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Oakland Vacation Rentals

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Dec 24 - Dec 25
Tomorrow
Dec 25 - Dec 26
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Oakland vacation rentals

Exterior
Cozy Farmhouse -minutes to town, miles from stress

Cozy Farmhouse -minutes to town, miles from stress

Cozy Farmhouse -minutes to town, miles from stress
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.
$380 nightly
The price is $405
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cozy Farmhouse -minutes to town, miles from stress
Exterior
Discover Oakland charm near Colby College 10 min

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.
$235 nightly
The price is $256
Jan 11 - Jan 12, 2026
Total with taxes and fees
Discover Oakland charm near Colby College 10 min
Exterior
Sister A-Frame in Woods B

Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
10.0 out of 10, Exceptional, (9)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
$210 nightly
The price is $228
Jan 1 - Jan 2, 2026
Total with taxes and fees
Sister A-Frame in Woods B
Property grounds
Central Maine Apartment offering 4 Seasons of Fun.

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 hosts were super friendly and attentive. The accommodations were cozy and quaint. It was extremely appreciated that they had coffee available. If we’re ever back in the area visiting Colby college we would definitely stay again. "
United States
Sounder a.
$221 nightly
The price is $241
Jan 5 - Jan 6, 2026
Total with taxes and fees
Central Maine Apartment offering 4 Seasons of Fun.
2 bedrooms, WiFi, bed sheets
The heart of the Belgrade Lakes

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
$215 nightly
The price is $234
Jan 4 - Jan 5, 2026
Total with taxes and fees
The heart of the Belgrade Lakes
Exterior
The Cabin Skowhegan

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
$192 nightly
The price is $209
Dec 25 - Dec 26
Total with taxes and fees
The Cabin Skowhegan
Property grounds
Private cabin on 30 acres, close to skiing, snowmobile & amenities

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.
$311 nightly
The price is $339
Dec 26 - Dec 27
Total with taxes and fees
Private cabin on 30 acres, close to skiing, snowmobile & amenities
Interior
High End Apartment in Downtown Hallowell

High End Apartment in Downtown Hallowell

High End Apartment in Downtown Hallowell
Hallowell
10.0 out of 10, Exceptional, (96)
"Beautiful place to stay. Having coffee with all the fixings already there along with snacks was great! Would definitely stay here again!"
United States
John H.
$189 nightly
The price is $206
Jan 2 - Jan 3, 2026
Total with taxes and fees
High End Apartment in Downtown Hallowell
Exterior
Angel Mist Retreat Garage Apartment

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.
$283 nightly
The price is $309
Dec 25 - Dec 26
Total with taxes and fees
Angel Mist Retreat Garage Apartment
Exterior detail
Large King Room

Large King Room

Large King Room
wilton
$195 nightly
The price is $213
Dec 25 - Dec 26
Total with taxes and fees
Large King Room
On the beach
The Getaway- A Cozy Lakeside Cabin

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.
$405 nightly
The price is $442
Dec 25 - Dec 26
Total with taxes and fees
The Getaway- A Cozy Lakeside Cabin
Property grounds
Cozy Cottage on water's edge of Lake Cobbosseecontee

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)
"Great views of the from the screened porch! Lots to loons too, a big bonus!"
United States
Randy P.
$309 nightly
The price is $337
Dec 25 - Dec 26
Total with taxes and fees
Cozy Cottage on water's edge of Lake Cobbosseecontee
Interior
Cute, new, modern duplex in renovated schoolhouse

Cute, new, modern duplex in renovated schoolhouse

Cute, new, modern duplex in renovated schoolhouse
2.0 star property
Skowhegan
$100 nightly
The price is $109
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cute, new, modern duplex in renovated schoolhouse
On the beach
The Retreat- A Relaxing Beachside Bungalow

The Retreat- A Relaxing Beachside Bungalow

The Retreat- A Relaxing Beachside Bungalow
Burnham
10.0 out of 10, Exceptional, (3)
"Great cabin and location "
United States
John V.
$375 nightly
The price is $409
Dec 25 - Dec 26
Total with taxes and fees
The Retreat- A Relaxing Beachside Bungalow
TV
The Hideout Cabin | Steps to the Beach

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.
$405 nightly
The price is $442
Dec 25 - Dec 26
Total with taxes and fees
The Hideout Cabin | Steps to the Beach
Outdoor spa tub
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP

Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP

Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
Whitefield
10.0 out of 10, Exceptional, (6)
"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.
$271 nightly
The price is $295
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
Outdoor dining
Minutes to Colby

Minutes to Colby

Minutes to Colby
Waterville
8.8 out of 10, Excellent, (22)
"Close to our event, great communication, clean, comfortable & cozy"
United States
Shelly B.
$174 nightly
The price is $190
Jan 5 - Jan 6, 2026
Total with taxes and fees
Minutes to Colby
Exterior detail
3350 Middle Road

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.
$308 nightly
The price is $336
Jan 5 - Jan 6, 2026
Total with taxes and fees
3350 Middle Road
Property grounds
Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards

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

Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards
Whitefield
9.8 out of 10, Exceptional, (30)
"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! "
United States
Ben R.
$206 nightly
The price is $225
Jan 6 - Jan 7, 2026
Total with taxes and fees
Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards
Property grounds
Every window has a spectacular lake view Low fees

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
$321 nightly
The price is $350
Jan 5 - Jan 6, 2026
Total with taxes and fees
Every window has a spectacular lake view Low fees
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

Maine Evergreen Hotel, an Ascend Collection Hotel

Maine Evergreen Hotel, an Ascend Collection Hotel

10/10 Excellent
"Clean & nicely decorated room & hotel. "
AmySue 1-night trip
Posted 2 days ago
Maine Evergreen Hotel, an Ascend Collection Hotel

Find out more about Oakland

Everything you need to know about Oakland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oakland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oakland vacation 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 low season months. For more hustle and bustle, you may prefer to visit Oakland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $209 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oakland rentals

At Expedia, we put the best Oakland vacation 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 vacation.

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.

Explore a world of travel with Expedia

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?

My Valhalla Farm: This Oakland vacation home rental is located in a rural location and has a garden, a barbecue grill, and free WiFi to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Other favorite homes for rent in Oakland are Cozy Long Pond Cottage: community access, private mooring & shared dock. and Classy AF Home Steps from Colby and Trails.

How many vacation rentals will I find in Oakland?

Choose from 28 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.