Oakville Vacation Rentals from AED 253: Search Short-Term Rentals

A cityscape with a prominent historic building with a golden dome, surrounded by green spaces and modern high-rise buildings.

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Our top choices for Oakville vacation rentals

A bench in a grassy area with a lake and trees in the background.

1. Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Oakville

AED 1,980 total

includes taxes & fees

16 Nov - 17 Nov

2. Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown

Elizabeth H.

AED 1,899 total

includes taxes & fees

16 Nov - 17 Nov

A white door with a glass panel, a white picket fence, and a wooden porch.

3. Bear Retreat - 2-bedroom house in Waterbury

Waterbury

Igor L.

AED 1,201 total

includes taxes & fees

22 Nov - 23 Nov

A building entrance with a brick facade, a green awning, and a glass door.

4. Cozy Studio apartment in delightful Waterbury with Central Air

Waterbury

"The place wasn’t how the pictures were on the app. It was hard to find the room. The keys for the room are very hard to open the room door . It’s like you have to struggle just to get inside . The room is inside of an abandoned building… some staff in the building was telling me that I shouldn’t be staying there or they wouldn’t stay there so it made me feel unsafe… the bed doesn’t match the head board. Everything just doesn’t match the images the host posted.."

zynaisha

AED 378 total

includes taxes & fees

8 Dec - 9 Dec

A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

5. The Overlook near South Farms in Litchfield County is Hospitality, integrated.

Morris

Joe K.

AED 971 total

includes taxes & fees

16 Nov - 17 Nov

A front view of a house with a wooden staircase leading to a front door, a small porch area, and a garage door.

6. 1-bedroom vacation home 22 minutes from Quinnipiac University

Wolcott

David G.

AED 1,405 total

includes taxes & fees

30 Nov - 1 Dec

A wooden deck with two white Adirondack chairs and a black lantern on a house with white siding.

7. Cozy One Bedroom Apartment Centrally Located in Southbury

Southbury

Lisbeth

AED 452 total

includes taxes & fees

3 Dec - 4 Dec

A modern kitchen with white cabinetry, stainless steel appliances, and a granite countertop.

8. #27- Luxury Collection

Southington

C B.

AED 1,835 total

includes taxes & fees

23 Nov - 24 Nov

A modern living room with a fireplace, leather sofas, a flat-screen TV, and large windows.

9. #30 - Spacious & Cozy!

Southington

Kaity B.

AED 2,421 total

includes taxes & fees

22 Nov - 23 Nov

A kitchen with a marble island, wooden cabinets, a clock, and a window with a view of trees.

10. The Jefferson Guest House, Spacious, Special Views

Litchfield

Jennifer A.

AED 1,380 total

includes taxes & fees

16 Nov - 17 Nov

A kitchen with wooden cabinets, granite countertops, and a stainless steel sink.

11. Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Southington

"We had a great, relaxing Thanksgiving holiday at this spacious Southington, CT home. It was the perfect spot to visit one of my daughters and be able to have my mother-in-law stay with us so we could cook and host Thanksgiving dinner. The house was well-stocked and supplied with everything we needed, and then some; which allowed us to have a stress-free holiday as if we were in our own home. We highly recommend this home and will keep it in mind for future extended stays in the area."

Cindy M.

AED 1,715 total

includes taxes & fees

20 Nov - 21 Nov

A modern kitchen with white cabinets, stainless steel appliances, and a black countertop.

12. Private Apartment in Southbury 105

Southbury

A spacious living room with a large window overlooking a lake, wooden ceiling, and comfortable seating.

13. Escape to Bantam Lake- With Fireplace and Hot tub!

Morris

Shannon M.

AED 1,678 total

includes taxes & fees

18 Nov - 19 Nov

A wooden porch with a concrete step leading to a door.

14. Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Cheshire

James P.

AED 694 total

includes taxes & fees

14 Dec - 15 Dec

A view through a window with a clear sky and lush greenery outside.

15. Private Apartment in Southbury 101

Southbury

Marissa G.

AED 870 total

includes taxes & fees

17 Nov - 18 Nov

A spacious living area with a sofa, coffee table, and a dining table with chairs. There is a kitchen area with cabinets and appliances.

16. Private Apartment in Southbury 104

Southbury

Daniel R.

AED 941 total

includes taxes & fees

30 Nov - 1 Dec

A living room with a blue sofa, patterned armchair, wooden coffee table, and a globe on a side table.

17. Brand New Platform #1

Wallingford Center

Cherie G.

AED 1,119 total

includes taxes & fees

14 Nov - 15 Nov

18. Private Apartment in Berlin

Berlin

Shaun L.

AED 992 total

includes taxes & fees

16 Nov - 17 Nov

A two-story house with a porch, surrounded by flowering plants.

19. Cozy Attic 10 min to Llitchfield

Torrington

Nicole N.

AED 1,256 total

includes taxes & fees

17 Nov - 18 Nov

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Find vacation rentals that suit your style

Top Oakville Hotel Reviews

A Courtyard by Marriott hotel with a modern design, featuring a central entrance and landscaped gardens.

