A lake surrounded by trees with autumn leaves.

Oakland Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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.
The price is CA $126
CA $311 total
includes taxes & fees
Nov 5 - Nov 6
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.
The price is CA $146
CA $351 total
includes taxes & fees
Nov 1 - Nov 2
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
The price is CA $161
CA $326 total
includes taxes & fees
Nov 5 - Nov 6
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.
The price is CA $257
CA $460 total
includes taxes & fees
Nov 1 - Nov 2
Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes
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.
The price is CA $207
CA $360 total
includes taxes & fees
Nov 8 - Nov 9
Cozy House in the heart of Waterville Maine.
A cozy cabin interior with a wooden floor, a sofa, a table, and a television mounted on the wall.

6. 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.
The price is CA $133
CA $214 total
includes taxes & fees
Nov 19 - Nov 20
Charming cabin in the birches right on the atv trail!
A modern living room with a flat-screen TV, a yellow armchair, a beige sofa, and a coffee table.

7. 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, (96 reviews)
"Cute place, quiet neighborhood close to downtown."
United States
Melissa F.
The price is CA $157
CA $313 total
includes taxes & fees
Nov 1 - Nov 2
Two bedroom Mid Century Modern apartment in Downtown Hallowell
A modern kitchen with a black refrigerator, dark cabinets, and a wooden dining table with a bench.

8. 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
The price is CA $168
CA $214 total
includes taxes & fees
Nov 1 - Nov 2
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.

9. 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.
The price is CA $216
CA $519 total
includes taxes & fees
Nov 5 - Nov 6
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
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

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.
The price is CA $168
CA $214 total
includes taxes & fees
Nov 1 - Nov 2
Whitsendsport unit 4 1 bedroom & queen pull out couch on 50 acres Smithfield
A modern building with a black exterior and a large glass entrance.

11. 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
The price is CA $157
CA $202 total
includes taxes & fees
Nov 6 - Nov 7
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
A bathroom with a white sink, wooden paneling, a mirror with a bead trim, and a view of a house through a window.

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

River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
Hallowell
10.0 out of 10, Exceptional, (3 reviews)
"Great place and great host. Right in the water and close to New York and Canada"
United States
Anthony R.
The price is CA $203
CA $253 total
includes taxes & fees
Oct 30 - Oct 31
River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
A stone fire pit with a red Adirondack chair and a picnic table with a striped umbrella in a grassy outdoor area.

13. 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.
The price is CA $188
CA $496 total
includes taxes & fees
Oct 30 - Oct 31
Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.
A covered porch with wicker furniture, a white door, and a welcome mat.

14. 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.
The price is CA $146
CA $261 total
includes taxes & fees
Nov 5 - Nov 6
Cozy cottage in the Winthrop Lakes Area
A cabin with a deck, a covered outdoor seating area, and a small porch.

15. 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, (150 reviews)
"We really enjoyed our stay here! The host was very nice and welcoming. The lake access was easy for boating and swimming. Wished that the place was cleaner when first arrived, but overall would highly recommend this place!"
United States
Justine M.
The price is CA $156
CA $200 total
includes taxes & fees
Nov 3 - Nov 4
Paddle, float, fish, or rope swing into the lake. Direct ATV trail access too!
A spacious room with a wooden floor, a striped rug, a black chair, and a dining table.

16. 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.
The price is CA $245
CA $430 total
includes taxes & fees
Oct 30 - Oct 31
Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
A large, two-story house with a well-lit front porch and multiple windows.

17. Elizabeth Cottage

Elizabeth Cottage
Mount Vernon
The price is CA $294
CA $605 total
includes taxes & fees
Nov 1 - Nov 2
Elizabeth Cottage
A two-story house with a front porch, a small tree, and a brick pathway.

18. Perfectly Located 1 Bedroom, newly remodeled

Perfectly Located 1 Bedroom, newly remodeled
Augusta
10.0 out of 10, Exceptional, (7 reviews)
"I’ve stayed in many rental properties and this one is by far the cleanest and nicest. Everything was exactly as described and there was even a second ac unit in the bedroom. It’s on a nice quiet street and convenient to many things. You truly can’t go wrong choosing to stay here."
United States
Lisa G.
Perfectly Located 1 Bedroom, newly remodeled
A large rock surrounded by lush greenery and flowering plants.

19. Wilson Lake Inn & Suites

Wilson Lake Inn & Suites
2.0 star property
Wilton
The price is CA $306
CA $333 total
includes taxes & fees
Nov 5 - Nov 6
Wilson Lake Inn & Suites
A large, red, two-story house with a balcony and a tower, surrounded by a fence and trees.

20. Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment
Pittsfield
10.0 out of 10, Exceptional, (15 reviews)
"Very quiet and lovely apartment. The host was very accommodating and attentive to my questions."
United States
Ruth W.
The price is CA $196
CA $437 total
includes taxes & fees
Oct 30 - Oct 31
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

Holiday Inn Express & Suites Waterville - North by IHG

Holiday Inn Express & Suites Waterville - North by IHG

8/10 Good
"Very clean,rooms not run down gd breakfast. very polite staff."
Sally 2-night trip
Posted 22 hours ago
Holiday Inn Express & Suites Waterville - North by IHG

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 $200 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.