Oakland Holiday Rentals from €83: Search Short-Term Rentals

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Holiday Rentals in Oakland

"Charming, spacious house. Easy check-in & well stocked kitchen. Lovely location. Overall a great visit!"

"Great place"

includes taxes & fees

30 Sept - 1 Oct

"Great spot for a special night out … beds were super comfortable "

includes taxes & fees

1 Oct - 2 Oct

Full-sized fridge, microwave, oven, stovetop

"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. "

"Great cottage to use as a base to discover the area. Well equipped, quiet and close to restaurants and shopping."

"Beautiful setting, very peaceful with lovely linens on the beds. The kitchen is fully stocked, the sitting room is comfortable and the outside decks are amazing. The little village of Chester was close by with a cozy pub offering live music on select nights and the local playhouse had local talent performing while we were there. We would stay again"

"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. "

"Spacious, clean, comfortable, and lots of room for people to spread out. We would happily return."

"Perfect house, perfect location, fabulous area to vacation!"

"Great time, went Peggy’s cove, Hubbard farm market, lunenburg and mahone bay"

"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. "

"Great house with tonnes of character, the hosts answered all questions we had and had good communication!"

"Short stay, unfortunately, but I’ll definitely be back. "

"Loved the area! Must try the black harbor distillery within walking distance. Would come back to the area in a heartbeat "

includes taxes & fees

6 Oct - 7 Oct

"We enjoyed the location and house. Made a great place to stay on the water near Peggy’s Cove and Lunenburg."

"Wonderful location! Charming Old House!"

"We had a wonderful time. You can’t beat the views!"

"What can I say? Lovely hosts, gorgeous cozy property, comfy beds, well-equipped kitchen, thoughtful information pack, board games in the cupboard, everything spotless, and in a great location within a few minutes walk of Lunenberg’s waterfront, shops and restaurants. Even the flowers at the front were in full bloom and smelled amazing! We toured Canada for 5 weeks, as a family of 4, staying in 14 different locations, and this house was my favourite. Thank you so much for a lovely stay! I only...

"As advertised and 2 minutes from the shore club."

includes taxes & fees

30 Sept - 1 Oct

"Lovely walking distance to the waterfront. Beautiful place to stay!"

includes taxes & fees

1 Oct - 2 Oct

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Top Oakland Hotel Reviews

Smugglers Cove Inn

10/10 Excellent

"Checking in was both smooth & pleasant. Room was clean, comfortable & well appointed. Room & washroom amenities were more than adequate. Location is fantastic. Many good restaurants just steps away from the hotel. Sushi by the Cove which is attached to the hotel has an excellent Japanese menu. Highly recommended!"

Atlantic View Motel and Cottages

10/10 Excellent

"We booked a cottage with queen bed. (The blue cottage) It's tiny, with a queen bed, refrigerator, microwave, eating area, bathroom with shower. Everything is tiny. The cottage is immaculately clean & you are encouraged to keep it that way (broom & dustpan, towel to wipe up spills). There is a BBQ available, and great views of the water to view the tall ships sail by! The electric outlets are a bit concerning. There is an outlet right next to the kitchen sink (not GFI), and one above the bed with a light that we were unable to turn off. We arrived early for our booking & were told rather abruptly that check in was 3PM. No offer to hold our luggage while we went into town. We really had no other interaction with the motel owner during our visit. But, the lady who cleans rooms was very friendly and even exchanged our wet towels for fresh ones. The motel is a distance from downtown Lunenburg. I think a bit far to walk. So, you likely need to drive in & park. And parking can be quite a challenge as the town can get very crowded. This is a very nice cottage in the motel if you are prepared for a small space. "

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

10/10 Excellent

"Beautiful setting, very peaceful with lovely linens on the beds. The kitchen is fully stocked, the sitting room is comfortable and the outside decks are amazing. The little village of Chester was close by with a cozy pub offering live music on select nights and the local playhouse had local talent performing while we were there. We would stay again"

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, apart-hotels, 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 €83 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.

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Holiday Rentals in Oakland

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Holiday Rentals in Oakland

Executive Ocean Front Estate with 2 Acres Overlooking Waters of Mahone Bay

Oakhill Pines Campground

Black Forest Cabins

Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg

One bedroom fully equipped Mahone Bay luxury cottage

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

Pebble Oceanside RV Retreat – Waterfront Hot Tub & Deck

Family Home In the Heart of the Village of Chester

Oceanfront 3-Bedroom Captain's House

Moonlight Cottage

Mahone Bay Hide-Away

Unique Ocean View Hilltop Retreat

Oceanfront Luxury Magical Views Sunset and Sunrise

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

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

Apple Orchard Cottage Lunenburg, Nova Scotia, Canada

Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia

Lunenburg's Cupcake House

Log Cabin #2 - Hubbards Beach

Remodelled historic suite w/nautical boho decor, in the UNESCO Town of Lunenburg

Top Oakland Hotel Reviews

Smugglers Cove Inn

Oakhill Pines Campground

Atlantic View Motel and Cottages

The Homeport Motel

Travelodge by Wyndham Bridgewater

Miller House By the Bay

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

Best Western Plus Bridgewater Hotel & Convention Centre

Fairmont House Bed & Breakfast

Find out more about Oakland

Frequently asked questions

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