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Oakland Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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.
$194 nightly
The price is $211
Nov 12 - Nov 13
Total with taxes and fees
Sister A-Frame in Woods B
Property grounds

2. 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.
$222 nightly
The price is $242
Nov 13 - Nov 14
Total with taxes and fees
Central Maine Apartment offering 4 Seasons of Fun.
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)
"Host was very accommodating "
United States
Maureen
$205 nightly
The price is $223
Nov 12 - Nov 13
Total with taxes and fees
The heart of the Belgrade Lakes
A wooden deck with outdoor furniture, a large potted plant, and string lights.

4. 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.
$225 nightly
The price is $245
Nov 13 - Nov 14
Total with taxes and fees
Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes
A cozy cabin interior with a wooden floor, a sofa, a table, and a television mounted on the wall.

5. 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.
$123 nightly
The price is $134
Nov 19 - Nov 20
Total with taxes and fees
Charming cabin in the birches right on the atv trail!
A modern RV kitchen with a built-in stove, sink, and refrigerator, a seating area, and a large window.

6. Fabulous 3-bedroom RV with direct access to the Sebasticook River!

Fabulous 3-bedroom RV with direct access to the Sebasticook River!
Benton
9.6 out of 10, Exceptional, (8 reviews)
"Beautiful camper and property! We loved it!"
United States
Tracy D.
$109 nightly
The price is $118
Nov 30 - Dec 1
Total with taxes and fees
Fabulous 3-bedroom RV with direct access to the Sebasticook River!
A modern kitchen with a black refrigerator, dark cabinets, and a wooden dining table with a bench.

7. 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
$132 nightly
The price is $144
Nov 13 - Nov 14
Total with taxes and fees
Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
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.

8. 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.
$222 nightly
The price is $242
Nov 15 - Nov 16
Total with taxes and fees
Cozy House in the heart of Waterville Maine.
A modern living room with a flat-screen TV, a yellow armchair, a beige sofa, and a coffee table.

9. 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, (97 reviews)
"Cute place, quiet neighborhood close to downtown."
United States
Melissa F.
$190 nightly
The price is $207
Nov 16 - Nov 17
Total with taxes and fees
Two bedroom Mid Century Modern apartment in Downtown Hallowell
A living room with a sofa, a coffee table, a rug, and a painting on the wall.

10. Country setting close to lake 1 bedroom queen bed sofa, full kitchens and bath

Country setting close to lake 1 bedroom queen bed sofa, full kitchens and bath
Smithfield
$125 nightly
The price is $136
Dec 1 - Dec 2
Total with taxes and fees
Country setting close to lake 1 bedroom queen bed sofa, full kitchens and bath
A room with a sliding glass door leading to a deck, a wooden table, and a chair.

11. 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.
$379 nightly
The price is $413
Nov 18 - Nov 19
Total with taxes and fees
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
A covered porch with wicker furniture, a white door, and a welcome mat.

12. 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.
$161 nightly
The price is $175
Nov 15 - Nov 16
Total with taxes and fees
Cozy cottage in the Winthrop Lakes Area
A modern building with a black exterior and a large glass entrance.

13. 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, (10 reviews)
"Excellent service and perfect for our stay. Would book again!"
United States
Scott
$143 nightly
The price is $155
Nov 21 - Nov 22
Total with taxes and fees
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
A large rock surrounded by lush greenery and flowering plants.

14. Wilson Lake Inn & Suites

Wilson Lake Inn & Suites
2.0 star property
Wilton
$143 nightly
The price is $156
Nov 15 - Nov 16
Total with taxes and fees
Wilson Lake Inn & Suites
A wooden deck with a railing and steps leading to a house.

15. Home Away From Home. Family friendly, comfortable- centrally located in Augusta

Home Away From Home. Family friendly, comfortable- centrally located in Augusta
Augusta
$225 nightly
The price is $245
Nov 12 - Nov 13
Total with taxes and fees
Home Away From Home. Family friendly, comfortable- centrally located in Augusta
A stone fire pit with a red Adirondack chair and a picnic table with a striped umbrella in a grassy outdoor area.

16. 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)
"Really neat cabin that has been added onto. The backstory was really cool to read. Highly recommend this cabin. Extremely peaceful and private. Highly recommend this host and staying here!"
United States
Blake B.
$294 nightly
The price is $321
Nov 22 - Nov 23
Total with taxes and fees
Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.
A large, two-story house with a well-lit front porch and multiple windows.

17. Elizabeth Cottage

Elizabeth Cottage
Mount Vernon
$389 nightly
The price is $414
Nov 15 - Nov 16
Total with taxes and fees
Elizabeth Cottage
A kitchen with a dining area, white cabinets, a stove, and a refrigerator.

18. Wilson Lake Inn

Wilson Lake Inn
3.0 star property
Wilton
9.0 out of 10, Wonderful, (2 reviews)
"Clean room . Quiet! Close to what we were in the area for."
United States
Patricia
$162 nightly
The price is $177
Nov 14 - Nov 15
Total with taxes and fees
Wilson Lake Inn
A modern building with a black exterior, a wooden-framed entrance, and a stone staircase leading up to a glass door.

19. Spacious modern living in a quite neighborhood

Spacious modern living in a quite neighborhood
Madison
10.0 out of 10, Exceptional, (2 reviews)
"Mila was always available when I needed anything. Very flexible and the place was nice."
United States
Donna B.
$134 nightly
The price is $147
Nov 15 - Nov 16
Total with taxes and fees
Spacious modern living in a quite neighborhood
A spacious living area with a large wooden dining table, a built-in kitchen island, and a view of the outdoors through large windows.

20. 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.
$344 nightly
The price is $375
Nov 13 - Nov 14
Total with taxes and fees
A soul soothing escape. Artistically built and lovingly maintained.
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

A hotel room with a large bed, a desk with a TV, a chair, a sofa, and a view of the city.
Lockwood Hotel

Lockwood Hotel

Lockwood Hotel
Waterville

10/10 Excellent

Had a wonderful stay at the Lockwood. The room, hotel and staff were all top shelf!
United States
Jeanne
Reviewed November 10, 2026
Lockwood 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 $118 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.

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.

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