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
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

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.
The price is ￥19,702
￥42,843 total
includes taxes & fees
Aug 13 - Aug 14
Sister A-Frame in Woods B
Exterior

2. Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (14 reviews)
"House very clean and convenient location for what we had going on. "
United States
Tammy W.
The price is ￥14,850
￥32,569 total
includes taxes & fees
Aug 13 - Aug 14
Discover Oakland charm near Colby College 10 min
2 bedrooms, WiFi, bed sheets

3. 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
The price is ￥18,788
￥38,286 total
includes taxes & fees
Aug 2 - Aug 3
The heart of the Belgrade Lakes
Outdoor dining

4. 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.
The price is ￥42,885
￥81,401 total
includes taxes & fees
Aug 10 - Aug 11
Peaceful retreat on farm minutes to lake. Bring kayak or canoe!
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.
The price is ￥18,379
￥28,047 total
includes taxes & fees
Aug 4 - Aug 5
Charming cabin in the birches right on the atv trail!
Paper towels

6. 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.
The price is ￥21,238
￥26,711 total
includes taxes & fees
Aug 3 - Aug 4
Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
Outdoor dining

7. Minutes to Colby

Minutes to Colby
Waterville
8.8 out of 10, Excellent, (23 reviews)
"Close to our event, great communication, clean, comfortable & cozy"
United States
Shelly B.
The price is ￥25,976
￥41,313 total
includes taxes & fees
Aug 3 - Aug 4
Minutes to Colby
Coffee/tea maker, fridge, microwave, oven

8. 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 ￥24,578
￥30,362 total
includes taxes & fees
Jul 31 - Aug 1
Whitsendsport unit 4 1 bedroom & queen pull out couch on 50 acres Smithfield
Interior

9. 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.
The price is ￥14,703
￥23,149 total
includes taxes & fees
Aug 11 - Aug 12
Fabulous 3-bedroom RV with direct access to the Sebasticook River!
Exterior

10. The Love Nest - a Cozy Lakefront Log Cabin

The Love Nest - a Cozy Lakefront Log Cabin
Farmington,
9.6 out of 10, Exceptional, (8 reviews)
"One-of-a-kind Nirvana If you are looking for peace beauty simplicity a d restoration at a soul level look no further. Everything you need and nothing you don't. Host, cabin, setting, amenities all superb. Thank you beyond words! "
United States
Tracy Ann L.
The price is ￥13,886
￥29,382 total
includes taxes & fees
Aug 22 - Aug 23
The Love Nest - a Cozy Lakefront Log Cabin
Exterior

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

Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Madison
9.2 out of 10, Wonderful, (7 reviews)
"Excellent service and perfect for our stay. Would book again!"
United States
Scott
The price is ￥21,761
￥27,281 total
includes taxes & fees
Aug 29 - Aug 30
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Exterior

12. 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.
The price is ￥24,578
￥43,757 total
includes taxes & fees
Aug 17 - Aug 18
Perfectly Located 1 Bedroom, newly remodeled
Property grounds

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, (44 reviews)
"Absolute gem with incredible quiet and privacy. It was only a mile from our daughter. House was incredibly well organized and provisioned. Everything imaginable was there!"
United States
Jeffrey K.
The price is ￥24,342
￥60,545 total
includes taxes & fees
Aug 23 - Aug 24
Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.
Terrace/patio

14. Cozy cottage in the Winthrop Lakes Area

Cozy cottage in the Winthrop Lakes Area
Winthrop
9.8 out of 10, Exceptional, (7 reviews)
"Lovely cottage! Everything we needed. The hosts were gracious and communicated well."
United States
Joshua
The price is ￥20,127
￥33,870 total
includes taxes & fees
Aug 29 - Aug 30
Cozy cottage in the Winthrop Lakes Area
Interior

15. 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.
The price is ￥25,290
￥31,305 total
includes taxes & fees
Aug 3 - Aug 4
River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
Exterior detail

16. 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.
The price is ￥22,194
￥27,753 total
includes taxes & fees
Aug 3 - Aug 4
Spacious modern living in a quite neighborhood
Exterior detail

17. Arden Cottage

Arden Cottage
Mount Vernon
The price is ￥34,308
￥70,785 total
includes taxes & fees
Aug 26 - Aug 27
Arden Cottage
Interior

18. 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
The price is ￥29,407
￥51,642 total
includes taxes & fees
Aug 29 - Aug 30
Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
Paper towels

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

Cozy new 1 bedroom, queen bed, and queen sofa bed, washer/dryers. Radiant heat.
Smithfield
10.0 out of 10, Exceptional, (1 review)
"Clean and new."
United States
erik s.
The price is ￥21,238
￥26,711 total
includes taxes & fees
Aug 1 - Aug 2
Cozy new 1 bedroom, queen bed, and queen sofa bed, washer/dryers. Radiant heat.
Exterior

20. Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment
Pittsfield
10.0 out of 10, Exceptional, (14 reviews)
"Great stay. Very comfortable, roomy, clean and good overall value."
United States
Rob K.
The price is ￥22,937
￥50,288 total
includes taxes & fees
Aug 3 - Aug 4
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

Comfort Inn & Suites Wilton

Comfort Inn & Suites Wilton

10/10 Excellent
"The place is like brand, new, clean, comfortable, no complaints, breakfast is your typical yogurt waffle fake eggs, it’s the only place I’ll stay in greater Farmington area"
Robert 1-night trip
Posted 13 hours ago
Comfort Inn & Suites Wilton

Find out more about Oakland

Search for holiday rentals in Oakland on Expedia! You can easily find your home rentals, villas, holiday apartments in Oakland using one of the methods below:

  • View our selection of featured holiday rentals in Oakland
  • Use the map to find apartments and other holiday homes in the Oakland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oakland while they last

Look no further and take a look at our great range of rental properties in Oakland!

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 33 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.