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Oakville Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Oakville vacation rentals

Interior

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

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Watertown
9.0 out of 10, Wonderful, (6 reviews)
"In town to visit our new grandchild. It was just my husband and me. It had more then enough room and was very comfortable."
United States
Elizabeth H.
The price is ￥34,357
￥84,088 total
includes taxes & fees
Sep 21 - Sep 22
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
House (3 Bedrooms) | Interior

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

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
3.0 star property
Oakville
The price is ￥42,828
￥84,564 total
includes taxes & fees
Sep 21 - Sep 22
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Exterior detail

3. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (7 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is ￥20,394
￥54,202 total
includes taxes & fees
Oct 8 - Oct 9
Bear Retreat - 2-bedroom house in Waterbury
Interior

4. Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Watertown
8.4 out of 10, Very good, (12 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is ￥13,962
￥19,194 total
includes taxes & fees
Sep 22 - Sep 23
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Interior

5. Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.

Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Waterbury
8.0 out of 10, Very good, (1 review)
"I had an emergency and was only able to stay one night, but enjoyed my stay "
United States
Dirk N.
The price is ￥17,257
￥22,983 total
includes taxes & fees
Sep 21 - Sep 22
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Interior

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

The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Morris
9.8 out of 10, Exceptional, (16 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is ￥33,729
￥43,338 total
includes taxes & fees
Sep 21 - Sep 22
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Exterior

7. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (36 reviews)
"Great place. Had everything we needed and was very clean."
United States
Niki B.
The price is ￥13,837
￥19,050 total
includes taxes & fees
Sep 27 - Sep 28
Cozy One Bedroom Apartment Centrally Located in Southbury
Exterior detail

8. 1-bedroom vacation home 22 minutes from Quinnipiac University

1-bedroom vacation home 22 minutes from Quinnipiac University
Wolcott
9.6 out of 10, Exceptional, (4 reviews)
"Very clean and the host was great "
United States
David G.
The price is ￥23,532
￥62,203 total
includes taxes & fees
Oct 1 - Oct 2
1-bedroom vacation home 22 minutes from Quinnipiac University
Interior

9. Cozy Studio apartment in delightful Waterbury with Central Air

Cozy Studio apartment in delightful Waterbury with Central Air
Waterbury
The price is ￥14,260
￥19,537 total
includes taxes & fees
Oct 2 - Oct 3
Cozy Studio apartment in delightful Waterbury with Central Air
3 bedrooms, desk, WiFi, bed sheets

10. Lakehaven • Hot Tub, Decks, Fires & More

Lakehaven • Hot Tub, Decks, Fires & More
Plymouth
The price is ￥54,343
￥135,138 total
includes taxes & fees
Oct 1 - Oct 2
Lakehaven • Hot Tub, Decks, Fires & More
Coffee/tea maker, fridge, microwave, oven

11. The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (9 reviews)
"Everything about Jefferson House was perfect. It was located in a beautiful part of Connecticut adjoining a state park. The house was beautifully decorated. The kitchen was fully equipped and had a large island for dining. The bed, pillows and living room furnishings were very comfortable. The house was well up-to-date with two TVs, a charging device with multiple cords, a double oven (!), and countless thoughtful touches. I cannot recommend it highly enough!"
United States
genevieve
The price is ￥45,746
￥59,238 total
includes taxes & fees
Sep 22 - Sep 23
The Jefferson Guest House, Spacious, Special Views
Outdoor dining

12. Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Collinsville
10.0 out of 10, Exceptional, (72 reviews)
"Wow! What a great place! The house is lovely, very clean, comfy beds and cozy seating. Amazing view and an unbeatable location!"
United States
Kristi M.
The price is ￥48,947
￥82,464 total
includes taxes & fees
Sep 28 - Sep 29
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Smart TV, fireplace

13. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (20 reviews)
"It was great!"
United States
Amanda T.
The price is ￥27,274
￥46,151 total
includes taxes & fees
Sep 21 - Sep 22
Pristine Cozy Walkable Downtown 2BR Getaway
Apartment (1 Bedroom) | Interior

14. Bristol Condo Near Espn HQ & Lake Compounce!

Bristol Condo Near Espn HQ & Lake Compounce!
3.5 star property
Bristol
The price is ￥27,454
￥49,227 total
includes taxes & fees
Sep 22 - Sep 23
Bristol Condo Near Espn HQ & Lake Compounce!
TV

15. #43- Modern Luxury Log Cabin Retreat - Fire Pit

#43- Modern Luxury Log Cabin Retreat - Fire Pit
Prospect
9.4 out of 10, Exceptional, (3 reviews)
"3.5 rounding up to 4. We had a good stay overall. I travel fairly often and tend to reserve 5 stars for places where every detail of the guest experience feels really thoughtfully considered. This home was comfortable and worked fine for our trip, but it felt a bit more basic compared to some other rentals I’ve stayed in."
United States
Lauren P.
The price is ￥30,047
￥70,323 total
includes taxes & fees
Sep 23 - Sep 24
#43- Modern Luxury Log Cabin Retreat - Fire Pit
TV

16. Newly Remodeled 1-BR Close to Everything yet Very Private

Newly Remodeled 1-BR Close to Everything yet Very Private
Wallingford
10.0 out of 10, Exceptional, (10 reviews)
"Very Clean with everything I needed. I will stay here again."
United States
David M.
The price is ￥18,512
￥45,762 total
includes taxes & fees
Sep 21 - Sep 22
Newly Remodeled 1-BR Close to Everything yet Very Private
Coffee/tea maker, fridge, microwave, oven

17. #27- Luxury Collection

#27- Luxury Collection
Southington
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful home, well designed and spacious rooms. Host was fantastic and communication was great! Thank you"
United States
C B.
The price is ￥38,440
￥80,131 total
includes taxes & fees
Oct 20 - Oct 21
#27- Luxury Collection
Smart TV, books, printers

18. Guest Fave Cape-Cod Style Retreat with Main-Level Bedroom bordering Farmington

Guest Fave Cape-Cod Style Retreat with Main-Level Bedroom bordering Farmington
New Britain
9.6 out of 10, Exceptional, (8 reviews)
"We enjoyed our trip and the house was perfect for us, 3 boys and their father. "
United States
Todd S.
Guest Fave Cape-Cod Style Retreat with Main-Level Bedroom bordering Farmington
Coffee/tea maker, fridge, microwave, oven

19. Private Apartment in Southbury 103

Private Apartment in Southbury 103
Southbury
9.4 out of 10, Exceptional, (6 reviews)
"It was amazing , clean and awesome and good time"
United States
Michael
The price is ￥17,100
￥38,922 total
includes taxes & fees
Sep 24 - Sep 25
Private Apartment in Southbury 103
TV

20. Newly Remodeled with deck. Close to town center

Newly Remodeled with deck. Close to town center
Wallingford
10.0 out of 10, Exceptional, (2 reviews)
"The apartment was perfect - size, location, furnishings and price. Will definitely return when I visit friends and family."
United States
Karen F.
The price is ￥18,512
￥45,762 total
includes taxes & fees
Sep 21 - Sep 22
Newly Remodeled with deck. Close to town center
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.
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Top Oakville Hotel Reviews

Days Inn by Wyndham Southington

Days Inn by Wyndham Southington

10/10 Excellent
"The room was clean, the breakfast was good. Staff were very helpful."
JoAnne 1-night trip
Posted 8 hours ago
Days Inn by Wyndham Southington

Find out more about Oakville

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Look no further and take a look at our great range of rental properties in Oakville!

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 Lake Quassapaug.

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.