A lake surrounded by trees with autumn leaves.

Oakland Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Oakland vacation rentals

A single-story house with a gray siding exterior, a white front door, and two flower planters on either side of the entrance.

1. Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (17 reviews)
"House very clean and convenient location for what we had going on. "
United States
Tammy W.
$214 nightly
The price is $233
Sep 28 - Sep 29
Total with taxes and fees
Discover Oakland charm near Colby College 10 min
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, (16 reviews)
"Kathleen was a wonderful host. My family and I found the property welcoming and relaxing. Great place to stay if you are looking for a laid back atmosphere and peaceful time in the country."
United States
Jared
$304 nightly
The price is $322
Sep 28 - Sep 29
Total with taxes and fees
Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes
A wooden cabin with a porch, a door, and a green chair.

3. 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.
$231 nightly
The price is $251
Sep 28 - Sep 29
Total with taxes and fees
Sister A-Frame in Woods B
A bedroom with a bed, a bedside table, a lamp, and a window with curtains.

4. The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.0 out of 10, Wonderful, (10 reviews)
"Host was very accommodating "
United States
Maureen
$210 nightly
The price is $229
Sep 28 - Sep 29
Total with taxes and fees
The heart of the Belgrade Lakes

5. Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.
Oakland
10.0 out of 10, Exceptional, (49 reviews)
"Apartment was comfortable and as described. I had a nice stay."
United States
kathy e.
$222 nightly
The price is $242
Sep 28 - Sep 29
Total with taxes and fees
Central Maine Apartment offering 4 Seasons of Fun.
A wooden deck with a table and chairs, a view of a house, and a tree.

6. Minutes to Colby

Minutes to Colby
Waterville
8.8 out of 10, Excellent, (26 reviews)
"Close to our event, great communication, clean, comfortable & cozy"
United States
Shelly B.
$224 nightly
The price is $244
Sep 28 - Sep 29
Total with taxes and fees
Minutes to Colby
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, (57 reviews)
"Great place, quiet neighborhood off the lake, very comfortable. Would definitely stay again!"
United States
Steve C.
$275 nightly
The price is $300
Sep 28 - Sep 29
Total with taxes and fees
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
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!

Fabulous 3-bedroom RV with direct access to the Sebasticook River!
Benton
9.6 out of 10, Exceptional, (4 reviews)
"Beautiful camper and property! We loved it!"
United States
Tracy D.
$130 nightly
The price is $142
Sep 28 - Sep 29
Total with taxes and fees
Fabulous 3-bedroom RV with direct access to the Sebasticook River!
A covered patio with a view of a lake, outdoor furniture, and a wooden deck.

9. Family's Paradise: 3BR/2BA,Game Room & Lake Access

Family's Paradise: 3BR/2BA,Game Room & Lake Access
Belgrade
10.0 out of 10, Exceptional, (11 reviews)
"This property is so special! The setting is absolutely gorgeous and the home itself is perfect both inside and out. We stayed here for a college graduation and had multiple generations-the layout was terrific for all of us. We especially loved sitting by the lake, enjoying the views from the screened in porch, and family time in the game room. The communication from the host was excellent and the entire process from beginning to end was seamless. We hope to return for another stay!"
United States
Jennifer E.
$820 nightly
The price is $894
Oct 26 - Oct 27
Total with taxes and fees
Family's Paradise: 3BR/2BA,Game Room & Lake Access
A two-story house with a balcony, surrounded by trees and a grassy yard.

10. Stunning Lakefront Retreat set on a Private point on North Pond, 9 acres w/beach

Stunning Lakefront Retreat set on a Private point on North Pond, 9 acres w/beach
Smithfield
10.0 out of 10, Exceptional, (3 reviews)
"Best vacation home ever!!! Host, property, and home met all of our families expections. Just perfect !"
United States
Dianne S.
$765 nightly
The price is $834
Sep 29 - Sep 30
Total with taxes and fees
Stunning Lakefront Retreat set on a Private point on North Pond, 9 acres w/beach
A cozy cabin interior with a wooden floor, a sofa, a table, and a television mounted on the wall.

