone 27 Properties Scugog 24 Properties

Complexes around Oshawa, ON


Bowmanville 10 Properties Comfort Inn 3 Properties Hilton Garden Inn 3 Properties Holiday Inn Express Whit 3 Properties Quality Whit 3 Properties Willow Pond Satellite Breakfast 3 Properties Durham Hotel Conference Centre 1 Properties Holiday Inn Express Oshawa Downtown Toronto Ihg Hotel 1 Properties Travelodge 1 Properties