Courtyard by Marriott Waterbury Downtown

Waterbury

10/10 Excellent

Courtney

An outdoor patio with a fire pit, wicker furniture, and a pergola structure.

Homewood Suites by Hilton Southington, CT

Southington

10/10 Excellent

Suzanne Martin

A breakfast buffet area with various food options and a bakery section.

Holiday Inn Express Southington by IHG

Southington

10/10 Excellent

Steffani

An outdoor seating area with fire pits and umbrellas, surrounded by modern buildings with large windows.

DoubleTree by Hilton Hotel Bristol, Connecticut

Bristol

10/10 Excellent

Susan

An outdoor patio area with a fire pit and seating, surrounded by a building with large windows and a parking lot.

Courtyard by Marriott Southington

Southington

10/10 Excellent

Christopher

A hotel room with a dining table, chairs, a sofa, a TV, a fireplace, and a door.

Residence Inn by Marriott Southington

Southington

10/10 Excellent

Anonymous traveler

A spacious hotel lobby with wooden beams, a central seating area, and large windows offering a view.

Heritage Hotel, Golf & Conference Center

Southbury

10/10 Excellent

Always a good stay. Been coming to this hotel with the family for at least a decade and I also worked here in my young adult life. The staff is always pleasant, the place is always clean. The pool was a little overcrowded for once and we were given wrist bands for the first time ever. There was a staff member checking we had them on yet 75% of the people there did not have them which I thought was odd. We did not get too enjoy the pool as much as we would have wanted, it’s a great pool but there...

Luz

A covered porch with white columns and black hanging lanterns.

The Milestone Inn

Woodbury

10/10 Excellent

Elin

A restaurant with wooden tables and chairs, a bar area, and hanging spherical light fixtures.

The Abner Hotel

Litchfield Historic District

10/10 Excellent

Karen

A Holiday Inn hotel with a covered entrance, multiple floors, and a well-lit facade.

Holiday Inn Cheshire - Southington by IHG

Southington

10/10 Excellent

I liked this hotel. The area was quiet, the staff was professional and the hotel was clean. My only setback was the keycard kept having issues so I had to make trips to front desk. Apart from that, the stay was fine and I would go back. Parking was always available. The hotel sold bkfast and lunches, but also offered free coffee all day. There were food places, including fast foods and diners, that were literally 2‐4 minutes away which was very convenient for the stay.

Constantia

A spacious lobby with high ceilings, a fireplace, comfortable seating, and a dining area with tables and chairs.

Hampton Inn & Suites Hartford/Farmington

Farmington

10/10 Excellent

Debora D.

A spacious living room with a fireplace, a curved sofa, and two armchairs. There are decorative wall sconces and a patterned rug on the floor.

Homewood Suites by Hilton Wallingford-Meriden

Wallingford

10/10 Excellent

Anonymous traveler

A Fairfield by Marriott hotel with a courtyard featuring outdoor seating and a fire pit.

Fairfield by Marriott Inn & Suites Wallingford New Haven

Wallingford

10/10 Excellent

Kelly

Frequently Asked Questions

Can I find vacation rentals in Oakville?

Yes, you can find vacation rentals close to popular attractions in Oakville, or you can choose a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental in Oakville?

Well laid out 2-bedroom private home in Washington-close to the green and depot: This vacation home rental near Oakville offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave. Make the most of the garden in this rental home to help you unwind.

What can I see and do in Oakville?

Explore the area and family-friendly sights such as Quassy Amusement Park, or get out into nature at a spot like Waterbury Green. In the larger area, you’ll find Palace Theatre and Abbey of Regina Laudis.

What’s a vacation rental in Oakville like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Oakville. Vacation rentals offer amenities like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from shared hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a small group gathering.

Oakville Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Oakville vacation rentals

1. Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

2. Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

3. Bear Retreat - 2-bedroom house in Waterbury

4. Cozy Studio apartment in delightful Waterbury with Central Air

5. The Overlook near South Farms in Litchfield County is Hospitality, integrated.

6. 1-bedroom vacation home 22 minutes from Quinnipiac University

7. Cozy One Bedroom Apartment Centrally Located in Southbury

8. #27- Luxury Collection

9. #30 - Spacious & Cozy!

10. The Jefferson Guest House, Spacious, Special Views

11. Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

12. Private Apartment in Southbury 105

13. Escape to Bantam Lake- With Fireplace and Hot tub!

14. Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

15. Private Apartment in Southbury 101

16. Private Apartment in Southbury 104

17. Brand New Platform #1

18. Private Apartment in Berlin

19. Cozy Attic 10 min to Llitchfield

Find vacation rentals that suit your style

Top Oakville Hotel Reviews

Courtyard by Marriott Waterbury Downtown

10/10 Excellent

Frequently Asked Questions

Can I find vacation rentals in Oakville?

What's the top vacation rental in Oakville?

What can I see and do in Oakville?

What’s a vacation rental in Oakville like?