Oakville Holidays from £595

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    Better together

    Save up to £335 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Packages with flights are ATOL protected

Your Oakville Holiday

Say goodbye to planning hassles and hello to a Oakville holiday package. With the finer details organised 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 holiday on Expedia.

Top Oakville Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Old Saybrook

Super 8 by Wyndham Old Saybrook

2 out of 5
per person
18 Oct - 25 Oct
found 1 day ago
Return flight included
London (LON) to New Haven (HVN)
7/10 Good! (888 reviews)
This was convenient to the highway and to a wedding we were attending at Water's Edge.

Reviewed on 15 Aug 2025

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
Old Saybrook Center
per person
18 Oct - 25 Oct
found 1 day ago
Return flight included
London (LON) to New Haven (HVN)
9.4/10 Exceptional! (1,003 reviews)
I love this property. But, very disappointed in the pool and lack of variety of food

Reviewed on 9 Aug 2025

James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast

4 out of 5
Old Saybrook Center
per person
18 Oct - 25 Oct
found 1 day ago
Return flight included
London (LON) to New Haven (HVN)
9.4/10 Exceptional! (16 reviews)
We loved the convenient location and beautiful historic building, but we were very disappointed in the level of cleanliness (a layer of dust on shelves and fireplace, cobwebs under furniture). There were some other issues (loose shower head, broken coffee maker). There's no one on site to address in person. It's a lovely place, but needs some attention. For the price, it should be better! :(

Reviewed on 1 May 2025

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
per person
18 Oct - 25 Oct
found 1 day ago
Return flight included
London (LON) to New Haven (HVN)
7.8/10 Good! (1,004 reviews)
Hotel was very clean, reasonable price, and convenient traveling

Reviewed on 12 Aug 2025

Oakville Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Population
9,000
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Lake Compounce, Quassy Amusement Park and Palace Theatre

Top hotels in Oakville

Wyndham Southbury

Wyndham Southbury

3 out of 5
1284 Strongtown Road, Southbury, CT
Fully refundableReserve now, pay when you stay
The price is £79 per night from 24 Aug to 25 Aug
£79
24 Aug - 25 Aug
includes taxes & fees
8/10 Very Good! (1,004 reviews)
Thumbs up
"Nice hotel, would stay again. Bartender Anthony was great."

Reviewed on 13 Aug 2025

Wyndham Southbury
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St, Southington, CT
Fully refundable
The price is £94 per night from 31 Aug to 1 Sept
£94
31 Aug - 1 Sept
includes taxes & fees
8.6/10 Excellent! (1,065 reviews)
"It was walking distance to Thompson’s point where the music festival I went to see was being held. The staff from the front desk to cleaning staff, were all very friendly. More hooks and/or towel bars in the bathroom. Other than the shelf/rack that all the towels were stored on that is IN THE SHOWER ..."

Reviewed on 15 Aug 2025

Holiday Inn Express Southington by IHG
Clarion Inn

Clarion Inn

3 out of 5
201 Washington Avenue, North Haven, CT
Fully refundableReserve now, pay when you stay
The price is £87 per night from 14 Sept to 15 Sept
£87
14 Sept - 15 Sept
includes taxes & fees
7.4/10 Good! (1,002 reviews)
"Staff are"

Reviewed on 13 Aug 2025

Clarion Inn
See all 602 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does an Oakville travel package cost?
We make it simple to explore the world, with Oakville packages starting from as little as £595. You'll have the flexibility to bundle your favourite hotels, airlines and car rental. For the ultimate getaway, why not add a few tours and activities to your itinerary?
If I'm not able to travel, can I cancel my Oakville travel package?
It's impossible to predict what the future holds, so it's comforting to know that you can cancel or change your Oakville travel package. If your booking was made in the last 24 hours, you may be entitled to a refund. If your booking is older, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal to learn more.
How do I get a cheap travel package to Oakville?
Our Oakville travel packages promise plenty of savings for the savvy wanderer. For the best deals, simply combine your flights, hotels and extras (including tours) into a convenient package. But great bargains are just the beginning of your next memorable adventure. When you book with Expedia, and you'll have over 550 airlines and 1,000,000 properties around the world to pick from. No matter your style or budget, there's a travel package here just for you.
Does Expedia offer Book Now, Pay Later Oakville holidays?
Your bank balance shouldn't get in the way of escaping on holiday, so Expedia has worked out a solution to help. Now that we've partnered with online lender Klarna, it's easier than ever to book your dream getaway without exhausting your savings. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your escape. Consider one of these flexible payment options:

  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna's convenient monthly instalment plans. If paying small amounts each month works for you, choose this option during the checkout process.
  • Pay in instalments holidays: If you want to pay off your escape in multiple transactions, holidays paid in instalments might be the right choice for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the full total upfront) makes it easier to hit that "book now" button, opt for a low deposit holiday payment plan with Klarna.

What are the top hotels in Oakville?
Get your holiday off to an excellent start by reserving a room at The Litchfield Inn. It's one of most popular properties in Oakville. Another top option is Americas Best Value Inn Torrington CT.
How far in advance should I book my Oakville holiday?
It all depends on the air carrier, but you can generally look up international flights on Expedia up to a year in advance. While it's generally recommended to book ahead of time, lucky travellers occasionally nab a cheaper seat only weeks before their intended journey.
What does an Expedia Oakville travel package include?
Car rentals, hotels and flights — we connect you to all the best deals. All you'll have to do is select your favourite combination. Once you've made your booking, you can add on the fun stuff like experiences and tours. Our travel packages make it simple to customize an exciting Oakville escape.
What should I know before booking an Oakville travel package?
Booking all the parts of your getaway together is one of the easiest ways to save. Combine your car rentals, airfares and hotels into a tidy package. But you're not limited to hotels. Expedia has all sorts of properties, including holiday rentals such as mountain cabins and serviced residences. The list goes on!
Can I choose my airline with an Oakville Expedia travel package?
Yes — that's the beauty of an Expedia travel package. You're in charge! We have more than 550 partner airlines worldwide, so you have options galore when creating your Oakville escape.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.