Oakland Vacation Rentals from CA $201: Short-Term Rentals for 2026

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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

Oakland

Amanda M.

CA $300 total

includes taxes & fees

Nov 10 - Nov 11

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

Oakland

Shana S.

CA $340 total

includes taxes & fees

Nov 8 - Nov 9

3. Central Maine Apartment offering 4 Seasons of Fun.

Oakland

kathy e.

CA $353 total

includes taxes & fees

Nov 8 - Nov 9

A bedroom with a bed, a bedside table, a lamp, and a window with curtains.

4. The heart of the Belgrade Lakes

Oakland

Maureen

CA $312 total

includes taxes & fees

Dec 7 - Dec 8

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.

Waterville

Rebecca B.

CA $345 total

includes taxes & fees

Nov 15 - Nov 16

A rustic stone house with a metal roof, surrounded by a grassy field and a large tree.

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

Smithfield

Sherrie

CA $202 total

includes taxes & fees

Dec 7 - Dec 8

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

Belgrade

Steve C.

CA $478 total

includes taxes & fees

Nov 8 - Nov 9

A modern RV kitchen with a built-in stove, sink, and refrigerator, a seating area, and a large window.

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

Benton

Hannah

CA $167 total

includes taxes & fees

Nov 30 - Dec 1

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

Hallowell

Melissa F.

CA $304 total

includes taxes & fees

Nov 9 - Nov 10

A modern kitchen with dark cabinets, a black refrigerator, and a wooden dining table with bar stools.

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

Smithfield

Mike F.

CA $202 total

includes taxes & fees

Dec 7 - Dec 8

A spacious living area with a large wooden dining table, a built-in kitchen island, and a view of the outdoors through large windows.

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

New Sharon

Matt W.

CA $534 total

includes taxes & fees

Nov 9 - Nov 10

A spacious room with a wooden floor, a striped rug, a black chair, and a dining table.

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

Winthrop

Laura M.

CA $411 total

includes taxes & fees

Dec 7 - Dec 8

A cozy cabin interior with a wooden floor, a sofa, a table, and a television mounted on the wall.

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

Fairfield

Tonilynne D.

CA $189 total

includes taxes & fees

Nov 19 - Nov 20

A stone fire pit with a red Adirondack chair and a picnic table with a striped umbrella in a grassy outdoor area.

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

Madison

Blake B.

CA $476 total

includes taxes & fees

Nov 9 - Nov 10

A modern kitchen with dark blue cabinets, a black refrigerator, and a wooden table with black cushioned benches.

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

Smithfield

Hailey M.

CA $203 total

includes taxes & fees

Nov 9 - Nov 10

A modern building with a black exterior and a large glass entrance.

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

Madison

Scott

CA $219 total

includes taxes & fees

Nov 8 - Nov 9

A deck with two Adirondack chairs, a metal fire pit, and a view of a lake surrounded by trees.

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

China

Anne S.

CA $729 total

includes taxes & fees

Nov 8 - Nov 9

A covered porch with wicker furniture, a white door, and a welcome mat.

18. Cozy cottage in the Winthrop Lakes Area

Winthrop

Treseanne A.

CA $239 total

includes taxes & fees

Nov 14 - Nov 15

A large, red, two-story house with a balcony and a tower, surrounded by a fence and trees.

19. Angel Mist Retreat Garage Apartment

Pittsfield

Ruth W.

CA $419 total

includes taxes & fees

Nov 8 - Nov 9

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Find vacation rentals that suit your style

Top Oakland Hotel Reviews

A hotel room with a bed, a sofa, a desk, and a chair.

Fireside Inn & Suites Waterville

Waterville

10/10 Excellent

Benjamin

A hotel lobby with a green sofa, a beige sofa, and two armchairs. There is a reception desk with a computer and a coffee machine.

Holiday Inn Express & Suites Waterville - North by IHG

Waterville

10/10 Excellent

Don&Ann

A modern hotel with a glass facade, outdoor seating area, and a well-lit entrance.

Lockwood Hotel

Waterville

10/10 Excellent

Hotel was clean and modern, with everything you need for an overnight stay. The personal highlight of our overnight stay was the bed - the king room bed was so comfy, I even asked for the mattress details upon check out! The Lavazza coffee/coffee maker made the best cup of in room coffee I have had. Hotel staff were friendly and accommodating (from the front desk to the restaurant). Free parking across the street from the hotel, and we were able to store our bikes in a storage room behind...

Kelly

A modern kitchen with a central island, bar stools, and a dining table.

The Elmwood

Waterville

10/10 Excellent

Alma

Maine Evergreen Hotel, an Ascend Collection Hotel

Augusta

10/10 Excellent

Tiffany

A rectangular swimming pool with a brick deck, surrounded by lounge chairs and umbrellas, with a building in the background.

The Towne Motel

Skowhegan

10/10 Excellent

Maxime

A hotel entrance with a covered patio, columns, and a sign indicating it is a Best Western Plus location.

Best Western Plus Waterville Grand Hotel

Waterville

10/10 Excellent

Denis

A Comfort Inn hotel with a covered entrance, multiple windows, and a brick facade.

Comfort Inn Augusta

Augusta

10/10 Excellent

I didn't expect to have such a great stay, given that the price was so low. Everyone there was very nice and helpful, especially Brenda working the breakfast room, and Peter at the front desk. The room was pretty big, I have two small children who had plenty of space to run around, and everyone really enjoyed their stay. Also the hotel is right next to the highway, so it's easy access. Plus the ninety nine restaurant just next door, and a mall about two minutes away.

Sebastien

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oakland vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oakland vacation rentals we have selected for you start as low as CA $201 per night. Entering your travel dates in the search wizard 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.

Oakland Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Oakland vacation rentals

1. Sister A-Frame in Woods B

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

3. Central Maine Apartment offering 4 Seasons of Fun.

4. The heart of the Belgrade Lakes

5. Cozy House in the heart of Waterville Maine.

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

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

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

9. Two bedroom Mid Century Modern apartment in Downtown Hallowell

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

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

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

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

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

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

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

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

18. Cozy cottage in the Winthrop Lakes Area

19. Angel Mist Retreat Garage Apartment

Find vacation rentals that suit your style

Top Oakland Hotel Reviews

Fireside Inn & Suites Waterville

10/10 Excellent

Find out more about Oakland

Oakland vacation rentals: An excellent choice for every season

How to find incredible deals on Oakland rentals

Frequently Asked Questions

Can I find vacation rentals in Oakland?

What are some of the best vacation rentals in Oakland?

How many vacation rentals will I find in Oakland?

What can I see and do in Oakland?

What are vacation rentals like in Oakland?