Search Vacation Homes in Oakland

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 395 Vacation Homes in Oakland with updated reviews, rates, and availability.

Newly renovated 5 bedroom house!

9.6 out of 10, Exceptional, (33)
"Loved the location very spacious and clean"
Newly renovated 5 bedroom house!

Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

10.0 out of 10, Exceptional, (34)
"Perfect for our family’s visit to West Point. Great location "
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

10.0 out of 10, Exceptional, (2)
"My family and I had a fantastic stay! The house was even more beautiful and spacious than we expected, making it the perfect home base for our weekend trip to Mount Peter. It was clean, cozy, and had everything we needed for a comfortable and relaxing stay. My parents live nearby in Warwick and this will definitely be my go-to VRBO recommendation for anyone visiting the area. We can’t wait to come back!"
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

Modern 4BD/3BA w/Parking & deck & 29 min>NYC

9.6 out of 10, Exceptional, (10)
"House was very nice and roomy. Area was nice also. Had an issue upstairs with refrigerator but used downstairs one as a backup."
Modern 4BD/3BA w/Parking & deck & 29 min>NYC

Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

2.0 star property
9.0 out of 10, Wonderful, (6)
"This property is great, our stay here was just amazing from start to finish. Communication with the host was great, we left some items there and the host was super accommodating. Would recommend this property very highly."
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

Your Oasis in the City w/ Jacuzzi , Parking, self check in and WiFi

8.0 out of 10, Very Good, (1)
"The property was clean and well taken care of and the communication with the owner was swift and reliable. "
The price is AED 632
AED 1,357 total
includes taxes & fees
31 Mar - 1 Apr
Your Oasis in the City w/ Jacuzzi , Parking, self check in and WiFi

Lakefront Luxury on Greenwood Lake

10.0 out of 10, Exceptional, (129)
"We were looking for a weekend in on the lake to relax and unwind and we got exactly that. The house was beautiful, clean and well maintained. Cheryl was attentive and came to help when needed. The views of the lake were breathtaking. Couldn’t have picked a better place. We can’t wait to come back! Thank you! "
Lakefront Luxury on Greenwood Lake

Cozy 2BR Home - 30 Min NYC - Yard + Free Streaming

Cozy 2BR Home - 30 Min NYC - Yard + Free Streaming

Family House 12 miles from NYC

10.0 out of 10, Exceptional, (15)
"The house was very clean and nicely updated. The four full bathrooms were especially useful when we returned from our day at the indoor water park. The kitchen was adequately stocked with supplies. The beds were comfortable and the linens were clean and soft.We did have an issue receiving the sign in code, but the issue was able to be resolved within the hour and the owner was responsive during our entire stay.The owner handled snow removal, which was nice, but the person who came to shovel...
The price is AED 1,157
AED 3,094 total
includes taxes & fees
30 Mar - 31 Mar
Family House 12 miles from NYC

Cozy 2-Bedroom Home allows you work remotely or hybrid with Wi-Fi

7.4 out of 10, Good, (6)
"He is very attentive helpful and always right on anything that arose"
Cozy 2-Bedroom Home allows you work remotely or hybrid with Wi-Fi

Large Family House On The Lake

9.6 out of 10, Exceptional, (56)
"It was perfect for us. We have stayed 7 guys and had a lot of fun. "
Large Family House On The Lake

Charming 2-bedroom house with AC, WiFi in marvelous Nyack

2.0 star property
Charming 2-bedroom house with AC, WiFi in marvelous Nyack

Cozy 1-bedroom Apt with WiFi and beautiful backyard view

9.0 out of 10, Wonderful, (2)
"The host was very receptive and quick to respond to messages. Listing is accurate. Easy in and out. Some noise through walls, but not at all disturbing. We had some difficulty getting the lights to turn off completely and were sleeping in low light for the night. "
The price is AED 290
AED 561 total
includes taxes & fees
6 Apr - 7 Apr
Cozy 1-bedroom Apt with WiFi and beautiful backyard view

Charming Hudson Valley 3-Bedroom Family Getaway

8.0 out of 10, Very Good, (2)
"Nice entryway, lots of room for shoes. 1st and 3rd floor bedrooms were spacious. Nice size livingroom. Need more cookware for kitchen, and would recommend fixing the exhaust fan in the bathroom, and a better foundation for the attic bed. Moving slats caused the mattress to sag, especially at the foot of the bed. We would stay again. "
Charming Hudson Valley 3-Bedroom Family Getaway

Lake Front Home w/Dock, Kayak, Canoe Right On Lake Hopatcong w/AC Wifi Huge Deck

Lake Front Home w/Dock, Kayak, Canoe Right On Lake Hopatcong w/AC Wifi Huge Deck

Luxe Living: Playground & Fireplace

10.0 out of 10, Exceptional, (1)
Luxe Living: Playground & Fireplace

Newark's Famility Favorite Place for 19 guests

2.0 out of 10, (1)
"I booked that place a few months back for my wedding party and when the day came I got the check-in info from the host. The check-in was at 3 pm, I went there at 5 pm, and when I got there I found some other guests inside the property. I was confused, the guests told me they were gonna be there until the next morning. So I called the host, and the host said she was sorry about it, she said there were two bookings from 2 different apps. She told me she was gonna refund me, which she did after she...
Newark's Famility Favorite Place for 19 guests

Spacious Village Gem, Family friendly

10.0 out of 10, Exceptional, (29)
"Second time staying here. Great space with a lot of room and amenities. Looking forward to staying again next year."
Spacious Village Gem, Family friendly

Modern Luxury Home near NYC FreeParking

4.0 star property
6.0 out of 10, (6)
"It was great! My family and I had a great time there together."
Modern Luxury Home near NYC FreeParking
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.
Don't see what you're looking for?
See all available properties in Oakland
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Oakland

Newly renovated 5 bedroom house!

9.6 out of 10, Exceptional, (33)
"Loved the location very spacious and clean"
Newly renovated 5 bedroom house!

2 BR+patio+workspace+parking near Seton Hall Univ.

8.6 out of 10, Excellent, (12)
"Everything is great…….. great host "
The price is AED 553
AED 1,368 total
includes taxes & fees
15 Apr - 16 Apr
2 BR+patio+workspace+parking near Seton Hall Univ.

Downtown Oasis 10 mins from Prudential Center!

2.0 star property
The price is AED 422
AED 761 total
includes taxes & fees
31 Mar - 1 Apr
Downtown Oasis 10 mins from Prudential 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.