Oakland Holiday Rentals from €125: Search Short-Term Rentals

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Our top choices for Oakland holiday rentals

A bedroom with a wooden ceiling, a bed with white bedding, a nightstand, a dresser, a chair, a window with a view of trees, and a patterned rug.

1. Black Forest Cabins

Mahone Bay

Julie

includes taxes & fees

9 Nov - 10 Nov

A tented accommodation with a bed, two chairs, and a view of a lake.

2. Luxury lakefront dome with private beach, close to nature and town!

Lunenburg

Maxime

includes taxes & fees

2 Nov - 3 Nov

A view of a waterfront property with a dock and a small building.

3. Oceanfront Luxury Magical Views Sunset and Sunrise

Western Shore

Cynthia K G.

includes taxes & fees

15 Nov - 16 Nov

A staircase with wooden balusters and a handrail, leading to a landing with a red door.

4. Romantic Getaway w/ King Bed in Historic Lunenburg (Suite 4)

Lunenburg

Patrick

includes taxes & fees

3 Nov - 4 Nov

A cozy cabin with a rustic interior, a wooden floor, a stove, a chair, and a view of a lake.

5. Mermaid's Retreat - Caribou Lake Cottage!

Mahone Bay

Josh

includes taxes & fees

5 Nov - 6 Nov

A wooden building with a sign reading "The Knot."

6. Red Barn Bed & Breakfast

Lunenburg

Kimberley K.

includes taxes & fees

2 Nov - 3 Nov

A wooden deck with a hot tub surrounded by trees.

7. Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

Windsor Road

Sandra

includes taxes & fees

1 Nov - 2 Nov

A small cabin with a deck, a door, and a window.

8. Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

Chester Basin

Suzanne

includes taxes & fees

30 Nov - 1 Dec

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Top Oakland Hotel Reviews

Oak Island Resort & Conference Centre

10/10 Excellent

"Property is beautiful! Staff are incredibly friendly and helpful. Even in the off season, and things being very quiet I was shocked to see how maintained the different areas were. Watching the sun rise, and set is stunning. We will be back :)"

The Homeport Motel

10/10 Excellent

"I did not expect this level of quality from a motel! The room was completely renovated and brand new, the TV was great for streaming, and the bed was really comfortable. I also loved being able to park right in front of my room! I stayed at several hotels during my trip to Nova Scotia, and this was easily the best place I stayed at. Highly recommend!"

The Dockside Inn & Restaurant

10/10 Excellent

"We had a wonderful room facing the harbor on the second floor. Fairly quiet because of the season but the view was wonderful--also helped that we had beautiful fall weather. Staff was excellent. They offered to let us use their washer and dryers when they were done with their daily needs when we inquired about doing a laundry. We chose to use a laundromat on outskirts of town where we were able to drop off and pick up later in day. Let us explore Lundenburg and its great selections of Victorian houses and the fishery museum. The restaurant while not fancy had a good selection of dishes. Would stay there again"

Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg

8/10 Good

"This is a wonderful location close enough to many attractions and isolated enough for a peaceful getaway. Deer roamed the property, kayaking for those who enjoy being on the water. Full windows across the front of this cottage offering a lovely view of the water, seagulls, night sky! You won’t find as many properties that are as clean and comfortable as here. It is a perfect place for two couples or four people. Your host Frank & Valerie are friendly, and all round nice people who will make your stay enjoyable! I had my 10 lb Cockapoo w me and she thoroughly enjoyed her stay as well. Plenty of places to go for a hike or leisurely walk. I visited Blue Rocks, two nearby beaches, Lunenberg, Mahone Bay on my way home where you can fill up with gas right in town. There are multiple cafes, restaurants & bistros if you prefer to eat out. A local grocery store in Lunenburg along the waterfront and another lovely one with a European flare in Rose Bay, look for the unusual and not those big chains. I visited from Oct 11 - 28, 2026, I had some beautiful days, some cooler day (I do enjoy sweater weather), so don’t hesitate to go as I did a little later in the season when the tourist traffic has calmed down. Many thanks to my hosts Frank & Valerie!"

