Oakville Vacation Packages 2026 from $465

Oakville flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

The Surfside Hotel

Lordship

$465

per person

Feb 13 - Feb 15

found 6 hours ago

Roundtrip non-stop flight included

Ontario (ONT) to New Haven (HVN)

A restaurant, free self parking, and wedding services are among this hotel's amenities. WiFi in public areas is free. Luggage storage is also provided.

Beechmont - Perfect for Family Retreat!

North End

$1,538

per person

Mar 20 - Mar 25

found 6 hours ago

Roundtrip flight included

Los Angeles (LAX) to New Haven (HVN)

This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a communal living room are also on offer.

Top Oakville hotels deals

Holiday Inn Express Southington by IHG

120 Laning St Southington CT

Free Cancellation

$89 nightly

$102 total

Feb 6 - Feb 7

Total with taxes and fees

This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

Courtyard by Marriott Waterbury Downtown

63 Grand St Waterbury CT

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$102 total

Jan 25 - Jan 26

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Self parking, a 24-hour business center, and a coffee shop are also offered.

Extended Stay America Suites Hartford Farmington

1 Batterson Park Rd Farmington CT

Free Cancellation

Reserve now, pay when you stay

$80 nightly

$92 total

Feb 2 - Feb 3

Total with taxes and fees

This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free on-the-go breakfast each morning. A safe deposit box is provided and the front desk is staffed around-the-clock.

Breakfast included

Pet friendly

Red Roof Inn Meriden

10 Bee St Meriden CT

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$102 total

Jan 9 - Jan 10

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the express check-out. There's a gym and multilingual staff can provide around-the-clock assistance.

Hamden Hotel and Suites – Hamden New Haven

2260 Whitney Ave Hamden CT

Free Cancellation

Reserve now, pay when you stay

$94 nightly

$108 total

Jan 9 - Jan 10

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. Business travelers can take advantage of the business center. Guests will appreciate freebies like continental breakfast and free self parking.

Breakfast included

Pet friendly

Holiday Inn Cheshire - Southington by IHG

64 Knotter Drive Southington CT

Free Cancellation

$96 nightly

$110 total

Jan 29 - Jan 30

Total with taxes and fees

This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the in-room fitness and perks like free self parking.

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much are vacation packages to Oakville?

With a Travelocity vacation package, you can live it up in Oakville for a mere $465. Flights, hotels and tours — we've got it all. You can save some cash just by bundling together your bookings. And with all of that taken care of before you leave, you can sit back, relax and enjoy the adventure.

Where can I get the best vacation package deals for Oakville?

Walking away with a great package deal to Oakville is a cinch with Travelocity. With 400 air carriers and 1,000,000 worldwide properties, you're flush with choice when picking your flights and hotels.

Why should I purchase my Oakville vacation package via Travelocity?

We've got destinations and experiences for every kind of globetrotter, superb service and support available 24/7. To top that off, we'll match any lower price you're able to find with our Price Match Guarantee.

Can I save on my Oakville car rental if I book it with a hotel or flight?

Sure can — and booking one of our Oakville vacation packages is the perfect way to go about this. Bundle any combination of a car, flight, hotel and experience and score serious discounts. The more you bundle, the more you save. There are loads of famous sights in Oakville that are worth a road trip, including Times Square (75 mi from Oakville). Nothing beats discovering amazing places like this with the freedom of your own rental car.