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Holiday Rentals in Oakland

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Check prices for these dates

In two weeks
24 Oct - 26 Oct
In two months
5 Dec - 7 Dec
In three months
2 Jan - 4 Jan
In four months
30 Jan - 1 Feb

Holiday Rentals in Oakland

Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Exterior

Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

9.4 out of 10, Exceptional, (63)
"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!"
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Cozy Long Pond Cottage: private mooring & shared dock
Outdoor dining

Cozy Long Pond Cottage: private mooring & shared dock

9.8 out of 10, Exceptional, (19)
"Very nice weekend and great host- very responsive!"
Cozy Long Pond Cottage: private mooring & shared dock
Sister A-Frame in Woods B
Exterior

Sister A-Frame in Woods B

10.0 out of 10, Exceptional, (6)
"Great stay. Would stay here again if in the area."
The price is €200
includes taxes & fees
9 Oct - 10 Oct
Sister A-Frame in Woods B
Central Maine Apartment offering 4 Seasons of Fun.
Property grounds

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"
The price is €214
includes taxes & fees
14 Oct - 15 Oct
Central Maine Apartment offering 4 Seasons of Fun.
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Interior

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. "
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
The Modern Maine Retreat
Dining

The Modern Maine Retreat

8.6 out of 10, Excellent, (13)
"Multi generation family in town to visit other family. Kitchen adequate for meal prep, "
The Modern Maine Retreat
Charming 1840s farmhouse with donkeys, wood stove, fire pit, and full kitchen
Exterior

Charming 1840s farmhouse with donkeys, wood stove, fire pit, and full kitchen

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! "
The price is €297
includes taxes & fees
9 Oct - 10 Oct
Charming 1840s farmhouse with donkeys, wood stove, fire pit, and full kitchen
NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.
Fridge, microwave, stovetop, coffee/tea maker

NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.

The price is €293
includes taxes & fees
1 Nov - 2 Nov
NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.
Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.
Exterior

Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.

9.4 out of 10, Exceptional, (132)
"Everything was great! We really enjoyed the peace and quiet."
The price is €129
includes taxes & fees
4 Nov - 5 Nov
Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.
Large Secluded Cabin on the Lake - Now booking 2+ night stays
Fridge, microwave, oven, stovetop

Large Secluded Cabin on the Lake - Now booking 2+ night stays

10.0 out of 10, Exceptional, (64)
"Great location! Amy is a fantastic host and she has provided everything for a relaxing stay on East Pond. "
Large Secluded Cabin on the Lake - Now booking 2+ night stays
Maine Cabin Masters Camp completely redone waiting for a Lake loving family !
Property grounds

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)"
Maine Cabin Masters Camp completely redone waiting for a Lake loving family !
Spacious Country Home w/ Hot Tub, near Colby/Thomas
TV

Spacious Country Home w/ Hot Tub, near Colby/Thomas

9.8 out of 10, Exceptional, (29)
"This house has everything for a weekend family vacay; you can spend the whole weekend enjoying the house & amenities such as the hot tub!"
Spacious Country Home w/ Hot Tub, near Colby/Thomas
Cozy House in the heart of Waterville Maine.
Smart TV

Cozy House in the heart of Waterville Maine.

9.6 out of 10, Exceptional, (45)
"Loved the cozy home! We would stay there again in a heartbeat. The only thing that we would have been nice is if there was a tv in the main bedroom, but that’s just a personal preference. "
Cozy House in the heart of Waterville Maine.
Nature lovers Paradise your own island
Exterior

Nature lovers Paradise your own island

9.8 out of 10, Exceptional, (69)
"Amazing property! "
Nature lovers Paradise your own island
Large New Lakeside Cottage Central Air
Exterior detail

Large New Lakeside Cottage Central Air

8.4 out of 10, Very good, (37)
"We loved the cabin, even in rainy weather. "
Large New Lakeside Cottage Central Air
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
Fridge, microwave, oven, stovetop

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

10.0 out of 10, Exceptional, (15)
"Beautiful property, had everything that was needed. Would definitely book again!"
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
Dining

Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion

9.8 out of 10, Exceptional, (37)
"Cute house with deck overlooking the pond with almost daily sightings of eagles, loons and ducks. We loved it here and would stay here again if we come back this way again. I hated to leave this cute home. "
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
Lakefront Cabin
Fridge, microwave, oven, stovetop

Lakefront Cabin

10.0 out of 10, Exceptional, (27)
"Enjoyed an awesome stay on the lake!! House was super and Kennith was a great host!"
Lakefront Cabin
Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards
Property grounds

Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards

9.8 out of 10, Exceptional, (28)
"We stayed in this cabin for two nights with our dog and it was very peaceful and fun! The cabin has a campfire, lots of batteries for charging, lights, battery fans, etc. There were many long walking trails with fun activities; like kayaking, axe throwing, a pizza oven… Exactly what we were looking for! Would stay again! "
The price is €198
includes taxes & fees
30 Oct - 31 Oct
Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards
Lakefront, Stunning Home only 30 min to Sugarloaf!
Interior

Lakefront, Stunning Home only 30 min to Sugarloaf!

10.0 out of 10, Exceptional, (36)
"The house was very comfortable. Grass and lake well maintained. Plenty of towels and the whirlpool bath was very a nice bonus. Kayaks were fun. "
Lakefront, Stunning Home only 30 min to Sugarloaf!
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

Comfort Inn & Suites Wilton

Comfort Inn & Suites Wilton

10/10 Excellent
"Great place to stay on our fall color trip "
Dennis 1-night trip
Posted 21 hours ago
Comfort Inn & Suites Wilton

Find out more about Oakland

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 €129 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. Some other top choices in Oakland are The Modern Maine Retreat and Charming 1840s farmhouse with donkeys, wood stove, fire pit, and full kitchen.

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.