Miller House By the Bay

8/10 Good

"This is a beautiful B&B and the owner is lovely. She is very chatty and helpful and made us breakfast in the morning. The location was also great! The only reason I didn't give five stars is because 'the hug' room was smaller than I anticipated. I knew it would be small, but it was quite tiny for two adults. I also didn't love that we had to share a bathroom with the rest of the guests but that's a personal thing. Would still stay here 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 €125 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 For The Birds Nature Shop, or get outside and enjoy nature at Mahone Bay Swimming Pool. Northern Sun Gallery & Gifts and Have A Yarn 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.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Oakland holiday rentals

1. Black Forest Cabins

2. Luxury lakefront dome with private beach, close to nature and town!

3. Oceanfront Luxury Magical Views Sunset and Sunrise

4. Romantic Getaway w/ King Bed in Historic Lunenburg (Suite 4)

5. Mermaid's Retreat - Caribou Lake Cottage!

6. Red Barn Bed & Breakfast

7. Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

8. Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

9. Downtown Bridgewater Suite near River and Trails

10. Luxurious 2 Bedroom with King and Queen bed and 1.5 Bathroom sleeps 6.

11. Luxury Coastal Dome - Private Hot Tub, Oceanfront Deck, Firepit & Parking

12. Welcome to our cozy/charming 2 Bedroom 1 Bath Apartment in Central Bridgewater

13. Coastal Dome Escape - Oceanfront, Private Hot Tub, Firepit and Deck

14. Spacious 1-Bedroom King Bed Suite w/ Deck (Suite 3)

15. Cozy Garden View Suite near Lunenburg Waterfront (Suite 6)

16. Charming Heritage Suite w/ Cozy Sunroom & Deck (Suite 1)

17. Abigael’s Apt Suite 1 BR 2 BED in Central Bridgewater

18. Relaxing King Bed Suite Close to Lunenburg Harbour (Suite 2)

19. Executive 1-Bedroom King Bed Suite in Lunenburg (Suite 5)

20. SUN, SAND, OCEAN, in Hubbards. What more do you need?

Find holiday rentals that suit your style

Top Oakland Hotel Reviews

Oak Island Resort & Conference Centre

The Homeport Motel

The Dockside Inn & Restaurant

Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg

Bridgewater Hotel

The Tuna Blue Inn and Restaurant

Best Western Plus Bridgewater Hotel & Convention Centre

Miller House By the Bay

Magnolia Inn

Find out more about Oakland

Frequently asked questions

Go further with the Expedia app

Holiday Rentals in Oakland

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Oakland holiday rentals

1. Black Forest Cabins

2. Luxury lakefront dome with private beach, close to nature and town!

3. Oceanfront Luxury Magical Views Sunset and Sunrise

4. Romantic Getaway w/ King Bed in Historic Lunenburg (Suite 4)

5. Mermaid's Retreat - Caribou Lake Cottage!

6. Red Barn Bed & Breakfast

7. Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

8. Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

9. Downtown Bridgewater Suite near River and Trails

10. Luxurious 2 Bedroom with King and Queen bed and 1.5 Bathroom sleeps 6.

11. Luxury Coastal Dome - Private Hot Tub, Oceanfront Deck, Firepit & Parking

12. Welcome to our cozy/charming 2 Bedroom 1 Bath Apartment in Central Bridgewater

13. Coastal Dome Escape - Oceanfront, Private Hot Tub, Firepit and Deck

14. Spacious 1-Bedroom King Bed Suite w/ Deck (Suite 3)

15. Cozy Garden View Suite near Lunenburg Waterfront (Suite 6)

16. Charming Heritage Suite w/ Cozy Sunroom & Deck (Suite 1)

17. Abigael’s Apt Suite 1 BR 2 BED in Central Bridgewater

18. Relaxing King Bed Suite Close to Lunenburg Harbour (Suite 2)

19. Executive 1-Bedroom King Bed Suite in Lunenburg (Suite 5)

20. SUN, SAND, OCEAN, in Hubbards. What more do you need?

Find holiday rentals that suit your style

Top Oakland Hotel Reviews

Oak Island Resort & Conference Centre

Find out more about Oakland

Frequently asked questions

Go further with the Expedia app