Oakville Vacations from $595

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Your Oakville Vacation

Say goodbye to planning hassles and hello to a Oakville vacation package. With the finer details organized before you go, you can focus on discovering every inch of this city, starting with Washington, which is great for nature, history and views. Any trip to Oakville has to include some sightseeing. Black Rock State Park is a superb place to begin exploring. A couple of clicks is all it takes to craft the ideal Oakville vacation on Expedia.

The Latest Oakville vacation packages

Price found within the past 48 hours. Click for updated prices.
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
Price was $665, price is now $595 per person
$595
per person
Mar 13 - Mar 16
found 15 hours ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
8.8/10 Excellent! (966 reviews)
Great stay overall. Wish it was easier to walk to good restaurants. Had to drive to good food.

Reviewed on Dec 27, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $2,095, price is now $1,387 per person
$1,387
per person
Mar 13 - Mar 16
found 15 hours ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
No reviews
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $827, price is now $689 per person
$689
per person
Mar 13 - Mar 16
found 14 hours ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
9.2/10 Wonderful! (908 reviews)
Everything was amazing

Reviewed on Dec 14, 2025

Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Price was $658, price is now $596 per person
$596
per person
Mar 13 - Mar 16
found 15 hours ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
8.6/10 Excellent! (1,184 reviews)
Very decent place to stay. This is my 2nd stay here. I'll definitely stay again!! The staff is amazing!

Reviewed on Dec 26, 2025

Quality Suites Stratford

Quality Suites Stratford

2.5 out of 5
Price was $695, price is now $629 per person
$629
per person
Mar 13 - Mar 16
found 15 hours ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
8/10 Very Good! (1,005 reviews)
Excellent place! Super clean, nice staff, great breakfast, comfortable!

Reviewed on Nov 26, 2025

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Oakville Hotel Deals

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Fully refundable
$82 nightly
The price is $94 total per night from Jan 2 to Jan 3
$94 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
8.6/10 Excellent! (1,181 reviews)
Great breakfast, very clean, comfortable bed, very friendly staff.

Reviewed on Dec 24, 2025

Holiday Inn Express Southington by IHG
Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
64 Knotter Drive Southington CT
Fully refundable
$92 nightly
The price is $106 total per night from Jan 4 to Jan 5
$106 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.2/10 Very Good! (1,006 reviews)
It was very well maintained, staff was nice.

Reviewed on Dec 19, 2025

Holiday Inn Cheshire - Southington by IHG
Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

3 out of 5
63 Grand St Waterbury CT
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $102 total per night from Dec 28 to Dec 29
$102 total
Dec 28 - Dec 29
Total with taxes and fees
8.4/10 Very Good! (1,073 reviews)
Place was very clean and well put together just in a bad area

Reviewed on Dec 21, 2025

Courtyard by Marriott Waterbury Downtown
See all 634 properties in Oakville
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.

Find the Best Oakville Vacation Packages

Oakville Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Population
9,000
Top Sights
Woodbury Ski Area, Pilgrim Mall Shopping Center and Glebe House Museum and The Gertrude Jekyll Garden

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Frequently asked questions

How much does an Oakville vacation package cost?
You'll find cheap prices from $595 on Expedia for your Oakville break. However, factors like the season, choice of hotel and length of stay will influence how much your vacation to Oakville costs.
What are the cheapest months to go to Oakville?
November, December and January are great times to look for cheap Oakville vacation packages. Traveling in quieter months means you can typically find better prices on hotels and flights.
How many days is enough for Oakville?
With a well-organized schedule, you can easily tick off the top Oakville sights in a few days. But if you want to discover lesser-known spots or take day trips, think about booking your Oakville vacation for longer.
How to find the best Oakville package deals?
Start your search for an Oakville package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Oakville package deal straight away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Oakville escape off to a flying start.
Is it cheaper to book an Oakville vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component separately. And you'll still enjoy the freedom to create a personalized Oakville vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Oakville?
If you have your Oakville travel dates locked in, book as soon as you can to grab some incredible deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Oakville?

  1. Choose when to travel: Check your calendar and get packing. Your preferred time of year and the type of activities available will also help you decide when to vacation in Oakville.
  2. Set your budget: Consider expenses like flights, meals and transportation when working out how much to save for your trip to Oakville. Then, pick a property that works with your budget, whether that's an economical stay or a more upscale getaway.
  3. Use our trip planning tool to explore Oakville: Research every part of your trip to Oakville with this comprehensive planner. Invite friends or family to collaborate on a group trip, search for stays or things to do and make bookings.
  4. Decide how long to go for: Now that you're up to speed on Oakville, you can work out the ideal length of your vacation. Pull together a draft itinerary and allocate enough time to cover everything you want to do.
  5. Bundle your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to choose an Oakville vacation package that brings all your bookings together.
  6. Add on excursions and experiences: Take a look at our travel guide to find some fun things to do in Oakville. Book tickets or make reservations before you go to save time and skip the hassle of searching for activities when you arrive.

Does Expedia offer Book Now, Pay Later Oakville vacation packages?
Your Oakville getaway should be an escape from your busy life, not a source of money worries. So to give you that extra flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.