A lake surrounded by trees with autumn leaves.

Oakland Vacation Rentals

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Oakland vacation rentals

A wooden cabin with a porch, a door, and a green chair.

1. Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
10.0 out of 10, Exceptional, (13 reviews)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
$203 nightly
The price is $221
Nov 3 - Nov 4
Total with taxes and fees
Sister A-Frame in Woods B
A wooden deck with outdoor furniture, a large potted plant, and string lights.

2. Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes

Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes
Oakland
10.0 out of 10, Exceptional, (18 reviews)
"We loved staying at the farm! My kids enjoyed meeting the horse and donkey on property. It was perfect for our family!"
United States
Shana S.
$369 nightly
The price is $394
Nov 1 - Nov 2
Total with taxes and fees
Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes
A bedroom with a bed, a bedside table, a lamp, and a window with curtains.

3. The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.2 out of 10, Wonderful, (11 reviews)
"It was amazing! Shawna was great! I forgot to add our pet on the original booking and she was so responsive and we got everything sorted out. The apartment was so comfortable and decorated beautifully! Great space from kids room with things to entertain them to calm adult bedroom. The kitchen was well stocked and had everything you could think of. We loved “the fluffy butt hut” chicken coop!!! This is a dream place, from veggie garden, pool, tree house, chicken coop. Love it! Will definitely...
United States
Tri C.
$215 nightly
The price is $234
Oct 26 - Oct 27
Total with taxes and fees
The heart of the Belgrade Lakes
Property grounds

4. Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.
Oakland
10.0 out of 10, Exceptional, (50 reviews)
"Apartment was comfortable and as described. I had a nice stay."
United States
kathy e.
$227 nightly
The price is $247
Nov 1 - Nov 2
Total with taxes and fees
Central Maine Apartment offering 4 Seasons of Fun.
A living room with a sectional sofa, a coffee table, and a patterned rug. There are two paintings on the walls, a lamp, and a potted plant.

5. Cozy House in the heart of Waterville Maine.

Cozy House in the heart of Waterville Maine.
Waterville
9.6 out of 10, Exceptional, (65 reviews)
"Clean and Cozy! Always perfect for our stay "
United States
Rebecca B.
$233 nightly
The price is $254
Nov 2 - Nov 3
Total with taxes and fees
Cozy House in the heart of Waterville Maine.
A modern kitchen with a black refrigerator, dark cabinets, and a wooden dining table with a bench.

6. Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine

Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
Smithfield
10.0 out of 10, Exceptional, (4 reviews)
"A lovely spot. It is extremely clean. The hostess has thought of everything! There are plenty of nice towels and facecloths and bedding. The bed is very comfortable. We have enjoyed our stay"
Canada
Sherrie
$150 nightly
The price is $164
Oct 23 - Oct 24
Total with taxes and fees
Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
A room with a sliding glass door leading to a deck, a wooden table, and a chair.

7. 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, (58 reviews)
"Great place, quiet neighborhood off the lake, very comfortable. Would definitely stay again!"
United States
Steve C.
$363 nightly
The price is $395
Nov 16 - Nov 17
Total with taxes and fees
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
A living room with a fireplace, a glass of white wine, a cutting board with cheese, and a remote control.

8. High End Apartment in Downtown Hallowell

High End Apartment in Downtown Hallowell
Hallowell
10.0 out of 10, Exceptional, (114 reviews)
"Bigger than I expected and one of the homier properties I have been to in a while. Great location to walk around town and minutes to Augusta. Will book again"
United States
Shawn
$185 nightly
The price is $202
Nov 2 - Nov 3
Total with taxes and fees
High End Apartment in Downtown Hallowell
A cozy cabin interior with a wooden floor, a sofa, a table, and a television mounted on the wall.

9. Charming cabin in the birches right on the atv trail!

Charming cabin in the birches right on the atv trail!
Fairfield
8.6 out of 10, Excellent, (9 reviews)
"The cabin was perfect for our two night stay. It was very clean and it felt just like being at home. Misty was a responsive host and I would definitely rent here again."
United States
Tonilynne D.
$140 nightly
The price is $153
Nov 19 - Nov 20
Total with taxes and fees
Charming cabin in the birches right on the atv trail!
A bathroom with a white sink, wooden paneling, a mirror with a bead trim, and a view of a house through a window.

10. River View Retreat, Hot Tub, Balcony, Kayaks & Bikes

River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
Hallowell
10.0 out of 10, Exceptional, (2 reviews)
"Great place and great host. Right in the water and close to New York and Canada"
United States
Anthony R.
$160 nightly
The price is $174
Oct 26 - Oct 27
Total with taxes and fees
River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
A modern kitchen with dark cabinets, a black refrigerator, and a wooden dining table with bar stools.

11. 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
8.0 out of 10, Very good, (1 review)
"Very clean and centrally located for the Belgrade Lakes. Nice people and I will definitely stay again."
United States
Mike F.
$150 nightly
The price is $164
Oct 31 - Nov 1
Total with taxes and fees
Whitsendsport unit 4 1 bedroom & queen pull out couch on 50 acres Smithfield
A spacious living area with a large wooden dining table, a built-in kitchen island, and a view of the outdoors through large windows.

