Oakland Vacation Rentals

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Check prices for these dates

In two weeks
Oct 24 - Oct 26
In one month
Nov 7 - Nov 9
In two months
Dec 5 - Dec 7
In three months
Jan 2 - Jan 4

Vacation Rentals in Oakland

Executive Ocean Front Estate with 2 Acres Overlooking Waters of Mahone Bay
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (31)
"Charming, spacious house. Easy check-in & well stocked kitchen. Lovely location. Overall a great visit!"
Executive Ocean Front Estate with 2 Acres Overlooking Waters of Mahone Bay
Oakhill Pines Campground
Cabin, Multiple Beds, Shared Bathroom | Desk, free WiFi

Oakhill Pines Campground

3.0 star property
9.0 out of 10, Wonderful, (16)
"Great place"
Oakhill Pines Campground
Black Forest Cabins
Meeting facility

Black Forest Cabins

3.0 star property
9.8 out of 10, Exceptional, (10)
"Great spot for a special night out … beds were super comfortable "
The price is ￥22,771
￥29,573 total
includes taxes & fees
Nov 2 - Nov 3
Black Forest Cabins
Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg
Full-size fridge, microwave, oven, stovetop

Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg

10.0 out of 10, Exceptional, (112)
"Wonderful. Great cottage."
Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg
One bedroom fully equipped Mahone Bay luxury cottage
Fridge, microwave, oven, stovetop

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."
The price is ￥15,855
￥28,919 total
includes taxes & fees
Oct 13 - Oct 14
One bedroom fully equipped Mahone Bay luxury cottage
Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring
Terrace/patio

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

9.6 out of 10, Exceptional, (34)
"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"
Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring
Pebble Oceanside RV Retreat – Waterfront Hot Tub & Deck
Outdoor dining

Pebble Oceanside RV Retreat – Waterfront Hot Tub & Deck

10.0 out of 10, Exceptional, (3)
"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
Family Home In the Heart of the Village of Chester
Terrace/patio

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
Oceanfront 3-Bedroom Captain's House
Dining

Oceanfront 3-Bedroom Captain's House

9.8 out of 10, Exceptional, (27)
"The property was just what we needed for our family. The location is great and close to the many things we wanted to do on our trip."
Oceanfront 3-Bedroom Captain's House
Moonlight Cottage
Exterior

Moonlight Cottage

9.2 out of 10, Wonderful, (15)
"Great time, went Peggy’s cove, Hubbard farm market, lunenburg and mahone bay"
Moonlight Cottage
Mahone Bay Hide-Away
TV

Mahone Bay Hide-Away

10.0 out of 10, Exceptional, (90)
"Great location, lovely town."
Mahone Bay Hide-Away
Unique Ocean View Hilltop Retreat
Exterior

Unique Ocean View Hilltop Retreat

10.0 out of 10, Exceptional, (175)
"Great hosts and amazing location"
Unique Ocean View Hilltop Retreat
Oceanfront Luxury Magical Views Sunset and Sunrise
2 bedrooms, desk, WiFi, bed sheets

Oceanfront Luxury Magical Views Sunset and Sunrise

9.6 out of 10, Exceptional, (18)
"We took day trips from Holly’s home all week, but the view off the balcony was a delight to return to. "
Oceanfront Luxury Magical Views Sunset and Sunrise
4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort
Fridge, microwave, oven, stovetop

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

8.4 out of 10, Very Good, (28)
"Beautiful view, the property owner was very responsive, they even had water in the fridge. Was perfect for our relaxing family getaway! "
The price is ￥19,026
￥25,063 total
includes taxes & fees
Oct 15 - Oct 16
4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort
Amazing ocean view/ private road/close to bayswater beach.
Fridge, microwave, oven, stovetop

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

8.6 out of 10, Excellent, (46)
"Great property for a quiet get away"
Amazing ocean view/ private road/close to bayswater beach.
Apple Orchard Cottage Lunenburg, Nova Scotia, Canada
Exterior

Apple Orchard Cottage Lunenburg, Nova Scotia, Canada

9.2 out of 10, Wonderful, (71)
"Older property with character. A bit quirky. Comfy beds and nice sheets etc. Good parking. Very clean. Modern appliances. Couldn't see how to access the 'beach'. A bit of TLC ..Fly screens, windows, doors could do with repair. Toilet flush flap not closing every time"
Apple Orchard Cottage Lunenburg, Nova Scotia, Canada
Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia
Property grounds

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

10.0 out of 10, Exceptional, (98)
"We had a wonderful time. You can’t beat the views!"
Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia
Lunenburg's Cupcake House
Exterior

Lunenburg's Cupcake House

10.0 out of 10, Exceptional, (4)
"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...
Lunenburg's Cupcake House
Log Cabin #2 - Hubbards Beach
Living area

Log Cabin #2 - Hubbards Beach

10.0 out of 10, Exceptional, (1)
"As advertised and 2 minutes from the shore club."
The price is ￥29,067
￥38,587 total
includes taxes & fees
Oct 7 - Oct 8
Log Cabin #2 - Hubbards Beach
Remodelled historic suite w/nautical boho decor, in the UNESCO Town of Lunenburg
Exterior

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

9.8 out of 10, Exceptional, (16)
"Lovely walking distance to the waterfront. Beautiful place to stay!"
The price is ￥28,538
￥58,922 total
includes taxes & fees
Oct 7 - Oct 8
Remodelled historic suite w/nautical boho decor, in the UNESCO Town of Lunenburg
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

Miller House By the Bay

Miller House By the Bay

10/10 Excellent
"Great location, very cute loft.Liked that we had a separate space from the main house. Great hostess, lots of recommendations for restaurants and things happening in the town."
Ellen 1-night trip
Posted 1 day ago
Miller House By the Bay

Find out more about Oakland

Find out more about Oakland

Search for holiday rentals in Oakland on Expedia! You can easily find your home rentals, villas, holiday apartments in Oakland using one of the methods below:

  • View our selection of featured holiday rentals in Oakland
  • Use the map to find apartments and other holiday homes in the Oakland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oakland while they last

Look no further and take a look at our great range of rental properties in Oakland!

Frequently asked questions

Can I find a vacation rental in Oakland?

Yes, there are vacation rentals near well known local attractions in Oakland, or you can select a more secluded option if you'd like a relaxing place to stay.

What's the top vacation rental in Oakland?

Executive Ocean Front Estate with 2 Acres Overlooking Waters of Mahone Bay: Visitors like this Oakland vacation home rental. It is located by the ocean and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

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 larger area.

What are vacation rentals like in Oakland?

Vacation rentals are privately owned accommodations you can stay in for several days or longer in Oakland. Vacation rentals provide amenities like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.