11. 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 Host was great, I highly recommend this spot, everything was super smooth and the cabin was beautiful. "
United States
Jason B.
$158 nightly
The price is $172
Oct 1 - Oct 2
Total with taxes and fees
Charming cabin in the birches right on the atv trail!
A modern kitchen with a black refrigerator, dark cabinets, and a wooden dining table with a bench.

12. 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, (3 reviews)
"WE were delighted in our accommodations. The apartment was lovely and very clean. Lynne was very responsive to my numerous questions. The location was centralized to hiking and biking trails and a quick jaunt to Augusta for the triathlon. I have to say that I slept like a baby too which is not a normal occurence for me. The mattress was so very comfortable. We would not hesitate to book here again. Thank you for a lovely visit."
United States
Cheri A.
$150 nightly
The price is $164
Oct 12 - Oct 13
Total with taxes and fees
Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
A spacious living area with a large wooden dining table, a built-in kitchen island, and a view of the outdoors through large windows.

13. 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, (30 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.
$355 nightly
The price is $386
Sep 29 - Sep 30
Total with taxes and fees
A soul soothing escape. Artistically built and lovingly maintained.
A large rock surrounded by lush greenery and flowering plants.

14. Wilson Lake Inn & Suites

Wilson Lake Inn & Suites
2.0 star property
Wilton
$204 nightly
The price is $223
Oct 9 - Oct 10
Total with taxes and fees
Wilson Lake Inn & Suites
A small, single-story house with a white exterior and a dark roof. It features a front door, two windows with shutters, and a small porch area.

15. Nightingale Cottage

Nightingale Cottage
Mount Vernon
6.0 out of 10, (1 review)
$385 nightly
The price is $409
Sep 28 - Sep 29
Total with taxes and fees
Nightingale Cottage
A modern building with a black exterior and a large glass entrance.

16. 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
Sep 28 - Sep 29
Total with taxes and fees
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
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 Lake, Dog Friendly, Lots of space for family gatherings
China
10.0 out of 10, Exceptional, (4 reviews)
"Perfect for family gatherings Home was very clean and well stocked Host responded quickly to all messages Love that it is pet friendly"
United States
Anne S.
$469 nightly
The price is $511
Oct 4 - Oct 5
Total with taxes and fees
China Lake, Dog Friendly, Lots of space for family gatherings
A large, red, two-story house with a balcony and a tower, surrounded by a fence and trees.

18. Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment
Pittsfield
10.0 out of 10, Exceptional, (15 reviews)
"Great stay. Very comfortable, roomy, clean and good overall value."
United States
Rob K.
$270 nightly
The price is $295
Sep 28 - Sep 29
Total with taxes and fees
Angel Mist Retreat Garage Apartment
A living room with a sofa, a coffee table, a rug, and a painting on the wall.

19. 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
$150 nightly
The price is $164
Oct 18 - Oct 19
Total with taxes and fees
Country setting close to lake 1 bedroom queen bed sofa, full kitchens and bath
A wooden kitchen with a large window, a black countertop, and three bar stools.

20. Welcome to "the east Madison chapel"

Welcome to "the east Madison chapel"
Madison
10.0 out of 10, Exceptional, (3 reviews)
"Great for kids. Lots of space. Convenient location. Plenty to do locally or venture out to explore. Recommend renting the golf cart to get back and forth down the camp road to the dock.. water is clear and clean, rock bottom at shore. Fast response from host who lives close by."
United States
Melissa B.
$621 nightly
The price is $677
Sep 28 - Sep 29
Total with taxes and fees
Welcome to "the east Madison chapel"
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

Holiday Inn Express & Suites Waterville - North by IHG

Holiday Inn Express & Suites Waterville - North by IHG

10/10 Excellent
"The hotel was perfect for our stay. Everything you need is nearby, including restaurants, fast-food options, gas stations, and Walmart. Breakfast is included, there is plenty of parking, and the hotel also has a pool. The rooms were very clean and smelled fresh, and the beds and pillows were comfortable. The location was definitely the highlight for me. I would absolutely stay here again."
Chrisnelia 3-night trip
Posted 6 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, 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 $142 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.