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Holiday Homes in Oakville

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Oakville holiday homes

A spacious living room with large windows, a fireplace, and a view of the outdoors.

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 NZ$958
includes taxes & fees
6 Oct - 7 Oct
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A staircase with a handrail, a potted plant with yellow flowers, and a sign above the stairs.

2. 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 NZ$261
includes taxes & fees
6 Oct - 7 Oct
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
A two-story house with a porch, a front door with a wreath, and a small garden area.

3. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (9 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is NZ$597
includes taxes & fees
6 Oct - 7 Oct
Bear Retreat - 2-bedroom house in Waterbury
A front view of a house with a wooden staircase leading to a front door, a small porch area, and a garage door.

4. 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 NZ$706
includes taxes & fees
6 Oct - 7 Oct
1-bedroom vacation home 22 minutes from Quinnipiac University
A modern kitchen with stainless steel appliances, a central island, and a dining area with a sofa.

5. #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 NZ$825
includes taxes & fees
20 Oct - 21 Oct
#27- Luxury Collection
A living room with a sectional sofa, a small side table, and a floor lamp.

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

Lakehaven • Hot Tub, Decks, Fires & More
Plymouth
The price is NZ$1,511
includes taxes & fees
6 Oct - 7 Oct
Lakehaven • Hot Tub, Decks, Fires & More
A living room with a grey sofa, red and yellow cushions, a wooden coffee table, and a TV on a wooden cabinet.

7. 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 NZ$521
includes taxes & fees
6 Oct - 7 Oct
Newly Remodeled 1-BR Close to Everything yet Very Private
A modern living room with a fireplace, leather sofas, a blue armchair, and large windows.

8. #30 - Spacious & Cozy!

#30 - Spacious & Cozy!
Southington
6.8 out of 10, (5 reviews)
"the house was great for our needs - it was nicely furnished fully stocked with the essentials in the kitchen. the host checked in when it was especially cold to ensure the heat and water were working correctly. the living room was very comfortable with leather reclining chairs and a gas fireplace that heated the room very well. We enjoyed how easy our stay was and recommend this location "
United States
Kaity B.
The price is NZ$833
includes taxes & fees
7 Oct - 8 Oct
#30 - Spacious & Cozy!
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

9. Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.2 out of 10, Wonderful, (15 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is NZ$525
includes taxes & fees
6 Oct - 7 Oct
Once the old Schools house now a newly furnished Apartment
A kitchen with wooden cabinets, granite countertops, and a stainless steel sink.

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

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Southington
10.0 out of 10, Exceptional, (3 reviews)
"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."
United States
Cindy M.
The price is NZ$1,262
includes taxes & fees
28 Oct - 29 Oct
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

11. Cozy private room in a shared home with a Full-size bed and private bathroom.

Cozy private room in a shared home with a Full-size bed and private bathroom.
New Milford
10.0 out of 10, Exceptional, (2 reviews)
"Clean and close to activitys"
United States
randall
The price is NZ$276
includes taxes & fees
3 Nov - 4 Nov
Cozy private room in a shared home with a Full-size bed and private bathroom.
A circular stone fire pit surrounded by large rocks and gravel, set in a forested area.

12. Sun Filled Lake House Living

Sun Filled Lake House Living
Avon
6.6 out of 10, (4 reviews)
"Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value"
United States
Joseph C.
The price is NZ$473
includes taxes & fees
26 Oct - 27 Oct
Sun Filled Lake House Living
A bedroom with a bed, a nightstand, a lamp, and a wooden wardrobe.

13. The Cottage by the Woods -private getaway to relax

The Cottage by the Woods -private getaway to relax
Meriden
The price is NZ$1,128
includes taxes & fees
6 Oct - 7 Oct
The Cottage by the Woods -private getaway to relax
A bedroom with a bed, two bedside tables with lamps, a dresser, and a door.

14. Collinsville River Escape / Fall Foliage, Deck & Yard

Collinsville River Escape / Fall Foliage, Deck & Yard
Collinsville
The price is NZ$294
includes taxes & fees
7 Oct - 8 Oct
Collinsville River Escape / Fall Foliage, Deck & Yard
A modern living room with hardwood flooring, a leather sofa, a round coffee table, and a wooden side table. There is a dining area with a table and chairs visible in the background.

15. Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
Shelton
The price is NZ$749
includes taxes & fees
6 Oct - 7 Oct
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
A patio with a table and chairs, a grill, and a view of a lake.

16. 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, (73 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is NZ$909
includes taxes & fees
19 Oct - 20 Oct
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
A two-story house with a front porch, a garage, and a well-maintained lawn.

17. Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
Middletown
9.6 out of 10, Exceptional, (19 reviews)
"The house was exactly what we were looking for, for a weekend away. Will surely book again, thank you!"
United States
Lee S.
The price is NZ$1,425
includes taxes & fees
6 Oct - 7 Oct
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
A patio area with wicker furniture and a brick floor.

18. The Old Avon 1800 Manor

The Old Avon 1800 Manor
Avon
7.0 out of 10, Good, (2 reviews)
"Wonderful place and host very responsive and friendly!"
United States
Anonymous traveller
The price is NZ$836
includes taxes & fees
12 Oct - 13 Oct
The Old Avon 1800 Manor
A room with a built-in bench along a wall with large windows, a door, and a tiled floor.

19. The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining

The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
New Milford
The price is NZ$1,417
includes taxes & fees
6 Oct - 7 Oct
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
A hot tub in a backyard with a house, trees, and a clear sky.

20. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is NZ$6,242
includes taxes & fees
6 Oct - 7 Oct
Las Flores Villa
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
"Great service"
Carwin 7-night trip
Posted 1 hour ago
Days Inn by Wyndham Southington

Find out more about Oakville

Oakville Holiday Homes information

Number of reviews
134
Accommodation
180 Holiday Homes
Lowest Price
NZ$261
Highest Price
NZ$6,242