Daybreak at lake, United States, Maine, Oakland

Oakland Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Oakland vacation rentals

Exterior

Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
10.0 out of 10, Exceptional, (11 reviews)
"Very clean and comfy. A pleasure to stay there. "
United States
Vicki W.
$179 nightly
The price is $195
Jun 24 - Jun 25
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
Oakland
10.0 out of 10, Exceptional, (9 reviews)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
$255 nightly
The price is $278
Jul 15 - Jul 16
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.
Oakland
10.0 out of 10, Exceptional, (47 reviews)
"Fantastic quiet location and beautiful property.Everything you could possibly need has been supplied and the property is absolutely spotless.The hosts communicated perfectly, including facilitating an extremely late check-in.We would highly recommend this property - and we are hoping to return in the summer.Thank you for a wonderful stay!"
United States
Stephen R.
$236 nightly
The price is $257
Jun 24 - Jun 25
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
Oakland
9.0 out of 10, Wonderful, (9 reviews)
"Host was very accommodating "
United States
Maureen
$214 nightly
The price is $233
Jul 2 - Jul 3
Total with taxes and fees
The heart of the Belgrade Lakes
Outdoor dining

Peaceful retreat on farm minutes to lake. Bring kayak or canoe!

Peaceful retreat on farm minutes to lake. Bring kayak or canoe!
Oakland
10.0 out of 10, Exceptional, (12 reviews)
"It was a great stay. The house is very comfortable"
United States
Benjamin C.
$380 nightly
The price is $405
Jun 24 - Jun 25
Total with taxes and fees
Peaceful retreat on farm minutes to lake. Bring kayak or canoe!
Room

The StarGazer Floating Dome

The StarGazer Floating Dome
Monmouth
$245 nightly
The price is $267
Jun 29 - Jun 30
Total with taxes and fees
The StarGazer Floating Dome
Smart TV

Charming cabin in the birches right on the atv trail!

Charming cabin in the birches right on the atv trail!
Fairfield
9.2 out of 10, Wonderful, (7 reviews)
"The Host was great, I highly recommend this spot, everything was super smooth and the cabin was beautiful. "
United States
Jason B.
$131 nightly
The price is $142
Jul 5 - Jul 6
Total with taxes and fees
Charming cabin in the birches right on the atv trail!
Terrace/patio

Hammock Haven Island Dome

Hammock Haven Island Dome
Monmouth
9.6 out of 10, Exceptional, (4 reviews)
"Could not have asked for a better way to end our vacation than a visit to this island. For being a sustainable space it does not lack in amenities conducive to comfort, and the setting is pristine. I had particular fondness for the rope swing!!"
United States
BlairR
$175 nightly
The price is $191
Jun 24 - Jun 25
Total with taxes and fees
Hammock Haven Island Dome
Exterior

The Love Nest - a Cozy Lakefront Log Cabin

The Love Nest - a Cozy Lakefront Log Cabin
Farmington,
9.6 out of 10, Exceptional, (8 reviews)
"One-of-a-kind Nirvana If you are looking for peace beauty simplicity a d restoration at a soul level look no further. Everything you need and nothing you don't. Host, cabin, setting, amenities all superb. Thank you beyond words! "
United States
Tracy Ann L.
$165 nightly
The price is $180
Jun 30 - Jul 1
Total with taxes and fees
The Love Nest - a Cozy Lakefront Log Cabin
Exterior

Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine

Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Madison
9.2 out of 10, Wonderful, (5 reviews)
"Excellent service and perfect for our stay. Would book again!"
United States
Scott
$142 nightly
The price is $155
Jun 24 - Jun 25
Total with taxes and fees
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Terrace/patio

Cozy cottage in the Winthrop Lakes Area

Cozy cottage in the Winthrop Lakes Area
Winthrop
9.8 out of 10, Exceptional, (6 reviews)
"Lovely cottage! Everything we needed. The hosts were gracious and communicated well."
United States
Joshua
Cozy cottage in the Winthrop Lakes Area
Exterior

Paddle, float, fish, or rope swing into the lake. Direct ATV trail access too!

Paddle, float, fish, or rope swing into the lake. Direct ATV trail access too!
Strong
9.4 out of 10, Exceptional, (141 reviews)
"Nice little cottage at a good price, thank you! "
United States
Jacob Z.
$148 nightly
The price is $161
Jun 24 - Jun 25
Total with taxes and fees
Paddle, float, fish, or rope swing into the lake. Direct ATV trail access too!
Property grounds

Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.

Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.
Madison
10.0 out of 10, Exceptional, (44 reviews)
"The cabin amd property were fantastic! Secluded location, loved the fire pit. Great central location for out door activities. "
United States
Susan Appt E.
$349 nightly
The price is $380
Jul 19 - Jul 20
Total with taxes and fees
Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.
Fridge, microwave, oven, stovetop

Whitsendsport unit 4 1 bedroom & queen pull out couch on 50 acres Smithfield

Whitsendsport unit 4 1 bedroom & queen pull out couch on 50 acres Smithfield
Smithfield
$160 nightly
The price is $174
Jun 24 - Jun 25
Total with taxes and fees
Whitsendsport unit 4 1 bedroom & queen pull out couch on 50 acres Smithfield
On the beach

The Retreat- A Relaxing Beachside Bungalow

The Retreat- A Relaxing Beachside Bungalow
Burnham
10.0 out of 10, Exceptional, (3 reviews)
"Great cabin and location "
United States
John V.
$409 nightly
The price is $446
Jun 24 - Jun 25
Total with taxes and fees
The Retreat- A Relaxing Beachside Bungalow
Interior

Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters

Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
Winthrop
$265 nightly
The price is $289
Jun 26 - Jun 27
Total with taxes and fees
Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
On the beach

The Getaway- A Cozy Lakeside Cabin

The Getaway- A Cozy Lakeside Cabin
Burnham
10.0 out of 10, Exceptional, (6 reviews)
"Such a great cabin and location. Super clean and a perfect getaway, we can’t wait to go back!"
United States
Sara D.
$589 nightly
The price is $642
Jun 29 - Jun 30
Total with taxes and fees
The Getaway- A Cozy Lakeside Cabin
Interior

Boat launch and Trailer parking, Dog Friendly, Lake Great Pond

Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
Belgrade
10.0 out of 10, Exceptional, (55 reviews)
"House was very comfortable and neat! Great location!"
United States
Brian D.
$760 nightly
The price is $828
Jul 22 - Jul 23
Total with taxes and fees
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
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
Whitefield
10.0 out of 10, Exceptional, (7 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.
$233 nightly
The price is $254
Jun 29 - Jun 30
Total with taxes and fees
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
Exterior

Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment
Pittsfield
10.0 out of 10, Exceptional, (14 reviews)
"Great stay. Very comfortable, roomy, clean and good overall value."
United States
Rob K.
$282 nightly
The price is $308
Jun 26 - Jun 27
Total with taxes and fees
Angel Mist Retreat Garage Apartment
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

Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

10/10 Excellent
"Seems as if they’re working to renovate. Hot tub was an actual hot tub and HOT. Pool was warm, breakfast was grab and go but a lot of options including pancakes and breakfast sandwiches. Staff was great."
Tabitha 1-night trip
Posted 1 hour ago
Fireside Inn & Suites Waterville

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 $161 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?

Cozy Long Pond Cottage: community access, private mooring & shared dock.: This Oakland vacation home rental is located on a lake and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. Our travelers also rate Peaceful retreat on farm minutes to lake. Bring kayak or canoe! as a favorite home for rent in Oakland.

How many vacation rentals will I find in Oakland?

Choose from 35 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.