A lake surrounded by trees with autumn leaves.

Oakland Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Oakland vacation rentals

Exterior

1. Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
10.0 out of 10, Exceptional, (10 reviews)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
$241 nightly
The price is $262
Aug 13 - Aug 14
Total with taxes and fees
Sister A-Frame in Woods B
2 bedrooms, WiFi, bed sheets

2. 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
$217 nightly
The price is $237
Aug 14 - Aug 15
Total with taxes and fees
The heart of the Belgrade Lakes
Outdoor dining

3. Peaceful retreat on farm minutes to lake. Bring kayak or canoe!

Peaceful retreat on farm minutes to lake. Bring kayak or canoe!
Oakland
10.0 out of 10, Exceptional, (14 reviews)
"It was a great stay. The house is very comfortable"
United States
Benjamin C.
$441 nightly
The price is $467
Aug 17 - Aug 18
Total with taxes and fees
Peaceful retreat on farm minutes to lake. Bring kayak or canoe!
Paper towels

4. 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, (2 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
Aug 14 - Aug 15
Total with taxes and fees
Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
Smart TV

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 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
Aug 17 - Aug 18
Total with taxes and fees
Charming cabin in the birches right on the atv trail!
Outdoor dining

6. Minutes to Colby

Minutes to Colby
Waterville
8.8 out of 10, Excellent, (24 reviews)
"Close to our event, great communication, clean, comfortable & cozy"
United States
Shelly B.
$233 nightly
The price is $254
Aug 17 - Aug 18
Total with taxes and fees
Minutes to Colby
Living area

7. 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
$171 nightly
The price is $186
Sep 1 - Sep 2
Total with taxes and fees
Country setting close to lake 1 bedroom queen bed sofa, full kitchens and bath
Exterior

8. 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, (8 reviews)
"Excellent service and perfect for our stay. Would book again!"
United States
Scott
$135 nightly
The price is $147
Sep 1 - Sep 2
Total with taxes and fees
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
TV

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, (90 reviews)
"House and community was amazing love the vibe of house experience was far and above expectations "
United States
Mike W.
$216 nightly
The price is $235
Sep 3 - Sep 4
Total with taxes and fees
Two bedroom Mid Century Modern apartment in Downtown Hallowell
Interior

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

Fabulous 3-bedroom RV with direct access to the Sebasticook River!
Benton
8.0 out of 10, Very Good, (1 review)
"Very clean and comfortable. Nice view of river. Very quiet & comfortable."
United States
Jack F.
$130 nightly
The price is $142
Aug 26 - Aug 27
Total with taxes and fees
Fabulous 3-bedroom RV with direct access to the Sebasticook River!
Interior

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, (56 reviews)
"Great place, quiet neighborhood off the lake, very comfortable. Would definitely stay again!"
United States
Steve C.
$500 nightly
The price is $545
Sep 3 - Sep 4
Total with taxes and fees
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
Exterior

12. Wilson Lake Inn & Suites

Wilson Lake Inn & Suites
2.0 star property
Wilton
$206 nightly
The price is $225
Aug 22 - Aug 23
Total with taxes and fees
Wilson Lake Inn & Suites
Interior

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.
$381 nightly
The price is $415
Aug 21 - Aug 22
Total with taxes and fees
A soul soothing escape. Artistically built and lovingly maintained.
Exterior

14. Perfectly Located 1 Bedroom, newly remodeled

Perfectly Located 1 Bedroom, newly remodeled
Augusta
10.0 out of 10, Exceptional, (4 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.
$257 nightly
The price is $280
Aug 13 - Aug 14
Total with taxes and fees
Perfectly Located 1 Bedroom, newly remodeled
Exterior

15. Wilson Lake Inn

Wilson Lake Inn
3.0 star property
Wilton
10.0 out of 10, Exceptional, (1 review)
"Clean room . Quiet! Close to what we were in the area for."
United States
Patricia
$214 nightly
The price is $233
Aug 18 - Aug 19
Total with taxes and fees
Wilson Lake Inn
Interior

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
10.0 out of 10, Exceptional, (2 reviews)
"The home was adorable, and beds were very comfortable. We checked out the dock (very convenient) though didn't spend any time in the lake, but she had lifejackets, pool noodles, and other lake amenities! Host was very responsive and helpful. We'd be delighted to stay here again!"
United States
Hannah
$290 nightly
The price is $316
Aug 29 - Aug 30
Total with taxes and fees
Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
Interior

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

River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
Hallowell
10.0 out of 10, Exceptional, (1 review)
"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
Aug 18 - Aug 19
Total with taxes and fees
River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
Property grounds

18. 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)
"The cabin amd property were fantastic! Secluded location, loved the fire pit. Great central location for out door activities. "
United States
Susan Appt E.
$342 nightly
The price is $373
Sep 3 - Sep 4
Total with taxes and fees
Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.
Exterior detail

19. Arden Cottage

Arden Cottage
Mount Vernon
$412 nightly
The price is $439
Aug 16 - Aug 17
Total with taxes and fees
Arden Cottage
Exterior detail

20. Peaceful Home in Central Maine

Peaceful Home in Central Maine
Sidney
9.0 out of 10, Wonderful, (9 reviews)
"Had a great experience, host was super responsive and even accommodated us outside the parameters of their listing! House was super cute!! Highly recommend!!"
United States
Jessica G.
$412 nightly
The price is $449
Aug 23 - Aug 24
Total with taxes and fees
Peaceful Home in Central Maine
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

Comfort Inn & Suites Wilton

Comfort Inn & Suites Wilton

10/10 Excellent
"Yes, the menu was fresh. "
corrine 1-night trip
Posted 1 hour ago
Comfort Inn & Suites Wilton

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?

Cozy Long Pond Cottage: community access, private mooring & shared dock.: This Oakland vacation home rental is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. Our travelers also rate Charming Lakeview House with Deck, Cozy Fireplace and firepit as a favorite home for rent in Oakland.

How many vacation rentals will I find in Oakland?

Choose from 32 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. Tree Spirits and East 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.