Oakville Vacations from $342

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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.
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
Price was $423, price is now $342 per person
$342
per person
Jan 1 - Jan 4
found 21 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to New Haven (HVN)
8.8/10 Excellent! (1,122 reviews)
The fan of the HVAC unit in the room was very loud.

Reviewed on Oct 24, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Price was $1,947, price is now $1,571 per person
$1,571
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
No reviews
Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
Price was $449, price is now $362 per person
$362
per person
Jan 1 - Jan 4
found 21 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to New Haven (HVN)
8.6/10 Excellent! (575 reviews)
Didn't get a chance to enjoy the breakfast or pool as intended, however customer service and cleanliness was outstanding! Plus they gave a small welcome bag with some water and little treats/snacks! Parking was easy, and location even though was by highway, was relatively quiet!

Reviewed on Oct 11, 2025

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
Price was $740, price is now $608 per person
$608
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to New Haven (HVN)
8.8/10 Excellent! (1,018 reviews)
Nice, clean room and friendly staff.

Reviewed on Oct 23, 2025

Simsbury Inn

Simsbury Inn

3.5 out of 5
Simsbury Center
Price was $1,460, price is now $1,285 per person
$1,285
per person
Dec 29 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
9.2/10 Wonderful! (270 reviews)
I loved my stay there. Beautiful rooms, the hot tub was great! Breakfast was decent but there are plenty of food options around town if you want something better!

Reviewed on Sep 29, 2025

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Oakville Hotel Deals

Red Roof Inn Meriden

Red Roof Inn Meriden

2 out of 5
10 Bee St, Meriden, CT
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $114 total per night from Oct 26 to Oct 27
$114 total
Oct 26 - Oct 27
Total with taxes and fees
7.2/10 Good! (1,001 reviews)
Excellent service. Good hotel for pets

Reviewed on Oct 18, 2025

Red Roof Inn Meriden
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St, Southington, CT
Fully refundable
$90 nightly
The price is $104 total per night from Nov 2 to Nov 3
$104 total
Nov 2 - Nov 3
Total with taxes and fees
8.6/10 Excellent! (1,139 reviews)
The room was clean and staff was friendly. We enjoyed the queen beds.

Reviewed on Oct 19, 2025

Holiday Inn Express Southington by IHG
Wyndham Southbury

Wyndham Southbury

3 out of 5
1284 Strongtown Road, Southbury, CT
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $107 total per night from Nov 2 to Nov 3
$107 total
Nov 2 - Nov 3
Total with taxes and fees
8/10 Very Good! (1,043 reviews)
Na

Reviewed on Oct 19, 2025

Wyndham Southbury
See all 593 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 $342 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.