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.

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Guest favorite

Loft in West Gardiner

4.98 out of 5 average rating, 111 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.

May 5 – 12

R2,283 ZAR per night

Guest favorite

Cabin in Skowhegan

4.82 out of 5 average rating, 401 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.

Dec 29 – Jan 5

R2,134 ZAR per night

Guest favorite

Home in Farmington

4.96 out of 5 average rating, 104 reviews

Carriage House

Renovated circa 1920 carriage house in a quaint New England college town. Eight-minute walk to busy downtown with restaurants, bars, shops, and grocery store. Elegant contemporary style. Open concept downstairs with sofa, daybed (napping in the sun!), and chef-designed kitchen. Second level with two queen beds and small balcony. Adjoins miles of walking trails and forest, full of wildlife. Less than 5-minute drive to a 1.5 mile running trail along the Sandy River, with refreshing swimming.

Jul 2 – 9

R3,050 ZAR per night

Guest favorite

Home in Oakland

4.97 out of 5 average rating, 29 reviews

Quaint Little Cottage

Clean, quiet, cozy, and includes extras that will make your stay a comfortable one. Located in the Belgrade Lakes region this home is nearby Colby and Thomas College, Maine General and NorthernLight Inland Hospital, centrally located between Waterville and Augusta, and 1 hour to the Maine coast as well as ski mountains. Enjoy hiking, fishing, exploring Maine, and more! For great dining options your commute is 10 minutes, or you can stay in and have delivery from one of our local eateries.

Oct 4 – 11

R3,029 ZAR per night

Guest favorite

Guesthouse in Orland

4.99 out of 5 average rating, 103 reviews

Cozy cottage in Orland Village-Penobscot Bay area

Charming cottage in Orland Village, 2 minutes from Bucksport, a short walk away from the Orland River and its estuary on the Penobscot Bay. Nestled on 3.5 acres of wooded land, 300 ft behind an 18th-century colonial house. Completely self-contained with equipped kitchen. Fast 400 Mbs cable internet/WiFi. 45 minutes to Acadia National Park, 30 min. to Belfast, 20 min. to Castine. Perfect base for hiking, kayaking, sailing, or discovering the maritime past of the area. Pet friendly!

Jan 17 – 24

R1,882 ZAR per night

Guest favorite

Apartment in Wilton

4.86 out of 5 average rating, 105 reviews

1 Bedroom Apartment in Downtown Wilton, Maine.

Simple 2nd floor, single bedroom apartment right in the heart of downtown Wilton, Maine. Just 300 yards from the beautiful Wilson Lake and next door to The Ambition Brewing Co and Calzolaio Pasta Co. This unit is ideal for visiting nurses and workers in the area. Just 5 miles from Franklin Memorial Hospital, and 8 miles from Downtown Farmington and the University of Maine at Farmington. Beautiful Mt. Blue State Park is a 30 minute scenic drive, and Sugar Loaf is within an hour.

May 22 – 29

R1,543 ZAR per night

Guest favorite

Cabin in Mercer

4.95 out of 5 average rating, 189 reviews

Haven Hill Homestead Cabin #1

We are located in the beautiful area of central Maine with amazing views that bring peace to the heart and calmness to the mind. We live away from town on a quiet dirt road with no street lights. We have beautiful views of North Pond and we have wonderful sunrises! We have a small hobby farm and guests can visit the animals if wanted. We are proud to be a pet loving environment. It is very peaceful here. We guarantee that you will have a memorable stay here at Haven Hill.

Jun 14 – 21

R2,512 ZAR per night

Guest favorite

Home in Waterville

4.79 out of 5 average rating, 143 reviews

Cozy House in Waterville

Our private Cozy House has just been renovated! We put in a new kitchen, bathroom, laundry room, and a big 4k smart tv. It's in a friendly neighborhood located in the heart of Waterville only five minutes from Colby College, Thomas College (by car) and just a few minutes from downtown Waterville. Everything is very close to our location. There's a Hannafords nearby, Maine General Hospital and many restaurants, schools and stores. We are located on a private dead-end driveway .

Sep 28 – Oct 5

R2,582 ZAR per night

Guest favorite

Home in Appleton

4.96 out of 5 average rating, 122 reviews

The Barn

I call my place "The Barn" because as I was finishing it it took the shape and feel of a barn. It's not a barn. It's a quiet post and beam open concept building (a Jamaica Cottages kit) set among the fields of Appleton Maine. You'll sleep in the loft or on a futon on the main floor. The bathroom is huge, 10X10, with a heated floor. It's an open concept kitchen and living space. From Appleton you are 20 miles away from the tourist destinations of Camden, Rockland, and Belfast.

May 21 – 28

R2,728 ZAR per night

Guest favorite

Apartment in Hallowell

4.98 out of 5 average rating, 300 reviews

Two Bedroom Mid Century Modern Downtown Apartment

Experience this amazing two bedroom Mid-Century Modern apartment in Downtown Hallowell. This is newly renovated & steps away from a variety of restaurants & pubs. It has all the fun and funky charm of the early 1960’s with bright colors, rich woods, clean lines & shag rugs. All the modern comforts including stainless steel appliances, vessel sinks, soaker tub & new beds. A couple miles from the State Capital and centrally located between Brunswick and Waterville.

Nov 14 – 21

R2,487 ZAR per night

Guest favorite

Cottage in Sidney

4.91 out of 5 average rating, 101 reviews

Waterfront Cottage

The Waterfront Eagle Pine Cottage sits directly on Snow Pond, just 15 minutes from Colby College and downtown Waterville and 1/2 mile from the New England Music Camp. Enjoy the BEST sunset views from the private dock and listen to the waves and loons at night. The private front deck is the perfect spot for a sunset cocktail after a day of swimming and kayaking from the sandy beach. You also have an outdoor hot soaking tub and access to barrel sauna. Paradise!

Sep 26 – Oct 3

R7,656 ZAR per night

Guest favorite

Cabin in Freedom

4.9 out of 5 average rating, 288 reviews

Cozy Lakefront Cabin in Freedom, ME

Our secluded, very quiet and private two bedroom cabin with loft features a bug-free screened-in porch on its large deck. The cabin overlooks peaceul Sandy Pond, inhabited by bald eagles, loons, and herons. Watch beautiful sunrises and sunsets, and swim, fish and kayak from our dock. We're close to coastal Belfast, Unity, MOFGA (annual Common Ground Fair), Waterville, Acadia and Camden. Eat at The Lost Kitchen, visit the Amish, hike the Hills to Sea Trail.

Dec 14 – 21

R1,574 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Oakland vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

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

Guest suite in Oakland

5.0 out of 5 average rating, 32 reviews

Cozy Studio Flat, Belgrade Lakes Region

Jan 8 – 15

R2,067 ZAR per night

Guest favorite

Cottage in Oakland

5.0 out of 5 average rating, 95 reviews

The Rocky Road Camp on East Pond

Oct 18 – 25

R2,975 ZAR per night

Guest favorite