Photo by Marc Maheu

Oakland Holiday Rentals

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Holiday Rentals in Oakland

Cozy Long Pond Cottage: private mooring & shared dock
9.8 out of 10, Exceptional, (19)
"Very nice weekend and great host- very responsive!"
United States
Marc W.
Cozy Long Pond Cottage: private mooring & shared dock
Sister A-Frame in Woods B
10.0 out of 10, Exceptional, (7)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is NZ$401
includes taxes & fees
20 Oct - 21 Oct
Sister A-Frame in Woods B
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
9.4 out of 10, Exceptional, (65)
"Great family camp right on the water with great views and paddle boats to play and fish the lake. Nice host, it was a peaceful stay!"
United States
Michael L.
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Classy AF Home Steps from Colby and Trails
10.0 out of 10, Exceptional, (48)
"Clean, comfortable and incredibly close to campus for a college visit."
United States
Patricia R.
Classy AF Home Steps from Colby and Trails
Central Maine Apartment offering 4 Seasons of Fun.
10.0 out of 10, Exceptional, (42)
"Very comfortable and clean VRBO!The hosts were very kind and easy to work with!!Great location for getting into Colby Highly recommend this location for people visiting in the area"
United States
Paul M.
The price is NZ$432
includes taxes & fees
28 Oct - 29 Oct
Central Maine Apartment offering 4 Seasons of Fun.
The Modern Maine Retreat
8.6 out of 10, Excellent, (13)
"Place was very clean, local to everything that we needed. Plenty of room for all 4 of us. I would definitely come back to this house if staying in Oakland again"
United States
Mark P.
The Modern Maine Retreat
Charming Guest House on Farm - Pets Welcome
10.0 out of 10, Exceptional, (7)
"Enjoyed a 2 night stay at this quiet country retreat. Our host was friendly and took time to visit. The kitchen was well stocked and it's a charming historic structure, equipped with modern conveniences. What more could you want! "
United States
Alvin W.
The price is NZ$627
includes taxes & fees
27 Oct - 28 Oct
Charming Guest House on Farm - Pets Welcome
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
9.2 out of 10, Wonderful, (26)
"Adorable cabin well stocked with plenty of space. Beautiful view! Nice and Clean. Needed help with the door lock and they were quick to respond and help. "
United States
Angela
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.
The price is NZ$546
includes taxes & fees
1 Nov - 2 Nov
NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.
Large Secluded Cabin on the Lake - Now booking 2+ night stays
10.0 out of 10, Exceptional, (66)
"It was a relaxing week It was fully equipped with everything we expected and more"
United States
Leslie R.
Large Secluded Cabin on the Lake - Now booking 2+ night stays
Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.
9.4 out of 10, Exceptional, (133)
"Everything was great! We really enjoyed the peace and quiet."
United States
Julie B.
The price is NZ$240
includes taxes & fees
4 Nov - 5 Nov
Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.
Maine Cabin Masters Camp completely redone waiting for a Lake loving family !
2.0 star property
10.0 out of 10, Exceptional, (7)
"Wonderful hosts, they thought of everything we might need including many nice extra touches! Beautiful quiet spot with the opportunity to paddle boat, kayak, canoe, swim, fish, enjoy campfires, outdoor grilling, observe wildlife (Osprey, Bald Eagle, Deer)"
United States
Diane S.
Maine Cabin Masters Camp completely redone waiting for a Lake loving family !
Spacious Country Home w/ Hot Tub, near Colby/Thomas
9.8 out of 10, Exceptional, (32)
"Wonderful location and beautiful property, very peaceful and convenient "
United States
Anne M.
Spacious Country Home w/ Hot Tub, near Colby/Thomas
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
10.0 out of 10, Exceptional, (252)
"Beautiful location and house is perfect for family with teenagers and perfect for enjoying the lake. In addition to lake activities which can’t be beat especially with swimable dick, cayaks and floaties, house has hot tub, pingpong table and flat part of back yard for play, no need to go anywhere. Nearby Hallowell is lovely with restaurants and cafes. I can’t say enough positive things about property!"
United States
Noelle F.
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
Cozy Cottage on water's edge of Lake Cobbosseecontee
8.8 out of 10, Excellent, (16)
"Perfect old fashion Maine cottage! Great sunsets!"
United States
Anita W.
The price is NZ$557
includes taxes & fees
19 Oct - 20 Oct
Cozy Cottage on water's edge of Lake Cobbosseecontee
Lighthouse Lane
10.0 out of 10, Exceptional, (67)
"We had a wonderful stay at Lighthouse Lane! The property was perfect with every detail thought out for guests! The views were spectacular and even better than what the listing photos show. We will definitely stay again! Thank you for being amazing hosts!"
United States
Keli H.
The price is NZ$838
includes taxes & fees
1 Nov - 2 Nov
Lighthouse Lane
Nature lovers Paradise your own island
9.8 out of 10, Exceptional, (70)
"Amazing property! "
United States
Emily H.
Nature lovers Paradise your own island
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
10.0 out of 10, Exceptional, (18)
"Beautiful property, had everything that was needed. Would definitely book again!"
United States
Rachel G.
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
9.8 out of 10, Exceptional, (37)
"House was great! Clean, bright, comfortable."
United States
Emily C.
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
2-bedroom apartment in charming Hallowell with AC
6.8 out of 10, (3)
"Easy check-in. Great location. Clean, comfortable and equipped as needed. Recommended."
United States
Scott F.
2-bedroom apartment in charming Hallowell with AC
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 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$240 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 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: private mooring & shared dock: This highly rated holiday home rental in Oakland is located on a lake, and has a fireplace, a selection of games 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. Our travellers also rate Charming historic guest house on farm 3 bedrooms wood stove pet friendly as a favourite home for rent in Oakland.

How many holiday rentals will I find in Oakland?

Choose from 29 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.