Holiday Rentals in Oakland

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Our top choices for Oakland holiday rentals

10.0 out of 10, Exceptional, (9 reviews)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is €194
includes taxes & fees
4 Mar - 5 Mar
Sister A-Frame in Woods B
10.0 out of 10, Exceptional, (43 reviews)
"Great hiking - nice views."
United States
Norbert A.
The price is €215
includes taxes & fees
9 Mar - 10 Mar
Central Maine Apartment offering 4 Seasons of Fun.
10.0 out of 10, Exceptional, (6 reviews)
"Very clean and comfy. A pleasure to stay there. "
United States
Vicki W.
The price is €216
includes taxes & fees
9 Mar - 10 Mar
Discover Oakland charm near Colby College 10 min
10.0 out of 10, Exceptional, (10 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 €296
includes taxes & fees
2 Mar - 3 Mar
Cozy getaway: farmhouse with wood stove & jacuzzi tub

Cabin in Skowhegan

The Cabin Skowhegan
9.8 out of 10, Exceptional, (52 reviews)
"Very quiet and relaxing - just what we wanted."
United States
Mary D.
The price is €179
includes taxes & fees
2 Mar - 3 Mar
The Cabin Skowhegan
9.2 out of 10, Wonderful, (7 reviews)
"Very neat cabin. Spacious all utilities and a fire pit"
United States
Lisa O.
The price is €149
includes taxes & fees
2 Mar - 3 Mar
Charming cabin in the birches right on the atv trail!
10.0 out of 10, Exceptional, (83 reviews)
"Great apartment, close to town, very clean, comfortable beds. Loved the little extras too.. coffee, creamer, etc! Will definitely stay again. "
United States
Rebekah B.
The price is €201
includes taxes & fees
3 Mar - 4 Mar
Two bedroom Mid Century Modern apartment in Downtown Hallowell
10.0 out of 10, Exceptional, (42 reviews)
"Everything was amazing"
United States
Antwan B.
The price is €316
includes taxes & fees
2 Mar - 3 Mar
Private cabin, 30 acres, 40 min to Sugarloaf. Can snowmobile, ATV and hike paths
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 €261
includes taxes & fees
2 Mar - 3 Mar
Angel Mist Retreat Garage Apartment

Apartment in Waterville

Minutes to Colby
8.8 out of 10, Excellent, (22 reviews)
"Easy check in and spacious apartment. Excellent location- within minutes of Colby and downtown restaurants. Super comfy living room to relax in after a full day of Parents Weekend:"
United States
Jodie M.
The price is €165
includes taxes & fees
2 Mar - 3 Mar
Minutes to Colby
8.8 out of 10, Excellent, (19 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 €282
includes taxes & fees
3 Mar - 4 Mar
Cozy Cottage on water's edge of Lake Cobbosseecontee
9.2 out of 10, Wonderful, (5 reviews)
"Excellent service and perfect for our stay. Would book again!"
United States
Scott
The price is €134
includes taxes & fees
4 Mar - 5 Mar
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
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 €264
includes taxes & fees
2 Mar - 3 Mar
Every window has a spectacular lake view Low fees
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 €236
includes taxes & fees
2 Mar - 3 Mar
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
The Escape | Steps to the Sand
9.8 out of 10, Exceptional, (9 reviews)
"We enjoyed our stay."
United States
Tyson W.
The price is €684
includes taxes & fees
2 Mar - 3 Mar
Family's Paradise: 3BR/2BA,Game Room & Lake Access
10.0 out of 10, Exceptional, (51 reviews)
"Great location!"
United States
Gail D.
The price is €314
includes taxes & fees
4 Mar - 5 Mar
Ice Fishing, Dog Friendly, Lake Great Pond

Cottage in Manchester

Lighthouse Lane
10.0 out of 10, Exceptional, (72 reviews)
"Very nice stay Beautiful lake views "
United States
Karen G.
The price is €258
includes taxes & fees
2 Mar - 3 Mar
Lighthouse Lane
The price is €134
includes taxes & fees
3 Mar - 4 Mar
Spacious modern living in a quite neighborhood
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 €425
includes taxes & fees
2 Mar - 3 Mar
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, 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 €258 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 getaway: farmhouse with wood stove & jacuzzi tub: This highly rated holiday home rental in Oakland is located in a rural location, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub. Our travellers also rate Cozy Long Pond Cottage: community access, private mooring & shared dock. as a favourite home for rent in Oakland.

How many holiday rentals will I find in Oakland?

Choose from 30 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.