12. A soul soothing escape. Artistically built and lovingly maintained.

A soul soothing escape. Artistically built and lovingly maintained.
New Sharon
10.0 out of 10, Exceptional, (31 reviews)
"Loved the cabin and the view!! Had a great stay, thank you to our host!! Would love to stay again "
United States
Matt W.
$360 nightly
The price is $392
Nov 2 - Nov 3
Total with taxes and fees
A soul soothing escape. Artistically built and lovingly maintained.
A spacious room with a wooden floor, a striped rug, a black chair, and a dining table.

13. 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
9.0 out of 10, Wonderful, (4 reviews)
"Very nice property, great location, nice decor, pet friendly, and good kitchen area."
United States
Laura M.
$285 nightly
The price is $311
Oct 26 - Oct 27
Total with taxes and fees
Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
A deck with two Adirondack chairs, a metal fire pit, and a view of a lake surrounded by trees.

14. China Lake, Dog Friendly, Lots of space for family gatherings

China Lake, Dog Friendly, Lots of space for family gatherings
China
10.0 out of 10, Exceptional, (5 reviews)
"We will miss this house and would be happy to come back again. The ac in every bedroom plus the main floor made the most humid days comfortable. And China Lake is a wonderful place to have a piece of to yourself."
United States
Lisa J.
$470 nightly
The price is $512
Nov 19 - Nov 20
Total with taxes and fees
China Lake, Dog Friendly, Lots of space for family gatherings
A stone fire pit with a red Adirondack chair and a picnic table with a striped umbrella in a grassy outdoor area.

15. 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, (45 reviews)
"Great experience"
United States
Chase D.
$321 nightly
The price is $350
Oct 23 - Oct 24
Total with taxes and fees
Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.
A modern living room with a flat-screen TV, a yellow armchair, a beige sofa, and a coffee table.

16. Two bedroom Mid Century Modern apartment in Downtown Hallowell

Two bedroom Mid Century Modern apartment in Downtown Hallowell
Hallowell
10.0 out of 10, Exceptional, (95 reviews)
"Cute place, quiet neighborhood close to downtown."
United States
Melissa F.
$222 nightly
The price is $242
Nov 1 - Nov 2
Total with taxes and fees
Two bedroom Mid Century Modern apartment in Downtown Hallowell
A covered porch with wicker furniture, a white door, and a welcome mat.

17. Cozy cottage in the Winthrop Lakes Area

Cozy cottage in the Winthrop Lakes Area
Winthrop
9.8 out of 10, Exceptional, (9 reviews)
"The property was lovely, and the host was wonderful!"
United States
Treseanne A.
$169 nightly
The price is $184
Nov 1 - Nov 2
Total with taxes and fees
Cozy cottage in the Winthrop Lakes Area
A modern building with a black exterior and a large glass entrance.

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

Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Madison
9.4 out of 10, Exceptional, (9 reviews)
"Excellent service and perfect for our stay. Would book again!"
United States
Scott
$133 nightly
The price is $144
Oct 25 - Oct 26
Total with taxes and fees
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
A modern kitchen with dark blue cabinets, a black refrigerator, and a wooden table with black cushioned benches.

19. Cozy new 1 bedroom, queen bed, and queen sofa bed, washer/dryers. Radiant heat.

Cozy new 1 bedroom, queen bed, and queen sofa bed, washer/dryers. Radiant heat.
Smithfield
9.0 out of 10, Wonderful, (2 reviews)
"The stay was nice, it was cute place and priced reasonably. The horses across the street were a fun surprise in the morning."
United States
Hailey M.
$150 nightly
The price is $164
Oct 28 - Oct 29
Total with taxes and fees
Cozy new 1 bedroom, queen bed, and queen sofa bed, washer/dryers. Radiant heat.
A large rock surrounded by lush greenery and flowering plants.

20. Wilson Lake Inn & Suites

Wilson Lake Inn & Suites
2.0 star property
Wilton
$161 nightly
The price is $175
Nov 1 - Nov 2
Total with taxes and fees
Wilson Lake Inn & Suites
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

Homewood Suites by Hilton Augusta

Homewood Suites by Hilton Augusta

8/10 Good
"It is tucked in a quiet area of the town but not so far away from everything essential: gas stations, fastfood/restaurants, and major roads."
Jenny 1-night trip
Posted 9 hours ago
Homewood Suites by Hilton Augusta

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 $147 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?

Stunning Belgrade Lakes Waterfront Retreat – Dock, Kayaks & Breathtaking Views!: This Oakland vacation home rental offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Some other top choices in Oakland are Cozy Long Pond Cottage: community access, private mooring & shared dock. and Charming Lakeview House with Deck, Cozy Fireplace and firepit.

How many vacation rentals will I find in Oakland?

Choose from 31 Expedia vacation rentals in Oakland for a memorable vacation.

What can I see and do in Oakland?

Belgrade Lakes Chain and Messalonskee Lake are a couple of lovely local spots to get outside and enjoy nature. East Pond and Great Pond are other places to visit while you're in town.

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.