Oakville Vacations from $407

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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.
La Quinta Inn & Suites by Wyndham New Haven

La Quinta Inn & Suites by Wyndham New Haven

3 out of 5
Long Wharf
Price was $515, price is now $407 per person
$407
per person
Oct 9 - Oct 12
found 5 hours ago
Roundtrip flight included
Nashville (BNA) to New Haven (HVN)
6/10 (1,308 reviews)
Hotel prices for a cheap motel experience

Reviewed on Jul 26, 2026

Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Save 100% on your flight
Price was $1,461, price is now $1,105 per person
$1,105
per person
Oct 9 - Oct 12
found 5 hours ago
Roundtrip flight included
Nashville (BNA) to New Haven (HVN)
9.2/10 Wonderful! (32 reviews)
Everything about the property & staff was AMAZING! Zero complaints, would 100% stay there again if in the area. Thank you!

Reviewed on Jul 24, 2026

Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
The Hill
Save 100% on your flight
Price was $1,597, price is now $1,214 per person
$1,214
per person
Oct 9 - Oct 12
found 5 hours ago
Roundtrip flight included
Nashville (BNA) to New Haven (HVN)
9.6/10 Exceptional! (85 reviews)
I had an amazing stay at the Hyatus. The property was exceptionally clean and well maintained, which made me feel comfortable from the moment I arrived. The location was perfect—convenient to everything I needed while still being quiet and peaceful, making it easy to relax after a busy week. Overall, it was a wonderful experience, and I would absolutely stay here again. Highly recommend!

Reviewed on Jul 6, 2026

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Save 100% on your flight
Price was $1,240, price is now $943 per person
$943
per person
Oct 9 - Oct 12
found 5 hours ago
Roundtrip flight included
Nashville (BNA) to New Haven (HVN)
2/10 (1 review)
The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host.

Reviewed on May 25, 2026

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Save 100% on your flight
Price was $945, price is now $722 per person
$722
per person
Oct 1 - Oct 5
found 8 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.2/10 Wonderful! (1,008 reviews)
I loved the location and the character of this property! Every person I encountered on the staff went above and beyond. I'm from the south so I appreciate the friendliness of these folks. I was greeted every time I came and went, which was a lot, and they truly seemed to care about my stay. The only negative I have is that they don't have a full-service restaurant on site. I stayed at the property for almost a week. It would have been nice to be able to eat in a night or two. Also, guests need to know that there is no parking. I was worried about that at first, but it turned out to be just fine. The Yale garage at Chapel and York was convenient, reasonably priced and safe, but I was nervous when I first realized that parking at this hotel is not an option. Overall, I enjoyed my stay and will come back if I am in the area again.

Reviewed on Jul 23, 2026

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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
$93 nightly
The price is $107 total per night from Aug 2 to Aug 3
$107 total
Aug 2 - Aug 3
Total with taxes and fees
8.6/10 Excellent! (1,392 reviews)
"We stayed at this property 2 years ago and had a great experience. This stay however was terrible. The initial room was way too small with a king bed they upgraded us to a slightly bigger room with 2 queen beds for a 7 day stay. Terrible accommodations for such a long stay. As we always stay at IHG ..."

Reviewed on Jul 26, 2026

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 Aug 2 to Aug 3
$107 total
Aug 2 - Aug 3
Total with taxes and fees
Wyndham Southbury
The Farmington Inn & Suites

The Farmington Inn & Suites

3 out of 5
827 Farmington Ave Farmington CT
Fully refundableReserve now, pay when you stay
$198 nightly
The price is $227 total per night from Jul 30 to Jul 31
$227 total
Jul 30 - Jul 31
Total with taxes and fees
8.8/10 Excellent! (1,007 reviews)
"I have stayed at Avon Old Farms Hotel a few times. I love the old world esthetic and stately lobby and rooms. I especially enjoy the canopy beds and the accomodations are elegant. The front desk receptionist could be more welcoming."

Reviewed on Jul 27, 2026

The Farmington Inn & Suites
See all 667 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 $407 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.