Oakland Vacation Rentals from SAR 287: Search Short-Term Rentals

A lake surrounded by dense forest and a rocky outcrop in the foreground.

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Our top choices for Oakland vacation rentals

A wooden cabin with a porch, a door, and a green chair.

1. Sister A-Frame in Woods B

Oakland

Amanda M.

SAR 794 total

includes taxes & fees

15 Nov - 16 Nov

2. Central Maine Apartment offering 4 Seasons of Fun.

Oakland

kathy e.

SAR 933 total

includes taxes & fees

17 Nov - 18 Nov

A bedroom with a bed, a bedside table, a lamp, and a window with curtains.

3. The heart of the Belgrade Lakes

Oakland

Maureen

SAR 839 total

includes taxes & fees

9 Dec - 10 Dec

A wooden deck with outdoor furniture, a large potted plant, and string lights.

4. Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes

Oakland

Shana S.

SAR 920 total

includes taxes & fees

13 Nov - 14 Nov

A cozy cabin interior with a wooden floor, a sofa, a table, and a television mounted on the wall.

5. Charming cabin in the birches right on the atv trail!

Fairfield

Tonilynne D.

SAR 540 total

includes taxes & fees

9 Dec - 10 Dec

A modern RV kitchen with a built-in stove, sink, and refrigerator, a seating area, and a large window.

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

Benton

Tracy D.

SAR 444 total

includes taxes & fees

30 Nov - 1 Dec

A modern kitchen with a black refrigerator, dark cabinets, and a wooden dining table with a bench.

7. Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine

Smithfield

Sherrie

SAR 540 total

includes taxes & fees

17 Nov - 18 Nov

A living room with a sectional sofa, a coffee table, and a patterned rug. There are two paintings on the walls, a lamp, and a potted plant.

8. Cozy House in the heart of Waterville Maine.

Waterville

Rebecca B.

SAR 908 total

includes taxes & fees

15 Nov - 16 Nov

A modern living room with a flat-screen TV, a yellow armchair, a beige sofa, and a coffee table.

9. Two bedroom Mid Century Modern apartment in Downtown Hallowell

Hallowell

Melissa F.

SAR 775 total

includes taxes & fees

16 Nov - 17 Nov

A living room with a sofa, a coffee table, a rug, and a painting on the wall.

10. Country setting close to lake 1 bedroom queen bed sofa, full kitchens and bath

Smithfield

SAR 511 total

includes taxes & fees

1 Dec - 2 Dec

A room with a sliding glass door leading to a deck, a wooden table, and a chair.

11. Boat launch and Trailer parking, Dog Friendly, Lake Great Pond

Belgrade

Steve C.

SAR 1,504 total

includes taxes & fees

15 Nov - 16 Nov

A covered porch with wicker furniture, a white door, and a welcome mat.

12. Cozy cottage in the Winthrop Lakes Area

Winthrop

Treseanne A.

SAR 659 total

includes taxes & fees

15 Nov - 16 Nov

A modern building with a black exterior and a large glass entrance.

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

Madison

Scott

SAR 642 total

includes taxes & fees

9 Dec - 10 Dec

A large rock surrounded by lush greenery and flowering plants.

14. Wilson Lake Inn & Suites

Wilton

SAR 650 total

includes taxes & fees

14 Nov - 15 Nov

A wooden deck with a railing and steps leading to a house.

15. Home Away From Home. Family friendly, comfortable- centrally located in Augusta

Augusta

SAR 920 total

includes taxes & fees

17 Nov - 18 Nov

A stone fire pit with a red Adirondack chair and a picnic table with a striped umbrella in a grassy outdoor area.

16. Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.

Madison

Blake B.

SAR 1,252 total

includes taxes & fees

9 Dec - 10 Dec

A large, two-story house with a well-lit front porch and multiple windows.

17. Elizabeth Cottage

Mount Vernon

SAR 1,552 total

includes taxes & fees

13 Dec - 14 Dec

A kitchen with a dining area, white cabinets, a stove, and a refrigerator.

18. Wilson Lake Inn

Wilton

Patricia

SAR 664 total

includes taxes & fees

16 Nov - 17 Nov

A modern building with a black exterior, a wooden-framed entrance, and a stone staircase leading up to a glass door.

19. Spacious modern living in a quite neighborhood

Madison

Donna B.

SAR 554 total

includes taxes & fees

11 Dec - 12 Dec

A spacious living area with a large wooden dining table, a built-in kitchen island, and a view of the outdoors through large windows.

20. A soul soothing escape. Artistically built and lovingly maintained.

New Sharon

Matt W.

