Oakland Holiday Rentals

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Holiday Rentals in Oakland

Oakhill Pines Campground

3.0 star property
8.2 out of 10, Very good, (12)
"Great place"
The price is NZ$168
includes taxes & fees
21 Sept - 22 Sept
Oakhill Pines Campground

Black Forest Cabins

3.0 star property
10.0 out of 10, Exceptional, (9)
"Great spot for a special night out … beds were super comfortable "
The price is NZ$468
includes taxes & fees
21 Oct - 22 Oct
Black Forest Cabins

4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort

8.4 out of 10, Very good, (27)
"This property was great for our one night stay as a group attending a show at the shore club. The patio and view is wonderful! Owner was in contact very quickly which was very much appreciated. "
The price is NZ$323
includes taxes & fees
6 Oct - 7 Oct
4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort

Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg

10.0 out of 10, Exceptional, (109)
"I wish we had more time to enjoy the cottage. There was so much to see in area, we were busy all day, but a comfy place to come home too. "
Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg

One bedroom fully equipped Mahone Bay luxury cottage

10.0 out of 10, Exceptional, (101)
"Great cottage to use as a base to discover the area. Well equipped, quiet and close to restaurants and shopping."
One bedroom fully equipped Mahone Bay luxury cottage

Pebble Oceanside RV Retreat – Waterfront Hot Tub & Deck

10.0 out of 10, Exceptional, (2)
"Beautiful location on the water, super friendly hosts. Location close to so many little towns with great food and amazing people. Trailer has everything that you need for your stay, they thought of everything. They made us feel welcome and we will be back for sure. We took our paddleboards out; he even lent us a fishing rod to use on the nearby Warf. "
Pebble Oceanside RV Retreat – Waterfront Hot Tub & Deck

Spectacular Oceanfront Living in Authentic Fishing Village

10.0 out of 10, Exceptional, (110)
"A family member was getting married in Hubbards this weekend and we were her decorating crew so needed somewhere to stay. The house was perfect it slept all 13 of us (10 adults, 3 little kids), it was clean, well maintained and had absolutely stunning views. Kelly was absolutely wonderful to deal with, we will definitely be back! "
Spectacular Oceanfront Living in Authentic Fishing Village

Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring

9.6 out of 10, Exceptional, (33)
"We loved the privacy and view of ocean. Loved watching the tide go in and out, that was so amazing. Missed having a sandy beach to walk on. Otherwise , fantastic. Golf course restaurant was amazing as well. "
Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring

Oceanfront 3-Bedroom Captain's House

10.0 out of 10, Exceptional, (25)
"Clean and lots of space for the four of us "
Oceanfront 3-Bedroom Captain's House

Family Home In the Heart of the Village of Chester

9.6 out of 10, Exceptional, (28)
"Spacious, clean, comfortable, and lots of room for people to spread out. We would happily return."
Family Home In the Heart of the Village of Chester

Ocean front cottage in the heart of Hubbards.

9.8 out of 10, Exceptional, (50)
"Excellent week with the kids. Hosts were great. "
Ocean front cottage in the heart of Hubbards.

The Salt + Soul Suite – Cozy Apt 5

10.0 out of 10, Exceptional, (1)
"Cozy little space for short term stay. Fairly well equipped. Appliances in good shape. Clean and tastefully decorated. Noisy road. No yard. Well situated close to amenities."
The price is NZ$321
includes taxes & fees
19 Oct - 20 Oct
The Salt + Soul Suite – Cozy Apt 5

Moonlight Cottage

9.2 out of 10, Wonderful, (14)
"Loved getting to come stay at the house that was the Grey Gull on Haven the TV show! The host was great with communicating and our stay was awesome."
Moonlight Cottage

Apple Orchard Cottage Lunenburg, Nova Scotia, Canada

9.2 out of 10, Wonderful, (70)
"Wonderful location! Charming Old House!"
Apple Orchard Cottage Lunenburg, Nova Scotia, Canada

Mahone Bay Town Center 2 Bedroom Apt. - Steps to Everything - Vacation Oasis

10.0 out of 10, Exceptional, (33)
"Everything was perfect with our stay."
Mahone Bay Town Center 2 Bedroom Apt. - Steps to Everything - Vacation Oasis

Oceanfront Luxury Magical Views Sunset and Sunrise

9.6 out of 10, Exceptional, (17)
"Short stay, unfortunately, but I’ll definitely be back. "
Oceanfront Luxury Magical Views Sunset and Sunrise

Mahone Bay Hide-Away

10.0 out of 10, Exceptional, (88)
"Loved this property. So cute and so very clean! Beautifully decorated and very well appointed. Walkable to great restaurants and coffee shops. Loved Mahone Bay and hope to be back. Will definitely stay at this wonderful cottage. "
Mahone Bay Hide-Away

Relax on the South Shore, steps from 2 beaches, ocean views & hot tub.

10.0 out of 10, Exceptional, (20)
"Great location and very well equipped."
Relax on the South Shore, steps from 2 beaches, ocean views & hot tub.

Amazing ocean view/ private road/close to bayswater beach.

8.6 out of 10, Excellent, (45)
"We enjoyed the location and house. Made a great place to stay on the water near Peggy’s Cove and Lunenburg."
Amazing ocean view/ private road/close to bayswater beach.

Beautiful Lakefront Home with 5 Bed/3 Baths, WiFi, tons of amenities!

10.0 out of 10, Exceptional, (34)
"Great house with basics to make it easy to stay."
Beautiful Lakefront Home with 5 Bed/3 Baths, WiFi, tons of amenities!
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 Oakland Hotel Reviews

Find out more about Oakland

Find out more about Oakland

Everything you need to know about Oakland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oakland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oakland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oakland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oakland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oakland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oakland holiday rentals we have selected for you start as low as NZ$168 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oakland rentals

At Expedia, we put the best Oakland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oakland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oakland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oakland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Oakland?

Yes, there are holiday rentals close to the most popular sights in Oakland, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Oakland has to offer?

4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort: This holiday home rental outside of Oakland is located by the ocean, and has a balcony, a garden and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What can I see and do in Oakland?

While exploring the area, visit family-friendly sights like Have A Yarn, or get outside and enjoy nature at Mahone Bay Swimming Pool. Cocoa Organic Spa & Boutique and Northern Sun Gallery & Gifts are a couple of places you'll find in the wider area.

What are holiday rentals like in Oakland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oakland. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for a small group gathering.