Search Cottages 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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 44 Cottages in Oakland with updated reviews, rates, and availability.

Mountain House Escape - 1 Hour from NYC
Exterior

Mountain House Escape - 1 Hour from NYC

10.0 out of 10, Exceptional, (7)
"We recently had the pleasure of staying at Deer Hill in Warwick, NY, and it truly exceeded our expectations. The property is set on three-acre expanse in a lovely, and ultra-quiet neighborhood. It was an ideal home for our annual family gathering, which includes our 3 adult children, spouses and two young grandchildren. The large in-ground pool was a hit, and was a source of fun and relaxation throughout our stay. The pool has a shallow end and an 8-foot deep end. The spacious great room served...
Mountain House Escape - 1 Hour from NYC
Cottage at Millpond Falls - Romantic Luxury Escape - Waterfall views in Warwick
The Cottage at Millpond Falls is a romantic getaway -- an luxury experience you won't forget.

Cottage at Millpond Falls - Romantic Luxury Escape - Waterfall views in Warwick

10.0 out of 10, Exceptional, (142)
"Such a beautiful location. The cottage is quant while having all the modern updates. The hosts have carefully left an array of coffee and welcome goodies, including fresh eggs from their ducks. Will be back! "
Cottage at Millpond Falls - Romantic Luxury Escape - Waterfall views in Warwick
Cozy Designer Cottage with Saltwater Pool
Pool

Cozy Designer Cottage with Saltwater Pool

10.0 out of 10, Exceptional, (2)
"Beautiful neighborhood. Safe easy accress. "
Cozy Designer Cottage with Saltwater Pool
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Dining

Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike

2.0 star property
8.0 out of 10, Very Good, (2)
"Nice"
The price is AED 1,036
AED 2,039 total
includes taxes & fees
22 Jan - 23 Jan
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
Home Sweet Home ...

Fenced Yard Private Lakes 7 Beaches Huge Fire Pit

9.8 out of 10, Exceptional, (98)
"Great Highland Lakes Cottage! Clean & well stocked kitchen. Be careful going up or down Breakneck Rd. Thus time of year every view is beautiful! We did lots of small road trips taking in the sites and autumnal views!!"
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
Lovely Home Near FDU & Holy Name Hospital!
Exterior

Lovely Home Near FDU & Holy Name Hospital!

3.0 star property
8.0 out of 10, Very Good, (1)
Lovely Home Near FDU & Holy Name Hospital!
Bright Irvington Home ~ 2 Mi to Prudential Center!
Living area

Bright Irvington Home ~ 2 Mi to Prudential Center!

3.0 star property
Bright Irvington Home ~ 2 Mi to Prudential Center!
A romantic cottage and artist's retreat looking down over an enchanted lake
Stunning views

A romantic cottage and artist's retreat looking down over an enchanted lake

9.4 out of 10, Exceptional, (96)
"We cannot overstate how perfect this cottage was for us to have a quiet retreat. The place has all you need to unwind and drink in the view. The owners went above and beyond (we stayed 2 full months!). Everything was lovely, thanks Julia :)"
A romantic cottage and artist's retreat looking down over an enchanted lake
NEW Spacious 5 bedrooms with Public Lake & Beach Access and Kayak!
Living area

NEW Spacious 5 bedrooms with Public Lake & Beach Access and Kayak!

10.0 out of 10, Exceptional, (5)
"The house is even more beautiful than the photos. From the spa-like bathrooms, to toys and books for kids, to the little extra amenities like qtips and bandaids, it was the perfect getaway for everyone in our party of all ages."
NEW Spacious 5 bedrooms with Public Lake & Beach Access and Kayak!
Cozy Newark Getaway ~ 15 Mi to Manhattan!
Living area

Cozy Newark Getaway ~ 15 Mi to Manhattan!

3.0 star property
Cozy Newark Getaway ~ 15 Mi to Manhattan!
Stylish Newark, New Jersey, Vacation Rental!
Living area

Stylish Newark, New Jersey, Vacation Rental!

3.0 star property
Stylish Newark, New Jersey, Vacation Rental!
Spacious East Orange Home: Steps to Elmwood Park!
Interior

Spacious East Orange Home: Steps to Elmwood Park!

3.0 star property
10.0 out of 10, Exceptional, (1)
Spacious East Orange Home: Steps to Elmwood Park!
Greenwood Lake Cottage w/ Shared Dock & Hot Tub!
Hewitt Vacation Rental | 1BR | 1BA | 350 Sq Ft | Stairs Required

Greenwood Lake Cottage w/ Shared Dock & Hot Tub!

