Oakville Vacations from $199

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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.
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
Price was $232, price is now $199 per person
$199
per person
Apr 9 - Apr 11
found 1 day ago
Roundtrip flight included
Detroit (DTW) to New Haven (HVN)
8/10 Very Good! (1,457 reviews)
Very good, I recommend it.

Reviewed on Feb 12, 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 $513, price is now $402 per person
$402
per person
Apr 9 - Apr 11
found 1 day ago
Roundtrip flight included
Detroit (DTW) to New Haven (HVN)
9.2/10 Wonderful! (908 reviews)
Loved everything about the hotel - great location, quaint and cozy rooms, clean, friendly staff and lots of character!

Reviewed on Feb 12, 2026

Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4 out of 5
The Hill
Save 100% on your flight
Price was $696, price is now $555 per person
$555
per person
Mar 27 - Mar 29
found 1 day ago
Roundtrip flight included
West Palm Beach (PBI) to New Haven (HVN)
9.4/10 Exceptional! (21 reviews)
The place could have been a little cleaner I found hair in the bed and crumbs and dirt in the couch and under it as well the walls were stained and the carpet was stained in the bedroom it definitely was a big difference from the first time I stayed there

Reviewed on Feb 16, 2026

The Surfside Hotel

The Surfside Hotel

2 out of 5
Lordship
Price was $371, price is now $309 per person
$309
per person
Apr 22 - Apr 25
just found
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.4/10 Exceptional! (168 reviews)
Great place, adorable and courteous staff!

Reviewed on Jan 1, 2026

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
Price was $438, price is now $378 per person
$378
per person
Mar 27 - Mar 29
found 1 day ago
Roundtrip flight included
West Palm Beach (PBI) to New Haven (HVN)
8.8/10 Excellent! (966 reviews)
Very modern new clean facilities

Reviewed on Feb 16, 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
$84 nightly
The price is $97 total per night from Mar 21 to Mar 22
$97 total
Mar 21 - Mar 22
Total with taxes and fees
8.6/10 Excellent! (1,218 reviews)
Great hot breakfast, quiet rooms. Overall looks nicely renovated, but there are some minor defects

Reviewed on Feb 13, 2026

Holiday Inn Express Southington by IHG
Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

2.5 out of 5
1 Batterson Park Rd Farmington CT
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $93 total per night from Feb 24 to Feb 25
$93 total
Feb 24 - Feb 25
Total with taxes and fees
7.8/10 Good! (999 reviews)
It is very rare , the floors were vinyl flooring instead of dirty carpets. Lots of parking spots, very quiete and good working ac system. I strongly recommend this hotel to everyone and I-84 connection is 20 seconds

Reviewed on Feb 4, 2026

Extended Stay America Suites Hartford Farmington
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 Mar 1 to Mar 2
$102 total
Mar 1 - Mar 2
Total with taxes and fees
8.4/10 Very Good! (1,139 reviews)
I have stayed at this hotel countless times and it continues to be the best in Waterbury. While a bit dated and in need of some updating, it is clean and comfortable. Being in the middle of the city, street noise can sometimes be an issue, but overall it is quiet. The best part of this hotel is the ...

Reviewed on Feb 18, 2026

Courtyard by Marriott Waterbury Downtown
See all 656 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 $199 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.