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Oakland Vacation Rentals

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49 rentals in Oakland.
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Classy AF Home Steps from Colby and Trails, vacation rental in Oakland

Classy AF Home Steps from Colby and Trails

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Updated Oakland Cottage w/Deck on McGrath Pond!, vacation rental in Oakland

Updated Oakland Cottage w/Deck on McGrath Pond!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Immaculate View On Webber Pond With Boat Rental Option, vacation rental in Oakland

Immaculate View On Webber Pond With Boat Rental Option

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Teaberry Cottage! Quiet Setting On The Lake, All The Modern Comforts Of Home, vacation rental in Oakland

Teaberry Cottage! Quiet Setting On The Lake, All The Modern Comforts Of Home

4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Peaceful Lakefront Getaway, vacation rental in Oakland

Peaceful Lakefront Getaway

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cabin on Long Pond, just steps to lake., vacation rental in Oakland

Cabin on Long Pond, just steps to lake.

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Beautiful Cottage In Wildewood Estates, vacation rental in Oakland

Beautiful Cottage In Wildewood Estates

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Large Lake House with Private Beach, Dock, Canoe & Kayak, vacation rental in Oakland

Large Lake House with Private Beach, Dock, Canoe & Kayak

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lakeside house on Webber Pond with small beach and wonderful views., vacation rental in Oakland

Lakeside house on Webber Pond with small beach and wonderful views.

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Luxury Family Home / Retreat Center on Great Pond, vacation rental in Oakland

Luxury Family Home / Retreat Center on Great Pond

7 bedrooms
9 bathrooms
Sleeps 16
Match: Sleeps
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3 Bedroom year round lakefront home on Three Mile Pond in South China, ME, vacation rental in Oakland

3 Bedroom year round lakefront home on Three Mile Pond in South China, ME

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Private and Calming Waterfront to the Rescue!, vacation rental in Oakland

Private and Calming Waterfront to the Rescue!

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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** Lakefront Home With All The Ammenities For A Relaxing Getaway!**, vacation rental in Oakland

** Lakefront Home With All The Ammenities For A Relaxing Getaway!**

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautifully renovated cottage on quiet lake, vacation rental in Oakland

Beautifully renovated cottage on quiet lake

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Summer Cottage on Clean Sheepscot Lake, vacation rental in Oakland

Summer Cottage on Clean Sheepscot Lake

4 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Family Cottage On Maranacook Lake  W/ WIFI, vacation rental in Oakland

Family Cottage On Maranacook Lake W/ WIFI

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lake House with Swim Area, Dock, Deck, Canoe, & Paddle Boat  (1BR+, Sleeps 6), vacation rental in Oakland

Lake House with Swim Area, Dock, Deck, Canoe, & Paddle Boat (1BR+, Sleeps 6)

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Get away from it all at this cottage on Lovejoy pond in Albion Maine, vacation rental in Oakland

Get away from it all at this cottage on Lovejoy pond in Albion Maine

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lake Front Chalet on Great Pond, vacation rental in Oakland

Lake Front Chalet on Great Pond

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Rustic lakefront home w/ private dock, wood fireplace & modern conveniences, vacation rental in Oakland

Rustic lakefront home w/ private dock, wood fireplace & modern conveniences

5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Beautiful Cottage With Double Decks On The Water And Incredible 180 Degree View, vacation rental in Oakland

Beautiful Cottage With Double Decks On The Water And Incredible 180 Degree View

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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A soul soothing escape. Kate-Ah-Den cabin is new & artistically built., vacation rental in Oakland

A soul soothing escape. Kate-Ah-Den cabin is new & artistically built.

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Little Beans Cottage, vacation rental in Oakland

Little Beans Cottage

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Twin Oaks on Great Pond, vacation rental in Oakland

Twin Oaks on Great Pond

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Maine Cabin on the Water, vacation rental in Oakland

Maine Cabin on the Water

5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Pristine Parker Pond - A Hidden Gem, vacation rental in Oakland

Pristine Parker Pond - A Hidden Gem

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Long Pond in Belgrade Lakes Region Maine Sleeps 12, vacation rental in Oakland

Long Pond in Belgrade Lakes Region Maine Sleeps 12

4 bedrooms
1 bathroom
Sleeps 12
Match: Sleeps
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Afterglow Cottage on Great Pond, vacation rental in Oakland

Afterglow Cottage on Great Pond

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Cozy House in the heart of Waterville Maine., vacation rental in Oakland

Cozy House in the heart of Waterville Maine.

