Oakland vacation rentals

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Top-rated vacation rentals in Oakland

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Loft in West Gardiner

4.98 out of 5 average rating, 110 reviews

Cozy, Efficiency Apartment with Hot Tub

Keep it simple at this peaceful, centrally-located efficiency apartment. 15 minutes to Gardiner and Augusta, 15 minutes to I95/295. Less than one hour from Portland. Walk along the stream, listen to the loons or enjoy relaxing in the hot tub. If you want to paddle in a kayak, you can do that too! Eagles regularly soar overhead. Queen size bed, love seat and room enough for a pack and pay or twin air mattress. A/C, full kitchen, Keurig, microwave, toaster, dishes. Wifi and cable. Roomy parking.

Feb 13 – 20

ﺩ.ﺇ438 per night
Guest favorite

Yurt in Appleton

4.96 out of 5 average rating, 221 reviews

SUMMER ROSE a Yurt for ALL Seasons

SUMMER ROSE - Overlooking the Field of Dreams pasture, and future pond, is a spacious wooden yurt with a spectacular ceiling, personal hot tub and "Hideout" a screened in sanctuary. The Appleton Retreat is situated on 120 acres of privately owned land. To the south, a short walk from Summer Rose, is the Pettengill Stream, a resource protected area where you can view wildlife or kayak; and to the north, a wooded trail leads to a secluded pond on 1,300 acres of Nature Conservancy protected land.

Feb 16 – 23

ﺩ.ﺇ598 per night
Guest favorite

Cabin in Skowhegan

4.82 out of 5 average rating, 399 reviews

The Cabin -Skowhegan

This guest house, main floor has living area, kitchen and dining area, 1 queen bed, with a daybed and trundler bed. Loft contains 2 twin beds. There is also a couch that could be used as a bed, full bathroom. Has no kitchen sink but has a kitchen area with microwave, large toaster oven, fridge/freezer, toaster and coffee maker, iron/board. Also has TV, DVD/blu ray player, Gas BBQ (May to November 1st.), as well as a picnic table, with benches and an out door fire pit and wood is supplied.

Mar 3 – 10

ﺩ.ﺇ398 per night

Popular amenities for Oakland vacation rentals

Stay near Oakland's top sights

Marden's4 locals recommend
Shaw's5 locals recommend
Early Bird Restaurant3 locals recommend
Buddies Groceries3 locals recommend
Sheba's Wicked Kitchen3 locals recommend
Riverside Farm Restaurant & Wine Market6 locals recommend

Other great vacation rentals in Oakland

Guest favorite

Home in Oakland

5.0 out of 5 average rating, 52 reviews

Cute 2-bedroom home in convenient central location

Nov 16 – 23

ﺩ.ﺇ624 per night
Guest favorite

Home in Oakland

4.95 out of 5 average rating, 86 reviews

The Modern Maine Retreat

Jun 30 – Jul 7

ﺩ.ﺇ972 per night
Guest favorite

Cottage in Oakland

4.9 out of 5 average rating, 31 reviews

Lakefront cottage in Belgrade Lakes

Aug 24 – 31

ﺩ.ﺇ1,055 per night
Guest favorite

Home in Oakland

4.99 out of 5 average rating, 73 reviews

Call of the Loon-Snow Pond (Messalonskee Lake)

Apr 17 – 24

ﺩ.ﺇ688 per night
Guest favorite

Home in Oakland

4.88 out of 5 average rating, 85 reviews

Lake-House on water, East Lake, Belgrade Lakes

Sep 4 – 11

ﺩ.ﺇ1,170 per night
Guest favorite

Home in Waterville

4.92 out of 5 average rating, 83 reviews

Sterling House

Sep 6 – 13

ﺩ.ﺇ598 per night
Guest favorite

Home in Augusta

5.0 out of 5 average rating, 10 reviews

Super cute waterfront cottage

Sep 12 – 19

ﺩ.ﺇ524 per night
Guest favorite

Home in Fairfield

4.9 out of 5 average rating, 31 reviews

Cozy home in Fairfield

Jun 12 – 19

ﺩ.ﺇ620 per night
Guest favorite

Home in Oakland

5.0 out of 5 average rating, 8 reviews

Quiet, 6 bedroom lakefront home with sandy beach

Feb 16 – 23

ﺩ.ﺇ2,292 per night
Guest favorite

Apartment in Skowhegan

5.0 out of 5 average rating, 14 reviews

Cozy, cute, new, tiny duplex

May 10 – 17

ﺩ.ﺇ471 per night
Guest favorite

Cottage in Farmington

4.98 out of 5 average rating, 82 reviews

The cottage at Marble Farm.

