Oakville, CT

Travel Guide

A cityscape with a prominent historic building with a golden dome, surrounded by green spaces and modern high-rise buildings.
A large, historic house with a porch and snow on the ground.
A waterfall in a forested area with clear water and surrounding rocks.
A grand hall with a colorful, circular ceiling design and a central statue.
A stone tower with people standing on its top.
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
$92 nightly
The price is $106 total per night from Sep 27 to Sep 28
$106 total
Sep 27 - Sep 28
Total with taxes and fees
Book a stay at this business-friendly hotel in Southington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Holiday Inn Express Southington by IHG
Wyndham Southbury

Wyndham Southbury

3 out of 5
1284 Strongtown Road Southbury CT
$87 nightly
The price is $100 total per night from Oct 22 to Oct 23
$100 total
Oct 22 - Oct 23
Total with taxes and fees
Book a stay at this business-friendly hotel in Southbury. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Wyndham Southbury
Clarion Inn North Haven - New Haven North

Clarion Inn North Haven - New Haven North

3 out of 5
201 Washington Avenue North Haven CT
Fully refundable
$111 nightly
The price is $128 total per night from Oct 18 to Oct 19
$128 total
Oct 18 - Oct 19
Total with taxes and fees
Book a stay at this business-friendly hotel in North Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Clarion Inn North Haven - New Haven North
See all 676 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.
Cozy cottage with AC and lake access in charming Connecticut suburb.

Cozy cottage with AC and lake access in charming Connecticut suburb.

Watertown CT
Stay at this cottage in Watertown. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Lake Winnemaug and Lake Quassapaug are located ...
9.6/10 Exceptional! (15 reviews)
"A very quiet and relaxing stay. The property was very clean and comfortable. The host was quick to respond and helpful. We have family in the area and would hope to stay here again."

Reviewed on Sep 13, 2026

Cozy cottage with AC and lake access in charming Connecticut suburb.
Well laid out 2-bedroom private home in Washington-close to the green and depot

Well laid out 2-bedroom private home in Washington-close to the green and depot

Washington CT
Stay at this vacation home in Washington. Enjoy a garden, laundry facilities, and patios. Popular attractions Hollister House Garden and Institute for American ...
10/10 Exceptional! (7 reviews)
"The house was lovely for 4 girls going away for the weekend. Cute living space set up well. Sarah was very communicative and helpful when I had a couple random questions. We came for the nearby Gilmore Girls weekend, only to find out we were in the ACTUAL town that inspired the show, Washington. ..."

Reviewed on Sep 6, 2026

Well laid out 2-bedroom private home in Washington-close to the green and depot
Private Annex/Former Artist Studio

Private Annex/Former Artist Studio

Washington CT
Stay at this vacation home in New Preston. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Mount Bushnell State Park and Lake Waramaug ...
10/10 Exceptional! (59 reviews)
"Charming cottage and clean. Communication from owner immediately responsive."

Reviewed on Aug 11, 2026

Private Annex/Former Artist Studio
See all 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.

Frequently asked questions

When is the best time to visit Oakville?
The best time to visit Oakville is from April through June. This period often brings pleasant weather for travelers to enjoy the destination. For fewer crowds and better value, the quieter months of December through February are a good option, offering a different experience with cooler temperatures and potential for snow.
What cuisines can you find in Oakville?
In Oakville you can find Italian cuisine, with classic dishes such as pasta, pizza, lasagna, and tiramisu. Travelers can also enjoy a variety of other options, including North American, European, Asian, and Latin American flavors, offering a diverse culinary experience.
Can I book a refundable hotel in Oakville?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Oakville by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Oakville with Expedia?
Expedia makes it easier to plan your Oakville trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Oakville?
The best choice depends on your travel style. Hotels in Oakville can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Oakville trip on Expedia?
Once you've booked your Oakville trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Oakville trip?
Expedia offers customer support before, during, and after your Oakville trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Oakville?
If it's your first trip to Oakville, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Oakville hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Oakville hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Oakville

A multi-tiered waterfall surrounded by autumn foliage.

Waterbury

A mountainous landscape with autumn foliage, a valley, and distant buildings.

Watertown

A weathered stone structure with steps and a small opening, surrounded by fallen leaves and moss.

Middlebury

A railway track curving through a forested hillside.

Thomaston

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