A lake surrounded by trees with autumn leaves.

Oakland Vacation Rentals

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Check prices for these dates

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

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 SAR 453
SAR 985 total
includes taxes & fees
20 Aug - 21 Aug
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
The price is SAR 432
SAR 876 total
includes taxes & fees
26 Aug - 27 Aug
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.
The price is SAR 887
SAR 1,755 total
includes taxes & fees
17 Aug - 18 Aug
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.
The price is SAR 488
SAR 614 total
includes taxes & fees
12 Sep - 13 Sep
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.
The price is SAR 422
SAR 645 total
includes taxes & fees
17 Aug - 18 Aug
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.
The price is SAR 597
SAR 954 total
includes taxes & fees
17 Aug - 18 Aug
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
The price is SAR 563
SAR 704 total
includes taxes & fees
9 Sep - 10 Sep
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
The price is SAR 439
SAR 561 total
includes taxes & fees
25 Aug - 26 Aug
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.
The price is SAR 507
SAR 945 total
includes taxes & fees
9 Sep - 10 Sep
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
9.0 out of 10, Wonderful, (2 reviews)
"Beautiful camper and property! We loved it!"
United States
Tracy D.
The price is SAR 338
SAR 532 total
includes taxes & fees
31 Aug - 1 Sep
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.
The price is SAR 1,088
SAR 2,045 total
includes taxes & fees
3 Sep - 4 Sep
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
The price is SAR 919
SAR 1,002 total
includes taxes & fees
22 Aug - 23 Aug
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.
The price is SAR 929
SAR 1,557 total
includes taxes & fees
21 Aug - 22 Aug
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.
The price is SAR 601
SAR 1,052 total
includes taxes & fees
27 Aug - 28 Aug
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
The price is SAR 825
SAR 899 total
includes taxes & fees
16 Aug - 17 Aug
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
The price is SAR 751
SAR 1,289 total
includes taxes & fees
23 Aug - 24 Aug
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.
The price is SAR 524
SAR 653 total
includes taxes & fees
18 Aug - 19 Aug
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.
The price is SAR 559
SAR 1,400 total
includes taxes & fees
3 Sep - 4 Sep
Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.
Exterior detail

19. Arden Cottage

Arden Cottage
Mount Vernon
The price is SAR 788
SAR 1,635 total
includes taxes & fees
13 Sep - 14 Sep
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.
The price is SAR 1,163
SAR 1,685 total
includes taxes & fees
23 Aug - 24 Aug
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

Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

8/10 Good
"Hot tub was well maintained. Hotel was in a good location."
Kristen 1-night trip
Posted 12 hours ago
Fireside Inn & Suites Waterville

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. Great Pond and Tree Spirits 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.