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Great Pond- Rustic, charming Log Cabin, vacation rental in Oakland

Great Pond- Rustic, charming Log Cabin

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Belgrade Lakes vacation home, vacation rental in Oakland

Belgrade Lakes vacation home

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Room near the Maine Statehouse, vacation rental in Oakland

Room near the Maine Statehouse

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Great Pond Shoreline- Charming Log Cabin, vacation rental in Oakland

Great Pond Shoreline- Charming Log Cabin

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Sandy River House - Retreat To Our Beautiful All-Renovated 200yo Village House, vacation rental in Oakland

Sandy River House - Retreat To Our Beautiful All-Renovated 200yo Village House

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Loon Loft on Pattee's Pond - Kayaks & Canoes - Fall 2020 Dates Available, vacation rental in Oakland

Loon Loft on Pattee's Pond - Kayaks & Canoes - Fall 2020 Dates Available

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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BELGRADE LAKES  MAINE ** GREAT POND **  2 BEDROOM COTTAGE 15 FEET FROM WATER, vacation rental in Oakland

BELGRADE LAKES MAINE ** GREAT POND ** 2 BEDROOM COTTAGE 15 FEET FROM WATER

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Appartamento Costa, vacation rental in Oakland

Appartamento Costa

2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Star Point on Snow Pond in the Belgrade Lakes, vacation rental in Oakland

Star Point on Snow Pond in the Belgrade Lakes

2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Room #1 at the Maple Hill Farm Inn -- Augusta and Hallowell, Maine, vacation rental in Oakland

Room #1 at the Maple Hill Farm Inn -- Augusta and Hallowell, Maine

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Room #4 at the Maple Hill Farm Inn – Augusta and Hallowell, Maine, vacation rental in Oakland

Room #4 at the Maple Hill Farm Inn – Augusta and Hallowell, Maine

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Room #6 at the Maple Hill Farm Inn – Augusta and Hallowell, Maine, vacation rental in Oakland

Room #6 at the Maple Hill Farm Inn – Augusta and Hallowell, Maine

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Room #5 at the Maple Hill Farm Inn – Augusta and Hallowell, Maine, vacation rental in Oakland

Room #5 at the Maple Hill Farm Inn – Augusta and Hallowell, Maine

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Room #7 at the Maple Hill Farm Inn – Augusta and Hallowell, Maine, vacation rental in Oakland

Room #7 at the Maple Hill Farm Inn – Augusta and Hallowell, Maine

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Room #3 at the Maple Hill Farm Inn – Augusta and Hallowell, Maine, vacation rental in Oakland

Room #3 at the Maple Hill Farm Inn – Augusta and Hallowell, Maine

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Room #8 at the Maple Hill Farm Inn – Augusta and Hallowell, Maine, vacation rental in Oakland

Room #8 at the Maple Hill Farm Inn – Augusta and Hallowell, Maine

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Room #2 at the Maple Hill Farm Inn – Augusta and Hallowell, Maine, vacation rental in Oakland

Room #2 at the Maple Hill Farm Inn – Augusta and Hallowell, Maine

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Tentrr Signature Site - Valley Acres, vacation rental in Oakland

Tentrr Signature Site - Valley Acres

1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Tentrr Signature Site - Fox Run Campsite, vacation rental in Oakland

Tentrr Signature Site - Fox Run Campsite

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Picturesque Freedom Log Cabin: Trails Nearby!, vacation rental in Oakland

NEW! Picturesque Freedom Log Cabin: Trails Nearby!

1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Clean, new Eco-friendly Camp: Hidden Treasure on Golden Pond, vacation rental in Oakland

Clean, new Eco-friendly Camp: Hidden Treasure on Golden Pond

3 bedrooms
2 bathrooms
Sleeps 1
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