Photo by Marc Maheu

Oakland Holiday Rentals

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Our top choices for Oakland holiday rentals

10.0 out of 10, Exceptional, (8 reviews)
"It was that was said to be The host was very nice and helpful . I enjoyed my stay "
United States
Andrea C.
The price is AU$532
includes taxes & fees
19 Jan - 20 Jan
Cozy getaway: farmhouse with wood stove & jacuzzi tub
10.0 out of 10, Exceptional, (43 reviews)
"Great hiking - nice views."
United States
Norbert A.
The price is AU$363
includes taxes & fees
22 Jan - 23 Jan
Central Maine Apartment offering 4 Seasons of Fun.
9.0 out of 10, Wonderful, (9 reviews)
"Host was very accommodating "
United States
Maureen
The price is AU$352
includes taxes & fees
1 Feb - 2 Feb
The heart of the Belgrade Lakes
2.0 star property
10.0 out of 10, Exceptional, (6 reviews)
"New, clean and had everything we needed. "
United States
Lara B.
The price is AU$386
includes taxes & fees
21 Jan - 22 Jan
Discover Oakland charm near Colby College 10 min
The price is AU$442
includes taxes & fees
17 Jan - 18 Jan
NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.

Holiday Home in Sidney

Peaceful Home in Central Maine
8.0 out of 10, Very good, (3 reviews)
"A great spot for all 7 of us. Nice house with zones for everyone. Lovely backyard. Big kitchen and dining table"
United States
Pat D.
The price is AU$592
includes taxes & fees
18 Jan - 19 Jan
Peaceful Home in Central Maine

Cabin in Skowhegan

The Cabin Skowhegan
9.8 out of 10, Exceptional, (50 reviews)
"Great place to stay. Highly recommend. Owner was very kind and helpful. Cabin was worth the money."
United States
Sue
The price is AU$316
includes taxes & fees
17 Jan - 18 Jan
The Cabin Skowhegan
The price is AU$317
includes taxes & fees
17 Jan - 18 Jan
Spacious King Room with AC, WiFi in Peaceful Wilton
9.8 out of 10, Exceptional, (45 reviews)
"Tina was great and very informative with places to visit and place to eat. Will definitely be checking in again "
United States
Nancy
The price is AU$529
includes taxes & fees
17 Jan - 18 Jan
Every window has a spectacular lake view Low fees
10.0 out of 10, Exceptional, (42 reviews)
"Everything was amazing"
United States
Antwan B.
The price is AU$508
includes taxes & fees
18 Jan - 19 Jan
Private cabin on 30 acres, close to skiing, snowmobile & amenities

Cottage in Manchester

Lighthouse Lane
10.0 out of 10, Exceptional, (70 reviews)
"Very nice stay Beautiful lake views "
United States
Karen G.
The price is AU$462
includes taxes & fees
20 Jan - 21 Jan
Lighthouse Lane
10.0 out of 10, Exceptional, (81 reviews)
"Great location and excellent accommodations. Just what we needed for this quick stay. We would definitely stay here again!"
United States
J K.
The price is AU$347
includes taxes & fees
1 Feb - 2 Feb
Two bedroom Mid Century Modern apartment in Downtown Hallowell
8.6 out of 10, Excellent, (18 reviews)
"Very quiet spot right on the lake, relatively easy to get to, close to town. Cabin is small, which was perfect for the two of us. "
United States
Stephanie P.
The price is AU$496
includes taxes & fees
17 Jan - 18 Jan
Cozy Cottage on water's edge of Lake Cobbosseecontee
2.0 star property
The Escape | Steps to the Sand
2.0 star property
9.8 out of 10, Exceptional, (8 reviews)
"We enjoyed our stay."
United States
Tyson W.
The price is AU$1,226
includes taxes & fees
20 Jan - 21 Jan
Family's Paradise: 3BR/2BA,Game Room & Lake Access
10.0 out of 10, Exceptional, (6 reviews)
"Great getaway! We loved all of the discoveries to be made both in the cabin and on the property. We stayed in Stella. It was adorable, functional, and very welcoming. We also enjoyed an outing to Kennebec Maine Cabin Masters only 20 min away! "
United States
Sandra L.
The price is AU$444
includes taxes & fees
18 Jan - 19 Jan
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
10.0 out of 10, Exceptional, (49 reviews)
"Great place for us to get in 2 days of golf and 2 days of fishing. House was clean and communication with host prior to arrival and during our stay was excellent. "
United States
Thomas B.
The price is AU$492
includes taxes & fees
21 Jan - 22 Jan
Ice Fishing, Dog Friendly, Lake Great Pond
10.0 out of 10, Exceptional, (14 reviews)
"Great stay. Very comfortable, roomy, clean and good overall value."
United States
Rob K.
The price is AU$462
includes taxes & fees
18 Jan - 19 Jan
Angel Mist Retreat Garage Apartment

Apartment in Waterville

Minutes to Colby
8.8 out of 10, Excellent, (22 reviews)
"Close to our event, great communication, clean, comfortable & cozy"
United States
Shelly B.
The price is AU$286
includes taxes & fees
19 Jan - 20 Jan
Minutes to Colby
8.8 out of 10, Excellent, (6 reviews)
"Great stay, property was a great fit for a few day stay to visit family."
United States
Amy M.
The price is AU$763
includes taxes & fees
18 Jan - 19 Jan
The Maine Lake House with an Amazing Sand Beach!
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

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 favourite 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 depend 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 AU$316 per night. Entering your travel dates in the search wizard might find you 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 holiday rentals 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. Oakland is known for its shopping and restaurants. Make sure you have time to check out the monuments while you're in the area.

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

Cozy Long Pond Cottage: community access, private mooring & shared dock.: This highly rated holiday home rental in Oakland is located on a lake, and has a fireplace, a patio and a BBQ 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. Our travellers also rate Beautiful lakeside 4 bedroom retreat with private dock and walkout basement as a favourite home for rent in Oakland.

How many holiday rentals will I find in Oakland?

Choose from 28 Expedia holiday rentals in Oakland for a memorable holiday.

What can I see and do in Oakland?

Explore the area and family-friendly sights such as Maine State Museum, or get out into nature at a spot like Belgrade Lakes Chain. Colby College and Tree Spirits 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 extras such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from public 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 standard hotel, which is another reason why a holiday rental is an attractive choice for families.