Photo by Marc Maheu

Oakland Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Oakland

Exterior
Cozy winter farmhouse with wood stove & jacuzzi tub near snow trails

Cozy winter farmhouse with wood stove & jacuzzi tub near snow trails

Oakland
10.0 out of 10, Exceptional, (7)
"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 ￥31,559
￥61,237 total
includes taxes & fees
Dec 17 - Dec 18
Cozy winter farmhouse with wood stove & jacuzzi tub near snow trails
Exterior
Sister A-Frame in Woods B

Sister A-Frame in Woods B

Oakland
10.0 out of 10, Exceptional, (8)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is ￥18,703
￥35,430 total
includes taxes & fees
Dec 8 - Dec 9
Sister A-Frame in Woods B
Living area
The heart of the Belgrade Lakes

The heart of the Belgrade Lakes

Oakland
9.0 out of 10, Wonderful, (9)
"Host was very accommodating "
United States
Maureen
The price is ￥12,539
￥29,798 total
includes taxes & fees
Dec 5 - Dec 6
The heart of the Belgrade Lakes
Front of property
My Valhalla Farm

My Valhalla Farm

3.5 star property
Oakland
The price is ￥34,893
￥53,541 total
includes taxes & fees
Dec 8 - Dec 9
My Valhalla Farm
Property grounds
Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.

Oakland
10.0 out of 10, Exceptional, (43)
"The place was clean, very spacious and comfortable. Having the laundry was helpful, so I didn’t have to worry about doing laundry when I got home late (also, I spilled coffee on the way there, so I’m glad the stain was gone)."
United States
Keeko
The price is ￥16,283
￥38,202 total
includes taxes & fees
Dec 5 - Dec 6
Central Maine Apartment offering 4 Seasons of Fun.
Fridge, microwave, oven, stovetop
Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min

2.0 star property
Oakland
10.0 out of 10, Exceptional, (6)
"New, clean and had everything we needed. "
United States
Lara B.
The price is ￥15,421
￥41,938 total
includes taxes & fees
Dec 22 - Dec 23
Discover Oakland charm near Colby College 10 min
Fridge, microwave, stovetop, coffee/tea maker
NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.

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

Oakland
The price is ￥24,146
￥48,463 total
includes taxes & fees
Dec 10 - Dec 11
NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.
Terrace/patio
The Cabin Skowhegan

The Cabin Skowhegan

Skowhegan
9.8 out of 10, Exceptional, (50)
"Great place to stay. Highly recommend. Owner was very kind and helpful. Cabin was worth the money."
United States
Sue
The price is ￥15,508
￥32,624 total
includes taxes & fees
Dec 5 - Dec 6
The Cabin Skowhegan
Fridge, microwave, oven, stovetop
Private cabin on 30 acres, close to skiing, snowmobile & amenities

Private cabin on 30 acres, close to skiing, snowmobile & amenities

Madison
10.0 out of 10, Exceptional, (42)
"The cabin amd property were fantastic! Secluded location, loved the fire pit. Great central location for out door activities. "
United States
Susan Appt E.
The price is ￥19,385
￥52,740 total
includes taxes & fees
Dec 5 - Dec 6
Private cabin on 30 acres, close to skiing, snowmobile & amenities
Fridge, microwave, oven, stovetop
The Beach Bum | Modern Cabin on the Sand

The Beach Bum | Modern Cabin on the Sand

Burnham
10.0 out of 10, Exceptional, (2)
"Nice cottage. Perfect location. Everything you need for a quiet beach stay on Unity pond. "
United States
Albert
The price is ￥25,827
￥63,745 total
includes taxes & fees
Dec 7 - Dec 8
The Beach Bum | Modern Cabin on the Sand
Property grounds
Cozy Cottage on water's edge of Lake Cobbosseecontee

Cozy Cottage on water's edge of Lake Cobbosseecontee

Manchester
8.6 out of 10, Excellent, (18)
"Check in was a breeze. Right on the lake. House was just the right size for me and my 3 adult sons. Was lovely to paddle, canoe or swim just walking down the porch stairs"
United States
Heather A.
The price is ￥20,238
￥49,444 total
includes taxes & fees
Dec 5 - Dec 6
Cozy Cottage on water's edge of Lake Cobbosseecontee
Fridge, microwave, oven, stovetop
Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment

Pittsfield
10.0 out of 10, Exceptional, (14)
"Great stay. Very comfortable, roomy, clean and good overall value."
United States
Rob K.
The price is ￥21,773
￥47,906 total
includes taxes & fees
Dec 5 - Dec 6
Angel Mist Retreat Garage Apartment
Exterior
Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.