SAR 1,407 total

includes taxes & fees

13 Nov - 14 Nov

View all properties

Find vacation rentals that suit your style

Top Oakland Hotel Reviews

A hotel lobby with a fireplace, two armchairs, a coffee table, and a wooden shelf above the fireplace.

Hampton Inn Waterville

Waterville

10/10 Excellent

Rob

A hotel room with a bed, a sofa, a desk, and a chair.

Fireside Inn & Suites Waterville

Waterville

10/10 Excellent

Anonymous traveler

A hotel lobby with a green sofa, a beige sofa, and two armchairs. There is a reception desk with a computer and a coffee machine.

Holiday Inn Express & Suites Waterville - North by IHG

Waterville

10/10 Excellent

We stayed here the weekend before and had a couple of small irritants but this stay was all but one irritant free. The previous room had plugs and usbs at both nightstands however this room only had them at one nightstand. It was mainly an irritant because it was on my side and I like to play on my phone before bed and needed to charge it which meant the cord was draped over my better half. So all in all it's a great place to stay. Pool area was nice too with towels and chairs and a handicap...

Tracy

A modern kitchen with a central island, bar stools, and a dining table.

The Elmwood

Waterville

10/10 Excellent

ANGELA

Maine Evergreen Hotel, an Ascend Collection Hotel

Augusta

10/10 Excellent

TODD

A living room with a wicker tray holding snacks, a television displaying a program, and a staircase leading to an upper level.

Maple Hill Farm Inn

Hallowell

10/10 Excellent

Anonymous traveler

An outdoor patio with a stone fire pit surrounded by wicker furniture and a pergola with string lights.

Homewood Suites by Hilton Augusta

Augusta

10/10 Excellent

Anonymous traveler

A hotel with a covered entrance, multiple floors, and a landscaped garden.

Comfort Inn & Suites Wilton

Wilton

10/10 Excellent

Anonymous traveler

A wooden dock extending into calm water, with a rowboat and a black chair.

Wilson Lake Inn

Wilton

10/10 Excellent

Anonymous traveler

A modern living room with a fireplace, a blue sofa, and a patterned ottoman.

Fairfield Inn & Suites by Marriott Augusta

Augusta

10/10 Excellent

Donna

The Skowhegan By Kasa

Skowhegan

10/10 Excellent

Rebekah

An indoor swimming pool with clear blue water, surrounded by white columns and large windows.

Senator Inn & Spa

Augusta

10/10 Excellent

We had an issue with parking after coming back from a night on the town. Someone had taken the space in front of our door. The vehicle owner said there was a first come first serve parking policy according to the Senator. It was winter with a lot of snow. I didn't want to have to walk around the building. Luckily there was a spot open a few rooms away. We enjoyed a great breakfast in the morning. Wait staff were awesome and attentive.

Jeffrey

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?

Stunning Belgrade Lakes Waterfront Retreat – Dock, Kayaks & Breathtaking Views!: This Oakland vacation home rental offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Some other top choices in Oakland are Cozy Long Pond Cottage: community access, private mooring & shared dock. and Charming Lakeview House with Deck, Cozy Fireplace and firepit.

How many vacation rentals will I find in Oakland?

Choose from 31 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. East Pond and Great 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.

Oakland Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Oakland vacation rentals

1. Sister A-Frame in Woods B

2. Central Maine Apartment offering 4 Seasons of Fun.

3. The heart of the Belgrade Lakes

4. Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes

5. Charming cabin in the birches right on the atv trail!

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

7. Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine

8. Cozy House in the heart of Waterville Maine.

9. Two bedroom Mid Century Modern apartment in Downtown Hallowell

10. Country setting close to lake 1 bedroom queen bed sofa, full kitchens and bath

11. Boat launch and Trailer parking, Dog Friendly, Lake Great Pond

12. Cozy cottage in the Winthrop Lakes Area

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

14. Wilson Lake Inn & Suites

15. Home Away From Home. Family friendly, comfortable- centrally located in Augusta

16. Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.

17. Elizabeth Cottage

18. Wilson Lake Inn

19. Spacious modern living in a quite neighborhood

20. A soul soothing escape. Artistically built and lovingly maintained.

Find vacation rentals that suit your style

Top Oakland Hotel Reviews

Hampton Inn Waterville

10/10 Excellent

Frequently Asked Questions

Can I find vacation rentals in Oakland?

What are some of the best vacation rentals in Oakland?

How many vacation rentals will I find in Oakland?

What can I see and do in Oakland?

What are vacation rentals like in Oakland?