10.0 out of 10, Exceptional, (2)
"Very clean, convenient, accessible and the host’s are Great too! Will stay again when in town"
Greenwood Lake Cottage w/ Shared Dock & Hot Tub!
Lakefront Getaway : Mountain & Lakes views
Property grounds

Lakefront Getaway : Mountain & Lakes views

10.0 out of 10, Exceptional, (4)
"The property is beautiful and relaxing, exactly what we needed. The house is cozy with full amenities needed if you were staying longer than just a few nights."
Lakefront Getaway : Mountain & Lakes views
Delightful Home w/ Fire Pit, Walk to Lake!
Living area

Delightful Home w/ Fire Pit, Walk to Lake!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Very clean, easy access perfect location near my family for a birthday, silvia was very quick to respond to any questions!!"
Delightful Home w/ Fire Pit, Walk to Lake!
Briarcliff Manor Estate w/ Hudson River Views
Living area

Briarcliff Manor Estate w/ Hudson River Views

3.0 star property
Briarcliff Manor Estate w/ Hudson River Views
Warwick Vacation Rental w/ Private Yard & Fire Pit
Living area

Warwick Vacation Rental w/ Private Yard & Fire Pit

3.0 star property
10.0 out of 10, Exceptional, (1)
"I was relieved to find that the property looks just like and even better than the pictures online. "
Warwick Vacation Rental w/ Private Yard & Fire Pit
Relaxing New York Home w/ Boat Dock & Lake View!
Living area

Relaxing New York Home w/ Boat Dock & Lake View!

2.5 star property
Relaxing New York Home w/ Boat Dock & Lake View!
All-season Vernon Township Lake House Retreat!
Exterior

All-season Vernon Township Lake House Retreat!

3.0 star property
All-season Vernon Township Lake House Retreat!
The Farm at Glenwood Mountain - Cotttage
Interior

The Farm at Glenwood Mountain - Cotttage

10.0 out of 10, Exceptional, (1)
"The house is perfect for a foursome buddy trip and Patrick was great to work with. Next time (and there definitely will be a next time!) we'll be utilizing the bbq and stocking the house with meats and produce from their Farm across the street. Couldn't have asked for more including the refrigerator full of IPA's! Now if we just played better on the course.......lol"
The Farm at Glenwood Mountain - Cotttage
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
Sign in
Sign up, it's free

Other property types in Oakland

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

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

7.4 out of 10, Good, (6)
"This is a beautiful home! Super clean, well equipped with everything you could conceivably need. The property owner is very responsonive and friendly. Book with absolute confidence!"
Cozy 2-Bedroom Home allows you work remotely or hybrid with Wi-Fi
Luxuriously furnished 4 bedroom apartment
Bathroom

Luxuriously furnished 4 bedroom apartment

8.2 out of 10, Very Good, (10)
"We did not make our flight to check in the first night. I tried to communicate with owner but NEVER got a response. Then when we did make it into town we drove to the property and quickly turned around and booked a new place. This house is the only decent thing on the block. It is in the hood and not safe for families to stay if you are not from the area or if you plan on going outside the house at all. I lost $ on this trip for not using the house but it was well worth the safety and comfort I...
Luxuriously furnished 4 bedroom apartment
Cozy Apartment-Just minutes from New York City
Living area

Cozy Apartment-Just minutes from New York City

9.4 out of 10, Exceptional, (3)
"My stay was uneventful. Nice property in a gorgeous neighborhood. The apartment is in the basement with quite a few stairs to go up and down but is cute and clean. There is a full kitch but you have to bring your own pans. No tv's in the bedroom which was ok with me because after being gone all day , all i wanted to do was go to sleep. I would recommend and stay again."
Cozy Apartment-Just minutes from New York City
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

Why book your cottage in Oakland with Expedia?
Expedia has some great cottages in Oakland, so start packing your bags for an unforgettable vacation on nature’s doorstep. If you have a budget, click on how much you want to spend and the star rating of your property. Or, make the most of our filters to search for cottages with a kitchen or a pool. We’ll help you find the perfect place whatever your style of travel or plans.
How can I find cheap cottages in Oakland?
With Expedia’s filter tool, locating cheap cottages in Oakland is a breeze. To discover stays that’ll make your wallet smile, narrow your search by budget, amenities and star rating.