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

Strong
9.4 out of 10, Exceptional, (137)
"Very relaxing!"
United States
Bradford B.
The price is ￥13,957
￥18,594 total
includes taxes & fees
Dec 5 - Dec 6
Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.
Interior
High End Apartment in Downtown Hallowell

High End Apartment in Downtown Hallowell

Hallowell
10.0 out of 10, Exceptional, (96)
"Such a great little space and town. Loved that it was walking distance to a little main street with shops and restaurants. Beautiful place. Great accomodations. "
United States
Kayla B.
The price is ￥17,369
￥31,948 total
includes taxes & fees
Jan 2 - Jan 3, 2026
High End Apartment in Downtown Hallowell
Property grounds
Every window has a spectacular lake view Low fees

Every window has a spectacular lake view Low fees

Wayne
9.8 out of 10, Exceptional, (45)
"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 ￥18,005
￥41,431 total
includes taxes & fees
Dec 9 - Dec 10
Every window has a spectacular lake view Low fees
Outdoor dining
Ice Fishing, Dog Friendly, Lake Great Pond

Ice Fishing, Dog Friendly, Lake Great Pond

Belgrade
10.0 out of 10, Exceptional, (48)
"The house was great, and the owners were very communicative and responsive. Would definitely recommend and stay again!"
United States
Jonathon R.
The price is ￥20,956
￥44,406 total
includes taxes & fees
Dec 8 - Dec 9
Ice Fishing, Dog Friendly, Lake Great Pond
On the beach
The Getaway- A Cozy Lakeside Cabin

The Getaway- A Cozy Lakeside Cabin

Burnham
10.0 out of 10, Exceptional, (6)
"Such a great cabin and location. Super clean and a perfect getaway, we can’t wait to go back!"
United States
Sara D.
The price is ￥25,712
￥68,533 total
includes taxes & fees
Dec 7 - Dec 8
The Getaway- A Cozy Lakeside Cabin
Exterior
Large King Room

Large King Room

wilton
The price is ￥25,278
￥31,610 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Large King Room
Property grounds
3350 Middle Road

3350 Middle Road

Sidney
8.0 out of 10, Very Good, (3)
"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 ￥41,918
￥52,313 total
includes taxes & fees
Dec 7 - Dec 8
3350 Middle Road
Fridge, microwave, oven, stovetop
The Hideout Cabin | Steps to the Beach

The Hideout Cabin | Steps to the Beach

Burnham
10.0 out of 10, Exceptional, (9)
"Amenities were great. Property was clean and quiet. Perfect for teens. Great view of the lake. Updated kitchen and grill was great for making family meals. Enjoyed making s'mores in the fire pit. Kayaks were so much fun. "
United States
Jamie M.
The price is ￥25,712
￥68,533 total
includes taxes & fees
Dec 7 - Dec 8
The Hideout Cabin | Steps to the 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Oakland Hotel Reviews

Maine Evergreen Hotel, an Ascend Collection Hotel

Maine Evergreen Hotel, an Ascend Collection Hotel

10/10 Excellent
"This hotel is amazing! From the friendly staff to the clean rooms it was a great experience. The restaurant was excellent as well. I was traveling on business and I will definitely return."
Kathleen 1-night trip
Posted 3 days ago
Maine Evergreen Hotel, an Ascend Collection Hotel

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 vacation rentals in Oakland?

Yes, there are vacation rentals close to popular sights in Oakland, or you can go with a secluded option if you want a relaxing place to 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 vacation rentals in Oakland?

Classy AF Home Steps from Colby and Trails: This Oakland vacation home rental offers a private yard, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Our travelers also rate Cozy Long Pond Cottage: private mooring & shared dock as a favorite home for rent in Oakland.

How many vacation rentals will I find in Oakland?

Choose from 29 Expedia vacation rentals in Oakland for a memorable vacation.

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 larger area.

What are vacation rentals like in Oakland?

Vacation rentals are private accommodations you can stay in for several days or more in Oakland. Vacation rentals offer extras such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for family gatherings.