Oakville Vacation Packages 2026 from $423

Oakville flight + hotel vacation packages

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

Pier Blue Inn Old Saybrook - Essex

Saybrook Manor

$423

per person

Jun 19 - Jun 21

found 19 hours ago

Roundtrip flight included

Fort Myers (RSW) to New Haven (HVN)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A picnic area and barbecue grills are also provided.

Beechmont - Perfect for Family Retreat!

North End

Save 100% on your flight

$2,540

per person

Jul 1 - Jul 8

found 1 day ago

Roundtrip flight included

Miami (MIA) 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.

Madison Beach Hotel

Madison Center

Save 100% on your flight

$1,048

per person

Jun 19 - Jun 21

found 19 hours ago

Roundtrip flight included

Fort Myers (RSW) to New Haven (HVN)

This smoke-free hotel features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Enjoy the gym and perks like free WiFi.

Hyatus Luxury Residences City Crossing

The Hill

Save 100% on your flight

$1,367

per person

May 15 - May 17

found 1 day ago

Roundtrip flight included

Fort Lauderdale (FLL) to New Haven (HVN)

This aparthotel features a 24-hour gym and a seasonal outdoor pool. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference center. Enjoy the a rooftop terrace and perks like free self parking and a free area shuttle.

Clarion Inn North Haven - New Haven North

$562

per person

Jun 11 - Jun 15

found 1 day ago

Roundtrip flight included

Tampa (TPA) to New Haven (HVN)

A restaurant and a 24-hour gym are featured at this hotel. 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.

Top Oakville hotels deals

Holiday Inn Express Southington by IHG

120 Laning St Southington CT

Free Cancellation

Reserve now, pay when you stay

$100 nightly

$115 total

Apr 19 - Apr 20

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.

Courtyard by Marriott Waterbury Downtown

63 Grand St Waterbury CT

Free Cancellation

Reserve now, pay when you stay

$94 nightly

$108 total

Apr 21 - Apr 22

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.

The Farmington Inn & Suites

827 Farmington Ave Farmington CT

Free Cancellation

Reserve now, pay when you stay

$145 nightly

$166 total

Apr 27 - Apr 28

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Business travelers can take advantage of the 24-hour business center. Enjoy the free continental breakfast each morning.

Heritage Hotel, Golf & Conference Center

522 Heritage Road Southbury CT

$137 nightly

$158 total

Apr 16 - Apr 17

Total with taxes and fees

A golf course and an indoor pool are featured at this smoke-free hotel. Enjoy the gym and perks like free self parking and free WiFi. Enjoy the outdoor tennis court and unwind at the bar/lounge and poolside bar.

Wyndham Southbury

1284 Strongtown Road Southbury CT

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$116 total

Apr 26 - Apr 27

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.

Clarion Inn North Haven - New Haven North

201 Washington Avenue North Haven CT

Free Cancellation

$98 nightly

$113 total

Apr 22 - Apr 23

Total with taxes and fees

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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 $423. 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.