Jun 10 – 17

ﺩ.ﺇ398 per night
Guest favorite

Cottage in Augusta

5.0 out of 5 average rating, 80 reviews

Modern Hideaway in Augusta

Apr 28 – May 5

ﺩ.ﺇ395 per night

Other great vacation rentals in Oakland

Superhost

Cottage in Oakland

4.83 out of 5 average rating, 12 reviews

Belgrade Lakes McGrath Pond

Jun 30 – Jul 7

ﺩ.ﺇ1,121 per night
Guest favorite

Home in Farmington

4.97 out of 5 average rating, 95 reviews

Carriage House

Apr 23 – 30

ﺩ.ﺇ513 per night
Guest favorite

Cabin in Starks

4.88 out of 5 average rating, 58 reviews

Private tiny cabin on six acres of trees

Mar 2 – 9

ﺩ.ﺇ361 per night
Guest favorite

Apartment in Pittsfield

4.89 out of 5 average rating, 38 reviews

Loft Retreat

Jun 11 – 18

ﺩ.ﺇ395 per night
Guest favorite

Apartment in Augusta

4.94 out of 5 average rating, 53 reviews

Downtown Augusta Studio - Newly Renovated #3

May 27 – Jun 3

ﺩ.ﺇ349 per night
Guest favorite

Apartment in Palermo

4.98 out of 5 average rating, 88 reviews

One bedroom apartment in rural Waldo County, Maine

Sep 17 – 24

ﺩ.ﺇ346 per night
Guest favorite

Home in Oakland

5.0 out of 5 average rating, 8 reviews

Lakefront cottage on East Pond

May 25 – Jun 1

ﺩ.ﺇ2,526 per night
Guest favorite

Cottage in China

4.99 out of 5 average rating, 77 reviews

Lake House on Three Mile Pond with Amazing views

May 4 – 11

ﺩ.ﺇ661 per night
Guest favorite

Guest suite in Chesterville

4.93 out of 5 average rating, 97 reviews

Rustic Ridge

Sep 1 – 8

ﺩ.ﺇ304 per night
Superhost

Apartment in Pittsfield

4.82 out of 5 average rating, 11 reviews

Book, Bed & Relax

Nov 23 – 30

ﺩ.ﺇ335 per night
Guest favorite

Apartment in Unity

4.98 out of 5 average rating, 41 reviews

The Heron's Nest Cozy apartment in the woods.

Dec 2 – 9

ﺩ.ﺇ525 per night
Guest favorite

Cottage in Belgrade

5.0 out of 5 average rating, 85 reviews

Lakefront Home, Sandy Beach, Belgrade Lakes Maine

Oct 26 – Nov 2

ﺩ.ﺇ1,049 per night

Quick stats about vacation rentals in Oakland

Total rentals

50 properties

Rentals with dedicated workspaces

20 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

30 properties are a good fit for families

Total number of reviews

1.4K reviews

Nightly prices starting at

ﺩ.ﺇ184 before taxes and fees

Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Oakland?

    Four-legged friends are welcome in Oakland. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Oakland?

    Yes! Work meets play with ease at over 20 vacation rentals in Oakland featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly house rentals in Oakland?

    Oakland has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Oakland?

    Experience the best of Oakland with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Oakland have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Oakland. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Oakland have wireless internet?

    Absolutely! We offer over 10 cottage rentals with wireless internet in Oakland. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Oakland have a bbq area?

    Absolutely! We offer over 10 house rentals with a bbq area in Oakland. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Oakland?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wireless internet, over 10 homes with a bbq area, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Kennebec County
  5. Oakland