Oakville Vacation Packages 2025/2026 from $420

Oakville flight + hotel vacation packages

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

Holiday Inn Cheshire - Southington by IHG

Save 100% on your flight

$420

per person

Jan 9 - Jan 16

found 1 day ago

Roundtrip flight included

Richmond (RIC) to New Haven (HVN)

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.

New Haven Hotel

Downtown New Haven

Save 100% on your flight

$459

per person

Jan 9 - Jan 16

found 1 day ago

Roundtrip flight included

Richmond (RIC) to New Haven (HVN)

A gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.

Graduate by Hilton New Haven

Downtown New Haven

Save 100% on your flight

$626

per person

Jan 9 - Jan 16

found 1 day ago

Roundtrip flight included

Richmond (RIC) to New Haven (HVN)

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A coffee shop and luggage storage are also provided.

Hampton Inn & Suites New Haven - South - West Haven

Save 100% on your flight

$517

per person

Jan 9 - Jan 16

found 1 day ago

Roundtrip flight included

Richmond (RIC) to New Haven (HVN)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.

The Blake Hotel

Downtown New Haven

Save 100% on your flight

$793

per person

Jan 9 - Jan 16

found 1 day ago

Roundtrip flight included

Richmond (RIC) to New Haven (HVN)

This smoke-free hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. There's a rooftop terrace on site, and laundry facilities and free newspapers are also offered.

Top Oakville hotels deals

Extended Stay America Suites Hartford Farmington

1 Batterson Park Rd Farmington CT

Free Cancellation

Reserve now, pay when you stay

$91 nightly

$105 total

Nov 23 - Nov 24

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

Wyndham Southbury

1284 Strongtown Road Southbury CT

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$107 total

Dec 1 - Dec 2

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking and a free area shuttle.

Pool

Pet friendly

Hamden Hotel and Suites – Hamden New Haven

2260 Whitney Ave Hamden CT

Free Cancellation

Reserve now, pay when you stay

$82 nightly

$94 total

Nov 23 - Nov 24

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 Express Southington by IHG

120 Laning St Southington CT

Free Cancellation

$95 nightly

$109 total

Nov 25 - Nov 26

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

Nov 23 - Nov 24

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.

Free WiFi

Restaurant

Clarion Inn

201 Washington Avenue North Haven CT

Free Cancellation

$95 nightly

$109 total

Nov 24 - Nov 25

Total with taxes and fees

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

Pool

Breakfast included

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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 $420. 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.